Binding of alkaloids by different hosts (native and modified cyclodextrins, cucurbiturils, calixarenes, and metal complexes of porphyrin and Salphen-type ligands), as well as receptor properties of alkaloid based hosts are reviewed. With alkaloids as guests, the largest binding constants and most significant spectral changes, in particular strong fluorescence enhancements induced by complexation with isoquinoline alkaloids, are observed with cucurbituril hosts. Cyclodextrins are successfully employed for improvement of solubility and for chiral separation of alkaloids of different types. Receptor properties of native and modified cinchona and bisbenzylisoquinoline alkaloids have attracted considerable attention for development of chiral selectors for analysis and separation.
LiuY, LiL, ZhangH-Y, FanZ, GuanX-D. (2003) Selective binding of chiral molecules of cinchona alkaloid by β- and γ-cyclodextrins and organoselenium-bridged bis(β-cyclodextrin)s. Bioorganic Chemistry, 31, 11–23.
2.
LiuY, ChenG-S, ChenY, DingF, ChenJ. (2005) Cyclodextrins as carriers for cinchona alkaloids: a pH-responsive selective binding system. Organic & Biomolecular Chemistry, 3, 2519–2523.
3.
SohajdaT, VargaE, IványiR, FejosI, SzenteL, Noszál B, BéniS. (2010) Separation of vinca alkaloid enantiomers by capillary electrophoresis applying cyclodextrin derivatives and characterization of cyclodextrin complexes by nuclear magnetic resonance spectroscopy. Journal of Pharmaceutical and Biomedical Analysis, 53, 1258–1266
4.
RibeiroL, CarvalhoRA, FerreiraDC, VeigaFJB (2005) Multicomponent complex formation between vinpocetine, cyclodextrins, tartaric acid and water-soluble polymers monitored by NMR and solubility studies. European Journal of Pharmaceutical Sciences, 24, 1–13.
5.
NieS, FanX, PengY, YangX, WangC, PanW. (2006) In vitro and in vivo studies on the complexes of vinpocetine with hydroxypropyl-β-cyclodextrin. Archives of Pharmacal Research, 30, 991–1001.
6.
MegyesiM, BiczókL, JablonkaiI. (2008) Highly sensitive fluorescence response to inclusion complex formation of berberine alkaloid with cucurbit[7]uril. Journal of Physical Chemistry C, 112, 3410–3416.
7.
MegyesiM, BiczókL. (2006) Considerable fluorescence enhancement upon supramolecular complex formation between berberine and p-sulfonated calixarenes. Chemical Physics Letters, 424, 71–76.
8.
YuJ-S, WeiF-D, GaoW, ZhaoC-C. (2002) Thermodynamic study on the effects of β-cyclodextrin inclusion with berberine. Spectrochimica Acta Part A, 58, 249–256.
9.
LiC-F, DuL-M, WuW-Y, ShengA-Z. (2010) Supramolecular interaction of cucurbit[n]urils and coptisine by spectrofluorimetry and its analytical application. Talanta, 80, 1939–1944.
10.
LiC-F, DuL-M, ZhangH-M. (2010) Study on the inclusion interaction of cucurbit[n]urils with sanguinarine by spectrofluorimetry and its analytical application. Spectrochimica Acta Part A, 75, 912–917.
11.
MiskolczyZ, MegyesiM, TarkanyiG, MizseiR, BiczokL. (2011) Inclusion complex formation of sanguinarine alkaloid with cucurbit[7]uril: inhibition of nucleophilic attack and photooxidation. Organic & Biomolecular Chemistry, 9, 1061–1070.
12.
LiC, LiJ, JiaX. (2009) Selective binding and highly sensitive fluorescent sensor of palmatine and dehydrocorydaline alkaloids by cucurbit[7]uril. Organic & Biomolecular Chemistry, 7, 2699–2703.
13.
MegyesiM, BiczokL. (2010) Considerable change of fluorescence properties upon multiple binding of coralyne to 4-sulfonatocalixarenes. Journal of Physical Chemistry B, 114, 2814–2819.
14.
LiC, XuQ, LiJ, JiaX. (2009) Highly effective binding and inverse fluorescent behavior of palmatine and l-tetrahydropalmatine alkaloids by p-sulfonatocalixarenes. Journal of Inclusion Phenomenon and Macrocyclic Chemistry, 64, 37–42.
15.
MartınL, LeonA, OlivesAI, del CastilloB, MartınMA. (2003) Spectrofluorimetric determination of stoichiometry and association constants of the complexes of harmane and harmine with β-cyclodextrin and chemically modified β-cyclodextrins. Talanta, 60, 493–503;
16.
MartınL, LeonA, MartınMA, del CastilloB, MenendezJC. (2003) Detection and characterization of cyclodextrin complexes with β-carboline derivatives by spectroscopic techniques. Journal of Pharmaceutical and Biomedical Analysis, 32, 991–1001.
