Oxidative stress has become widely viewed as an underlying condition in a number of diseases, such as ischemia–reperfusion disorders, central nervous system disorders, cardiovascular conditions, cancer, and diabetes. Thus, natural and synthetic antioxidants have been actively sought. Superoxide dismutase is a first line of defense against oxidative stress under physiological and pathological conditions. Therefore, the development of therapeutics aimed at mimicking superoxide dismutase was a natural maneuver. Metalloporphyrins, as well as Mn cyclic polyamines, Mn salen derivatives and nitroxides were all originally developed as SOD mimics. The same thermodynamic and electrostatic properties that make them potent SOD mimics may allow them to reduce other reactive species such as peroxynitrite, peroxynitrite-derived CO3·−, peroxyl radical, and less efficiently H2O2. By doing so SOD mimics can decrease both primary and secondary oxidative events, the latter arising from the inhibition of cellular transcriptional activity. To better judge the therapeutic potential and the advantage of one over the other type of compound, comparative studies of different classes of drugs in the same cellular and/or animal models are needed. We here provide a comprehensive overview of the chemical properties and some in vivo effects observed with various classes of compounds with a special emphasis on porphyrin-based compounds. Antioxid. Redox Signal. 13, 877–918.
AbashkinYG, BurtSK. (Salen)MnIII compounds as nonpeptidyl mimics of catalase. Mechanism-based tuning of catalase activity: a theoretical study. Inorg Chem, 44:1425–1432. 2005.
2.
AbidiP, Leers-SuchetaS, CortezY, HanJ, AzharS. Evidence that age-related changes in p38 MAP kinase contribute the decreased steroid production by adrenocortical cells from old rats. Aging Cell, 7:168–178. 2008.
3.
AdamO, LaufsU. Antioxidant effects of statins. Arch Toxicol, 82:885–892. 2008.
4.
AgadjanianH, MaJ, RentsendorjA, VallupiralliV, HwangJY, MahammedA, FarkasDL, GrayHB, GrossZ, Medina-KauweLK. Tumor detection and elimination by a targeted gallium corrole. Proc Natl Acad Sci USA, 106:6105–6110. 2009.
5.
AgadjanianH, WeaverJJ, MahammedA, RentsendorjA, BassS, KimJ, DmochowskiIJ, MargalitR, GrayHB, GrossZ, Medina-KauweLK. Specific delivery of corroles to cells via noncovalent conjugates with viral proteins. Pharm Res, 23:367–377. 2006.
6.
AladagMA, TurkozY, SahnaE, ParlakpinarH, GulM. The attenuation of vasospasm by using a SOD mimetic after experimental subarachnoidal haemorrhage in rats. Acta Neurochir (Wien), 145:673–676. 2003.
7.
AlexandreJ, NiccoC, ChereauC, LaurentA, WeillB, GoldwasserF, BatteuxF. Improvement of the therapeutic index of anticancer drugs by the superoxide dismutase mimic, mangafodipir. J Natl Cancer Inst, 98:236–244. 2006.
Al-MaghrebiM, FridovichI, BenovL. Manganese supplementation relieves the phenotypic deficits seen in superoxide-dismutase-null Escherichia coli. Arch Biochem Biophys, 402:104–109. 2002.
10.
AmatoRJ, JacJ, Hernandez-McClainJ. Motexafin gadolinium for the treatment of metastatic renal cell carcinoma: phase II study results. Clin Genitourin Cancer, 6:73–78. 2008.
AndrievskyGV, BruskovVI, TykhomyrovAA, GudkovSV. Peculiarities of the antioxidant and radioprotective effects of hydrated C60 fullerene nanostuctures in vitro and in vivo. Free Radic Biol Med, 47:786–793. 2009.
13.
AnjemA, VargheseS, ImlayJA. Manganese import is a key element of the OxyR response to hydrogen peroxide in Escherichia coli. Mol Microbiol, 72:844–858. 2009.
14.
ArchibaldFS, FridovichI. The scavenging of superoxide radical by manganous complexes: In vitro. Arch Biochem Biophys, 214:452–463. 1982.
15.
ArchibaldFS, FridovichI. Manganese, superoxide dismutase, and oxygen tolerance in some lactic acid bacteria. J Bacteriol, 145:422–451. 1981.
16.
AronovitchY, GodingerD, IsraeliA, KrishnaMC, SamuniA, GoldsteinS. Dual activity of nitroxides as pro- and antioxidants: catalysis of copper-mediated DNA breakage and H2O2 dismutation. Free Radic Biol Med, 42:1317–1325. 2007.
17.
AroraM, KumarA, KaundalRK, SharmaSS. Amelioration of neurological and biochemical deficits by peroxynitrite decomposition catalysts in experimental diabetic neuropathy. Eur J Pharmacol, 596:77–83. 2008.
18.
AsayamaS, KawamuraE, NagaokaS, KawakamiH. Design of manganese porphyrin modified with mitochondrial signal peptide for a new antioxidant. Mol Pharm, 3:468–470. 2006.
19.
AslanM, CortA, YucelI. Oxidative and nitrative stress markers in glaucoma. Free Radic Biol Med, 45:367–376. 2008.
20.
AslanM, RyanTM, AdlerB, TownesTM, ParksDA, ThompsonJA, ToussonA, GladwinMT, TarpeyMM, PatelRP, Batinić-HaberleI, WhiteCR, FreemanBA. Oxygen radical inhibition of nitric-oxide dependent vascular function in sickle cell disease. Proc Natl Acad Sci U S A, 98:15215–15220. 2001.
21.
AstonK, RathN, NaikA, SlomczynskaU, SchallOF, RileyDP. Computer-aided design (CAD) of Mn(II) complexes: superoxide dismutase mimetics with catalytic activity exceeding the native enzyme. Inorg Chem, 40:1779–1789. 2001.
22.
AviezerD, CottonS, DavidM, SegevA, KhaselevN, GaliliN, GrossZ, YayonA. Porphyrin analogues as novel antagonists of fibroblast growth factor and vascular endothelial growth factor receptor binding that inhibit endothelial cell proliferation, tumor progression, and metastasis. Cancer Res, 60:2973–2980. 2000.
BakerK, Bucay MarcusC, HuffmanK, MalfroyB, DoctrowS. Synthetic combined superoxide dismutase/catalase mimetics are protective as a delayed treatment in a rat stroke model: a key role for reactive oxygen species in ischemic brain injury. J Pharmacol Exp Ther, 284:215–221. 1998.
25.
BarneseK, GrallaEB, CabelliDE, ValentineJS. Manganous phosphate acts as a superoxide dismutase. J Am Chem Soc, 130:4604–4606. 2008.
26.
BarretteWCJr, SawyerDT, FreeJA, AsadaK. Potentiometric titrations and oxidation-reduction potentials of several iron superoxide dismutases. Biochemistry, 22:624–627. 1983.
27.
BartesaghiS, Ferrer-SuetaG, PeluffoG, ValezV, ZhangH, KalyanaramanB, RadiR. Protein tyrosine nitration in hydrophilic and hydrophobic environments. Amino Acids, 32:501–515. 2007.
28.
Batinić-HaberleI, BenovLT. An SOD mimic protects NADP+-dependent isocitrate dehydrogenase against oxidative inactivation. Free Radic Res, 42:618–624. 2008.
29.
Batinić-HaberleI, BenovL, SpasojevićI, FridovichI. The ortho effect makes manganese (III) meso-tetrakis(N-methylpyridinium-2-yl)porphyrin (MnTM-2-PyP) a powerful and potentially useful superoxide dismutase mimic. J Biol Chem, 273:24521–24528. 1998.
30.
Batinić-HaberleI, SpasojevićI, HambrightP, BenovL, CrumblissAL, FridovichI. The relationship between redox potentials, proton dissociation constants of pyrrolic nitrogens, and in vitro and in vivo superoxide dismutase activities of manganese(III) and iron(III) cationic and anionic porphyrins. Inorg Chem, 38:4011–4022. 1999.
31.
Batinić-HaberleI, CuzzocreaS, RebouçasJS, Ferrer-SuetaG, Emanuela MazzonE, Di PaolaR, RadiR, SpasojevićI, BenovL, SalveminiD. Pure MnTBAP selectively scavenges peroxynitrite over superoxide: comparison of pure and commercial MnTBAP samples to MnTE-2-PyP in two different models of oxidative stress injuries, SOD-specific E. coli model and carrageenan-induced pleurisy. Free Radic Biol Med, 46:192–201. 2009.
32.
Batinic-HaberleI, Gauter-FleckensteinB, KosI, FleckensteinK, SpasojevicI, VujaskovicZ. MnTnHex-2-PyP5+ structural characteristics, lipophilicity and bioavailability contribute to its high potency in pulmonary radioprotection. 55th Radiation Research Society Meeting: Savannah, 2009PS6.40 (Book of abstracts)143.
Batinić-HaberleI, NdengeleMM, CuzzocreaS, RebouçasJS, MasiniE, SpasojevićI, SalveminiD. Lipophilicity is a critical parameter that dominates the efficacy of metalloporphyrins in blocking morphine tolerance through peroxynitrite-mediated pathways. Free Radic Biol Med, 46:212–219. 2009.
Batinić-HaberleI, SpasojevićI, StevensRD, HambrightP, NetaP, Okado-MatsumotoA, FridovichI. New class of potent catalysts of O2·− dismutation. Mn(III) methoxyethylpyridyl- and methoxyethylimidazolylporphyrins. J Chem Soc Dalton Trans, 1696–1702. 2004.
39.
Batinic-HaberleI, SpasojevicI, TseHM, TovmasyanA, St. ClairDK, VujaskovicZ, DewhirstMW, PiganelliJD. Design of Mn porphyrins for treating oxidative stress injuries and their redox-based regulation of cellular transcriptional activities. Amino Acids, 2010(in press).
