Biophysical evaluation of two red-shifted hypocrellin B derivatives as novel PDT agents

Journal of Photochemistry and Photobiology B: Biology

Volumn 94, Issue 1, 2009, Pages 38-44

  Paul, Bibbin T ^a   Babu, Mani S ^b   Santhoshkumar, Thankayyan R ^b   Karunagaran, Devarajan ^b   Selvam, Govindan S ^a   Brown, Kevin ^c   Woo, Thomas ^c   Sharma, Sanjay ^c   Naicker, Selvaraj ^c   Murugesan, Ramachandran ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b RAJIV GANDHI CENTRE FOR BIOTECHNOLOGY   (India)

^c Quest PharmaTech Inc   (Canada)

Author keywords

Cytotoxicity; DNA damage; Human colon cancer cell; Hypocrellin; Photodynamic therapy; Photosensitization

Indexed keywords

CYCLOHEXANE 1,2 DIAMINO HYPOCRELLIN B; DNA; HYPOCRELLIN B DERIVATIVE; N,N DIMETHYLAMINOPROPYL HYPOCRELLIN B; PHOTOSENSITIZING AGENT; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOPHYSICS; CELL STRAIN HCT116; CELL VIABILITY; COLON CANCER; CONTROLLED STUDY; DNA DAMAGE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; GEL ELECTROPHORESIS; HUMAN; HUMAN CELL; HYDROPHILICITY; LD 50; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BIOPHYSICAL PROCESSES; CELL LINE, TUMOR; CELL SURVIVAL; COLOR; DNA CLEAVAGE; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; MOLECULAR STRUCTURE; OXYGEN; PERYLENE; PHOTOCHEMISTRY; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; QUINONES; SPECTROPHOTOMETRY; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES; WATER;

EID: 57749206211     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2008.09.007     Document Type: Article

References (29)

