The inhibitory action of pyrrolidine alkaloid, 1,4-dideoxy-1,4-imino-D-ribitol, on eukaryotic DNA polymerases

Biochemical and Biophysical Research Communications

Volumn 304, Issue 1, 2003, Pages 78-85

  Mizushina, Yoshiyuki ^a   Xu, Xianai ^a   Asano, Naoki ^b   Kasai, Nobuyuki ^c   Kato, Atsushi ^d   Takemura, Masaharu ^e   Asahara, Hitomi ^f   Linn, Stuart ^f   Sugawara, Fumio ^c   Yoshida, Hiromi ^a   Sakaguchi, Kengo ^c  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b HOKURIKU UNIVERSITY   (Japan)

^c TOKYO UNIVERSITY OF SCIENCE   (Japan)

^d UNIVERSITY OF TOYAMA   (Japan)

^e NAGOYA UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^f UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

1,4 Dideoxy 1,4 imino D ribitol; DNA polymerase; Enzyme inhibitor; Pyrrolidine alkaloid

Indexed keywords

1,4 DIDEOXY 1,4 IMINO DEXTRO RIBITOL; DEOXYRIBONUCLEASE I; DEOXYRIBOSE; DNA DIRECTED DNA POLYMERASE ALPHA; DNA POLYMERASE; GLYCOSIDASE; NITROGEN; PENTOSE; PYRROLIDINE ALKALOID; PYRROLIDINE DERIVATIVE; RIBITOL; RNA DIRECTED DNA POLYMERASE; RNA POLYMERASE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; ENZYME ACTIVITY; ENZYME BINDING; ENZYME KINETICS; PRIORITY JOURNAL; PURIFICATION;

BOVINAE; EUKARYOTA; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; MORUS (PLANT); MORUS ALBA; PROKARYOTA;

EID: 0037466484     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-291X(03)00540-0     Document Type: Article

References (51)