BayneAC, SohalRS. Effects of superoxide dismutase/catalase mimetics on life span and oxidative stress resistance in the housefly, Musca domestica. Free Radic Biol Med, 32:1229–1234. 2002.
42.
BenatarM. Lost in translation: treatment trials in the SOD1 mouse and in human ALS. Neurobiol Dis, 26:1–13. 2007.
43.
BendixJ, DmochowskiIJ, GrayHB, MahammedA, SimkhovichL, GrossZ. Structural electrochemical and photophysical properties of gallium(III) 5,10,15-tris(pentafluorophenyl)corrole. Angew Chem Int Ed, 39:4048–4051. 2000.
44.
BenovL, Batinić-HaberleI. A manganese porphyrin SOD mimic suppresses oxidative stress and extends the life span of streptozotocin-diabetic rats. Free Radic Res, 38:81–88. 2005.
45.
BianchiC, WakiyamaH, FaroR, KhanT, McCullyJD, LevitskyS, SzabóC, SellkeFW. A novel peroxynitrite decomposer catalyst (FP-15) reduces myocardial infarct size in an in vivo peroxynitrite decomposer and acute ischemia-reperfusion in pigs. Ann Thorac Surg, 74:1201–1207. 2002.
46.
BoilleeS, VeldeVC, ClevelandDW. ALS: a disease of motor neurons and their nonneuronal neighbors. Neuron, 52:39–59. 2006.
47.
BonelloS, ZahringerC, BelAibaRS, DjordjevicT, HesssJ, MichielsC, KietzmannT, GorlachA. Reactive oxygen species activate the HIF-1a promoter via a functional NFκB site. Arterioscl Thromb Vasc Biol, 27:755–761. 2007.
48.
BottinoR, BalamuruganAN, BerteraS, PietropaoloM, TruccoM, PiganelliJD. Preservation of human islet cell functional mass by anti-oxidative action of a novel SOD mimic compound. Diabetes, 51:2561–1567. 2002.
49.
BottinoR, BalamuruganAN, TseH, ThirunavukkarasuC, GeX, ProfozichJ, MiltonM, ZiegenfussA, TruccoM, PiganelliJD. Response of human islets to isolation stress and the effect of antioxidant treatment. Diabetes, 53:2559–2568. 2004.
50.
BoucherLJ. Manganese Schiff's base complexes-II: synthesis and spectroscopy of chloro-complexes of some derivatives of (salicylaldehydeethylenediimato) manganese(III)J Inorg Nucl Chem, 36:531–536. 1974.
51.
BrazierMW, DoctrowSR, MastersCL, CollinsSJ. A manganese-superoxide dismutase/catalase mimetic extends survival in a mouse model of human prion disease. Free Radic Biol Med, 45:184–192. 2008.
52.
BrownNS, BicknellR. Hypoxia and oxidative stress in breast cancer: oxidative stress: its effects on the growth, metastatic potential and response to therapy of breast cancer. Breast Cancer Res, 3:323–327. 2001.
53.
BuchlerJW, KokischW, SmithPD. Cis, trans, and metal effects in transition metal porphyrins. Struct Bond, 34:79–134. 1978.
54.
CarnieriN, HarrimanA, PorterG. Photochemistry of manganese porphyrins, part 6: oxidation-reduction equilibria of manganese(III) porphyrins in aqueous solution. J Chem Soc Dalton Trans, 931–938. 1982.
55.
CarrerasMC, PoderosoJJ. Mitochondrial nitric oxide in the signaling of cell integrated responses. Am J Physiol Cell Physiol, 292:C1569–C1580. 2006.
56.
CastelloPR, DrechselDA, DayBJ, PatelM. Inhibition of mitochondrial hydrogen peroxide production by lipophilic metalloporphyrins. J Pharmacol Exp Ther, 324:970–976. 2008.
57.
CernanecJM, WeinbergBJ, Batinić-HaberleI, GuilakF, FermorB. Influence of oxygen tension on interleukin-1-induced peroxynitrite formation and matrix turnover in articular cartilage. J Rheumatol, 34:401–407. 2007.
58.
ChangLY, CrapoJD. Inhibition of airway inflammation and hyperreactivity by an antioxidant mimetic. Free Radic Biol Med, 33:379–386. 2002.
59.
ChangLY, SubramanianM, YoderBA, DayBJ, EllisonMC, SundayME, CrapoJD. A catalytic antioxidant attenuates alveolar structural remodeling in bronchopulmonary dysplasia. Am J Respir Crit Care Med, 167:57–64. 2003.
CrowJP, CalinasanNY, ChenJ, HillJL, BealMF. Manganese porphyrin given at symptom onset markedly extends survival of ALS mice. Ann Neurol, 58:258–265. 2005.
68.
CrowJP. Administration of Mn porphyrin and Mn texaphyrin at symptom onset extends survival of ALS mice. Medicinal Inorganic Chemistry. SesslerJS, DoctrowSR, McMurrayTJ, LippardSJ. Washington, DC: American Chemical Society, 2005; 295–318.
69.
CrowJP. Peroxynitrite scavenging by metalloporphyrins and thiolates. Free Radic Biol Med, 28:1487–1494. 2000.
70.
CsiszarA, WangM, LakattaEG, UngvariZI. Inflammation and endothelial dysfunction during aging: role of NF-κB. J Appl Physiol, 105:1333–1341. 2008.
71.
CsontT, ViappianiS, SawickaJ, SleeS, AltarejosJY, Batinić-HaberleI, SchulzR. The involvement of superoxide and iNOS-derived NO in cardiac dysfunction induced by pro-inflammatory cytokines. J Mol Cell Cardiol, 39:833–840. 2005.
72.
CulottaVC, YangM, HallMD. Manganese transport and trafficking: lessons learned from Saccharomyces cerevisiae. Eukaryot Cell, 4:1159–1165. 2005.
73.
CuzzocreaS, CostantinoG, MazzonE, ZingarelliB, De SarroA, CaputiAP. Protective effects of Mn(III)tetrakis (4-benzoic acid) porphyrin (MnTBAP), a superoxide dismutase mimetic, in paw oedema induced by carrageenan in the rat. Biochem Pharmacol, 58:171–176. 1999.
74.
CuzzocreaS, MazzonD, DugoL, CaputiAP, RileyDP, SalveminiD. Protective effects of M40403, a superoxide dismutase mimetic in a rodent model of colitis. Eur J Pharmacol, 432:79–89. 2001.
CuzzocreaS, ZingarelliB, ConstantinoG, CaputiAP. Beneficial effects of Mn(III) tetrakis (4-benzoic acid) porphyrin (MnTBAP), a superoxide dismutase mimetic, in a carrageenan-induced pleurisy. Free Radic Biol Med, 26:25–33. 1999.
77.
DarocziB, KariG, ZenginAY, ChinnaiyanP, Batinić-HaberleI, RodeckU, DickerAP. Radioprotective effects of two superoxide dismutase (SOD) mimetics and the nanoparticle DF-1 in a vertebrate zebrafish model (abstract)48th ASTRO, Annual Meeting of the American Society for Radiation Oncology, 2006.
DayBJ, KariyaC. A novel class of cytochrome P450 reductase redox cycling: cationic manganoporphyrins. Toxicol Sci, 85:713–719. 2005.
80.
DayBJ, Batinić-HaberleI, CrapoJD. Metalloporphyrins are potent inhibitors of lipid peroxidation. Free Radic Biol Med, 26:730–736. 1999.
81.
DayBJ, ShawenS, LiochevSI, CrapoJD. A metalloporphyrin superoxide dismutase mimetic protects against paraquat-induced endothelial cell injury, in vitro. J Pharmacol Exp Ther, 275:1227–1232. 1995.
82.
DayBJ. Antioxidants as potential therapeutics for lung fibrosis. Antioxid Redox Signal, 10:355–370. 2008.
83.
DayBJ. Catalase and glutathione peroxidase mimics. Biochem Pharmacol, 77:285–296. 2009.
84.
DecraeneD, SmaersK, GanD, MammoneT, MatsuiM, MaesD, DeclercqL, GarmynM. A synthetic superoxide dismutase/catalase mimetic (EUK-134) inhibits membrane-damage-induced activation of mitogen-activated protein kinase pathways and reduces p53 accumulation in ultraviolet B-exposed primary human keratinocytes. J Invest Dermatol, 122:484–491. 2004.
85.
DeFreitas-SilvaG, RebouçasJS, SpasojevićI, BenovL, IdemoriYM, Batinić-HaberleI. SOD-like activity of Mn(II) β-octabromo-meso-tetrakis(N-methylpyridinium-3-yl)porphyrin equals that of the enzyme itself. Arch Biochem Biophys, 477:105–112. 2008.
86.
DennisKE, AschnerJL, MilatovicD, SchmidtJW, AschnerM, KaplowitzMR, ZhangY, FikeCD. NADPH oxidases and reactive oxygen species at different stages of chronic hypoxia-induced pulmonary hypertension in newborn piglets. Am J Physiol Lung Cell Mol Physiol, 297:L596–L607. 2009.
87.
DesideriA, FalconiM, ParisiV, MoranteS, RotilioG. Is the activity-linked electrostatic gradient of bovine Cu, Zn superoxide dismutases conserved in homologous enzymes irrespective of the number and distribution of charges?Free Radic Biol Med, 5:313–317. 1988.
88.
DessolinJ, SchulerM, QuinartA, De GiorgiF, GhosezL, IchasF. Selective targeting of synthetic antioxidants to mitochondria; towards a mitochondrial medicine for neurodegenerative diseases?Eur J Pharmacol, 447:155–161. 2002.
89.
DewhirstM, CaoY, MoellerB. Cycling hypoxia and free radicals regulate angiogenesis and radiotherapy response. Nat Rev Cancer, 8:425–437. 2008.
90.
