Structural analysis of catechin derivatives as mammalian DNA polymerase inhibitors

Biochemical and Biophysical Research Communications

Volumn 333, Issue 1, 2005, Pages 101-109

  Mizushina, Yoshiyuki ^a   Saito, Akiko ^b   Tanaka, Akira ^c   Nakajima, Noriyuki ^c   Kuriyama, Isoko ^a   Takemura, Masaharu ^d   Takeuchi, Toshifumi ^e   Sugawara, Fumio ^e   Yoshida, Hiromi ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b Biotechnology Center   (Japan)

^c TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^d MIE UNIVERSITY   (Japan)

^e TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

( ) Epigallocatechin gallate; Anti inflammation; DNA polymerase ; DNA polymerase ; Enzyme inhibitor; Tea catechins

Indexed keywords

CATECHIN; DEOXYRIBONUCLEASE I; DNA; DNA DIRECTED DNA POLYMERASE; DNA NUCLEOTIDYLEXOTRANSFERASE; ENZYME INHIBITOR; EPICATECHIN; EPICATECHIN GALLATE; EPIGALLOCATECHIN; EPIGALLOCATECHIN GALLATE; GALLOCATECHIN; GALLOCATECHIN GALLATE; RNA POLYMERASE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; COMPETITIVE INHIBITION; DNA METABOLISM; DNA TEMPLATE; DRUG ACTIVITY; DRUG INHIBITION; ENZYME INHIBITION; ENZYME SUBSTRATE; IC 50; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; CATECHIN; COMPUTER SIMULATION; DNA-DIRECTED DNA POLYMERASE; ENZYME INHIBITORS; HUMANS; MAMMALS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; REPRODUCIBILITY OF RESULTS; SPECIES SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP;

BOVINAE; MAMMALIA; PROKARYOTA;

EID: 20444490681     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2005.05.093     Document Type: Article

References (47)

