Chemopreventive action of xanthone derivatives on photosensitized DMA damage

Photochemistry and Photobiology

Volumn 81, Issue 2, 2005, Pages 314-319

  Hirakawa, Kazutaka ^a   Yoshida, Mami ^b   Nagatsu, Akito ^c   Mizukami, Hajime ^c   Rana, Virendra ^d   Rawat, Mohan Singh Maniyari ^d   Oikawa, Shinji ^b   Kawanishi, Shosuke ^b  

^a SHIZUOKA UNIVERSITY   (Japan)

^b MIE UNIVERSITY   (Japan)

^c NAGOYA CITY UNIVERSITY   (Japan)

^d H N B GARHWAL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; PHOTOSENSITIZING AGENT; RIBOFLAVIN; XANTHONE DERIVATIVE;

ANIMAL; ARTICLE; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; DNA DAMAGE; DOSE RESPONSE; DRUG ANTAGONISM; DRUG EFFECT; ENERGY TRANSFER; HUMAN; RADIATION EXPOSURE; SPECTROFLUOROMETRY; TUMOR CELL LINE; ULTRAVIOLET RADIATION;

ANIMALS; CATTLE; CELL LINE, TUMOR; DNA; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; ENERGY TRANSFER; HUMANS; MOLECULAR STRUCTURE; PHOTOSENSITIZING AGENTS; RIBOFLAVIN; SPECTROMETRY, FLUORESCENCE; ULTRAVIOLET RAYS; XANTHONES;

EID: 17444363351     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2004-07-29-RA-252.1     Document Type: Article

References (46)