DhanasekaranA, KotamrajuS, KarunakaranC, KalivendiSV, ThomasS, JosephJ, KalyanaramanB. Mitochondria superoxide dismutase mimetic inhibits peroxide-induced oxidative damage and apoptosis: role of mitochondrial superoxide. Free Radic Biol Med, 39:567–583. 2005.
91.
DharA, KaundalRK, SharmaSS. Neuroprotective effects of FeTMPyP: a peroxynitrite decomposition catalyst in global cerebral ischemia model in gerbils. Pharmacol Res, 54:311–316. 2006.
92.
DikalovS, LosikT, ArbisrJL. Honokiol is a potent scavenger of superoxide and peroxyl radicals. Biochem Pharm, 76:589–596. 2008.
93.
DoctrowS, HuffmanK, Bucay-MarcusC, ToccoG, MalfroyE, AdinolfiCA, KrukH, BakerK, LazarowychN, MascarenhasJ, MalfroyB. Salen-manganese complexes as catalytic scavengers of hydrogen peroxide and cytoprotective agents: structure-activity relationship. J Med Chem, 45:4549–4558. 2002.
94.
DoctrowSR, BaudryM, HuffmanK, MalfroyB, MelovS. Salen-manganese complexes: multifunctional catalytic antioxidants protective in models for neurodegenerative diseases of aging in Medicinal Inorganic Chemistry. American Chemical Society Symposium Series 903. SesslerJS, DoctrowSR, McMurrayTJ, LippardSJ. ACS and Oxford University Press, 2005; 319–347.
95.
DoyleT, BryantL, Batinić-HaberleI, LittleJ, CuzzocreaS, MasiniE, SpasojevićI, SalveminiD. Supraspinal inactivation of mitochondrial superoxide dismutase is a source of peroxynitrite in the development of morphine antinociceptive tolerance. Neuroscience, 164:702–710. 2009.
96.
DuW, AdamZ, RaniR, ZhangX, PangQ. Oxidative stress in Fanconi anemia hematopoiesis and disease progression. Antioxid Redox Signal, 10:1909–1921. 2008.
DuganLL, TuretskyTM, DuC, LobnerD, WheelerM, AlmliCR, ShenCK, LuhTY, ChoiDW, LinTS, ChoiDW. Carboxyfullerenes as neuroprotective agents. Proc Natl Acad Sci U S A, 94:9434–9439. 1997.
99.
EckshtainM, ZilbermannI, MahammedA, SaltsmanA, OkunZ, MaimonE, CohenH, MeyersteinD, GrossZ. Superoxide dismutase activity of corrole metal complexes. Dalton Trans, 7879–7882. 2009.
100.
EllerbyRM, CabelliDE, GradenJA, ValentineJS. Copper-zinc superoxide dismutase: why not pH-dependent?J Am Chem Soc, 118:6556–6561. 1996.
101.
EpperlyMW, MelendezJA, ZhangX, NieS, PearceL, PetersonJ, FranicolaD, DixonT, GreenbergerBA, KomanduriP, WangH, GreenbergerJS. Mitochondrial targeting of a catalase transgene product by plasmid liposomes increases radioresistance in vitro and in vivo. Radiat Res, 171:588–595. 2009.
102.
EricD, CoulterED, EmersonJP, KurtzDMJr, CabelliDE. Superoxide reactivity of rubredoxin oxidoreductase (desulfoferrodoxin) from Desulfovibrio vulgaris: a pulse radiolysis study. J Am Chem Soc, 122:11555–11556. 2000.
103.
FailliP, BaniD, BenciniA, CantoreM, Di Cesare MannelliL, GhekardiniC, GiorgiC, InnocentiM, RugiF, SpepiA, UdistiR, ValtancoliB. A novel manganese complex effective as superoxide anion scavenger and therapeutic agent against cell and tissue oxidative injury. J Med Chem, 52:7273–7283. 2009.
104.
FaraggiM, PeretzP, WeinraubD. Chemical properties of water-soluble porphyrins: 4. the reduction of a “picket-fence-like” iron(III) complex with superoxide oxygen couple. Int J Radiat Biol, 49:951–968. 1986.
105.
FaulknerKM, LiochevSI, FridovichI. Stable Mn(III) porphyrins mimic superoxide dismutase in vitro and substitute for it in vivo. J Biol Chem, 269:23471–23476. 1994.
106.
Ferrer-SuetaG, RadiR. Chemical biology of peroxynitrite: kinetics, diffusion, and radicals. ACS Chem Biol, 4:161–177. 2009.
107.
Ferrer-SuetaG, Batinić-HaberleI, SpasojevićI, FridovichI, RadiR. Catalytic scavenging of peroxynitrite by isomeric Mn(III) N-methylpyridylporphyrins in the presence of reductants. Chem Res Toxicol, 12:442–449. 1999.
108.
Ferrer-SuetaG, HannibalL, Batinić-HaberleI, RadiR. Reduction of manganese porphyrins by flavoenzymes and submitochondrial particles and the catalytic redox cycle of peroxynitrite. Free Radic Biol Med, 41:503–512. 2006.
109.
Ferrer-SuetaG, QuijanoC, AlvarezB, RadiR. Reactions of manganese porphyrins and manganese-superoxide dismutase with peroxynitrite. Methods Enzymol, 349:23–37. 2002.
110.
Ferrer-SuetaG, VitturiD, Batinić-HaberleI, FridovichI, GoldsteinS, CzapskiG, RadiR.Reactions of manganese porphyrins with peroxynitrite and carbonate radical anion. J Biol Chem, 278:27432–27438. 2003.
111.
Figueroa-RomeroC, SadidiM, FeldmanEL. Mechanism of disease: the oxidative stress theory of diabetic neuropathy. Rev Endocr Metab Disord, 9:301–314. 2008.
112.
FinstererJ. Is atherosclerosis a mitochondrial disorder?Vasa, 36:229–240. 2008.
FisherAEO, HagueTA, ClarkeCL, NaughtonDP. Catalytic superoxide scavenging by metal complexes of the calcium chelator EGTA and contrast agent EHPG. Biochem Biophys Chem Commun, 323:163–167. 2004.
115.
FisherAEO, NaughtonDP. Metal ion chelating peptides with superoxide dismutase activity. Biomed Pharmacother, 59:158–162. 2005.
FriedLE, ArbiserJL. Honokiol, a multifunctional antiangiogenic and antitumor agent. Antiox Redox Signal, 11:1139–1148. 2009.
122.
FukuiH, MoraesCT. The mitochondrial impairment, oxidative stress and neurodegeneration connection: reality or just an attractive hypothesis. Trends Neurosci, 31:251–256. 2007.
123.
Gauter-FleckensteinB, FleckensteinK, OwzarK, JianC, Batinić-HaberleI, VujaskovićZ. Comparison of two Mn porphyrin-based mimics of superoxide-dismutase (SOD) in pulmonary radioprotection. Free Radic Biol Med, 44:982–989. 2008.
124.
Gauter-FleckensteinB, FleckensteinK, OwzarK, JiangC, RebouçasJS, Batinić-HaberleI, VujaskovićZ. Early and late administration of antioxidant mimic MnTE-2-PyP5+ in mitigation and treatment of radiation-induced lung damage. Free Radic Biol Med, 2010, DOI:10.1016/j.freeradbiomed.2010.01.020.
125.
GauuanPJF, TrovaMP, Gregor-BorosL, BocckinoSB, CrapoJD, DayBJ. Superoxide dismutase mimetics: structure-activity relationship study of MnTBAP analogues. Bioorg Med Chem, 10:3013–3021. 2002.
126.
GenoveseT, MazzonE, EspositoE, Di PaolaR, MurthyK, NevilleL, BramantiP, CuzzocreaS. Effects of a metalloporphyrinic peroxynitrite decomposition catalyst, ww-85, in a mouse model of spinal cord injury. Free Radic Res, 43:631–645. 2009.
127.
GershmanZ, GoldbergI, GrossZ. DNA binding and catalytic properties of positively charged corroles. Angew Chem Int Ed, 46:4320–4324. 2007.
GharbiN, PressacM, HadchouleM, Szwarch, WilsonSR, MoussaF. [60]Fullerene is a powerful antioxidant in vivo with no acute or subacute toxicity. Nano Lett, 5:2578–2585. 2005.
130.
GiblinGMP, BocPC, CampbellIB, NacockAP, RoomansS, MillsGI, MolloyC, TranterGE, WalkerAL, DoctrowSR, HuffmanK, MalfroyB. 6,6'-Bis(2-hydroxyphenyl)-2,2'-bipyridine manganese(III) complexes: a novel series of superoxide dismutase and catalase mimetics. Bioorg Med Chem Lett, 11:1367–1370. 2001.
131.
GilesSS, Batinić-HaberleI, PerfectJR, CoxGM. Cryptococcus neoformans mitochondrial superoxide dismutase: an essential link between antioxidant function and high temperature growth. Eukariot Cell, 4:46–54. 2005.
132.
GloireG, PietteJ. Redox regulation of nuclear post-translational; modifications during NF-κB activation. Antioxid Redox Signal, 11:2209–2222. 2009.
GoldsteinS, SamuniA. Kinetics and mechanism of peroxyl radical reactions with nitroxides. J Phys Chem A, 111:1066–1072. 2007.
135.
GoldsteinS, CzapskiG, HellerA. Osmium tetraoxide, used in the treatment of arthritic joints, is a fast mimic of superoxide dismutase. Free Radic Biol Med, 38:839–45. 2005.
136.
GoldsteinS, FridovichI, CzapskiG. Kinetic properties of Cu, Zn-superoxide dismutase as a function of metal content: order restored. Free Radic Biol Med, 41:937–941. 2006.
137.
GoldsteinS, MereneyG, RussoA, SamuniA. The role of oxoammonium cation in the SOD-like activity of cyclic nitroxides. J Am Chem Soc, 125:789–795. 2003.
138.
GoldsteinS, SamuniA, MerenyiG. Kinetics of the reaction between nitroxide and thiyl radicals: nitroxides as antioxidants in the presence of thiols. J Phys Chem A, 112:8600–8605. 2008.