1. Dougherty J.T., Gomer J.L., Henderson B.W., Jori G., Kessel D., Korbelick M., Moan J., and Peng Q. Photodynamic therapy. J. Natl. Cancer Inst. 190 (1998) 889-905
2. Chin W., Lau W., Cheng C., and Olivo M. Evaluation of Hypocrellin B in a human bladder tumor model in experimental photodynamic therapy: biodistribution, light dose and drug-light interval effects. Int. J. Oncol. 25 (2004) 623-629
3. Yang H., Wu T., Zhang M., and Zhang Z. A novel photosensitizer 2-butylamino-2-demethoxy-hypocrellin B (2-BA-2-DMHB) - its photodynamic effects on HeLa cells: efficacy and apoptosis. Biochim. Biophys. Acta 1540 (2001) 22-31
4. Yu-Ying H., and Li-Jin J. Synthesis and EPR investigations of new aminated hypocrellin derivatives. Free Radic. Biol. Med. 20 (2000) 1642-1650
5. Kalyanaraman B., Felix C.C., and Sealy R.C. Photoionization of melanine precursors: an electron spin resonance investigation using the spin trap 5,5-dimethyl-1-pyrroline-1-oxide (DMPO). Photochem. Photobiol. 36 (1982) 5-12
6. Xu S., Chen S., Zhang M., and Shen T.A. Novel method for the preparation of amino-substituted hypocrellin B. Bioorg. Med. Chem. Lett. 11 (2001) 2045-2047
7. Anto R.J., Maliekal T.T., and Karunagaran D. L-929 cells harboring ectopically expressed RelA resist curcumin-induced apoptosis. J. Biol. Chem. 275 (2000) 15601-15604
8. Mosinger J., and Micka Z. Quantum yields of singlet oxygen of metal complexes of meso-tetrakis (sulphonatophenyl) porphine. Photochem. Photobiol. A 107 (1997) 77-82
9. Lee P.C.C., and Rodgers M.A. Laser flash photokinetic studies of rose Bengal sensitized photodynamic interactions of nucleotides and DNA. Photochem. Photobiol. 45 (1987) 79-86
10. Inbaraj J.J., Gandhidasan R., and Murugesan R. Cytotoxicity and superoxide anion generation by some naturally occurring quinines. Free Radic. Biol. Med. 26 (1999) 1072-1078
11. Lion Y., Demelle M., and Van De Vorst A. New method of detecting singlet oxygen production. Nature 263 (1976) 442-443
12. Koppenol W.H., and Butler J. The radiation chemistry of cytochrome c. Isr. J. Chem. 24 (1984) 14-21
13. Rajendran M., Inbaraj J.J., Gandhidasan R., and Murugesan R. Photodynamic action of damnacanthal and nordamncanthal. Photochem. Photobiol. 162 (2004) 615-623
14. Buettner G.R., and Oberley L.W. Considerations in the spin trapping of superoxide and hydroxyl radical in aqueous systems using 5,5-dimethyl-1-pyrroline-1-oxide. Biochem. Biophys. Res. Commun. 83 (1978) 69-74
15. Diwu Z. Novel therapeutic and diagnostic applications of hypocrellins and hypericin. Photochem. Photobiol. 61 (1995) 529-539
16. Jori G. Tumor photosensitizer: approaches to enhance the selectivity and efficiency of photodynamic therapy. J. Photochem. Photobiol. B 36 (1996) 87-93
17. Rajendran M., Gandhidasan R., and Murugesan R. Photosensitization and photoinduced DNA cleavage by four naturally occurring anthraquinones. J. Photochem. Photobiol. 168 (2004) 67-73
18. Brezova V., Valko M., Breza M., Morris H., Telser J., Dvoranova D., Kaiserova K., Varecka L., Mazur M., and Leibfritz D. Role of radicals and singlet oxygen in photoactivated DNA cleavage by the anticancer drug camptothecin: an electron paramagnetic resonance study. J. Phys. Chem. B 107 (2003) 2415-2425
19. 60 in an oxygen-saturated aqueous solution. J. Phys. Chem. B 106 (2002) 2372-2380
20. Yang H., Wu T., Zhang M., and Zhang Z. A novel photosensitizer, 2-butylamino-2-demethoxy-hypocrellin B (2-BA-2-DMHB) - its photodynamic effects on HeLa cells: efficacy and apoptosis. Biochim. Biophys. Acta 1540 (2001) 22-31
21. Finkelstein E., Rosen G.M., and Rauckman E.J. Production of hydroxyl radical by decomposition of superoxide spin-trapped adducts. Mol. Pharmacol. 21 (1982) 262-265
22. Ben-Hur E., Carmichael A., Riesz P., and Rosenthal I. Photochemical generation of superoxide radical and the cytotoxicity of phthalocyanines. Int. J. Radiat. Biol. 48 (1985) 837-846
23. Buettner G.R. Spin trapping: ESR parameters of spin trapping. Free Radic. Biol. Med. 3 (1987) 259-303
24. Xu S., Chen S., Zhang M., and Shen T. Hypocrellin derivative with improvements of red absorption and active oxygen species generation. Bioorg. Med. Chem. Lett. 14 (2004) 1499-1501
25. Singh I., Ogata R., Moore T., Chang C.W.J., and Scheuer P.J. Electronic spectra of substituted naphthoquinones. Tetrahedron 24 (1968) 6053-6073
26. He Y., Liu H., An J., Han R., and Jiang L. Photodynamic action of hypocrellin dyes: structure-activity relationships. Dyes Pigments 44 (2000) 63-67
27. Diwu Z.J., and Lown J.W. Photosensitization with anticancer agents 12. Perlyenequinoid pigments, a novel type of singlet oxygen sensitizer. J. Photochem. Photobiol. A 64 (1992) 273-287
28. Xu S., Zhang X., Chen S., Zhang M., and Shen T. EPR studies of photodynamic properties of a novel potential photodynamic therapeutic agent: photogeneration of semiquinone radical anion and active oxygen species. Photochem. Photobiol. Sci. 2 (2003) 871-876
29. Lee H., Zhou Z., Chen S., Zhang M., and Shen T. New long wavelength ethanolamino-substituted hypocrellin: photodynamic activity and toxicity to MGC803 cancer cell. Dyes Pigments 68 (2006) 1-10