1. U. Hubscher, G. Maga, and S. Spadari Eukaryotic DNA polymerases Annu. Rev. Biochem. 71 2002 133 163
2. S. Kimura, Y. Uchiyama, N. Kasai, S. Namekawa, A. Saotome, T. Ueda, T. Ando, T. Ishibashi, M. Oshige, T. Furukawa, T. Yamamoto, J. Hashimoto, and K. Sakaguchi A novel DNA polymerase homologous to Escherichia coli DNA polymerase I from a higher plant, rice (Oryza sativa L.) Nucleic Acids Res. 30 2002 1585 1592
3. A.G. So, and K.M. Downey Eukaryotic DNA replication Crit. Rev. Biochem. Mol. Biol. 27 1992 129 155
4. Y. Mizushina, N. Tanaka, H. Yagi, T. Kurosawa, M. Onoue, H. Seto, T. Horie, N. Aoyagi, M. Yamaoka, A. Matsukage, S. Yoshida, and K. Sakaguchi Fatty acids selectively inhibit eukaryotic DNA polymerase activities in vitro Biochim. Biophys. Acta 1308 1996 256 262
5. Y. Mizushina, S. Yoshida, A. Matsukage, and K. Sakaguchi The inhibitory action of fatty acids on DNA polymerase β Biochim. Biophys. Acta 1336 1997 509 521
6. Y. Mizushina, T. Ohkubo, T. Date, T. Yamaguchi, M. Saneyoshi, F. Sugawara, and K. Sakaguchi Mode analysis of a fatty acid molecule binding to the N-terminal 8-kDa domain of DNA polymerase β: a 1:1 complex and binding surface J. Biol. Chem. 274 1999 25599 25607
7. Y. Mizushina, F. Sugawara, A. Iida, and K. Sakaguchi Structural homology between DNA binding sites of DNA polymerase β and DNA topoisomerase II J. Mol. Biol. 304 2000 385 395
8. Y. Mizushina, T. Tsuzuki, T. Eitsuka, T. Miyazawa, K. Kobayashi, H. Ikawa, I. Kuriyama, Y. Yonezawa, M. Takemura, H. Yoshida, and K. Sakaguchi Inhibitory action of conjugated C18-fatty acids on DNA polymerases and DNA topoisomerases Lipids 39 2004 977 983
9. Y. Mizushina, N. Takahashi, L. Hanashima, H. Koshino, Y. Esumi, J. Uzawa, F. Sugawara, and K. Sakaguchi Lucidenic acid O and lactone, new terpene inhibitors of eukaryotic DNA polymerases from a basidiomycete, Ganoderma lucidum Bioorg. Med. Chem. 7 1999 2047 2052
10. Y. Mizushina, T. Ohkubo, F. Sugawara, and K. Sakaguchi Structure of lithocholic acid binding to the N-terminal 8-kDa domain of DNA polymerase β Biochemistry 39 2000 12606 12613
11. Y. Mizushina, N. Kasai, F. Sugawara, A. Iida, H. Yoshida, and K. Sakaguchi Three-dimensional structural model analysis of the binding site of lithocholic acid, an inhibitor of DNA polymerase β and DNA topoisomerase II J. Biochem. (Tokyo) 130 2001 657 664
12. Y. Mizushina, N. Kasai, K. Miura, S. Hanashima, M. Takemura, H. Yoshida, F. Sugawara, and K. Sakaguchi Structural relationship of lithocholic acid derivatives binding to the N-terminal 8-kDa domain of DNA polymerase β Biochemistry 43 2004 10669 10677
13. S. Takahashi, S. Kamiski, Y. Mizushina, K. Sakaguchi, F. Sugawara, and T. Nakata Total synthesis of dehydroaltenusin Tetrahedron Lett. 44 2003 1875 1877
14. S. Hanashima, Y. Mizushina, T. Yamazaki, K. Ohta, S. Takahashi, H. Sahara, K. Sakaguchi, and F. Sugawara Synthesis of sulfoquinovosylacylglycerols, inhibitors of eukaryotic DNA polymerase α and β Bioorg. Med. Chem. 9 2001 367 376
15. C. Murakami, T. Yamazaki, S. Hanashima, S. Takahashi, K. Ohta, H. Yoshida, F. Sugawara, K. Sakaguchi, and Y. Mizushina Structure-function relationship of synthetic sulfoquinovosyl-acylglycerols as mammalian DNA polymerase inhibitors Arch. Biochem. Biophys. 403 2002 229 236
16. C. Murakami, T. Yamazaki, S. Hanashima, S. Takahashi, M. Takemura, S. Yoshida, K. Ohta, H. Yoshida, F. Sugawara, K. Sakaguchi, and Y. Mizushina A novel DNA polymerase inhibitor and a potent apoptosis inducer: 2-mono-O-acyl-3-O-(α-d-sulfoquinovosyl)-glyceride with stearic acid Biochim. Biophys. Acta 1645 2003 72 80
17. C. Murakami, M. Takemura, H. Yoshida, F. Sugawara, K. Sakaguchi, and Y. Mizushina Analysis of cell cycle regulation by 1-mono-O-acyl-3-O-(α-d- sulfoquinovosyl)-glyceride (SQMG), an inhibitor of eukaryotic DNA polymerases Biochem. Pharmacol. 66 2003 541 550
18. C. Murakami, M. Takemura, Y. Sugiyama, S. Kamisuki, H. Asahara, M. Kawasaki, T. Ishidoh, S. Linn, S. Yoshida, F. Sugawara, H. Yoshida, K. Sakaguchi, and Y. Mizushina Vitamin A-related compounds, all-trans retinal and retinoic acids, selectively inhibit activities of mammalian replicative DNA polymerases Biochim. Biophys. Acta 1574 2002 85 92
19. Y. Mizushina, X. Xu, K. Matsubara, C. Murakami, I. Kuriyama, M. Oshige, M. Takemura, N. Kato, H. Yoshida, and K. Sakaguchi Pyridoxal 5′-phosphate is a selective inhibitor in vivo of DNA polymerase α and ε Biochem. Biophys. Res. Commun. 312 2003 1025 1032
20. Y. Mizushina, X. Xu, C. Murakami, T. Okano, M. Takemura, H. Yoshida, and K. Sakaguchi Selective inhibition of mammalian DNA polymerase α by vitamin D2 and D3 J. Pharmacol. Sci. 92 2003 283 290