139.
GoldsteinS, SamuniA, MerenyiG. Reactions of nitric oxide, peroxynitrite and carbonate radicals with nitroxides and their corresponding oxoammonium cations. Chem Res Toxicol, 17:250–257. 2004.
140.
GoldsteinS, SamuniA, HidegK, MerenyiG. Structure-activity relationship of cyclic nitroxides as SOD mimics and scavengers of nitrogen dioxide and carbonate radicals. J Phys Chem A, 110:3679–3685. 2006.
141.
GonzalezPK, ZhuangJ, DoctrowSR, MalfroyB, BensonPF, MenconiMJ, FinkMP. EUK-8 a synthetic superoxide dismutase and catalase mimetic ameliorates acute lung injury in endotoxemic swine. J Pharmacol Exp Ther, 275:798–806. 2002.
142.
GridleyDS, MakindeAY, LuoX, RizviA, CrapoJD, DewhirstMW, MoellerBJ, PearlsteinRD, SlaterJM. Radiation and a metalloporphyrin radioprotectant in a mouse prostate tumor model. Anticancer Res, 27:3101–3109. 2007.
143.
GrossZ, GaliliN, SaltsmanI. The first direct synthesis of corroles from pyrrole. Angew Chem Int Ed, 38:1427–1429. 1999.
144.
HaberA, MahammedA, FuhrmanB, VolkovaN, ColemanR, HayekT, AviramM, GrossZ. Amphiphilic/bipolar metallocorroles that catalyze the decomposition of reactive oxygen and nitrogen species, rescue lipoproteins from oxidative damage, and attenuate atherosclerosis. Angew Chem Int Ed, 47:7896–7900. 2008.
145.
HalliwellB, GutteridgeJMC. Free Radical Biology and Medicine, 4th. Oxford: Oxford University Press, 2007.
146.
HalliwellB. Are polyphenols antioxidants or pro-oxidants? What do we learn from cell culture and in vivo studies. Arch Biochem Biophys, 476:107–112. 2008.
147.
HahnSM, DeLucaAM, CoffinD, KrishnaCM, MitchellJB. In vivo radioprotection and effects on blood pressure of the stable free radical nitroxides. Int J Radiat Oncol Biol Phys, 42:839–842. 1998.
148.
HashemySI, UngerstedtJS, AvvalFZ, HolmgrenA. Motexafin gadolinium, a tumor-selective drug targeting thioredoxin reductase and ribonucleotide reductase. J Biol Chem, 281:10691–10697. 2006.
149.
HeckertEG, KarakotiAS, SealS, SelfWT. The role of cerium redox state in the SOD mimetic activity of nanoceria. Biomaterials, 29:2705–2709. 2008.
150.
HeckertEG, SealS, SelfWT. Fenton-like reaction catalyzed by rare earth inner transition metal cerium. Environ Sci Technol, 42:5014–5019. 2008.
151.
HidalfoC, DonosoP. Crosstalk between calcium and redox signaling: from molecular mechanisms to health implications. Antioxid Redox Signal, 10:1275–1312. 2008.
152.
HolleyAK, DharSK, XuY, St ClairDK. Manganese superoxide dismutase: beyond life and death. Amino Acids, 2010(in press).
HyodoF, SouleBP, MatsumotoK-I, MatusmotoS, CookJA, HyodoE, SowersA, KrishnaMC, MitchellJB. Assessment of tissue redox status using metabolic responsive contrast agents and magnetic resonance imaging. J Pharm Pharmacol, 60:1049–1060. 2008.
157.
IlanY, RabaniJ, FridovichI, PasternackRF. Superoxide dismuting activity of iron porphyrin. Inorg Nucl Chem Lett, 17:93–96. 1981.
158.
JacksonIL, ChenL, Batinić-HaberleI, VujaskovićZ. Superoxide dismutase mimetic reduces hypoxia-induced O2·−, TGF-β, and VEGF production by macrophages. Free Radic Res, 41:8–14. 2007.
159.
JacksonIL, Gaunter-FleckensteinBM, Batinić-HaberleI, PoultonS, ZhaoY, DewhirstMW, VujaskovićZ.Hyperthermia enhances the anti-angiogenic effect of metalloporphyrin mimetic of superoxide dismutase. 24th Annual Meeting of the European Society for Hyperthermic Oncology: Prague, Czech Republic, 2007.
160.
JanGP, BischaD, BottleSE. Synthesis and properties of novel porphyrin spin probes containing isoindoline nitroxides. Free Radic Biol Med, 43:111–116. 2007.
161.
JaramilloMC, FryeJB, CrapoJD, BriehlMM, TomeME. Increased manganese superoxide dismutase expression or treatment with manganese porphyrin potentiates dexamethasone-induced apoptosis in lymphoma cells. Cancer Res, 69:5450–5457. 2009, DOI:10.1158/0008-5472.CAN-08-4031.
162.
JensenAW, WilsonSR, SchusterDI. Biological applications of fullerenes. Bioorg Med Chem, 4:767–779. 1996.
163.
JiangJ, KurnikovI, BelikovaNA, XiaoJ, ZhaoQ, AmoscatoAA, BraslauR, StuderA, FinkMP, GreenbergerJS, WipfP, KaganVE. Structural requirements for optimized delivery, inhibition of oxidative stress and antiapoptotic activity of targeted nitroxides. J Pharmacol Exp Ther, 32:1050–1060. 2007.
164.
JungC, RongY, DoctrowS, BaudryM, MalfroyB, XuZ. Synthetic superoxide/dismutase/catalase mimetics reduce oxidative stress and prolong survival in a mouse amyotrophic lateral sclerosis model. Neurosci Lett, 304:157–160. 2001.
165.
KachadourianR, Batinić-HaberleI, FridovichI. Mn(III)Cl4T-2-PyP5+ exhibits a high superoxide dismuting rate. Free Radic Biol Med, 25:S17. 1998.
166.
KachadourianR, Batinić-HaberleI, FridovichI. Syntheses and SOD-like activities of partially (1–4) β-chlorinated derivatives of manganese(III) meso-tetrakis(N-methylpyridinium-2-yl)porphyrin. Inorg Chem, 38:391–396. 1999.
167.
KachadourianR, JohnsonCA, MinE, SpasojevićI, DayBJ. Flavin-dependent antioxidant properties of a new series of meso-N,N'-dialkyl-imidazolium substituted manganese(III) porphyrins. Biochem Pharmacol, 67:77–85. 2004.
168.
KajitaM, HikosakaK, IitsukaM. Kanayama A, Toshima N, and Miyamoto Y. Platinum nanoparticle is a useful scavenger of superoxide anion and hydrogen peroxide. Free Radic Res, 41:615–626. 2007.
169.
KangJL, LeeHS, JungHJ, KimHJ. Iron tetrakis (N-methyl-4'-pyridyl) porphyrinato inhibits proliferative activity of thymocytes by blocking activation of p38 mitogen-activated protein kinase, nuclear factor-kappaB, and interleukin-2 secretion. Toxicol Appl Pharmacol, 191:147–155. 2003.
170.
KangJL, LeeHS, PackIS, LeonardS, CastranovaV. Iron tetrakis (N-methyl-4'-pyridyl) porphyrinato (FeTMPyP) is a potent scavenging antioxidant and an inhibitor of stimulant-induced NF-κB activation of raw 264.7 macrophages. J Toxicol Environ Health A, 64:291–310. 2001.
171.
KeaneyM, MatthijssensF, SharpeM, VanfleterenJ, GemsD. Superoxide dismutase mimetics elevate superoxide dismutase activity in vivo but do not retard aging in the nematode Caenorhabditis elegans. Free Radic Biol Med, 37:239–250. 2004.
172.
KhaldiMZ, ElouilH, GuiotY, HenquinJC, JonasJC. Antioxidants N-acetyl-L-cysteine and manganese(III) tetrakis (4-benzoic acid)porphyrin do not prevent β-cell disfunction in rat islets cultured in high glucose for 1 wk. Am J Physiol Endocrinol Metab, 29:E137–E146. 2006.
173.
KimJ, TakahashiM, ShimizuT, ShirasawaT, KajitaM, KanayamaA, MiyamotoY. Effects of a potent antioxidant, platinum nanoparticle, on the lifespan of Caenorhabditis elegans. Mech Ageing Dev, 129:322–331. 2008.
174.
Klug-RothD, FridovichI, RabbaniJ. Pulse radiolytic investigations of superoxide catalyzed disproportionation: mechanism for bovine superoxide dismutase. J Am Chem Soc, 95:2786–2790. 1973.
KonorevEA, KotamrajuS, ZhaoH, ShasiH, KalivendiS, JosephJ, KalyanaramanB. Paradoxical effects of metalloporphyrins on doxorubicin-induced apoptosis: scavenging of reactive species versus induction of heme oxygenase-1. Free Radic Biol Med, 33:988–997. 2002.
KosI, BenovL, SpasojevićI, RebouçasJS, Batinić-HaberleI. High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based SOD mimics compensates for their lower antioxidant potency and makes them equally effective as ortho analogues in protecting E. coli. J Med Chem, 52:7868–7872. 2009.
179.
KosI, RebouçasJS, DeFreitas-SilvaG, SalveminiD, VujaskovićZ, DewhirstMW, SpasojevićI, Batinić-HaberleI. The effect of lipophilicity of porphyrin-based antioxidants: comparison of ortho and meta isomers of Mn(III) N-alkylpyridylporphyrins. Free Radic Biol Med, 47:72–78. 2009.
180.
KosI, RebouçasJS, ShengH, WarnerDS, SpasojevićI, Batinić-HaberleI. Oral availability of MnTE-2-PyP5+, a potent antioxidant and cellular redox modulator. Free Radic Biol Med, 45:S86. 2008.