1. International Agency for Research on Cancer Working Group (1992) Solar and ultraviolet radiation. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 55. IARC, Lyon, France.
2. Burrows, C. I. and J. G. Muller (1998) Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98, 1109-1151.
3. Klecak, G., F. Urbach and H. Urwyler (1997) Fluoroquinolone antibacterials enhance UVA-induced skin tumors. J. Photochem. Photobiol. B: Biol. 37, 174-181.
4. Makinen, M., P. D. Forbes and F. Stenback (1997) Quinolone antibacterials: a new class of photochemical carcinogens. J. Photochem. Photobiol. B: Biol. 37, 182-187.
5. Ito, K., S. Inoue, K. Yamamoto and S. Kawanishi (1993) 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in double-stranded DNA by UV radiation with riboflavin. /. Biol. Chem. 268, 13221-13227.
6. Kawanishi, S., S. Inoue, S. Sano and H. Aiba (1986) Photodynamic guanine modification by hematoporphyrin is specific for single-stranded DNA with singlet oxygen as a mediator. J. Biol. Chem. 261, 6090-6095.
7. Hirakawa, K., H. Suzuki, S. Oikawa and S. Kawanishi (2003) Sequence-specific DNA damage induced by ultraviolet A-irradiated folic acid via its photolysis product Arch. Biochem. Biophys. 410, 261-268.
8. Kawanishi, S., Y. Hiraku and S. Oikawa (2001) Sequence-specific DNA damage induced by UVA radiation in the presence of endogenous and exogenous photosensitizes. Curr. Probl. Dermatol. 29, 74-82.
9. Dolmans, D. E., D. Fukumura and R. K. Jain (2003) Photodynamic therapy for cancer. Nat. Rev. Cancer 3, 380-387.
10. Slaga, T. J. (1995) Inhibition of the induction of cancer by antioxidants. In Nutrition and bio/technology in heart disease and cancer (Edited by J. B. Longenecker, D. Kritchevski and M. K. Drezner), Vol. 369, pp. 167-174. Plenum Publishing Corp., New York.
11. Yamashita, N., M. Murata, S. Inoue, M. J. Burkitt, L. Milne and S. Kawanishi (1998) α-Tocopherol induces oxidative damage to DNA in the presence of copper(II) ions. Chem. Res. Toxicol. 11, 855-862.
12. Murata, M. and S. Kawanishi (2000) Oxidative DNA damage by vitamin A and its derivative via Superoxide generation. J. Biol. Chem. 275, 2003-2008.
13. Nitta, Y., K. Kamiya, M. Tanimoto, O. Kagimoto, O. Niwa and K. Yokoro (1991) Effects of administration natural vitamin E on spontaneous hepatocarcinogenesis and N-nitrosoamine initiated tumors in mice. J. Toxicol. Pathol. 4, 55-61.
14. The alpha-tocopherol, beta carotene cancer prevention study group (1994) The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers. N. Engl. J. Med. 330, 1029-1035.
15. Omenn, G. S., G. E. Goodman, M. D. Thornquist, J. Balmes, M. R. Cullen, A. Glass, I. P. Keogh, F. L. Meyskens Jr., B. Valanis, J. H. Williams Jr., S. Barnhart, M. G. Cherniack, C. A. Brodkin and S. Hammar (1996) Risk factors for lung cancer and for intervention effects in CARET, the beta-carotene and retinol efficacy trial. J. Natl. Cancer Inst. 88, 1550-1559.
16. Menkovic, N., K. Savikin-Fodulovic, V. Bulatovic, I. Aljancic, N. Juranic. S. Macura, V. Vajs and S. Milosavljevic (2002) Xanthones from Swertia punctata. Phytochemistry 61, 415-420.
17. 60Co-irradiated mice. Phytomedicine 6, 85-88.
18. Bajpai, M. B., R. K. Asthana, N. K. Sharma, S. K. Chatterjee and S. K. Mukherjee (1991) Hypoglycemic effect of swerchirin from the hexane fraction of Swertia chirayita. Planta Med. 57, 102-104.
19. Basnet, P., S. Kadota, M. Shimizu, Y. Takata, M. Kobayashi and T. Namba (1995) Bellidifolin stimulates glucose uptake in rat 1 fibroblasts and ameliorates hyperglycemia in streptozotocin (STZ)-induced diabetic rats. Planta Med. 61, 402-405.
20. Basnet, P., S. Kadota, M. Shimizu and T. Namba (1994) Bellidifolin: a potent hypoglycemic agent in streptozotocin (STZ)-induced diabetic rats from Swertia japonica. Planta Med. 60, 507-511.
21. Nair, U. J., R. A. Floyd, J. Nair, V. Bussachini, M. Friesen and H. Bartsch (1987) Formation of reactive oxygen species and of 8- hydroxydeoxyguanosine in DNA in vitro with betel quid ingredients. Chem. Biol. Interact. 63, 157-169.
22. Mukherjee, K. S., C. K. Chakraborty, T. P. Bhattacharjee and S. Laha (1991) A xanthone from Swertia chirayita. Phytochemistry 30, 1037-1039.
23. Fukamiya, N., M. Okano, K. Kondo and K. Tagahara (1990) Xanthone from Swertia punicea. J. Nat. Prod. 53, 1543-1547.
