Photodynamic effects of two hydroxyanthraquinones

Biochimica et Biophysica Acta - General Subjects

Volumn 1622, Issue 2, 2003, Pages 65-72

  Rajendran, M ^a   Ramasamy, S ^b   Rajamanickam, C ^b   Gandhidasan, R ^b   Murugesan, R ^b  

^a N M S S V N COLLEGE   (India)

^b MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

5,5 dimethyl 1 pyrroline N oxide (DMPO); Anthraquinone; Singlet oxygen; Spin trapping; Superoxide anion

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ANTHRAQUINONE DERIVATIVE; CYNODONTIN; CYNODONTIN 5,8 DIMETHYL ETHER; CYTOCHROME C; EDETIC ACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; BLEACHING; ELECTRON; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; MONITORING; PHOTODYNAMICS; PRIORITY JOURNAL; RACEMIC MIXTURE; REDUCTION; SPECTRUM;

EID: 0038105311     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-4165(03)00100-4     Document Type: Article

References (35)

1. Powis G. Free radical formation by antitumor quinones. Free Radic. Biol. Med. 6:1989;63-101.
2. Moore H.W., Czerniak R., Hamdan A. Natural quinones as quinone methide precursors - ideas in rational drug design. Drug Expl. Clin. Res. 12:1986;475-494.
3. Dichancaite E., Cenas N., Kalvelyte A., Serapiniene N. Toxicity of daunorubicin and naphthaquinones to HL-60 cells: an involvement of oxidative stress. Biochem. Mol. Biol. Int. 41:1997;987-994.
4. Reszka K.J., Kolodziejczyk P., Lown J.W. Photosensitization by antitumor agents: 3. Spectroscopic evidence for superoxide and hydroxyl radical production by anthrapyrazole-sensitized oxidation of NADH. Free Radic. Biol. Med. 2:1986;267-274.
5. Diwu Z.J., Lown J.W. Photosensitization with anticancer agents. 20-EPR studies on the photodynamic action of phleichrome: formation of semiquinone radical and activated oxygen species on illumination with visible light. Free Radic. Biol. Med. 18:1995;357-363.
6. Ray S., Ponnathpur V., Huang Y., Tang C., Mahoney M.E., Ibrado A.M., Bullock G., Bhalla K. 1-beta-D-arabinofuranosylcytosine-, mitoxantrone-, and paclitaxel-induced apoptosis in HL-60 cells: improved method for detection of internucleosomal DNA fragmentation. Cancer Chemother. Pharmacol. 34:1994;365-371.
7. Reszka K.J., Bilski P., Chignell C.F., Hartley J.A., Khan N., Souhami R.L., Mendonca A.J., Lown J.W. Photosensitization by anticancer agents: 11. Mechanisms of photosensitization of human leukemic cells by diaminoanthraquinones: singlet oxygen and radical reactions. J. Photochem. Photobiol., B Biol. 15:1992;317-335.
8. Andreoni A., Colasanti A., Malatesta V., Riccio P., Roberti G. Enhancement of antitumor drug cytotoxicity via laser photoactivation. Photochem. Photobiol. 53:1991;797-805.
9. Shiraki T., Sugiura Y. Visible light induced DNA cleavage by the hybrid antitumor antibiotic dynemicin A. Biochemistry. 29:1990;9795-9798.
10. Reszka K., Lown J.W. Photosensitization of anticancer agents-8. One-electron reduction of mitoxantrone: an EPR and spectrophotometric study. Photochem. Photobiol. 50:1989;297-304.
11. Hartley J.A., Reszka K., Lown J.W. Photosensitization by antitumor agents: 7. Correlation between anthracenedione-photosensitized DNA damage, NADH oxidation and oxygen consumption following visible light illumination. Photochem. Photobiol. 48:1988;19-25.
12. Reszka K.J., Bilski P., Chignell C.F., Hartley J.A., Khan N., Souhami R.L., Mendoca A.J., Lown J.W. Photosensitisation by antitumor agents: 11. Mechanisms of photosensitisation of human leukemic cells by diaminoanthraquinones: singlet oxygen and radical reactions. J. Photochem. Photobiol. 15:1992;317-335.