LahayeD, MuthukumaranK, HungCH, GrykoD, RebouçasJS, SpasojevićI, Batinić-HaberleI, LindseyJS. Design and synthesis of manganese porphyrins with tailored lipophilicity: investigation of redox properties and superoxide dismutase activity. Bioorg Med Chem, 15:7066–7086. 2007.
183.
LamMA, PattisonDI, BottleSE, KeddieDJ, DaviesMJ. Nitric oxide and nitroxides can act as efficient scavengers of protein-derived free radicals. Chem Res Toxicol, 21:211–2119. 2008.
184.
LeeJ, HuntJA, GrovesJT. Mechanisms of iron porphyrins reactions with peroxynitrite. J Am Chem Soc, 120:7493–7501. 1998.
185.
LeeJ, HuntJA, GrovesJT. Manganese porphyrins as redox-coupled peroxynitrite reductases. J Am Chem Soc, 120:6053–6061. 1998.
186.
LeeJH, ParkJW. A manganese porphyrin complex is a novel radiation protector. Free Radic Biol Med, 37:272–283. 2004.
187.
LeeJH, LeeYM, ParkJW. Regulation of ionizing radiation-induced apoptosis by a manganese porphyrin complex. Biochem Biophys Res Commun, 334:298–305. 2005.
188.
LiF, SonveauxPP, RabbaniZN, LiuS, YanB, HuangQ, VujaskovićZ, DewhirstMW, LiC-H. Regulation of HIF-1α stability through S-nitrosylation. Mol Cell, 26:63–74. 2007.
189.
LiQX, LuoQH, LiYZ, ShenMC. A study on the mimics of Cu-Zn superoxide dismutase with high activity and stability: two copper(II) complexes of 1,4,7-triazacyclononane with benzimidazole groups. Dalton Trans, 2329–2335. 2004.
190.
LiS, YanT, YangJ-Q, OberleyTD, OberleyLW. The role of cellular glutathione peroxidase redox regulation in the suppression of tumor cell growth by manganese superoxide dismutase. Cancer Res, 60:3927–3939. 2000.
191.
LiangHL, HiltonG, MortensenJ, RegnerK, JohnsonCP, NilakantanV. MnTMPyP, a cell-permeant SOD mimetic, reduces oxidative stress and apoptosis following renal ischemia-reperfusion. Am J Physiol Renal Physiol, 296:F266–F276. 2008.
192.
LiangL-P, HuasngJ, FultonR, DayBJ, PatelM. An orally active catalytic metalloporphyrin protects against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine neurotoxicity in vivo. J Neurosci, 27:4326–4333. 2007.
193.
LinY-T, HoangH, HsiehSI, RangelN, FosterAL, SampayoJN, LithgowGJ, SrinivasanC. Manganous ion supplementation accelerates wild type development, enhances stress resistance, and rescues the life span of a short-lived Caenorhabditis elegans mutant. Free Radic Biol Med, 40:1185–1193. 2006.
194.
LingX, LiuD. Temporal and spatial profile of cell loss after spinal cord injury: reduction by a metalloporphyrin. J Neurosci Res, 85:2175–2185. 2007.
195.
LiochevSI, FridovichI. Superoxide from glucose oxidase or from nitroblue tetrazolium?Arch Biochem Biophys, 318:408–410. 1995.
196.
LiuJ-Y, LiX-F, LiY-Z, ChangWB, HuangA-J. Oxidation of styrene by various oxidants with different kinds of metalloporphyrins. J Mol Catal A: Chem, 187:163–167. 2002.
197.
MableyJG, PacherP, BaiP, WallaceR, GoonesekeraS, ViragL, SouthanGJ, SzabóC. Suppression of intestinal polyposis in Apcmin/+ mice by targeting the nitric oxide or poly(ADP-ribose) pathways. Mutat Res, 548:107–116. 2004.
198.
MacarthurH, WestfallTC, RileyDP, MiskoTP, SalveminiD. Inactivation of catecholamines by superoxide gives new insights on the pathogenesis of septic shock. Proc Natl Acad Sci U S A, 97:9753–9758. 2000.
199.
MackensenGB, PatelM, ShengH, CalviCL, Batinić-HaberleI, DayBJ, LiangLP, FridovichI, CrapoJD, PearlsteinRD, WarnerDS. Neuroprotection from delayed post-ischemic administration of a metalloporphyrin catalytic antioxidant in the rat. J Neurosci, 21:4582–4592. 2001.
200.
MahammedA, GrossZ. Iron and manganese corroles are potent catalysts for the decomposition of peroxynitrite. Angew Chem Int Ed, 45:6544–6547. 2006.
201.
MakindeAY, Luo-OwenX, RizviA, CrapoJD, PearlsteinRD, SlaterJM, GridleyDS. Effect of a metalloporphyrin antioxidant (MnTE-2-PyP) on the response of a mouse prostate cancer model to radiation. Anticancer Res, 29:107–118. 2009.
MaoXW, CrapoJD, MekonnenT, LindseyN, MartinezP, GridleyDS, SlaterJM. Radioprotective effect of a metalloporphyrin compound in rat eye model. Curr Eye Res, 34:62–72. 2009.
204.
MarozA, KelsoGF, SmithRAJ, WareDC, AndersonRF. Pulse radiolysis investigation on the mechanism of the catalytic action of Mn(II)-pentaazamacrocycle compounds as superoxide dismutase mimetics. J Phys Chem A, 112:4929–4935. 2008.
205.
MartiMA, BariSE, EstrinDA, DoctorovichF. Discrimination of nitroxyl and nitric oxide by water-soluble Mn(III) porphyrins. J Am Chem Soc, 127:4680–4684. 2005.
206.
MartinRC, LiuQ, WoJM, RayMb, LiY. Chemoprevention of acrinogenic progression to esophageal adenocarcinoma by the manganese superoxide dismutase supplementation. Clin Cancer Res, 13:5176–5182. 2007.
207.
MasiniE, BaniD, VannacciA, PierpaoliS, MannaioniPF, ComhairSAA, XuW, MuscoliC, ErzurumSC, SalveminiD. Reduction of antigen-induced respiratory abnormalities an airway inflammation in sensitized guinea pigs by a superoxide dismutase mimetic. Free Radic Biol Med, 39:520–531. 2005.
208.
MasiniE, CuzzocreaS, MazzonE, MarzoccaC, MannaioniPF, SalveminiD. Protective effects of M40403, a selective superoxide dismutase mimetic, in myocardial ischaemia and reperfusion injury in vivo. Br J Pharmacol, 136:905–917. 2002.
209.
MatsukawaN, YasuharaT, HaraK, XuL, MakiM, YuG, KanekoY, OjikaK, HessDC, BorlonganCV. Therapeutic targets and limits of minocycline neuroprotection in experimental ischemic stroke. BMC Neurosci, 10:126. 2009.
210.
MatthijssensF, BackP, BraeckmanBP, VanfleterenJR. Prooxidant activity of the superoxide dismutase (SOD)-mimetic EUK-8 in proliferating and growth-arrested Escherichia coli cells. Free Radic Biol Med, 45:708–715. 2008.
211.
MaybauerDM, MaybauerMO, SzabóC, WestphalM, TraberLD, EnkhbaatarP, MurthyKG, NakanoY, SalzmanAL, HerndonDN, TraberDL. Lung-protective effects of the metalloporphyrinic peroxynitrite decomposition catalyst WW-85 in interleukin-2 induced toxicity. Biochem Biophys Res Commun, 377:786–791. 2008.
212.
McCordJM, FridovichI. Superoxide dismutase: an enzymatic function for erythrocuprein (hemocuprein)J Biol Chem, 244:6049–6055. 1969.
213.
McDonaldMC, d'Emamnuele Di Villa BlancaR, WaymanNS, PintoA, SharpeMA, CuzzocreaS, ChatterjeePK, ThiemermannC. A superoxide dismutase mimetic with catalase activity (EUK-8) reduces the organ injury in endotoxic shock. Eur J Pharmacol, 466:181–189. 2003.
MehtaMP, ShapiroWR, PhanSC, GervaisR, CarrieC, ChabotP, PatchellRA, GlantzMJ, RechtL, LangerC, SurRK, RoaWH, MaheMA, FortinA, NiederC, MeyersCA, SmithJA, MillerRA, RenschlerMF. Motexafin gadolinium combined with prompt whole brain radiotherapy prolongs time to neurologic progression in non-small-cell lung cancer patients with brain metastases: results of a phase III trial. Int J Radiat Oncol Biol Phys, 73:1069–1076. 2009.
216.
MelovS, RavenscroftJ, MalikS, GillMS, WalkerDW, ClaytonPE, WallaceDC, MalfroyB, DoctrowSR, LithgowGJ. Extension of life-span with superoxide dismutase/catalase mimetics. Science, 289:1567–1569. 2000.
217.
MetzJA, SmithD, MickR, LustigR, MitchellJ, CherakuriM, GlatsteinE, HahnSM. A phase I study of topical tempol for the prevention of alopecia induced by whole brain radiotherapy. Clin Cancer Res, 10:6411–6417. 2004.
218.
MichelE, NauserT, SutterB, BoundsPL, KoppenolWH. Kinetics properties of Cu, Zn-superoxide dismutase as a function of metal content. Arch Biochem Biophys, 439:234–240. 2005.
219.
MillerRJ, James-KrackeM, SunGY, SunAY. Oxidative and inflammatory pathways in Parkinson's disease. Neurochem Res, 34:55–65. 2009.
220.
MocellinS, BronteV, NittiD. Nitric oxide, a double edged sword in cancer biology: searching for therapeutic opportunities. Med Res Rev, 27:317–352. 2007.
MoellerBJ, CaoY, LiCY, DewhirstMW. Radiation activates HIF-1 to regulate vascular radiosensitivity in tumors: role of oxygenation, free radicals and stress granules. Cancer Cell, 5:429–441. 2004.
223.