DeviprasadGR, D'SouzaF. (2000) Molecular recognition directed porphyrin chemosensor for selective detection of nicotine and cotinine. Chemical Communications, 1915–1916.
19.
Escudero-AdánEC, Benet-BuchholzJ, KleijAW. (2008) Supramolecular adsorption of alkaloids by metallosalphen complexes. Inorganic Chemistry, 47, 4256–4263.
20.
ZhouY, YuH, ZhangL, XuH, WuL, SunJ, WangL. (2009) A new spectrofluorometric method for the determination of nicotine base on the inclusion interaction of methylene blue and cucurbit[7]uril. Microchimica Acta, 164, 63–68.
21.
WarhurstDC, CraigJC, AdaguIS, MeyerDJ, LeeSY. (2003) The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids. Malaria Journal, 2, 26–40.
22.
MinkL, MaZ, OlsenRA, JamesJN, ShollDS, MuellerLJ, ZaeraF. (2008) The physico-chemical properties of Cinchona alkaloids, responsible for their unique performance in chiral catalysis. Topics in Catalysis, 48, 120–127.
23.
SchneiderH-J, YatsimirskyAK, (2008) Selectivity in supramolecular host–guest complexes. Chemical Society Reviews, 37263–277.
24.
MaitiM, KumarGS. (2007) Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives. Medicinal Research Reviews, 27, 649–695;
25.
MaitiM, KumarGS. (2007) Protoberberine alkaloids: physicochemical and nucleic acid binding properties. Topics in Heterocyclic Chemistry, 10, 155–209;
26.
GiriP, KumarGS. (2010) Molecular recognition of poly(A) targeting by protoberberine alkaloids: in vitro biophysical studies and biological perspectives. Molecular BioSystems, 6, 81–88;
27.
BhadraK, KumarGS. (2010) Isoquinoline alkaloids and their binding with DNA: calorimetry and thermal analysis applications. Mini-Reviews in Medicinal Chemistry, 10, 1235–1247.
28.
(a) IslamMd. M, BasuA, HossainM, SureshkumarG, HothaS, KumarGS. (2011) Enhanced DNA binding of 9-o-amino alkyl ether analogs from the plant alkaloid berberine. DNA and Cell Biology, 30, 123–133;
29.
BhadraK, KumarGS. (2011) Interaction of berberine, palmatine, coralyne, and sanguinarine to quadruplex DNA: A comparative spectroscopic and calorimetric study. Biochimica et Biophysica Acta, 1810, 485–496;
30.
IslamMd. M, PandyaP, KumarS, KumarGS. (2009) RNA targeting through binding of small molecules: Studies on t-RNA binding by the cytotoxic protoberberine alkaloid coralyne. Molecular BioSystems, 5, 244–254.
31.
MegyesiM, BiczokL. (2007) Berberine alkaloid as a sensitive fluorescent probe for bile salt aggregates. Journal of Physical Chemistry B, 111, 5635–5639.
32.
SchneiderH-J, HacketF, RüdigerV, IkedaH. (1998) NMR studies of cyclodextrins and cyclodextrin complexes, Chemical Reviews, 98, 1755–1786.
33.
SchonefeldK, LudwigR, FellerK-H. (2006) Fluorescence studies of host–guest interaction of a dansyl amide labeled calix[6]arene. Journal of Fluorescence, 16, 449–454.
34.
SongCE. (Ed.) (2009) Cinchona Alkaloids in Synthesis and Catalysis, Wiley-VCH, Weinheim.
35.
LahJ, MaierNM, LindnerW, VesnaverG. (2001) Thermodynamics of binding of (R)- and (S)-dinitrobenzoyl leucine to Cinchona alkaloids and their tert-butylcarbamate derivatives in methanol: Evaluation of enantioselectivity by spectroscopic (CD, UV) and microcalorimetric (ITC) titrations. Journal of Physical Chemistry, B, 105, 1670–1678.
36.
MaierNM, NicolettiL, LammerhoferM, LindnerW. (1999) Enantioselective anion exchangers based on Cinchona alkaloid-derived carbamates: Influence of C8/C9 stereochemistry on chiral recognition. Chirality, 11, 522–528;
37.
MaierNM, SchefzickS, LombardoGM, FelizM, RissanenK, LindnerW, LipkowitzKB. (2002) Elucidation of the chiral recognition mechanism of Cinchona alkaloid carbamate-type receptors for 3,5-dinitrobenzoyl amino acids. Journal of the American Chemical Society, 124, 8611–8629.
38.
SchuurB, WinkelmanJGM. HeeresHJ. (2008) Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a Cinchona alkaloid extractant. Industrial & Engineering Chemistry Research, 47, 10027–10033.
39.