13. Reszka K., Kolodziejczyk P., Tsoungas P.G., Lown J.W. Photosensitisation by antitumor agents: 6. Production superoxide radical and hydrogen peroxide during illumination of diaminoanthracendiones in the presence of NADH in aqueous solutions: an EPR study. Photochem. Photobiol. 47:1988;625-633.
14. Inbaraj J.J., Gandhidasan R., Murugesan R. Photodynamic action of some naturally occurring quinones: formation of reactive oxygen species. J. Photochem. Photobiol., A Chem. 124:1999;95-99.
15. Inbaraj J.J., Krishna M.C., Gandhidasan R., Murugesan R. Cytotoxicity, redox cycling and photodynamic action of two naturally occurring quinones. Biochim. Biophys. Acta. 1472:1999;462-470.
16. Tikkanen L., Matsushima T., Natori S. Mutagenicity of anthraquinones in the Salmonella preincubation test. Mutat. Res. 116:1983;297-304.
17. Chari V.M., Neelakantan S., Seshadri T.R. Constitution of tectoleafquinone - a synthetic study. Indian J. Chem. 7:1969;40-43.
18. Kalyanaraman B., Felix C.C., Sealy R.C. Photoionisation of melanin precursors: an electron spin resonance investigation using the spin trap 5,5-dimethyl-1-pyrroline-1-oxide (DMPO). Photochem. Photobiol. 36:1982;5-12.
19. Lion Y., Demelle M., Van De Vorst A. New method of detecting singlet oxygen production. Nature. 263:1976;442-443.
20. Moan J., Wold E. Detection of singlet oxygen production by ESR. Nature. 279:1979;450-451.
21. Kraljic I., El Mohsni S. A new method for the detection of singlet oxygen in aqueous solution. Photochem. Photobiol. 28:1978;577-581.
22. Gandin E., Lion Y., Van de Vorst A. Quantum yield of singlet oxygen production by Xanthene derivatives. Photochem. Photobiol. 37:1983;271-278.
23. Gandin E., Lion Y. J. Photochem. 30:1982;77-81.
24. Lee P.C.C., Rodgers M.A.J. Laser flash photokinetic studies of rose bengal sensitised photodynamic interactions of nucleotides and DNA. J. Photochem. Photobiol. 45:1987;79-86.
25. Koppenol W.H., Butler J. The radiation chemistry of cytochrome c. Isr. J. Chem. 24:1984;11-16.
26. Wu T., Shen J., Song A., Chen S., Zhang M., Shen T. Photodynamic action of amino substituted hypocrellins: EPR studies on the photogeneration of active oxygen and free radical species. J. Photochem. Photobiol., B Biol. 57:2000;14-21.
27. Diwu Z., Lown J.W. Hypocrellins and their uses in photosensitisation. Photochem. Photobiol. 52:1990;609-616.
28. Wilkinson E., Brummer J.G. Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen solution. J. Phys. Chem. Ref. Data. 10:1981;809-999.
29. Rosenthal I., Krishna C.M., Riesz P., Ben-Hur E. The role of molecular oxygen in the photodynamic effect of phthalocyanines. Radiat. Res. 107:1986;136-142.
30. Diwu Z., Lown J.W. Photosensitization with anticancer agents: 15. Perylenequinoid pigments as potential photodynamic therapeutic agent: formation of semiquinone radicals and reactive oxygen species on illumination. J. Photochem. Photobiol., B Biol. 18:1993;131-143.
31. Ben-Hur E., Carmichael A., Riesz P., Rosenthal I. Photochemical generation of superoxide anion radical and the cytotoxicity of phthalocyanines. Int. J. Radiat. Biol. 48:1985;837-846.
32. Buettner G.R. Spin trapping: ESR parameters of spin adducts. Free Radic. Biol. Med. 3:1987;259-303.
33. Driebergenm R.J., Verboom W., Reinhoudt D.N., Lelieved P. Electrochemistry of potential bioreductive alkylating quinones: its use in the development of new aziridinylquinones. Anticancer Res. 6:1986;605-620.
34. Hansch C., Leo A., Vnger S.H., Kim K.H., Nikaitaini D., Lien E.J. Aromatic substituent constants for structure-activity relationship. J. Med. Chem. 16:1973;1207-1216.
35. Driscoll J.S., Hazard G.F. Jr., Wood H.B. Jr., Goldin A. Structure-antitumor activity relationships among quinone derivatives. Cancer Chemother. Rep., Part 2. 4(2):1974;. (April).