Acylated catechin derivatives: Inhibitors of DNA polymerase and angiogenesis

Frontiers in Bioscience - Elite

Volumn 3 E, Issue 4, 2011, Pages 1337-1348

  Mizushina, Yoshiyuki ^a   Saito, Akiko ^b   Horikawa, Keiko ^c   Nakajima, Noriyuki ^c   Tanaka, Akira ^c   Yoshida, Hiromi ^a   Matsubara, Kiminori ^a,d  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b OSAKA ELECTRO COMMUNICATION UNIVERSITY   (Japan)

^c TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^d HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Acylated catechin derivative; Angiogenesis; Anti cancer; Catechin; Cultured cell growth; DNA polymerase; E.C.2.7.7.7; Enzyme inhibitor; HUVEC

Indexed keywords

3 O ACYLCATECHIN DERIVATIVE; 3 O ACYLEPICATECHIN DERIVATIVE; ANGIOGENESIS INHIBITOR; ANTINEOPLASTIC AGENT; CATECHIN; DNA POLYMERASE; EPICATECHIN; STEARIC ACID; UNCLASSIFIED DRUG; DNA DIRECTED DNA POLYMERASE; ENZYME INHIBITOR;

ACYLATION; ANGIOGENESIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BASEMENT MEMBRANE; CELL CULTURE; CELL VIABILITY; CHEMICAL MODIFICATION; COLON CARCINOMA; CONTROLLED STUDY; DNA METABOLISM; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; MALE; NONHUMAN; RAT; SIGNAL TRANSDUCTION; UMBILICAL VEIN ENDOTHELIAL CELL; ANIMAL; CHEMISTRY; DRUG ANTAGONISM; NEOVASCULARIZATION (PATHOLOGY); WISTAR RAT;

EUKARYOTA; MAMMALIA;

ACYLATION; ANIMALS; CATECHIN; DNA-DIRECTED DNA POLYMERASE; ENZYME INHIBITORS; NEOVASCULARIZATION, PATHOLOGIC; RATS; RATS, WISTAR;

EID: 80052934687     PISSN: 19450494     EISSN: 19450508     Source Type: Journal    
DOI: 10.2741/e337     Document Type: Article

References (57)

