Interaction of echinomycin with guanine: Electrochemistry and spectroscopy studies

Biophysical Chemistry

Volumn 111, Issue 3, 2004, Pages 259-265

  Li, Nan ^a   Guo, Liping ^b   Jiang, Junguang ^a   Yang, Xiurong ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

Adsorptive transfer stripping cyclic voltammetry; Echinomycin; FTIR; Guanine; Interaction; UV Vis

Indexed keywords

ALANINE; ANTINEOPLASTIC AGENT; BUFFER; CARBON; ECHINOMYCIN; GLASS; GUANINE; PHOSPHATE;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG BINDING; DRUG DNA INTERACTION; DRUG STRUCTURE; ELECTROCHEMISTRY; ELECTRODE; HYDROGEN BOND; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; SPECTROSCOPY; ULTRAVIOLET SPECTROSCOPY; VISIBLE ADSORPTION SPECTROSCOPY;

ADSORPTION; ANTIBIOTICS, ANTINEOPLASTIC; ECHINOMYCIN; ELECTROCHEMISTRY; GUANINE; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 6344226809     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2004.06.007     Document Type: Article

References (39)

1. Gilpin R.K. Pharmaceuticals and related drugs. Anal. Chem. 69:1997;145R-163R
2. Erdem A., Ozsoz M. Electrochemical DNA biosensors based on DNA-drug interactions. Electroanalysis. 14:2002;965-974
3. Yang X.L., Wang A.H.J. Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol. Ther. 83:1999;181-215
4. Corbaz R., Ettlinger L., Gäumann E., Keller-Schierlein W., Kradolfer F., Neipp L., Prelog V., Reusser P., Zähner H. Stoffwechselprodukte von Actinomyceten 7, Echinomycin. Helv. Chim. Acta. 40:1957;199-204
5. Waring M.J. The molecular basis of specific recognition between echinomycin and DNA. Molecular Basis of Specificity in Nucleic Acid-Drug Interactions. 1990;225-245 Kluwer Academic, Dordercht
6. Dell A., Williams D.H., Morris H.R., Smith G.A., Feeney J., Roberts G.C.K. Structure revision of the antibiotic echinomycin. J. Am. Chem. Soc. 97:1975;2479-2502
7. Waring M.J. Echinomycin, Triostin and Related Antibiotics. 1977;173-194 Springer-Verlag, Berlin
8. Waring M.J., Wakelin L.P.G. Echinomycin: a bifuncitional intercalating antibiotic. Nature. 252:1974;653-657
9. Bailly C., Hamy F., Waring M.J. Cooperativity in the binding of echinomycin to DNA fragments containing closely spaced CpG sites. Biochemistry. 35:1996;1150-1161
10. Van Dyke M.M., Dervan P.B. Echinomycin binding sites on DNA. Science. 225:1984;1122-1127
11. Bailly C., Genle D., Hamy F. Localized chemical-reactivity in DNA associated with the sequence-specific bisintercalation of echinomycin. Biochem. J. 300:1994;165-173
12. Gao X.L., Patel D.J. NMR studies of echinomycin bisintercalation complexes with d(A1-C2-G3-T4) and d(T1-C2-G3-A4) duplexes in aqueous solution: sequence-dependent formation of Hoogsteen A1.cntdot.T4 and Watson-Crick T1.cntdot.A4 base pairs flanking the bisintercalation site. Biochemistry. 27:1988;1744-1751
13. 2. Biochemistry. 30:1991;2483-2494
14. 2-2echinomycin complex: conformational changes between echinomycin binding-sites. Nucleic Acids Res. 20:1992;2411-2420
15. Wang A.H-J., Ughetto G., Quigley G.J., Hakoshima T., Van Der Marel G.A., Van Boom J.H., Rich A. The molecular structure of a DNA-triostin a complex. Science. 225:1984;1115-1121
16. Quigley G.J., Ughetto G., van der Marel G.A., van Boom J.H., Wang A.H.-J., Rich A. Non-Watson-Crick GC and AT base pairs in a DNA-antibiotic complex. Science. 232:1986;1255-1258
17. Costantino P., Santis P.D., Ughetto G. Circular dichroism studies on the echinomycin-DNA complex. FEBS Lett. 88:1978;349-352
18. Fox K.R., Waring M.J. Stopped-flow kinetic studies on the interaction between echinomycin and DNA. Biochemistry. 23:1984;2627-2633