MoonKH, HoodBL, MukhopadhyayP, RajeshM, AbdelmegeedMA, KwonYI, ConradsTP, VeenstraTD, SongBJ, PacherP. Oxidative inactivation of key mitochondrial proteins leads to dysfunction and injury in hepatic ischemia reperfusion. Gastroenterology, 135:1344–1357. 2008.
224.
MoriscotC, CandelS, SauretV, Kerr-ConteJ, RichardMJ, FavrotMC, BenhamouPY. MnTMPyP, a metalloporphyrin-based superoxide dismutase/catalase mimetic, protects INS-1 cells and human pancreatic islets from an in vitro oxidative challenge. Diabetes Metab, 33:44–53. 2007.
225.
MunroeW, KingsleyC, DurazoA, GrallaEB, ImlayJA, SrinivasanC, ValentineJS. Only one of a wide assortment of manganese-containing SOD mimicking compounds rescues the slow aerobic growth phenotype of both Escherichia coli and Saccharomyces cerevisiae strains lacking superoxide dismutase enzymes. J Inorg Biochem, 101:1875–1882. 2007.
226.
MurphyCK, FeyEG, WatkinsBA, WongV, RothsteinD, SonisST. Efficacy of superoxide dismutase mimetic M40403 in attenuating radiation-induced oral mucositis in hamsters. Clin Cancer Res, 14:4292–4297. 2008.
227.
MurphyMP, SmithRAJ. Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annu Rev Pharmacol Toxicol, 47:629–656. 2007.
MuscoliC, CuzzocreaS, NdengeleMM, MollaceV, PorrecaF, FabriziF, EspositoE, MasiniM, MatuschakGM, SalveminiD.Therapeutic manipulation of peroxynitrite attenuates the development of opiate-induced antinociceptive tolerance. J Clin Invest, 117:1–11. 2007.
230.
MuscoliC, CuzzocreaS, RileyDP, ZweierJL, ThiemermannC, WangZ-Q, SalveminiD. On the selectivity of superoxide dismutase mimetics and its importance in pharmacological studies. Br J Pharmacol, 140:445–460. 2003.
NaiduBV, FragaC, SalzmanAL, SzabóC, VerrierED, MulliganMS. Critical role of reactive nitrogen species in lung ischemia-reperfusion injury. J Heart Lung Transplant, 22:784–793. 2003.
233.
NdengeleMM, MuscoliC, WangQ-Z, DoyleTM, MatuschakGM, SalveminiD. Superoxide potentiates NF-κB activation and modulates endotoxin-induced cytokine production in alveolar macrophages. Shock, 23:186–193. 2005.
234.
NepomucenoMF, TabakM, VercesiAE. Opposite effects of Mn(III) and Fe(III) forms of meso-tetrakis(4-N-methyl pyridiniumyl) porphyrins on isolated rat liver mitochondria. J Bioenerg Biomembr, 34:41–47. 2002.
235.
NilssonJ, BengtssonE, FredriksonGN, BjorkbackaH. Inflammation and immunity in diabetic vascular complications. Curr Opin Lipidol, 19:519–524. 2008.
OberleyLW, LeuthauserSW, PasternackRF, OberleyTD, SchuttL, SorensonJR. Anticancer activity of metal compounds with superoxide dismutase activity. Agents Actions, 15:535–538. 1984.
238.
ObrosovaIG, MableyJG, ZsengellérZ, CharniauskayaT, AbatanOI, GrovesJT, SzabóC. Role for nitrosative stress in diabetic neuropathy: evidence from studies with peroxynitrite decomposition catalyst. FASEB J, 19:401–403. 2005.
239.
OhseT, NagaokaS, ArakawaY, KawakamiH, NakamuraK. Cell death by reactive oxygen species generated from water-soluble cationic metalloporphyrins as superoxide dismutase mimics. J Inorg Biochem, 85:201–208. 2001.
240.
Okado-MatsumotoA, FridovichI. Subcellular distribution of superoxide dismutases (SOD) in rat liver. J Biol Chem, 276:38388–38393. 2001.
241.
Okado-MatsumotoA, Batinić-HaberleI, FridovichI. Complementation of SOD deficient Escherichia coli by manganese porphyrin mimics of superoxide dismutase. Free Radic Biol Med, 37:401–410. 2004.
242.
OkunZ, KupershmidtL, AmitT, MandelS, Bar-AmO, YoudimMBH, GrossZ. Manganese corroles prevent intracellular nitration and subsequent death of insulin-producing cells. ACS Chem Biol, 4:910–914. 2009.
243.
OlcottA, ToccoG, TianJ, ZekzerD, FukutoJ, IgnarroL, KaufmanDL. A salen-manganese catalytic free radical scavenger inhibits type 1 diabetes and islet allograft rejection. Diabetes, 53:2574–2580. 2004.
ParkW, LimD. Effect of oligo(ethylene glycol) group on the antioxidant activity of manganese salen complexes. Bioorg Med Chem Lett, 19:614–617. 2009.
246.
PasternackRF, HalliwellB. Superoxide dismutase activities of an iron porphyrin and other iron complexes. J Am Chem Soc, 101:1026–1031. 1979.
247.
PasternackRF, SkowronekWRJr. Catalysis of the disproportionation of superoxide by metalloporphyrins. J Inorg Biochem, 11:261–267. 1979.
248.
PasternackRF, BanthA, PasternackJM, JohnsonCS. Catalysis of the disproportionation of superoxide by metalloporphyrins, III. J Inorg Biochem, 15:261–267. 1981.
249.
PasternackRF, GibbsEJ, VillafrancaAC. Interactions of porphyrins with nucleic acids. Biochemistry, 22:2406–2414. 1983.
250.
PasternackRF, GibbsEJ, VillafrancaAC. Interactions of porphyrins with nucleic acids. Biochemistry, 22:5409–5417. 1983.
PeretzP, SolomonD, WeinraubD, FaraggiM. Chemical properties of water-soluble porphyrins, 3: the reaction of superoxide radicals with some metalloporphyrins. Int J Radiat Biol, 42:449–456. 1982.
253.
PérezMJ, CederbaumAI. Antioxidant and pro-oxidant effects of a manganese porphyrin complex against CYP2E1-dependent toxicity. Free Radic Biol Med, 33:111–127. 2002.
QuickKL, AliSS, ArchR, XiongC, WozniakD, DuganLL. A carboxyfullerene SOD mimetic improves cognition and extends the lifespan of mice. Neurobiol Aging, 289:117–128. 2008.
257.
RabbaniZ, Batinić-HaberleI, AnscherMS, HuangJ, DayBJ, AlexanderE, DewhirstMW, VujaskovićZ. Long term administration of a small molecular weight catalytic metalloporphyrin antioxidant AEOL10150 protects lungs from radiation-induced injury. Int J Radic Oncol Biol Phys, 67:573–580. 2007.
RabbaniZN, SpasojevićI, ZhangX, MoellerBJ, HaberleS, Vasquez-VivarJ, DewhirstMW, VujaskovićZ, Batinić-HaberleI. Antiangiogenic action of redox-modulating Mn(III) meso-tetrakis(N-ethylpyridinium-2-yl)porphyrin, MnTE-2-PyP5+, via suppression of oxidative stress in a mouse model of breast tumor. Free Radic Biol Med, 47:992–1004. 2009.
260.
RahmanI, AdcockIM. Oxidative stress and redox regulation of lung inflammation in COPD. Eur Respir J, 28:219–242. 2006.
261.
RebouçasJS, de CarvalhoMEMD, IdemoriYM. Perhalogenated 2-pyridylporphyrin complexes: synthesis, self-coordinating aggregation properties, and catalytic studies. J Porphyrins Phthalocyanines, 6:50–57. 2002.
262.
RebouçasJS, DeFreitas-SilvaG, IdemoriYM, SpasojevićI, BenovL, Batinić-HaberleI. Impact of electrostatics in redox modulation of oxidative stress by Mn porphyrins: protection of SOD-deficient Escherichia coli via alternative mechanism where Mn porphyrin acts as a Mn carrier. Free Radic Biol Med, 45:201–210. 2008.
263.
RebouçasJS, KosI, VujaskovićZ, Batinić-HaberleI. Determination of residual manganese in Mn porphyrin-based superoxide dismutase (SOD) and peroxynitrite reductase mimics. J Pharm Biomed Anal, 50:1088–1091. 2009.
264.
RebouçasJS, SpasojevićI, Batinić-HaberleI. Pure manganese(III) 5,10,15,20-tetrakis(4-benzoic acid)porphyrin (MnTBAP) is not a superoxide dismutase mimic in aqueous systems: a case of structure-activity relationship as a watchdog mechanism in experimental therapeutics and biology. J Inorg Biol Chem, 13:289–302. 2008.
265.
RebouçasJS, SpasojevićI, Batinić-HaberleI. Quality of Mn-porphyrin-based SOD mimics and peroxynitrite scavengers for preclinical mechanistic/therapeutic purposes. J Pharm Biomed Anal, 48:1046–1049. 2008.
266.
RebouçasJS, SpasojevićI, TjahjonoDH, RichaudA, MéndezF, BenovL, Batinić-HaberleI. Redox modulation of oxidative stress by Mn porphyrin-based therapeutics: the effect of charge distribution. Dalton Trans, 1233–1242. 2008.
267.
ReddiAR, JensenLT, NaranuntaratA, RosenfeldL, LeungE, ShahR, CulottaVC. The overlapping roles of manganese and Cu/ZnSOD in oxidative stress protection. Free Radic Biol Med, 46:154–162. 2009.
268.
ReesMD, BottleSE, Fairfull-SmithKE, MalleE, WhitelockJM, DaviesMJ. Inhibition of myeloperoxidase-mediated hypochlorous acid production by nitroxides. Biochem J, 421:79–86. 2009.
269.