1. Mizushina Y., Ohkubo T., Date T., Yamaguchi T., Saneyoshi M., Sugawara F., Sakaguchi K. 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.
2. Mizushina Y., Ohkubo T., Sugawara F., Sakaguchi K. Structure of lithocholic acid binding to the N-terminal 8-kDa domain of DNA polymerase β Biochemistry. 39:2000;12606-12613.
3. Mizushina Y., Tanaka N., Yagi H., Kurosawa T., Onoue M., Seto H., Horie T., Aoyagi N., Yamaoka M., Matsukage A., Yoshida S., Sakaguchi K. Fatty acids selectively inhibit eukaryotic DNA polymerase activities in vitro. Biochim. Biophys. Acta. 1308:1996;256-262.
4. Mizushina Y., Yoshida S., Matsukage A., Sakaguchi K. The inhibitory action of fatty acids on DNA polymerase β Biochim. Biophys. Acta. 1336:1997;509-521.
5. Mizushina Y., Sagisaka M., Sakai H., Abe M., Sakaguchi K. Mode analysis of binding of fatty acids to mammalian DNA polymerases. Biochim. Biophys. Acta. 1486:2000;211-218.
6. Mizushina Y., Tanaka N., Kitamura A., Tamai K., Ikeda M., Takemura M., Sugawara F., Arai T., Matsukage A., Yoshida S., Sakaguchi K. The inhibitory effect of novel triterpenoid compounds, fomitellic acids, on DNA polymerase β Biochem. J. 330:1998;1325-1332.
7. Tanaka N., Kitamura A., Mizushina Y., Sugawara F., Sakaguchi K. Fomitellic acids, triterpenoid inhibitors of eukaryotic DNA polymerases from a basidiomycete, Fomitella fraxinea. J. Nat. Prod. 61:1998;193-197.
8. Mizushina Y., Iida A., Ohta K., Sugawara F., Sakaguchi K. Novel triterpenoids inhibit both DNA polymerase and DNA topoisomerase. Biochem J. 350:2000;757-763.
9. Murakami C., Ishijima K., Hirota M., Sakaguchi K., Yoshida H., Mizushina Y. Novel anti-inflammatory compounds from Rubus sieboldii, triterpenoids, are inhibitors of mammalian DNA polymerases. Biochim. Biophys. Acta. 1596:2002;193-200.
10. Mizushina Y., Watanabe I., Togashi H., Hanashima L., Takemura M., Ohta K., Sugawara F., Koshino H., Esumi Y., Uzawa J., Matsukage A., Yoshida S., Sakaguchi K. An ergosterol peroxide, a natural product that selectively enhances the inhibitory effect of linoleic acid on DNA polymerase β Biol. Pharm. Bull. 21:1998;444-448.
11. Mizushina Y., Takahashi N., Hanashima L., Koshino H., Esumi Y., Uzawa J., Sugawara F., Sakaguchi K. Lucidenic acid O and lactone, new terpene inhibitors of eukaryotic DNA polymerases from a basidiomycete, Ganoderma lucidum. Bioorg. Med. Chem. 7:1999;2047-2052.
12. Mizushina Y., Hanashima L., Yamaguchi T., Takemura M., Sugawara F., Saneyoshi M., Matsukage A., Yoshida S., Sakaguchi K. A mushroom fruiting body-inducing substance inhibits activities of replicative DNA polymerases. Biochem. Biophys. Res. Commun. 249:1998;17-22.
13. Mizushina Y., Watanabe I., Ohta K., Takemura M., Sahara H., Takahashi N., Gasa S., Sugawara F., Matsukage A., Yoshida S., Sakaguchi K. Studies on inhibitors of mammalian DNA polymerase α and β: sulfolipids from a pteridophyte, Athyrium niponicum. Biochem. Pharmacol. 55:1998;537-541.
14. Ohta K., Mizushina Y., Hirata N., Takemura M., Sugawara F., Matsukage A., Yoshida S., Sakaguchi K. Sulfoquinovosyldiacylglycerol, KM043, a new potent inhibitor of eukaryotic DNA polymerases and HIV-reverse transcriptase type 1 from a marine red alga, Gigartina tenella. Chem. Pharm. Bull. 46:1998;684-686.
15. Ohta K., Mizushina Y., Hirata N., Takemura M., Sugawara F., Matsukage A., Yoshida S., Sakaguchi K. Action of a new mammalian DNA polymerase inhibitor, sulfoquinovosyldiacylglycerol. Biol. Pharm. Bull. 22:1999;111-116.
16. Hanashima S., Mizushina Y., Ohta K., Yamazaki T., Sugawara F., Sakaguchi K. Structure-activity relationship of a novel group of mammalian DNA polymerase inhibitors, synthetic sulfoquinovosylacylglycerols. Jpn. J. Cancer Res. 91:2000;1073-1083.