1. C. S. Yang, J. M. Landau, M. T. Huang and H. L. Newmark: Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu Rev Nutr 21, 381-406 (2001) (Pubitemid 32695277)
2. C. S. Yang, J. Y. Chung, G. Yang, S. K. Chhabra and M. J. Lee: Tea and tea polyphenols in cancer prevention. J Nutr 130, 472S-478S (2000) (Pubitemid 30073776)
3. J. Folkman: Angiogenesis in cancer, vascular, rheumatoid and other disease. Nat Med 1, 27-31 (1995)
4. Y. Cao: Antiangiogenic cancer therapy. Semin Cancer Biol 14, 139-145 (2004) (Pubitemid 38234756)
5. K. Matsubara, M. Mori, Y. Matsuura and N. Kato: Pyridoxal 5'-phosphate and pyridoxal inhibit angiogenesis in serum-free rat aortic ring assay. Int J Mol Med 8, 505-508 (2001)
6. S. Komatsu, N. Yanaka, K. Matsubara and N. Kato: Antitumor effect of vitamin B6 and its mechanisms. Biochim Biophys Acta 1647, 127-130 (2003) (Pubitemid 38234644)
7. K. Matsubara, S. Komatsu, T. Oka and N. Kato: Vitamin B6-mediated suppression of colon tumorigenesis, cell proliferation, and angiogenesis (review). J Nutr Biochem 14, 246-250 (2003) (Pubitemid 36794261)
8. K. Matsubara, M. Mori, H. Matsumoto, K. Hori and K. Miyazawa: Antiangiogenic properties of a sulfated galactan isolated from a marine alga, Codium cylindricum. J Appl Phycol 15, 87-90 (2003) (Pubitemid 36435000)
9. K. Matsubara, C. Xue, X. Zhao, M. Mori, T. Sugawara and T. Hirata: Effects of middle molecular weight fucoidans on in vitro and ex vivo angiogenesis of endothelial cells. Int J Mol Med 15, 695-699 (2005)
10. T. Sugawara, K. Matsubara, R. Akagi, M. Mori and T. Hirata: Antiangiogenic activity of brown algae fucoxanthin and its deacetylated product, fucoxanthinol. J Agric Food Chem 54, 9805-9810 (2006) (Pubitemid 46158974)
11. P. Ganesan, K. Matsubara, T. Ohkubo, Y. Tanaka, K. Noda, T. Sugawara and T. Hirata: Anti-angiogenic effect of siphonaxanthin from green alga, Codium fragile. Phytomedicine, in press.
12. K. Matsubara, T. Kaneyuki, T. Miyake and M. Mori: Antiangiogenic activity of nasunin, an antioxidant anthocyanin, in eggplant peels. J Agric Food Chem 53, 6272-6275 (2005) (Pubitemid 41169372)
13. K. Matsubara, M. Mori and Y. Mizushina: Petasiphenol which inhibits DNA polymerase lambda activity is an inhibitor of in vitro angiogenesis. Oncol Rep 11, 447-451 (2004)
14. K. Matsubara, H. Matsumoto, Y. Mizushina, M. Mori, N. Nakajima, M. Fuchigami, H. Yoshida and T. Hada: Inhibitory effect of glycolipids from spinach on in vitro and ex vivo angiogenesis. Oncol Rep 14, 157-160 (2005)
15. 3 on DNA polymerase and angiogenesis. Int J Mol Med 22, 381-387 (2008)
16. T. Kayashima, M. Mori, H. Yoshida, Y. Mizushina and K. Matsubara: 1, 4-Naphthoquinone is a potent inhibitor of human cancer cell growth and angiogenesis. Cancer Lett 278, 34-40 (2009)
17. T. Kayashima, M. Mori, R. Mizutani, K. Nishio, K. Kuramochi, K. Tsubaki, H. Yoshida, Y. Mizushina and K. Matsubara: Synthesis and biological evaluation of vitamin K derivatives as angiogenesis inhibitor. Bioorg Med Chem 18, 6305-6309 (2010)
18. A. Kornberg and T. A. Baker: DNA replication, second edition, W. H. Freeman (ed), New York, Chapter 6, 197-225 (1992)
19. K. Bebenek and T. A. Kunkel: DNA Repair and Replication: Advances in Protein Chemistry, W. Yang (ed), San Diego, 137-165 (2004)
20. E. C. Friedberg, W. J. Feaver and V. L. Gerlach: The many faces of DNA polymerases: strategies for mutagenesis and for mutational avoidance. Proc Natl Acad Sci USA 97, 5681-5683 (2000) (Pubitemid 30367454)
21. A. G. So and K. M. Downey: Eukaryotic DNA replication. Crit Rev Biochem Mol Biol 27, 129-155 (1992)
