β-Sitosterol-3-O-β-d-glucopyranoside: A eukaryotic DNA polymerase λ inhibitor

Journal of Steroid Biochemistry and Molecular Biology

Volumn 99, Issue 2-3, 2006, Pages 100-107

  Mizushina, Yoshiyuki ^a   Nakanishi, Rumi ^a   Kuriyama, Isoko ^a   Kamiya, Kohei ^a   Satake, Toshiko ^a   Shimazaki, Noriko ^b   Koiwai, Osamu ^b   Uchiyama, Yukinobu ^b   Yonezawa, Yuko ^a   Takemura, Masaharu ^c   Sakaguchi, Kengo ^b   Yoshida, Hiromi ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c MIE UNIVERSITY   (Japan)

Author keywords

Sitosterol 3 O d glucopyranoside; DNA polymerase ; Enzyme inhibitor; Proline rich region; Steroidal glycoside

Indexed keywords

DNA DIRECTED DNA POLYMERASE ALPHA; DNA DIRECTED DNA POLYMERASE DELTA; DNA DIRECTED DNA POLYMERASE EPSILON; DNA POLYMERASE; DNA POLYMERASE LAMBDA; GLUCOSE; GLYCOSIDE; NUCLEOTIDYLTRANSFERASE INHIBITOR; PARATHION; PRIMER DNA; SITOGLUSIDE; SITOSTEROL; UNCLASSIFIED DRUG; DNA DIRECTED DNA POLYMERASE BETA; DNA POLYMERASE BETA2; ENZYME INHIBITOR; GLUCOSIDE; PEPTIDE FRAGMENT; SITOSTEROL 3 O GLUCOPYRANOSIDE; SITOSTEROL DERIVATIVE; SITOSTEROL-3-O-GLUCOPYRANOSIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; DNA TEMPLATE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME STRUCTURE; ENZYME SUBSTRATE; MAMMAL; ONION; ANIMAL; BINDING SITE; CATALYSIS; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DROSOPHILA MELANOGASTER; DRUG ANTAGONISM; ENZYMOLOGY; EUKARYOTIC CELL; GENETICS; HUMAN; ISOLATION AND PURIFICATION; KINETICS; MUTATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; STRUCTURE ACTIVITY RELATION;

ALLIUM CEPA; EUKARYOTA; MAMMALIA;

ANIMALS; BINDING SITES; CATALYSIS; CATTLE; DNA POLYMERASE BETA; DOSE-RESPONSE RELATIONSHIP, DRUG; DROSOPHILA MELANOGASTER; ENZYME INHIBITORS; EUKARYOTIC CELLS; GLUCOSE; GLUCOSIDES; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MUTATION; ONIONS; PEPTIDE FRAGMENTS; RATS; SITOSTEROLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33745727524     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2005.12.007     Document Type: Article

References (35)