17. Ohta K., Hanashima S., Mizushina Y., Yamazaki T., Saneyoshi M., Sugawara F., Sakaguchi K. Studies on a novel DNA polymerase inhibitor group, synthetic sulfoquinovosylacylglycerols: inhibitory action on cell proliferation. Mutat. Res. 467:2000;139-152.
18. Hanashima S., Mizushina Y., Yamazaki T., Ohta K., Takahashi S., Koshino H., Sahara H., Sakaguchi K., Sugawara F. Structural determination of sulfoquinovosyldiacylglycerol by chiral syntheses. Tetrahedron Lett. 41:2000;4403-4407.
19. Ohta K., Mizushina Y., Yamazaki T., Hanashima S., Sugawara F., Sakaguchi K. Specific interaction between an oligosaccharide on the tumor cell surface and the novel antitumor agents, sulfoquinovosylacylglycerols. Biochem. Biophys. Res. Commun. 288:2001;893-900.
20. Hanashima S., Mizushina Y., Yamazaki T., Ohta K., Takahashi S., Sahara H., Sakaguchi K., Sugawara F. Synthesis of sulfoquinovosylacylglycerols, inhibitors of eukaryotic DNA polymerase α and β Bioorg. Med. Chem. 9:2001;367-376.
21. Mizushina Y., Sugiyama Y., Yoshida H., Hanashima S., Yamazaki T., Kamisuki S., Ohta K., Takemura M., Yamaguchi T., Matsukage A., Yoshida S., Saneyoshi M., Sugawara F., Sakagauchi K. Galactosyldiacylglycerol, a mammalian DNA polymerase α-specific inhibitor from a sea alga, Petalonia bingbamiae. Biol. Pharm. Bull. 24:2001;982-987.
22. Murakami C., Yamazaki T., Hanashima S., Takahashi S., Ohta K., Yoshida H., Sugawara F., Sakaguchi K., Mizushina Y. Structure-function relationship of synthetic sulfoquinovosyl-acylglycerols as mammalian DNA polymerase inhibitors. Arch. Biochem. Biophys. 403:2002;229-236.
23. Murakami C., Takemura M., Sugiyama Y., Kamisuki S., Asahara H., Kawasaki M., Ishidoh T., Linn S., Yoshida S., Sugawara F., Yoshida H., Sakaguchi K., Mizushina Y. Vitamin A-related compounds, all-trans retinal and retinoic acids, selectively inhibit activities of mammalian replicative DNA polymerases. Biochim. Biophys. Acta. 1574:2001;85-92.
24. Sakaguchi K., Sugawara F., Mizushina Y. Inhibitors of eukaryotic DNA polymerases. Seikagaku. 74:2002;244-251.
25. Asano N., Oseki K., Tomioka E., Kizu H., Matsui K. N-containing suger from Morus alba and their glycosidase inhibitory activities. Carbohydr. Res. 259:1994;243-255.
26. Asano N., Yasuda K., Kizu H., Kato A., Fan J.Q., Nash R.J., Fleet G.W.J., Molyneux R. Novel α-L-fucosidase inhibitors from the bark of Angylocalyx pynaertii (Leguminosae). Eur. J. Biochem. 268:2001;35-41.
27. Asano N., Oseki K., Kizu H., Matsui K. Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases. J. Med. Chem. 37:1994;3701-3706.
28. Yasuda K., Kizu H., Yamashita T., Kameda Y., Kato A., Nash R.J., Fleet G.W.J., Molyneux R.J., Asano N. New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii. J. Nat. Prod. 65:2002;198-202.
29. Asano N., Kato A., Miyauchi M., Kizu H., Kameda Y., Watson A.A., Nash R.J., Fleet G.W.J. Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis. J. Nat. Prod. 61:1998;625-628.
30. Tamai K., Kojima K., Hanaichi T., Masaki S., Suzuki M., Umekawa H., Yoshida S. Structural study of immunoaffinity-purified DNA polymerase α-DNA primase complex from calf thymus. Biochim. Biophys. Acta. 950:1988;263-273.
31. Date T., Yamaguchi M., Hirose F., Nishimoto Y., Tanihara K., Matsukage A. Expression of active rat DNA polymerase β in Escherichia coli. Biochemistry. 27:1988;2983-2990.
32. Shoji-Kawaguchi M., Izuta S., Tamiya-Koizumi K., Suzuki M., Yoshida S. Selective inhibition of DNA polymerase ε by phosphatidylinositol. J. Biochem. (Tokyo. 117:1995;1095-1099.
33. Chui G.S., Linn S. Purification of mammalian polymerases: DNA polymerase ε Methods Enzymol. 262:1995;93-98.