22. K. Sakaguchi, F. Sugawara and Y. Mizushina: Inhibitors of eukaryotic DNA polymerases. Seikagaku 74, 244-251 (2002)
23. G. Maga and U. Hubscher: Repair and translesion DNA polymerases as anticancer drug targets. Anticancer Agents Med Chem 8, 431-447 (2008) (Pubitemid 351761428)
24. Y. Mizushina, A. Saito, A. Tanaka, N. Nakajima, I. Kuriyama, M. Takemura, T. Takeuchi, F. Sugawara and H. Yoshida: Structural analysis of catechin derivatives as mammalian DNA polymerase inhibitors. Biochem Biophys Res Commun 333, 101-109 (2005) (Pubitemid 40813452)
25. K. Matsubara, A. Saito, A. Tanaka, N. Nakajima, R. Akagi, M. Mori and Y. Mizushina: Catechin conjugated with fatty acid inhibits DNA polymerase and angiogenesis. DNA Cell Biol 25, 95-103 (2006) (Pubitemid 43271413)
26. K. Matsubara, A. Saito, A. Tanaka, N. Nakajima, R. Akagi, M. Mori and Y. Mizushina: Epicatechin conjugated with fatty acid is a potent inhibitor of DNA polymerase and angiogenesis. Life Sci 80, 1578-1585 (2007) (Pubitemid 46412366)
27. K. Tamai, K. Kojima, T. Hanaichi, S. Masaki, M. Suzuki, H. Umekawa and S. Yoshida: Structural study of immunoaffinity-purified DNA polymerase alpha-DNA primase complex from calf thymus. Biochim Biophys Acta 950, 263-273 (1988)
28. T. Date, M. Yamaguchi, F. Hirose, Y. Nishimoto, K. Tanihara and A. Matsukage: Expression of active rat DNA polymerase beta in Escherichia coli. Biochemistry 27, 2983-2990 (1988)
29. S. Umeda, T. Muta, T. Ohsato, C. Takamatsu, N. Hamasaki and D. Kang: The D-loop structure of human mtDNA is destabilized directly by 1-methyl-4- phenylpyridinium ion (MPP+), a parkinsonism-causing toxin. Eur J Biochem 267, 200-206 (2000) (Pubitemid 30029754)
30. 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, 248-256 (2004) (Pubitemid 38718084)
31. N. Aoyagi, S. Matsuoka, A. Furunobu, A. Matsukage and K. Sakaguchi: Drosophila DNA polymerase delta: Purification and characterization. J Biol Chem 269, 6045-6050 (1994)
32. N. Aoyagi, M. Oshige, F. Hirose, K. Kuroda, A. Matsukage and K. Sakaguchi: DNA polymerase epsilon from Drosophila melanogaster. Biochem Biophys Res Commun 230, 297-301 (1997) (Pubitemid 27211988)
33. R. K. Hamatake, H. Hasegawa, A. B. Clark, K. Bebenek, T. A. Kunkel and A. Sugino: Purification and characterization of DNA polymerase II from the yeast Saccharomyces cerevisiae. Identification of the catalytic core and a possible holoenzyme form of the enzyme. J Biol Chem 265, 4072-4083 (1990)
34. K. Sakaguchi, Y. Hotta and H. Stern: Chromatin-associated DNA polymerase activity in meiotic cells of lily and mouse. Cell Struct Funct 5, 323-334 (1980)
35. Y. Mizushina, H. Yagi, N. Tanaka, T. Kurosawa, H. Seto, K. Katsumi, M. Onoue, H. Ishida, A. Iseki, T. Nara, K. Morohashi, T. Horie, Y. Onomura, M. Narusawa, N. Aoyagi, K. Takami, M. Yamaoka, Y. Inoue, A. Matsukage, S. Yoshida and K. Sakaguchi: Screening of inhibitor of eukaryotic DNA polymerases produced by microorganisms. J Antibiot (Tokyo) 49, 491-492 (1996) (Pubitemid 26178955)
36. 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, 256-262 (1996) (Pubitemid 26290686)
37. Y. Mizushina, S. Yoshida, A. Matsukage and K. Sakaguchi: The inhibitory action of fatty acids on DNA polymerase beta. Biochim Biophys Acta 1336, 509-521 (1997) (Pubitemid 27467053)
38. A. Ogawa, T. Murate, M. Suzuki, Y. Nimura and S. Yoshida: Lithocholic acid, a putative tumor promoter, inhibits mammalian DNA polymerase beta. Jpn J Cancer Res 89, 1154-1159 (1998) (Pubitemid 29007996)
