The interaction of cytosine with AuCl4−, under electrospray ionization mass spectrometric conditions, is discussed. On the basis of respective full scan mass spectra and product ion spectra, obtained in positive and negative ion mode, it has been deduced that cytosine is very prone to form Au(I)-containing complexes. The complexes may be formed in the gas phase by decomposition of Au(III)-containing complexes and also in the electrospray ionization source as a result of the occurrence of redox process. It has also been found that the interaction of cytosine with Au+ is stronger than that with Cu+ or Ag+, although taking into account the electrostatic attraction, it is not expected.
PatilYPNethajiM.Simultaneous co-ordination of three cytosine ligands displaying different binding sites around the copper centres. RSC Adv2014;
4: 44938–44942.
2.
KrilovDGomziVHerakJN.A new cytosine-copper paramagnetic complex: spectroscopic study. Spectrochim Acta Part A2008;
70: 1238–1242.
3.
KalyanaramanSKrishnakumarVGanesanK.Vibrational spectroscopic analysis of cytosine monohydrate and its copper(II) complex. Spectrochim Acta Part A2007;
66: 1340–1346.
4.
KrilovDLekićABešićE, et al.
EPR study of a copper center in a single crystal of cytosine monohydrate. J Inorg Biochem2005;
99: 886–889.
5.
SelviPTMuraliMPalaniandavarM, et al.
X-ray crystal structure of tetrakis(1-methylcytosine)copper(II) perchlorate dihydrate: effect of 1-methyl substitution on cytosine on the spectral and redox behavior. Inorg Chim Acta2002;
340: 139–146.
6.
PalaniandavarMSomasundaramLMManoharH.Stabilisation of unusual simultaneous binding of four cytosine nucleobases to copper(II) by a novel network of bifurcated hydrogen bonding. J Chem Soc Dalton Trans1996; 1333–1340.
7.
TranQDPalacioE.Synthesis and structure of cytosine dichloride cuprate: direct binding of copper to cytosine. Acta Cryst1990;
CA6: 1220–1223.
8.
MikulskiCMLeeCJTranTB.Cytosine complexes with copper(II) perchlorate. Inorg Chim Acta1987;
136: L13–L15.
9.
GaoJBerdenGRodgersMT, et al.
Interaction of Cu+ with cytosine and formation of i-motif-like C–M+–C complexes: alkali versus coinage metals. Phys Chem Chem Phys2016;
18: 7269–7277.
10.
Correia dos SantosMMSousaPMPModestoAMM, et al.
Voltammetric behaviour of copper complexes with cytosine and its nucleoside.Bioelectrochem Bioenerg1998;
45: 267–273.
11.
ZhengYYangCYangF, et al.
Real-time study of interactions between cytosine-cytosine pairs in DNA oligonucleotides and silver ions using dual polarization interferometry. Anal Chem2014;
86: 3849–3855.
12.
LinaresFGarcía-FernándezELópez-GarzónFJ, et al.
Multifunctional behavior of molecules comprising stacked cytosine–AgI–cytosine base pairs; towards conducting and photoluminescence silver-DNA nanowires. Chem Sci2019;
10: 1126–1137.
13.
WangYRitzoBGuL-Q.Silver(I) ions modulate the stability of DNA duplexes containing cytosine, methylcytosine and hydroxymethylcytosine at different salt concentrations. RSC Adv2015;
5: 2655–2658.
14.
OnoACaoSTogashiH, et al.
Specific interactions between silver(I) ions and cytosine-cytosine pairs in DNA duplexes. Chem Commun2008; 4825–4827.
15.
XuYZhangCDuH, et al.
Fluorometric detection of silver(I) using cytosine-Ag(I)-cytosine pair formation, DNA assembly and the and logic operation of a multiple-component DNAzyme. Microchim Acta2019;
186: 522.
16.
KimJHKimKBParkJS, et al.
Single cytosine-based electrochemical biosensor for low-cost detection of silver ions. Sens Actuators B2017;
245: 741–746.
17.
XieWYHuangWTLiNB, et al.
Silver(I) ions and cysteine detection based on photoinduced electron transfer mediated by cytosine-Ag+-cytosine base pairs. Analyst2011;
136: 4130–4133.
18.
LangMLiQHuangH, et al.
Highly sensitive exonuclease III-assisted fluorometric determination of silver(I) based on graphene oxide and self-hybridization of cytosine-rich ss-DNA. Microchim Acta2016;
183: 1659–1665.
19.
QiaoHYHongMLTianX, et al.
Cytosine-rich DNA decorated gold nanoparticles surface enhanced Raman-scattering platform for sensitive and selective detection of silver ions. Anal Sci2013;
29: 991–996.
20.
XuGWangGXiupingH, et al.
An ultrasensitive electrochemical method for detection of Ag+ based on cyclic amplification of exonuclease III activity on cytosine-Ag+-cytosine. Analyst2013;
138: 6900–6906.
21.
Espinosa LealLAKarpenkoASwaseyS, et al.
The role of hydrogen bonds in the stabilization of silver-mediated cytosine tetramers. J Phys Chem Lett2015;
6: 4061–4066.
22.
GuerraCFMiguelPJSCebolladaA, et al.
Rationalizing the structural variability of the exocyclic amino groups in nucleobases and their metal complexes: cytosine and adenine. Chem Eur J2014;
20: 9494–9499.
23.
ChoK-HJooS-W.Tautomerism of cytosine on silver, gold, and copper: Raman spectroscopy and density functional theory calculation study. Bull Korean Chem Soc2008;
29: 69–74.
24.
SchimanskiAFreisingerEErxlebenA, et al.
Interactions between [AuX4]− (X=C1, CN) and cytosine and guanine model nucleobases: salt formation with (hemi-) protonated bases, coordination, and oxidative degradation of guanine. Inorgan Chim Acta1998;
283: 223–232.
25.
BressanMEttorreRRigoP.NMR studies of the interaction between cytosine and gold complexes. J Magn Reson1977;
26: 43–41.
26.
HadjiliadisNPneumatikakisGBasosiR.Gold complexes of purine and pirimidine nucleosides. J Inorg Biochem1981;
14: 115–126.
27.
FrańskaMKonowałE.Nucleoside-AuCl4− interactions as studied by electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom2019;
33: 1164–1168.
28.
HendersonWMcIndoeJS.Mass spectrometry of inorganic, coordination and organometallic compounds.
Milton, Queensland:
John Wiley & Sons, Ltd, 2005, p. 117.
29.
SlenoLVolmerDA.Ion activation methods for tandem mass spectrometry. J Mass Spectrom2004;
39: 1091–1112.
30.
FrańskiR.Gas phase hydration of polyethylene glycol-metal cation complexes. J Mass Spectrom2019;
54: 88–91.
31.
MonajjemiMKetabiSZadehMH, et al.
Simulation of DNA bases in water: comparison of the monte carlo algorithm with molecular mechanics force fields. Biochemistry2006;
71: S1–S8.
32.
ShaoPKuangX-YDingL-P, et al.
Structures, electrophilic properties, and hydrogen bonds of cytidine, uridine, and their radical anions: microhydration effects. J Chem Phys2013;
139: 024305.
33.
MoserAGuzaRTretyakovaN, et al.
Density functional study of the influence of C5 cytosine substitution in base pairs with guanine. Theor Chem Acc2009;
122: 179–188.
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