HallettAJ, KwantGJ, de VriesJG. (2009) Continuous separation of racemic 3,5-dinitrobenzoyl-amino acids in a centrifugal contact separator with the aid of Cinchona-based chiral host compounds. Chemistry European Journal, 15, 2111–2120.
CzerwenkaC, ZhangMM, KahligH, MaierNM, LipkowitzKB, LindnerW. (2003) Chiral recognition of peptide enantiomers by Cinchona alkaloid derived chiral selectors: Mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling. Journal of Organic Chemistry, 68, 8315–8327.
42.
Uccello-BarrettaG, MirabellaF, BalzanoF, SalvadoriP. (2003) C11 versus C9 carbamoylation of quinine: a new class of versatile polyfunctional chiral solvating agents, Tetrahedron: Asymmetry, 14, 1511–1516.
43.
Uccello-BarrettaG, BardoniS, BalzanoF, SalvadoriP. (2001) Versatile chiral auxiliaries for NMR spectroscopy based on carbamoyl derivatives of dihydroquinin. Tetrahedron: Asymmetry, 12, 2019–2023.
44.
Uccello-BarrettaG, BalzanoF, SalvadoriP. (2005) Rationalization of the multireceptorial character of chiral solvating agents based on quinine and its derivatives: Overview of selected NMR investigations. Chirality, 17, S243–S248.
45.
Uccello-BarrettaG, VanniL, BalzanoF. (2009) NMR Enantiodiscrimination phenomena by quinine C9-carbamates. European Journal of Organic Chemistry, 860–869.
46.
RudzinskaE, BerlickiL, KafarskiP, LammerhoferM, MuchaA. (2009) Cinchona alkaloids as privileged chiral solvating agents for the enantiodiscrimination of N-protected aminoalkanephosphonates-a comparative NMR study. Tetrahedron: Asymmetry, 20, 2709–2714.
47.
Uccello-BarrettaG, VanniL, BerniMG, BalzanoF. (2011) NMR enantiodiscrimination by pentafluorophenylcarbamoyl derivatives of quinine: C10 versus C9 derivatization. Chirality, 23, 417–423.
48.
BozkurtS, DurmazM, YilmazM, SiritA. (2008) Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids. Tetrahedron: Asymmetry, 19, 618–623.
49.
KacprzakK, GawronskiJ. (2003) Bifunctional receptor triad for efficient recognition of mono- and dicarboxylic acids. Chemical Communications, 1532–1533.
ShammaM. (1972) The Isoquinoline Alkaloids. Academic Press, New York;
52.
KwanCY, AchikeF. (2002) Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: cardiovascular effects and mechanisms of action. Acta Pharmacologica Sinica, 1057–1068.
53.
KingH. (1935) Curare Alkaloids. Part 1. Tubocurarine. Journal of the Chemical Society, 1381–1389.
54.
Godoy-AlcántarC, EliseevAV, YatsimirskyAK. (1996) Molecular recognition by natural macrocycles. Part I. d-Tubocurarine as a host molecule for organic anions. Journal of Molecular Recognition, 9, 54–64.
55.
Godoy-AlcántarC, NelenMI, EliseevAV, YatsimirskyAK. (1999) Molecular recognition by natural macrocycles. Part II. Esterolytic activity and chiral discrimination of amino acid derivatives by the zwitterionic form of (1)-tubocurarine. Journal of the Chemical Society, Perkin Transactions. 2, 353–361.
56.
NairUB., ArmstrongDW, HinzeWL. (1998) Characterization and evaluation of d-(+)-tubocurarine chloride as a chiral selector for capillary electrophoretic enantioseparations. Analytical Chemistry, 70, 1059–1065.
57.
LaraKO, Godoy-AlcántarC, RiveraIL, EliseevAV, YatsimirskyAK. (2001) Complexation of dicarboxylates and phosphates by a semisynthetic alkaloid-based cyclophane in water. Journnl of Physical Organic Chemistry, 14, 453–462.
58.
Ochoa LaraK, Godoy-AlcántarC, EliseevAV, YatsimirskyAK. (2004) Recognition of α-amino acid derivatives by N, N'-dibenzylatedS, S-(+)-tetrandrine. Organic & Biomolecular Chemistry, 2, 1712–1718.
59.
Moreno-CorralR, Ochoa-LaraK. (2008) Complexation studies of nucleotides by tetrandrine derivatives bearing anthraquinone and acridine groups. Supramolecular Chemistry, 20, 427–435.
StanculescuI, MandravelC, DelattreF, LandyD, WoiselP, SurpateanuG. (2003) Cation binding characteristics of tetrandrine studied by UV-Vis absorption and fluorescence spectroscopies. Journal of Photochemistry and Photobiology A, 161, 79–85.
62.
SchneiderH.-J. (2009) Binding mechanisms in supramolecular complexes. Angewandte Chemie - International Edition, 48, 3924–3977.