RileyDP, LennonPJ, NeumannWL, WeissRH. Toward the rational design of superoxide dismutase mimics: mechanistic studies for the elucidation of substituent effects on the catalytic activity of macrocyclic manganese(II) complexes. J Am Chem Soc, 119:6522–6528. 1997.
270.
RobakJ, GryglewskiRJ. Bioactivity of flavonoids. Pol J Pharmacol, 48:555–564. 1996.
271.
RoberstonL, HartleyR. Synthesis of N-arylpyridinium salts bearing a nitron spin trap as potential mitochondria-targeted antioxidants. Tetrahedron, 65:5284–5292. 2009.
272.
RosenthalRA, HuffmanKD, FisetteLW, DamphousseCA, CallawayWB, MalfroyB, DoctrowSR. Orally available Mn porphyrins with superoxide dismutase and catalase activity. J Biol Inorg Chem, 14:979–991. 2009.
273.
RubboH, RadiR. Protein and lipid nitration: role in redox signaling and injury. Biochim Biophys Acta, 1780:1318–1324. 2008.
SaltsmanI, BotoshanskyM, GrossZ. Facile synthesis of ortho-pyridyl-substituted corroles, molecular structures of analogous porphyrins. Tetrahedron Lett, 49:4163–4166. 2008.
276.
SalveminiD, DoyleTM, CuzzocreaS. Superoxide, peroxynitrite and oxidative/nitrative stress in inflammation. Biochem Soc Trans, 34:965–970. 2006.
277.
SalveminiD, WangZ-Q, ZweierJL, SamouilovA, MacarthurH, MiskoTOP, CurrieMG, CuzzocreaS, SikorskiJA, RileyDP. A nonpeptidyl mimic of superoxide dismutase with therapeutic activity in rats. Science, 286:304–306. 1999.
278.
SamlowskiWE, PetersonR, CuzzocreaS, MacarthurH, BurtonD, McGregorJR, SalveminiD. A nonpeptidyl mimic of superoxide dismutase, M40403, inhibits dose-limiting hypotension associated with interleukin-2 and increases its antitumor effects. Nat Med, 9:750–755. 2009.
279.
SanchezRJ, SrinivasanC, MunroeWH, WallaceMA, MartinsJ, KaoTY, LeK, GrallaEB, ValentineJS. Exogenous manganous ion at millimolar levels rescues all known dioxygen-sensitive phenotypes of yeast lacking CuZnSOD. J Biol Inorg Chem, 10:913–923. 2005.
280.
SatohM, TakayanagiI. Pharmacological studies on fullerene (C60), a novel carbon allotrope, and its derivatives. J Pharmacol Sci, 100:513–518. 2006.
281.
SchubertR, ErkerL, BarlowC, YakushijiH, LarsonD, RussoA, MitchellJB, Wynshaw-BorisA. Cancer chemoprevention by the antioxidant tempol in Atm-mice. Hum Mol Genet, 13:1793–1802. 2004.
282.
SesslerJL, MillerRA. Texaphyrins: new drugs with diverse clinical applications in radiation and photodynamic therapy. Biochem Pharmacol, 59:733–739. 2000.
283.
SharmaSS, GuptaS. Neuroprotective effect of MnTMPyP, a superoxide dismutase/catalase mimetic in global cerebral ischemia is mediated through reduction of oxidative stress and DNA fragmentation. Eur J Pharmacol, 561:72–79. 2007.
284.
SharpeMA, OllossonR, StewartVC, ClarkJB. Oxidation of nitric oxide by oxomanganese-salen complexes: a new mechanism for cellular protection by superoxide dismutase/catalase mimetics. Biochem J., 366:97–107. 2002.
285.
ShenJ, IjaimiNE, ChkoundaM, GrosCP, BarbeJ-M, ShaoJ, GuilardR, KadishKM. Solvent, anion and structural effects on the redox potentials and UV-visible spectral properties of mononuclear manganese corroles. Inorg Chem, 47:7717–7727. 2008.
ShengH, SpasojevićI, WarnerDS, Batinić-HaberleI. Mouse spinal cord compression injury is ameliorated by intrathecal manganese(III) porphyrin. Neurosci Lett, 366:220–225. 2004.
288.
ShengH, YangW, FukudaS, TseHM, PaschenW, JohnsonK, Batinić-HaberleI, CrapoJD, PearlsteinRD, PiganelliJ, WarnerDS. Long-term neuroprotection from a potent redox-modulating metalloporphyrin in the rat. Free Radic Biol Med, 47:917–923. 2009.
289.
ShimanovichR, HannahS, LynchV, GerasimchukN, ModyTD, MagdaD, SesslerJ, GrovesJT. Mn(II)-texaphyrin as a catalyst for the decomposition of peroxynitrite. J Am Chem Soc, 123:3613–3614. 2001.
290.
ShohamA, HadziahmetovicM, DunaiefJL, MydlarskiMB, SchipperHM. Oxidative stress in diseases of human cornea. Free Radic Biol Med, 45:1047–1055. 2008.
291.
ShuklaS, GuptaS. Suppression of constitutive and tumor necrosis factor α-induced nuclear factor (NF-κB activation and induction of apoptosis by apigenin in human prostate carcinoma PC-3 cells: correlation with down-regulation of NF-κB–responsive genes. Clin Cancer Res, 10:3169–3178. 2004.
292.
SilvaD. Suppression of cancer invasiveness by dietary compounds. Mini Rev Med Chem, 8:677–688. 2008.
293.
SolomonD, PeretzP, FaraggiM. Chemical properties of water-soluble porphyrins, 1: the reaction of iron(IIII) tetrakis(4-N-methylpyridyl)porphyrin with superoxide radical dioxygen couple. J Phys Chem, 86:1842–1849. 1982.
294.
SompolP, IttaratW, TangpongJ, ChenY, DoubinskaiaI, Batinić-HaberleI, Mohammad AbdulH, ButterfieldA, St ClairDK. Alzheimer's disease: an insight into the mechanisms of oxidative stress-mediated mitochondrial injury. Neuroscience, 153:120–130. 2008.
295.
Soukhova-O'HaraGK. Ortines RV, Gu Y, Nozdrachev AD, Prabhu SD, and Gozal D. Postnatal intermittent hypoxia and developmental programming of hypertension in spontaneously hypertensive rats. Hypertension, 52:156–162. 2008.
296.
SouleBP, HyodoF, MatsumotoK, SimoneNL, CookJA, KrishnaMC, MitchellJB. The chemistry and biology of nitroxide compounds. Free Radic Biol Med, 42:1632–1650. 2007.
297.
SouleBP, HyodoF, MatsumotoK-I, SimoneNL, CookJA, KrishnaMC, MitchellJB. Therapeutic and clinical applications of nitroxide compounds. Antioxid Redox Signal, 9:1731–1743. 2007.
298.
SouzaJM, PeluffoG, RadiR. Protein tyrosine nitration: functional alteration or just a biomarker?Free Radic Biol Med, 45:357–366. 2008.
299.
SpasojevićI, Batinić-HaberleI. Manganese(III) complexes with porphyrins and related compounds as catalytic scavengers of superoxide. Inorg Chim Acta, 317:230–242. 2001.
SpasojevićI, Batinić-HaberleI, RebouçasJS, IdemoriYM, FridovichI. Electrostatic contribution in the catalysis of O2·− dismutation by superoxide dismutase mimics. J Biol Chem, 278:6831–6837. 2003.
302.
SpasojevićI, Batinić-HaberleI, StevensRD, HambrightP, ThorpeAN, GrodkowskiJ, NetaP, FridovichI. Manganese(III) biliverdin IX dimethylester. a powerful catalytic scavenger of superoxide employing the Mn(III)/Mn(IV) redox couple Inorg Chem, 40:726–739. 2001.
303.
SpasojevićI, ChenY, NoelTJ, FanP, ZhangL, RebouçasJS, St ClairDK, Batinić-HaberleI. Pharmacokinetics of the potent redox modulating manganese porphyrin, MnTE-2-PyP5+ in plasma and major organs of B6C3F1 mice. Free Radic Biol Med, 45:943–949. 2008.
304.
SpasojevićI, ColvinOM, WarshanyKR, Batinić-HaberleI. New approach to the activation of anti-cancer pro-drug by metalloporphyrin-based cytochrome P450 mimics in all-aqueous biologically relevant system. J Inorg Biochem, 100:1897–1902. 2006.
305.
SpasojevicI, ShengH, WarnerDS, Batinic-HaberleI. Metalloporphyrins are versatile and powerful therapeutics: biomimetics of SOD, peroxyredoxin, and cyt P450. 2nd World Conference on Magic Bullets (Ehrlich II): Nurnberg, 2008.
SrinivasanV, DoctrowS, SinghVK, WhitnallMH. Evaluation of EUK-189, a synthetic superoxide dismutase/catalase mimetic as radiation countermeasure. Immunopharmacol Immunotoxicol, 30:271–290. 2008.
308.
StavrovskayaIG, KristalBS. The powerhouse takes control of the cell: is the mitochondrial permeability transition a viable therapeutic target against neuronal dysfunction and death?Free Radic Biol Med, 38:687–697. 2005.
309.
StefanuttiG, PierroA, SmithVV, KleinNJ, EatonS. Peroxynitrite decomposition catalyst FeTMPyP provides partial protection against intestinal ischemia and reperfusion injury in infant rats. Pediatr Res, 62:43–48. 2007.
StrimpakosAS, SharmaRA. Curcumin: preventive and therapeutic properties in laboratory studies and clinical trials. Antioxid Redox Signal, 10:511–545. 2008.
312.
SunH-L, LiuY-N, HuangY-T, PanS-L, HuangD-J, GuhJ-H, LeeF-Y, KuoS-C. YC-1 inhibits HIF-1 expression in prostate cancer cells: contribution of Akt/NF-kB signaling to HIF-1α accumulation during hypoxia. Oncogene, 26:3941–3951. 2007.
313.