24. 13C NMR spectroscopy of substituted xanthones II. Tetrahedron 35, 2035-2038.
25. Kanamori, H., I. Sakamoto, M. Mizuta, K. Hashimoto and O. Tanaka (1984) Studies on mutagenicity of Swertiae Herba. I. Identification of the mutagenic components. Chem. Pharm. Bull. 32, 2290-2295.
26. Otsuka, H. (1999) Triptexanthosides A-E: xanthone glycosides from aerial parts of Tripterospermum japonicum. Chem. Pharm. Bull. 47, 962-965.
27. Chumakov, P. (1990) EMBL Data Library, accession number X54156. European Molecular Biology Laboratory, Heidelberg, Germany.
28. Serrano, M., G. J. Hannon and D. A. Beach (1993) A new regulatory motif in cell-cycle control causing specific inhibition of cyclin D/CDK4. Nature 366, 704-707.
29. Capon, D. J., E. Y. Chen, A. D. Levinson, P. H. Seeburg and D. V. Goeddel (1983) Complete nucleotide sequences of the T24 human bladder carcinoma oncogene and its normal homologue. Nature 302, 33-37.
30. Yamashita, N., M. Murata, S. Inoue, Y. Hiraku, T. Yoshinaga and S. Kawanishi (1998) Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II). Mutat. Res. 397, 191-201.
31. Oikawa, S., K. Murakami and S. Kawanishi (2003) Oxidative damage to cellular and isolated DNA by homocysteine: implications for carcinogenesis. Oncogene 22, 3530-3538.
32. Yamamoto, K. and S. Kawanishi (1991) Site-specific DNA damage induced by hydrazine in the presence of manganese and copper ions; the role of hydroxyl radical and hydrogen atom. J. Biol. Chem. 266, 1509-1515.
33. Yamamoto, K. and S. Kawanishi (1989) Hydroxyl free radical is not the main active species in site-specific DNA damage induced by copper(II) ion and hydrogen peroxide. J. Biol. Chem. 264, 15435-15440.
34. Maxam, A. M. and W. Gilbert (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 65, 499-560.
35. Hirakawa, K., M. Yoshida, S. Oikawa and S. Kawanishi (2003) Base oxidation at 5′ site of GG sequence in double-stranded DNA induced by UVA in the presence of xanthone analogues: relationship between the DNA-damaging abilities of photosensitizes and their HOMO energies. Photochem. Photobiol. 77, 349-355.
36. Sugiyama, H. and I. Saito (1996) Theoretical studies of GG-specific photocleavage of DNA via electron transfer significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-form DNA. J. Am. Chem. Soc. 118, 7063-7068.
37. Yoshioka, Y., Y. Kitagawa, Y. Takano, K. Yamaguchi, T. Nakamura and I. Saito (1999) Experimental and theoretical studies on the selectivity of GGG triplets toward one-electron oxidation in B-form DNA. J. Am. Chem. Soc. 121, 8712-8719.
38. Kawai, K., T. Takada, S. Tojo and T. Majima (2003) Kinetics of weak distance-dependent hole transfer in DNA by adenine-hopping mechanism. J. Am. Chem. Soc. 125, 6842-6843.
39. Bruner, S. D., D. P. G. Norman and G. L. Verdine (2000) Structural basis for recognition and repair of the endogenous mutagen 8-oxoguanine in DNA. Nature 403, 859-866.
40. Shibutani, S., M. Takeshita and A. P. Grollman (1991) Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 349, 431-434.
41. Kino, K., I. Saito and H. Sugiyama (1998) Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-aminoimidazolone as a major guanine oxidation product. J. Am. Chem. Soc. 120, 7373-7374.
42. Kino, K. and H. Sugiyama (2001) Possible cause of G-C→C-G transversion mutation by guanine oxidation product, imidazolone. Chem. Biol. 8, 369-378.
43. McBride, T. J., J. E. Schneider, R. A. Floyd and L. A. Loeb (1992) Mutations induced by methylene blue plus light in single-stranded M13mp2. Proc. Natl. Acad. Sci. USA 89, 6866-6870.
44. Negishi, K. and W. Hao (1992) Spectrum of mutations in singlestranded DNA phage M13mp2 exposed to sunlight: predominance of G-to-C transversion. Carcinogenesis 13, 1615-1618.
45. Hirakawa, K., S. Oikawa, Y. Hiraku, I. Hirosawa and S. Kawanishi (2002) Catechol and hydroquinone have different redox properties responsible for their differential DNA-damaging ability. Chem. Res. Toxicol. 15, 76-82.
46. Massad, W., S. Criado, S. Bertolotti, A. Pajares, I. Gianoni, J. P. Escalada, F. Amat-Gucrri and N. A. García (2004) Photodegradation of the herbicide Norflurazon sensitised by Riboflavin. A kinetic and mechanistic study. Chemosphere 57, 455-461.