Interaction of 9,10-anthraquinone with adenine and 2′-deoxyadenosine

Biophysical Chemistry

Volumn 136, Issue 1, 2008, Pages 59-65

  Bose, Adity ^a   Sarkar, Achintya K ^b   Basu, Samita ^a  

^a SAHA INSTITUTE OF NUCLEAR PHYSICS   (India)

^b PRESIDENCY UNIVERSITY   (India)

Author keywords

2 deoxyadenosine; 9,10 anthraquinone; Adenine; Aromaticity; Hydrogen bonding; Magnetic field effect

Indexed keywords

ACETONITRILE; ADENINE; ANTHRAQUINONE; DEOXYADENOSINE; WATER;

ARTICLE; ELECTRON TRANSPORT; MICELLE; PRIORITY JOURNAL;

ADENINE; ANTHRAQUINONES; DEOXYADENOSINES; HYDROGEN BONDING; MAGNETICS; SPECTRUM ANALYSIS;

EID: 44349121674     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2008.04.011     Document Type: Article

References (38)

1. Zagotto G., Supino R., Favini E., Morto S., and Palumbo M. New 1,4-anthracene-9,10-dione derivatives as potential anticancer agents. Il Farmaco 55 (2000) 1-5
2. Breslin D.T., and Schuster G.B. Anthraquinone photonucleases: mechanisms for GG-selective and nonselective cleavage of double-stranded DNA. J. Am. Chem. Soc. 118 (1996) 2311-2319
3. Bergeron F., Nair V.K., and Wagner J.R. Near-UV induced interstrand cross-links in anthraquinone-DNA duplexes. J. Am. Chem. Soc. 128 (2006) 14798-14799
4. Ma J., Lin W., Wang W., Han Z., Yao S., and Lin N. Characterization of reactive intermediates in laser photolysis of nucleoside using of sodium salt anthraquinone-2-sulfonic acid as photosensitizer. Radiat. Phys. Chem. 54 (1999) 491-497
5. Li H., Yao S., Zuo Z., Wang W., Zhang J., and Lin N. Characterization of the reactive intermediates in laser flash photolysis of adenine, adenosine and dAMP using acetone as photosensitizer. J. Photochem. Photobiol., B Biol. 28 (1995) 65-70
6. Nikogosyan D.N., Angelov D., Soep B., and Lindqvist L. Direct measurement of excited singlet-state lifetime in the homologous sequence adenine, adenosine, adenosine 5′-monophosphate and in calf thymus DNA. Chem. Phys. Lett. 252 (1996) 322-326
7. Crespo-Hernández C.E., Martínez L., González-Sierra A.E., Irizarry L.R., Vázquez A.D., and Arce R. The 254 nm low intensity and 266 nm laser photochemistry of adenosine: effect of pH and concentration on the reactive precursors of the principal products, adenine and FAPyAde. J. Photochem. Photobiol., A Chem. 152 (2002) 123-133
8. Lu C.Y., Yao S.D., and Lin N.Y. Photooxidation of 2′-deoxyguanosine 5′-monophosphate (dGMP) by flavin adenine dinucleotide (FAD) via electron transfer: a laser photolysis stud. Chem. Phys. Lett. 330 (2000) 389-396
9. A. Bose, D. Dey, S. Basu, Laser flash photolysis and magnetic-field-effect on interaction of thymine and thymidine with menadione: role of sugar in controlling reaction pattern, Sci. Technol. Adv. Mater. (in press).
10. A. Bose, D. Dey, S. Basu, Interactions of guanine and guanosine hydrate with quinones: a laser flash photolysis and magnetic field effect study, J. Phys. Chem., A (in press).
11. Sengupta T., Choudhury S.D., and Basu S. Medium-dependent electron and H atom transfer between 2′-deoxyadenosine and menadione: a magnetic field effect study. J. Am. Chem. Soc. 126 (2004) 10589-10593
12. Bergeron F., Klarskov K., Hunting D.J., and Wagner J.R. Near-UV photolysis of 2-methyl-1,4-naphthoquinone-DNA duplexes: characterization of reversible and stable interstrand cross-links between quinone and adenine moieties. Chem. Res. Toxicol. 20 (2007) 745-756
13. Ly D., Kan Y., Armitage B., and Schuster G.B. Cleavage of DNA by irradiation of substituted anthraquinones: intercalation promotes electron transfer and efficient reaction at GG steps. J. Am. Chem. Soc. 118 (1996) 8747-8748
14. Koch T., Ropp J.D., Sliger S.G., and Schuster G.B. Photocleavage of DNA, irradiation of quinone containing reagents converts supercoiled to linear DNA. Photochem. Photobiol. 58 (1993) 554-558
15. Ma J., Lin W., Wang W., Han Z., Yao S., and Lin N. Triplet state mechanism for electron transfer oxidation of DNA. J. Photochem. Photobiol., B Biol. 57 (2000) 76-81