1. Bebenek K., and Kunkel T.A. In: Yang W. (Ed). DNA Repair and Replication, Advances in Protein Chem vol. 69 (2004), Elsevier, San Diego 137-165
2. Friedberg E.C., Feaver W.J., and Gerlach V.L. The many faces of DNA polymerases: strategies for mutagenesis and for mutational avoidance. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 5681-5683
3. Mizushina Y., Tanaka N., Yagi H., Kurosawa T., Onoue M., Seto H., Horie T., Aoyagi N., Yamaoka M., Matsukage A., Yoshida S., and 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., and Sakaguchi K. The inhibitory action of fatty acids on DNA polymerase β. Biochim. Biophys. Acta 1336 (1997) 509-521
5. Mizushina Y., Takahashi N., Ogawa A., Tsurugaya K., Koshino H., Takemura M., Yoshida S., Matsukage A., Sugawara F., and Sakaguchi K. The cyanogenic glucoside, prunasin (d-mandelonitrile-β-d-glucoside), is a novel inhibitor of DNA polymerase β. J. Biochem. (Tokyo) 126 (1999) 430-436
6. Mizushina Y., Kamisuki S., Mizuno T., Takemura M., Asahara H., Linn S., Yamaguchi T., Matsukage A., Hanaoka F., Yoshida S., Saneyoshi M., Sugawara F., and Sakaguchi K. Dehydroaltenusin, a mammalian DNA polymerase α inhibitor. J. Biol. Chem. 275 (2000) 33957-33961
7. Mizushina Y., Kamisuki S., Kasai N., Shimazaki N., Takemura M., Asahara H., Linn S., Yoshida S., Matsukage A., Koiwai O., Sugawara F., Yoshida H., and Sakaguchi K. A plant phytotoxin, solanapyrone A, is an inhibitor of DNA polymerase β and λ. J. Biol. Chem. 277 (2002) 630-638
8. Mizushina Y., Xu X., Asahara H., Takeuchi R., Oshige M., Shimazaki N., Takemura M., Yamaguchi T., Kuroda K., Linn S., Yoshida H., Koiwai O., Saneyoshi M., Sugawara F., and Sakaguchi K. A sulphoquinovosyl diacylglycerol is a DNA polymerase ε inhibitor. Biochem. J. 370 (2003) 299-305
9. Mizushina Y., Kasai N., Miura K., Hanashima S., Takemura M., Yoshida H., Sugawara F., and Sakaguchi K. Structural relationship of lithocholic acid derivatives binding to the N-terminal 8-kDa domain of DNA polymerase β. Biochemistry 41 (2004) 10669-10677
10. Kuriyama I., Asano N., Kato I., Ikeda K., Takemura M., Yoshida H., Sakaguchi K., and Mizushina Y. Dipeptide alcohol-based inhibitors of eukaryotic DNA polymerase α. Bioorg. Med. Chem. 13 (2005) 2187-2196
11. Garcia-Diaz M., Dominguez O., Lopez-Fernandez L.A., de Lera L.T., Saniger M.L., Ruiz J.F., Parraga M., Garcia-Ortiz M.J., Kirchhoff T., del Mazo J., Bernad A., and Blanco L. DNA polymerase λ (Pol λ), a novel eukaryotic DNA polymerase with a potential role in meiosis. J. Mol. Biol. 301 (2000) 851-867
12. Bork P., Hofmann K., Bucher P., Neuwald A.F., Altschul S.F., and Koonin E.V. A superfamily of conserved domains in DNA damage-responsive cell cycle checkpoint proteins. FASEB J. 11 (1997) 68-76
13. Tamai K., Kojima K., Hanaichi T., Masaki S., Suzuki M., Umekawa H., and Yoshida S. Structural study of immunoaffinity-purified DNA polymerase α-DNA primase complex from calf thymus. Biochim. Biophys. Acta 950 (1988) 263-273
14. Date T., Yamaguchi M., Hirose F., Nishimoto Y., Tanihara K., and Matsukage A. Expression of active rat DNA polymerase β in Escherichia coli. Biochemistry 27 (1988) 2983-2990
15. Oshige M., Takeuchi R., Ruike R., Kuroda K., and Sakaguchi K. Subunit protein-affinity isolation of Drosophila DNA polymerase catalytic subunit. Protein Expr. Purif. 35 (2004) 248-256
16. Shimazaki N., Yoshida K., Kobayashi T., Toji S., Tamai T., and Koiwai O. Over-expression of human DNA polymerase λ in E. coli and characterization of the recombinant enzyme. Genes Cells 7 (2002) 639-651