21. Y. Mizushina, M. Hirota, C. Murakami, T. Ishidoh, S. Kamisuki, N. Shimazaki, M. Takemura, M. Perpelescu, M. Suzuki, H. Yoshida, F. Sugawara, O. Koiwai, and K. Sakaguchi Some anti-chronic inflammatory compounds are DNA polymerase λ-specific inhibitors Biochem. Pharmacol. 66 2003 1935 1944
22. Y. Mizushina, H. Yoshida, K. Sakaguchi, Inhibition of DNA polymerase λ suppresses 12-O-tetradecanoylphorbol-13-acetate-induced-inflammation, Curr. Med. Chem.-Anti-Inflammatory Anti-Allergy Agents (2005) in press.
23. Z. Chen, Q.Y. Zhu, D. Tsang, and Y. Huang Degradation of green tea catechins in tea drinks J. Agric. Food Chem. 49 2001 477 482
24. 2+ mediated oxidative modification of low density lipoprotein Biol. Pharm. Bull. 17 1994 1567 1572
25. I.E. Dreosti, M.J. Wargovich, and C.S. Yang Inhibition of carcinogenesis by tea: the evidence from experimental studies Crit. Rev. Food Sci. Nutr. 37 1997 761 770
26. R. Amarowicz, R.B. Pegg, and D.A. Bautista Antibacterial activity of green tea polyphenols against Escherichia coli K 12 Nahrung 44 2000 60 62
27. S. Sakanaka, M. Kim, M. Taniguchi, and T. Yamamoto Antibacterial substances in Japanese green tea extract against Streptococcus mutants, a cariogenic bacterium Agric. Biol. Chem. 53 1989 2307 2311
28. K. Mabe, M. Yamada, I. Oguni, and T. Takahashi In vitro and in vivo activities of tea catechins against Helicobacter pylori Antimicrob. Agents Chemother 43 1999 1788 1791
29. N. Ahmad, and H. Mukhtar Green tea polyphenols and cancer: biologic mechanisms and practical implications Nutr. Rev. 57 1999 78 83
30. J.L. Buschman Green tea and cancer in humans: a review of the literature Nutr. Cancer 31 1998 51 57
31. M.G. Hertog, E.J. Feskens, P.C. Hollman, M.B. Katan, and D. Kromhout Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study Lancet 342 1993 1007 1011
32. K. Imai, and K. Nakachi Cross sectional study of effects of drinking green tea on cardiovascular and liver disease Biochem. Med. J. 310 1985 693 696
33. C.S. Yang Tea and health Nutrition 15 1999 946 949
34. K. Tamai, K. Kojima, T. Hanaichi, S. Masaki, M. Suzuki, H. Umekawa, and S. Yoshida Structural study of immunoaffinity-purified DNA polymerase α-DNA primase complex from calf thymus Biochim. Biophys. Acta 950 1988 263 273
35. T. Date, M. Yamaguchi, F. Hirose, Y. Nishimoto, K. Tanihara, and A. Matsukage Expression of active rat DNA polymerase β in Escherichia coli Biochemistry 27 1988 2983 2990
36. M. Oshige, R. Takeuchi, R. Ruike, K. Kuroda, and K. Sakaguchi Subunit protein-affinity isolation of Drosophila DNA polymerase catalytic subunit Protein Expr. Purif. 35 2004 248 256
37. C. Masutani, R. Kusumoto, S. Iwai, and F. Hanaoka Mechanisms of accurate translesion synthesis by human DNA polymerase η EMBO J. 19 2000 3100 3109
38. A. Tissier, E.G. Frank, J.P. McDonald, S. Iwai, F. Hanaoka, and R. Woodgate Misinsertion and bypass of thymine-thymine dimers by human DNA polymerase ι EMBO J. 19 2000 5259 5266
39. E. Ohashi, T. Ogi, R. Kusumoto, S. Iwai, C. Masutani, F. Hanaoka, and H. Ohmori Error-prone bypass of certain DNA lesions by the human DNA polymerase κ Genes Dev. 14 2000 1589 1594
40. N. Shimazaki, K. Yoshida, T. Kobayashi, S. Toji, T. Tamai, and O. Koiwai Over-expression of human DNA polymerase λ in E. coli and characterization of the recombinant enzyme Genes Cells 7 2000 639 651
41. K. Sakaguchi, Y. Hotta, and H. Stern Chromatin-associated DNA polymerase activity in meiotic cells of lily and mouse Cell Struct. Funct. 5 1980 323 334
42. C. Nakayama, and M. Saneyoshi Inhibitory effects of 9-β-D- xylofuranosyladenine 5′-triphosphate on DNA-dependent RNA polymerase I and II from cherry salmon (Oncorhynchus masou) J. Biochem. (Tokyo) 97 1985 1385 1389
43. B.C. Lu, and K. Sakaguchi An endo-exonuclease from meiotic tissues of the basidiomycete Coprinus cinereus: Its purification and characterization J. Biol. Chem. 266 1991 21060 21066
44. M. Gschwendt, W. Kittstein, G. Furstenberger, and F. Marks The mouse ear edema: a quantitatively evaluable assay for tumor promoting compounds and for inhibitors of tumor promotion Cancer Lett. 25 1984 177 185
45. E. Hecker Carcinogenesis 2 1978 11 48
46. H. Fujiki, and T. Sugimura Adv. Cancer Res. 49 1987 223 264
47. Y. Nakamura, A. Murakami, Y. Ohto, K. Torikai, T. Tanaka, and H. Ohigashi Suppression of tumor promoter-induced oxidative stress and inflammatory responses in mouse skin by a superoxide generation inhibitor 1′-acetoxychavicol acetate Cancer Res. 58 1995 4832 4839