16. Song Q.H., Yao S.D., Li H.C., Zuo Z.H., Zhang J.S., and Lin N.Y. Characterization of reactive intermediates in laser photolysis of guanine and its derivatives using acetone as photosensitizer: the pH dependence. J. Photochem. Photobiol., A Chem. 95 (1996) 223-229
17. In: Tanimoto Y., and Fujiwara Y. (Eds). Handbook of Photochem. Photobiol. (2003), American Scientific Publishers, California
18. Steiner U.E., and Ulrich T. Magnetic field effects in chemical kinetics and related phenomena. Chem. Rev. 89 (1989) 51-147
19. In: Gould I.R., Turro N.J., and Zimmt N.B. (Eds). Adv. Phys. Org. Chem. (1980), Academic Press, London
20. Bhattacharya K., and Chowdhury M. Environmental and magnetic field effects on exciplex and twisted charge transfer emission. Chem. Rev. 93 (1993) 507-535
21. Boxer S.G., Chidsey C.E.D., and Roelofs M.G. Magnetic field effects on reaction yields in the solid state: an example from photosynthetic reaction centers. Ann. Rev. Phys. Chem. 34 (1983) 389-417
22. Chowdhury A., and Basu S. Interactions between 9,10-anthraquinone and aromatic amines in homogeneous and micellar media: a laser flash photolysis and magnetic field effect study. J. Lumin. 121 (2006) 113-122
23. Wetmore S.D., Boyd R.J., and Eriksson L.A. Theoretical investigation of adenine radicals generated in irradiated DNA components. J. Phys. Chem. B, 102 (1998) 10602-10614
24. Evangelista F.A., Paul A., and Schaefer III H.F. Radicals derived from adenine: prediction of large electron affinities with a considerable spread. J. Phys. Chem. A, 108 (2004) 3565-3571
25. Sakaguchi Y., and Hayashi H. Laser-photolysis study of the photochemical reactions of naphthoquinones in a sodium dodecyl sulfate micelle under high magnetic fields. J. Phys. Chem. 88 (1984) 1437-1440
26. Wakasa M., Hayashi H., Mikami Y., and Takeda T. Reversion of magnetic field effects observed in the reaction of a triplet-born radical pair consisting of two equivalent sulfur-centered radicals. J. Phys.Chem. 99 (1995) 13181-13186
27. Joule J.A., and Mills K. Heterocyclic Chemistry. 4th edition (2000), Blackwell publishing, Oxford, UK
28. Rodgers M.T., and Armentrout P.B. Influence of d orbital occupation on the binding of metal ions to adenine. J. Am. Chem. Soc. 124 (2002) 2678-2691
29. Cysewski P. An ab initio study on nucleic acid bases aromaticities. J. Mol. Struc., Theochem. 714 (2005) 29-34
30. Nowick J.S., Chen J.S., and Noronha. Molecular recognition in micelles: the roles of hydrogen bonding and hydrophobicity in adenine-thymine base-pairing in SDS micelles. J. Am. Chem. Soc. 115 (1993) 7636-7644
31. Bose A., Dey D., and Basu S. Structure-dependent switchover of reaction modes: a laser flash photolysis and magnetic field effect study. J. Photochem. Photobiol., A Chem. 186 (2007) 130-134
32. Tanimoto Y., Udagawa H., and Itoh M. Magnetic field effects on the primary photochemical processes of anthraquinones in SDS micelles. J. Phys. Chem. 87 (1983) 724-726
33. Tanimoto Y., Shimizu K., and Itoh M. Magnetic field effect on the photosensitized oxidation reaction of 1,3-diphenylisobenzofuran in SDS micellar solutions. J. Am. Chem. Soc., 106 (1984) 7257-7258
34. Steenken S. Purine bases, nucleosides, and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e- and OH adducts. Chem. Rev. 89 (1989) 503-520
35. Finar I.L. Organic Chemistry vol. I (1988), Pearson Education, Singapore
36. Wetmore S.D., Boyd R.J., and Eriksson L.A. A comprehensive study of sugar radicals in irradiated DNA. J. Phys. Chem., B 102 (1998) 7674-7686
37. Hamza A., Broch H., and Vasilescu D. Quantum molecular simulation of the H abstraction at C4′ of DNA sugar moiety by the free radical OH. J. Mol. Struc. (Theochem) 491 (1999) 237-247
38. Nakatani K., Shirai J., Sando S., and Saito I. Dibenzoyldiazomethane-acridine conjugate: a novel DNA photofootprinting agent. Tetrahedron Lett. 38 (1997) 6047-6050