34. Tamiya-Koizumi K., Murate T., Suzuki M., Simbulan C.G., Nakagawa M., Takamura M., Furuta K., Izuta S., Yoshida S. Inhibition of DNA primase by sphingosine and its analogues parallels with their growth suppression of cultured human leukemic cells. Biochem. Mol. Biol. Int. 41:1997;1179-1189.
35. ′ -triphosphates and related nucleotides on DNA-dependent RNA polymerases I and II from the cherry salmon (Oncorhynchus masou) J. Biochem. (Tokyo). 97:1985;1385-1389.
36. Soltis D.A., Uhlenbeck O.C. Isolation and characterization of two mutant forms of T4 polynucleotide kinase. J. Biol. Chem. 257:1982;11332-11339.
37. Lu B.C., Sakaguchi K. An endo-exonuclease from meiotic tissues of the basidiomycete Coprinus cinereus: its purification and characterization. J. Biol. Chem. 266:1991;21060-21066.
38. Kim N.W., Piatyszek M.A., Prowse K.R., Haley C.B., West M.D., Ho P.L.C., Coviello G.M., Wright W.E., Weinrich S.L., Shay J.W. Specific association of human telomerase activity with immortal cells and cancer. Science. 266:1994;2011-2015.
39. Ueno T., Takahashi H., Oda M., Mizunuma M., Yokoyama A., Goto Y., Mizushina Y., Sakaguchi K., Hayashi H. Inhibition of human telomerase by rubromycins: implication of spiroketal system of the compounds as an active moiety. Biochemistry. 39:2000;5995-6002.
40. Mizushina Y., Iida A., Ohta K., Sugawara F., Sakaguchi K. Novel triterpenoids inhibit both DNA polymerase and DNA topoisomerase. Biochem. J. 350:2000;757-763.
41. Burgers P.M., Koonin E.V., Bruford E., Blanco L., Burtis K.C., Christman M.F., Copeland W.C., Friedberg E.C., Hanaoka F., Hinkle D.C., Lawrence C.W., Nakanishi M., Ohmori H., Prakash L., Prakash S., Reynaud C.A., Sugino A., Todo T., Wang Z., Weill J.C., Woodgate R. Eukaryotic DNA polymerases: proposal for a revised nomenclature. J. Biol. Chem. 276:2001;43487-43490.
42. Kimura S., Uchiyama Y., Kasai N., Namekawa S., Saotome A., Ueda T., Ando T., Ishibashi T., Oshige M., Furukawa T., Yamamoto T., Hashimoto J., Sakaguchi K. 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.
43. Delarue M., Poch O., Tordo N., Moras D., Argos P. An attempt to unify the structure of polymerases. Protein Eng. 3:1990;461-467.
44. Wang T.S. Eukaryotic DNA polymerases. Annu. Rev. Biochem. 60:1991;513-552.
45. Clayton D.A. Mitochondrial DNA replication. DePamphilis M.L. DNA Replication in Eukaryotic Cells. 1996;1015-1027 Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
46. Lindahl T., Satoh M.S., Dianov G. Enzymes acting at strand interruptions in DNA. Philos. Trans. R. Soc. Lond. B. Biol. Sci. 347:1995;57-62.
47. Sobol R.W., Horton J.K., Kuhn R., Gu H., Singhal R.K., Prasad R., Rajewsky K., Wilson S.H. Requirement of mammalian DNA polymerase-β in base-excision repair. Nature. 379:1996;183-186.
48. Lindahl T., Karran P., Wood R.D. DNA excision repair pathways. Curr. Opin. Genet. Dev. 7:1997;158-169.
49. Matsumoto Y., Sahara H., Fujita T., Hanashima S., Yamazaki T., Takahashi S., Sugawara F., Mizushina Y., Ohta K., Takahashi N., Jimbow K., Sakaguchi K., Sato N. A novel immunosuppressive agent, SQDG, derived from sea urchin. Transplant. Proc. 32:2000;2051-2053.
50. Sahara H., Hanashima S., Yamazaki T., Takahashi S., Sugawara F., Ohtani S., Ishikawa M., Mizushina Y., Ohta K., Shimozawa K., Gasa S., Jimbow K., Sakaguchi K., Sato N., Takahashi N. Anti-tumor effect of chemically synthesized sulfolipids based on sea urchin's natural sulfonoquinovosylmonoacylglycerols. Jpn. J. Cancer Res. 93:2002;85-92.
51. Matsumoto Y., Sahara H., Fujita T., Shimozawa K., Takenouchi M., Torigoe T., Hanashima S., Yamazaki T., Takahashi S., Sugawara F., Mizushina Y., Ohta K., Takahashi N., Gasa S., Jimbow K., Sakaguchi K., Sato N. An immunosuppressive effect by synthetic sulfonolipids deduced from sulfonoquinovosyl diacylglycerols of sea urchin. Transplantation. 74:2002;261-267.