19. Hasoň S., Dvořák J., Jelen F., Vetterl V. Interaction of DNA with echinomycin at the mercury electrode surface as detected by impedance and chronopotentiometric measurements. Talanta. 56:2002;905-913
20. Paleèek E., Fojta M. Detecting DNA hybridization and damage. Anal. Chem. 73:2001;74A-83A
21. Jelen F., Erdem A., Paleček E. Cyclic voltammetry of echinomycin and its interaction with double-stranded and single-stranded DNA adsorbed at the electrode. Bioelectrochemistry. 55:2002;165-167
22. Leroy J.L., Gao X., Misra V., Guéron M., Patel D.J. Proton exchange in DNA-luzopeptin and DNA-echinomycin bisintercalation complexes: rates and processes of base-pair opening. Biochemistry. 31:1992;1407-1415
23. Gallego J., Luque F.J., Orozco M., Burgos C., Alvarez-Builla J., Rodrigo M.M., Gago F. DNA sequence-specific reading by echinomycin: role of hydrogen bonding and stacking interactions. J. Med. Chem. 37:1994;1602-1609
24. Wang H.S., Ju H.X., Chen H.Y. Simultaneous determination of guanine and adenine in DNA using an electrochemically pretreated glassy carbon electrode. Anal. Chim. Acta. 461:2002;243-250
25. Kepley L.J., Bard A.J. Ellipsometric, electrochemical, and elemental characterization of the surface phase produced on glassy carbon electrodes by electrochemical activation. Anal. Chem. 60:1988;1459-1467
26. Stará V., Kopanica M. Determination of some quinoxaline-N-dioxide derivatives by adsorptive stripping voltammetry. Anal. Chim. Acta. 186:1986;21-30
27. Cai X.H., Rivas G., Farias P.A.M., Shiraishi H., Wang J. Evaluation of different carbon electrodes for adsorptive stripping analysis of nucleic acids. Electroanalysis. 8:1996;753-758
28. Beilby A.L., Sasaki T.A., Stern H.M. Electrochemical pretreatment of carbon electrodes as a function of potential, pH, and time. Anal. Chem. 67:1995;976-980
29. Bard A.J., Faulkner L.R. Electrochemical Methods Fundamentals and Applications. 1980;Wiley, New York
30. Brett C.M.A., Oliveira A.M., Serrano S.H.P. On the adsorption and electrochemical oxidation of DNA at glassy carbon electrodes. J. Electroanal. Chem. 306:1994;225-231
31. Brabec V. 314 - electrochemical oxidation of nucleic acids and proteins at graphite electrode qualitative aspects. Bioelectrochem. Bioenerg. 7:1980;69-82
32. Paleček E. Topics in Bioelectrochemistry and Bioenergetics. 1983;Wiley, London
33. Seibert E., Chin A.S., Pfleiderer W. pH-Dependent spectroscopy and electronic structure of the guanine analogue 6,8-dimethylisoxanthopterin. J. Phys. Chem., A. 107:2003;178-185
34. Medina M.Á., Ramírez F.J., Ruiz-Chica J., Chavarría T., López-Navarrete J.T., Sánchez-Jiménez F. DNA-chlorophniramine interaction studied by spectroscopic techniques. Biochim. Biophys. Acta. 1379:1998;129-133
35. Neault J.F., Tajmir-Riahi H.A. DNA-chlorophyllin interaction. J. Phys. Chem., B. 102:1998;1610-1614
36. Wang Z.X., Liu D.L., Dong S.J. In-situ FTIR study on adsorption and oxidation of native and thermally denatured calf thymus DNA at glassy carbon electrodes. Biophys. Chem. 89:2001;87-94
37. Kasende O.E., Szczepaniak K., Person W.B., Huyskens T.Z. Infrared and Raman spectra of alkylated guanine derivatives. J. Mol. Struct. 435:1997;17-33
38. Wang Z.X., Liu D.L., Dong S.J. In situ infrared spectroelectrochemical studies on adsorption and oxidation of nucleic acids at glassy carbon electrode. Bioelectrochemistry. 53:2001;175-181
39. Colarusso P., Zhang K.Q., Guo B.J., Bernath P.F. The infrared spectra of uracil, thymine, and adenine in the gas phase. Chem. Phys. Lett. 269:1997;39-48