SzabóC, MableyJG, MoellerSM, ShimanovichR, PacherP, ViragL, SorianoVG, Van DuzerJH, WilliamsW, SalzmanAL, GrovesJT. Part I: Pathogenetic role of peroxynitrite in the development of diabetes and diabetic vascular complications: studies with FP15, a novel potent peroxynitrite decomposition catalyst. Mol Med, 8:571–580. 2002.
314.
TauskelaJS, BrunetteE, KiedrowskiL, LortieK, HewittM, MorleyP. Unconventional neuroprotection against Ca2+-dependent insults by metalloporphyrin catalytic antioxidants. J Neurochem, 98:1234–1342. 2006.
315.
TauskelaJS, BrunetteE, O'ReillyN, MealingG, ComasT, GendronTF, MonetteR, MorleyP. An alternative Ca2+-dependent mechanism of neuroprotection by metalloporphyrin class of superoxide dismutase mimetics. FASEB J, 19:1734–1736. 2005.
316.
TawfikHE, CenaJ, SchulzR, KaufmanS. Role of oxidative stress in multiparity-induced endothelial disfunction. Am J Physiol Heart Circ Physiol, 295:H1736–H1742. 2008.
317.
ToyokuniS. Molecular mechanisms of oxidative stress-induced carcinogenesis: from epidemiology to oxygenomics. IUBMB Life, 60:441–447. 2008.
318.
TrnkaJ, BlaikieFH, LoganA, SmithRAJ, MurphyMP. Antioxidant properties of MitoTEMPOL and its hydroxylamine. Free Radic Res, 43:4–12. 2009.
319.
TrnkaJ, BlaikieFH, SmithRA, MurphyMP. A mitochondria-targeted nitroxide is reduced to its hydroxylamine by ubiquinol in mitochondria. Free Radic Biol Med, 44:1406–1419. 2008.
320.
TrostchanskyA, Ferrer-SuetaG, BatthyányC, BottiH, Batinić-HaberleI, RadiR, RubboH. Peroxynitrite flux-mediated LDL oxidation is inhibited by manganese porphyrins in the presence of uric acid. Free Radic Biol Med, 35:1293–1300. 2003.
321.
TrovaMP, GauuanPJF, PechulisAD, BubbSM, BocckinoSB, CrapoJD, DayBJ. Superoxide dismutase mimetics, part 2: synthesis and structure-activity relationship of glyoxylate- and glyoxamide-derived metalloporphyrins. Bioorg Med Chem, 11:2695–2707. 2003.
322.
TseH, MiltonMJ, PiganelliJD. Mechanistic analysis of the immunomodulatory effects of a catalytic antioxidant on antigen-presenting cells: implication for their use in targeting oxidation/reduction reactions in innate immunity. Free Radic Biol Med, 36:233–247. 2004.
323.
UngvariZ, Parrado-FernandezC, CsiszarA, de CaboR. Mechanisms underlying caloric restriction and lifespan regulation: implications for vascular aging. Circ Res, 102:519–528. 2008.
324.
Van EmpelVPM, BertrandAT, Van OortRJ, Van der NagelR, EngelenM, Van RijenHV, DoevendansPA, CrijnsHJ, AckermanSL, SluiterW, De WindtLJ. EUK-8, a superoxide dismutase and catalase mimetic, reduces cardiac oxidative stress and ameliorates pressure overload-induced heart failure in the harlequin mouse mutant. J Am Coll Cardiol, 48:824–832. 2006.
325.
VanceCK, MillerAF. A simple proposal that can explain the inactivity of metal-substituted superoxide dismutases. J Am Chem Soc, 120:461–467. 1998.
326.
VianiGA, MantyaGB, FonsecaEC, De FendiLI, AfonsoSL, StefanoEJ. Whole brain radiotherapy with radiosensitizer for brain metastases. J Exp Clin Cancer Res, 28:47. 2009.
VujaskovićZ, Batinić-HaberleI, RabbaniZN, FengQ-F, KangSK, SpasojevićI, SamulskiTV, FridovichI, DewhirstMW, AnscherMS. A small molecular weight catalytic metalloporphyrin antioxidant with superoxide dismutase (SOD) mimetic properties protects lungs from radiation-induced injury. Free Radic Biol Med, 33:857–863. 2002.
329.
WangZ-Q, PoreccaF, CuzzocreaS, GalenK, LightfootR, MasiniE, MuscoliE, MollaceV, NdengeleM, IschirpoulosH, SalveminiD. A newly identified role for superoxide in inflammatory pain. J Pharmacol Exp Ther, 309:869–878. 2004.
330.
WangJF. Defects of mitochondrial electron transport chain in bipolar disorder: implications for mood-stabilizing treatment. Can J Psychiatry, 52:753–762. 2007.
331.
WatanabeT, OwadaS, KobayashiHP, KawakamiH, NagaokaS, MurakamiE, IshiuchiA, EnomotoT, JinnouchiY, SakuraiJ, TobeN, KoizumiS, ShimamuraT, AsakuraT, NakanoH, OtsuboT. Protective effects of MnTM2Py4P and Mn-salen against small bowel ischemia/reperfusion injury in rats an in vivo and ex vivo electron paramagnetic resonance technique with a spin probe. Transplant Proc, 39:3002–3006. 2007.
332.
WeinraubD, PeretzP, FaraggiM. Chemical properties of water-soluble porphyrins, 1. Equilibria between some ligands and iron(III) tetrakis(4-N-methylpyridyl)porphyrin. J Phys Chem, 86:1839–1842. 1982.
333.
WerinraubD, LevyP, FaraggiM. Chemical properties of water-soluble porphyrins, 5. Reactions of some manganese (III) porphyrins with the superoxide and other reducing radicals. Int J Radiat Biol, 50:649–658. 1986.
334.
WilcoxCS, PearlmanA. Chemistry and antihypertensive effects of tempol and other nitroxides. Pharmacol Rev, 60:418–469. 2009.
335.
WinterbournCC. Reconciling the chemistry and biology of reactive species. Nat Chem Biol, 4:278–286. 2008.
336.
WinterbournCC, HamptonMB. Thiol chemistry and specificity in redox signaling. Free Radic Biol Med, 45:549–561. 2008.
337.
Wise-FaberowskiL, WarnerDS, SpasojevićI, Batinić-HaberleI. The effect of lipophilicity of Mn (III) ortho N-alkylpyridyl- and diortho N, N'-imidazolylporphyrins in two in-vitro models of oxygen and glucose deprivation-induced neuronal death. Free Radic Res, 43:329–339. 2009.
338.
WolakM, van EldikR. Mechanistic studies on peroxide activation by a water-soluble iron(III)–porphyrin: implications for O-O bond activation in aqueous and nonaqueous solvents. Chem Eur J, 13:4873–4883. 2007and references therein.
339.
WolfG, HannkenT, SchroedrR, ZahnerG, ZiyadehFN, StahlRAK. Antioxidant treatment induces transcription and expression of transforming growth factor β in cultured renal proximal tubular cells. FEBS Lett, 488:154–159. 2001.
340.
WuAS, KiaeiM, AguirreN, CrowJP, CalingasanNY, BrowneSE, BealMF. Iron porphyrin treatment extends survival in transgenic animal model of amyotrophic lateral sclerosis. J Neurochem, 85:142–150. 2003.
WuZ, ZhangJ, ZhaoB. Superoxide anion regulates the mitochondrial free Ca2+ through uncoupling proteins. Antioxid Redox Signal, 11:1805–1818. 2009.
343.
XuY, LiuB, ZweierJL, HeG. Formation of hydrogen peroxide and reduction of peroxynitrite via dismutation of superoxide at reperfusion enhances myocardial blood flow and oxygen consumption in postischemic mouse heart. J Pharmacol Exp Ther, 327:402–410. 2008.
344.
YadavaN, NichollsDG. Spare respiratory capacity rather than oxidative stress regulates glutamate excitotoxicity after partial respiratory inhibition of mitochondrial complex I with rotenone. J Neurosci, 27:7310–7317. 2007.
345.
YanH, ParsonsDW, JinG, McLendonR, RasheedBA, YuanW, KosI, Batinić-HaberleI, JonesS, RigginsGJ, FriedmanH, FriedmanA, ReardonD, HerndonJ, KinzlerKW, VelculescuVE, VogelsteinB, BignerDD. IDH1 and IDH2 mutations in gliomas. N Engl J Med, 360:765–773. 2009.
346.
YeX, FelsD, DedeugdC, DewhirstMW, LeongK, Batinic-HaberleI. The in vitro cytotoxic effects of Mn(III) alkylpyridylporphyrin/ascorbate system on four tumor cell lines. Free Radic Biol Med, 47:S136. 2009.
347.
YinJ-J, LaoF, FuPP, WamerWG, ZhaoY, WangPC, QiuY, SunB, XingG, DongJ, LiangX-J, ChenC. The scavenging of reactive oxygen species and potential for the cell protection by functionalized fullerene materials. Biomaterials, 3:611–621. 2009.
348.
YuL, JiX, DerrickM, DrobyshevskyA, LiuT, Batinic-HaberleI, TanS. Testing new porphyrins in in vivo model system: effect of Mn porphyrins in animal model of cerebral palsy (abstract)Sixth International Conference on Porphyrins and Phthalocyanines, New Mexico, 2010.
349.
YudohK, ShishidoK, MurayamaH, YanoM, MatsubayashiK, TakadaH, NakamuraH, MasukoK, KatoT, NishiokaK. Water-soluble C60 fullerene prevents degradation of articular cartilage in osteoarthritis via down-regulation of chondrocyte catabolic activity and inhibition of cartilage degeneration during disease development. Arthritis Rheum, 56:3307–3318. 2007.
350.
ZhaoY, ChaiswingL, OberleyTD, Batinić-HaberleI, St ClairW, EpsteinCJ, St ClairD. A mechanism-based antioxidant approach for the reduction of skin carcinogenesis. Cancer Res, 65:1401–1405. 2005.