17. Tomikawa A., Seno M., Sato-Kiyotaki K., Ohtsuki C., Hirai T., Yamaguchi T., Kawaguchi T., Yoshida S., and Saneyoshi M. Synthetic nucleosides and nucleotides. 40. Selective inhibition of eukaryotic DNA polymerase a by 9-(β-d-arabinofuranosyl)-2-(p-n-butylanilino) adenine 5′-triphosphate (BuAaraATP) and its 2′-up azido analog: synthesis and enzymatic evaluations. Nucleos. Nucleot. 17 (1998) 487-501
18. Aoyagi N., Matsuoka S., Furunobu A., Matsukage A., and Sakaguchi K. Drosophila DNA polymerase δ: purification and characterization. J. Biol. Chem. 269 (1994) 6045-6050
19. Aoyagi N., Oshige M., Hirose F., Kuroda K., Matsukage A., and Sakaguchi K. DNA polymerase ε from Drosophila melanogaster. Biochem. Biophys. Res. Commun. 230 (1997) 297-301
20. Sakaguchi K., Hotta Y., and Stern H. Chromatin-associated DNA polymerase activity in meiotic cells of lily and mouse. Cell Struct. Funct. 5 (1980) 323-334
21. Uchiyama Y., Kimura S., Yamamoto T., Ishibashi T., and Sakaguchi K. Plant DNA polymerase λ, a DNA repair enzyme that functions in plant meristematic and meiotic tissues. Eur. J. Biochem. 271 (2004) 2799-2807
22. Ogawa A., Murate T., Suzuki M., Nimura Y., and Yoshida S. Lithocholic acid, a putative tumor promoter, inhibits mammalian DNA polymerase β. Jpn. J. Cancer Res. 89 (1998) 1154-1159
23. Tamiya-Koizumi K., Murate T., Suzuki M., Simbulan C.G., Nakagawa M., Takemura M., Furuta K., Izuta S., and 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
24. Nakayama C., and Saneyoshi M. 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
25. Soltis D.A., and Uhlenbeck O.C. Isolation and characterization of two mutant forms of T4 polynucleotide kinase. J. Biol. Chem. 257 (1982) 11332-11339
26. Lu B.C., and Sakaguchi K. An endo-exonuclease from meiotic tissues of the basidiomycete Coprinus cinereus: its purification and characterization. J. Biol. Chem. 266 (1991) 21060-21066
27. Aoufouchi S., Flatter E., Dahan A., Faili A., Bertocci B., Storck S., Delbos F., Cocea L., Gupta N., Weill J.C., and Reynaud C.A. Two novel human and mouse DNA polymerases of the polX family. Nucleic Acids Res. 28 (2000) 3684-3693
28. Nagasawa K., Kitamura K., Yasui A., Nimura Y., Ikeda K., Hirai M., Matsukage M., and Nakanishi M. Identification and characterization of human DNA polymerase β 2, a DNA polymerase β-related enzyme. J. Biol. Chem. 275 (2000) 31233-31238
29. Ito J., and Braithwaite D.K. Compilation and alignment of DNA polymerase sequences. Nucleic Acids Res. 19 (1991) 4045-4057
30. Braithwaite D.K., and Ito J. Compilation, alignment, and phylogenetic relationships of DNA polymerases. Nucleic Acids Res. 21 (1993) 787-802
31. Dominguez O., Ruiz J.F., Lain de Lera T., Garcia-Diaz M., Gonzalez M.A., Kirchhoff T., Martinez A.C., Bernad A., and Blanco L. DNA polymerase mu (Pol μ), homologous to TdT, could act as a DNA mutator in eukaryotic cells. EMBO J. 19 (2000) 1731-1742
32. Oliver S.G., van der Aart Q.J., Agostoni-Carbone M.L., Aigle M., Alberghina L., Alexandraki D., Antoine G., Anwar R., Ballesta J.P., Benit P., et al. The complete DNA sequence of yeast chromosome III. Nature 357 (1992) 38-46
33. Bork P., Ouzounis C., Sander C., Scharf M., Schneider R., and Sonnhammer E. Comprehensive sequence analysis of the 182 predicted open reading frames of yeast chromosome III. Protein Sci. 1 (1992) 1677-1690
34. Oliveros M., Yanez R.J., Salas M.L., Salas J., Vinuela E., and Blanco L. Characterization of an African swine fever virus 20-kDa DNA polymerase involved in DNA repair. J. Biol. Chem. 272 (1997) 30899-30910
35. Taladriz S., Hanke T., Ramiro M.J., Garcia-Diaz M., Garcia De Lacoba M., Blanco L., and Larraga V. Nuclear DNA polymerase β from Leishmania infantum: cloning, molecular analysis and developmental regulation. Nucleic Acids Res. 29 (2001) 3822-3834