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Abstract

The electrochemical behavior of 6-furfurylaminopurine(6-KT) and 6-mercaptopurine(6-MP) on a mercury electrode has been investigated using cyclic voltammetry and differential pulse voltammetry.It is found that there are two pairs of redox waves for 6-KT and 6-MP on the mercury electrode controlled by diffusion and adsorption,respectively.The anodic peak currents of the diffusion-controlled wave increase with the adding concentration of 6-substituted purines.A good linear relationship for 6-KT and 6-MP is revealed in the concentration range from 0.1 to 50.0 μmol·L-1.Based on the effects of accumulating time and pH values on the cathodic peak potentials and currents of adsorption-controlled waves,their adsorption mechanism is discussed.The experimental results show that there are interactions of 6-KT and 6-MP with DNA via the intercalative mode partly and electrostatic action,respectively.

Keywords

6-furfurylaminopurine, 6-mercaptopurine, DNA, electrochemical behavior

Publication Date

2008-02-28

Online Available Date

2008-02-28

Revised Date

2008-02-28

Received Date

2008-02-28

References

[1]Barciszewski J,Rattan S I S,Siboska G,et al.Kinetin—45 years on[J].Plant Sci,1999,148:37-45.
[2]Nelson J A,Carpenter J W,Adamson ML.Mechanismof Action of 6-thiogunine,6-mercaptopurine and 8-aza-guanine[J].Cancer Res,1975,35:2872-2877.
[3]Cao X N,Lin L,Zhou Y Y,et al.Study of the interac-tion of 6-mercaptopurine with protein by microdialysiscoupled with LC and electrochemical detection based onfunctionalized multi-wall carbon nanotubes modified e-lectrode[J].J Pharmaceut Biomed,2003,32:505-512.
[4]Zhou C F,Du X S,Li H.Studies of interactions amongcobalt(III)polypyridyl complexes,6-mercaptopurineand DNA[J].Bioelectrochemistry,2007,70:446-451.
[5]Shen X C,Jiang L F,Liang H,et al.Determination of6-mercaptopurine based on the fluorescence enhance-ment of Au nanoparticles[J].Talanta,2006,69:456-462.
[6]Wu H,Wang HG.Studies of the influence of the sur-factant sodium dodecyl sulfate on the fluorescence prop-erties of kinetin[J].Anal Chim Acta,1996,329:161-164.
[7]Yang H F,Liu Y L,Liu Z M,et al.Raman mappingand in situ SERS spectroelectrochemical studies of 6-mercaptopurine SAMs on the gold electrode[J].J PhysChem B,2005,109:2739-2744.
[8]Chu H,Yang HF,Huan S Y,et al.Orientation of 6-mercaptopurine SAMs at the silver electrode as studiedby Raman mapping and in situ SERS[J].J Phys ChemB,2006,110:5490-5497.
[9]Lakomska I,Pazderski L,Sitkowski J,et al.Multinu-clear NMR spectroscopy and antiproliferative activity invitro of platinum(II)and palladium(II)complexes with6-mercaptopurine[J].J Mol Struct,2004,707:241-247.
[10]Madue o R,Sevilla J M,Pineda T,et al.A voltam-metric study of 6-mercaptopurine monolayers on poly-crystalline gold electrodes[J].J Electroanal Chem,2001,506:92-98.
[11]Sevilla J M,Pineda T,Madue o R,et al.Character-ization of 6-mercaptopurine monolayers on Hg surfaces[J].J Electroanal Chem,1998,442:107-112.
[12]Madue o R,Pineda T,Sevilla J M,et al.The kinet-ics of the dissolution of 6-mercaptopurine self-assem-bled monolayers on Au(111)and Hg electrodes[J].J Electroanal Chem,2005,576:197-203.
[13]Cao X N,Lin L,Zhou Y Y,et al.Amperometric de-termination of 6-mercaptopurine on functionalizedmulti-wall carbon nanotubes modified electrode by liq-uid chromatography coupled with microdialysis and itsapplication to pharmacokinetics in rabbit[J].Talan-ta,2003,60:1063-1070.
[14]Liu C H(刘彩红),Li H(李红),Zhu W(朱伟).The interaction of Cu(phen)22+with 6-mercaptopurineon a rotating platinum disk[J].Acta Phys Chim Sin(in Chinese),2004,20(4):440-444.
[15]Ballesteros Y,Gonzalez de la Huebra M J,QuintanaM C,et al.Voltamperometric determination of kinetinwith a carbon paste modified electrode[J].Micro-chem J,2003,74:193-202.
[16]Reichmann M E,Rice S A,Thomas C A,et al.Afurhter examination of the molecular weight and size ofdeoxy pentose nucleic acid[J].J Am Chem Soc,1954,76:3047-3053.
[17]Holderna-Natkaniec K,Natkaniec I,KasperkowiakW,et al.The IINS,IR and DFT studies of hydrogenbonds in 6-furfuryl and 6-benzylaminopurines[J].JMol Struct,2006,790:94-113.
[18]Madue o R,Pineda T,Sevilla J M,et al.An electro-chemical study of 6-thioguanine monolayers on a mer-cury electrode in acid and neutral solutions[J].JElectroanal Chem,2004,565:301-310.
[19]Bard A J,Faulkner L R.Electrochemical methods[M].New York:John Wiley&Sons,1980.522.
[20]Li H(李红),Ji L N(计亮年),Li W S(李伟善),et al.Progress in electrochemical studies of deoxyribo-nucleic acid[J].Chinese J Inorg Chem(in Chinese),2003,19(3):225-231.
[21]Zhao Y D(赵元弟),Pang D W(庞代文),Wang ZL(王宗礼),et al.Electrochemical deoxyribonucleicacid sensors[J].Chinese J Anal Chem(in Chinese),1996,24(3):364-368.
[22]Lu J X(卢继新),Zhang G Z(张贵珠),Huang Z N(黄志娜),et al.Study on the mechanism of the in-teraction between mercaptopurine metal complexes andcalf thymus DNA[J].Acta Chim Sinica(in Chi-nese),2002,60(6):967-972.
[23]Ye B X(冶保献),Muhetaer T(木合塔尔.吐尔洪),Qu S(曲松).Electrochemical studies of inter-action between anticancer drug 6-mercaptopurine andDNA[J].J Anal Sci(in Chinese),2004,20(4):364-366.

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