39. K. Tamiya-Koizumi, T. Murate, M. Suzuki, C. G. Simbulan, M. Nakagawa, M. Takemura, K. Furuta, S. Izuta and S. Yoshida: Inhibition of DNA primase by sphingosine and its analogues parallels with their growth suppression of cultured human leukemic cells. Biochem Mol Biol Int 41, 1179-1189 (1997) (Pubitemid 27232077)
40. 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, 1385-1389 (1985) (Pubitemid 15098407)
41. D. A. Soltis and O. C. Uhlenbeck: Isolation and characterization of two mutant forms of T4 polynucleotide kinase. J Biol Chem 257, 11332-11339 (1982) (Pubitemid 13203366)
42. 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, 21060-21066 (1991) (Pubitemid 21908574)
43. T. Mosmann: Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65, 55-63 (1983) (Pubitemid 14203433)
44. M. Mori, Y. Sadahira, S. Kawasaki, T. Hayashi, K. Notohara and M. Awai: Capillary growth from reversed rat aortic segments cultured in collagen gel. Acta Pathol Jpn 38, 1503-1512 (1988) (Pubitemid 19063126)
45. S. Kawasaki, M. Mori and M. Awai: Capillary growth of rat aortic segments cultured in collagen gel without serum. Acta Pathol Jpn 39, 712-718 (1989) (Pubitemid 20055673)
46. Y. Cao and R. Cao: Angiogenesis inhibited by drinking tea. Nature 398, 381 (1999)
47. R. F. Nicosia and A. Ottinetti: Growth of microvessels in serum-free matrix culture of rat aorta. Lab Invest 63, 115-122 (1990)
48. E. A. Kruger, P. H. Duray, M. G. Tsokos, D. J. Venzon, S. K. Libutti, S. C. Dixon, M. A. Rudek, J. Pluda, C. Allerga and W. D. Figg: Endostatin inhibits microvessel formation in the ex vivo rat aortic ring angiogenesis assay. Biochem Biophys Res Commun 268, 183-191 (2000) (Pubitemid 30116631)
49. T. G. Zogakis, N. G. Costouros, E. A. Kruger, S. Forbes, M. He, M. Qian, A. L. Feldman, W. D. Figg, H. R. Alexander, E. T. Liu, E. C. Kohn and S. K. Libutti: Microarray gene expression profiling of angiogenesis inhibitors using the rat aortic ring assay. Biotechniques 33, 664-666, 668, 670 (2002)
50. Y. Mizushina: Specific inhibitors of mammalian DNA polymerase species. Biosci Biotechnol Biochem 73, 1239-1251 (2009)
51. A. H. Jr. Vagnucci and W. W. Li: Alzheimer's disease and angiogenesis. Lancet 361, 605-608 (2003) (Pubitemid 36207483)
52. Y. Cao, R. Cao and E. Bråkenhielm: Antiangiogenic mechanisms of dietderived polyphenols. J Nutr Biochem 13, 380-390 (2002)
53. S. Uesato, Y. Kitagawa, Y. Hara, H. Tokuda, M. Okuda, Y. X. Mou, T. Mukainaka and H. Nishino: Antitumor promoting activities of 3-Oacyl-(-) epigallocatechins. Bioorg Med Chem Lett 10, 1673-1675 (2000) (Pubitemid 30495238)
54. J. P. E. Spencer, H. Schroeter, G. Kuhnle, S. K. S. Srai, R. M. Tyrrell, U. Hahn and C. Rice-Evans: Epicatechin and its in vivo metabolite, 3'-O-methyl epicatechin, protect human fibroblasts from oxidative-stress-induced cell death involving caspase-3 activation. Biochem J 354, 493-500 (2001) (Pubitemid 32269712)
55. S. Lamy, D. Gingras and R. Béliveau: Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation. Cancer Res 62, 381-385 (2000)
56. K. Murakami-Murofushi, S. Kobayashi, K. Onimura, M. Matsumoto, M. Shioda, S. Yoshida, M. Shoji and H. Murofushi: Selective inhibition of DNA polymerase-alpha family with chemically synthesized derivatives of PHYLPA, a unique Physarum lysophosphatidic acid. Biochim Biophys Acta 1258, 57-60 (1995)
57. A. Patti, C. Sanfilippo, M. Piattelli and G. Nicolosi: Use of Mucor miehei lipase in the preparation of long chain 3-O-acylcatechins. J Mol Catal B: Enzym 10, 577-582 (2000) (Pubitemid 30645945)