Monoacetylcurcumin: A new inhibitor of eukaryotic DNA polymerase λ and a new ligand for inhibitor-affinity chromatography

Biochemical and Biophysical Research Communications

Volumn 337, Issue 4, 2005, Pages 1288-1295

  Mizushina, Yoshiyuki ^a   Ishidoh, Tomomi ^a   Takeuchi, Toshifumi ^b   Shimazaki, Noriko ^b   Koiwai, Osamu ^b   Kuramochi, Kouji ^b   Kobayashi, Susumu ^b   Sugawara, Fumio ^b   Sakaguchi, Kengo ^b   Yoshida, Hiromi ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Affinity column chromatography; Curcumin; DNA polymerase ; Enzyme inhibitor; Monoacetylcurcumin

Indexed keywords

ACETYLCURCUMIN; CURCUMIN; DNA NUCLEOTIDYLEXOTRANSFERASE; DNA POLYMERASE; DNA PRIMASE; ENZYME INHIBITOR; PANCREATIC RIBONUCLEASE; POL PROTEIN; POLYNUCLEOTIDE 5' HYDROXYL KINASE; RNA DIRECTED DNA POLYMERASE; RNA POLYMERASE; SEPHAROSE; TELOMERASE; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN MOTIF;

ANIMALS; CATTLE; CHROMATOGRAPHY, AFFINITY; CURCUMIN; DNA POLYMERASE BETA; DROSOPHILA MELANOGASTER; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; ISOENZYMES; KINETICS; LIGANDS; MOLECULAR STRUCTURE; RATS;

BOVINAE; EUKARYOTA; HUMAN IMMUNODEFICIENCY VIRUS 1; MAMMALIA; PROKARYOTA;

EID: 27144540442     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2005.10.005     Document Type: Article

References (37)

1. K. Bebenek, T.A. Kunkel, in: W. Yang, (Ed.), DNA Repair and Replication, Advances in Protein Chemistry, Elsevier, San Diego, vol. 69, 2004, pp. 137-165.
2. U. Hubscher, G. Maga, and S. Spadari Eukaryotic DNA polymerases Annu. Rev. Biochem. 71 2002 133 163
3. 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
4. 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
5. 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
6. Y. Mizushina, S. Kamisuki, T. Mizuno, M. Takemura, H. Asahara, S. Linn, T. Yamaguchi, A. Matsukage, F. Hanaoka, S. Yoshida, M. Saneyoshi, F. Sugawara, and K. Sakaguchi Dehydroaltenusin, a mammalian DNA polymerase α inhibitor J. Biol. Chem. 275 2000 33957 33961
7. 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
8. Y. Mizushina, S. Kamisuki, N. Kasai, N. Shimazaki, M. Takemura, H. Asahara, S. Linn, S. Yoshida, A. Matsukage, O. Koiwai, F. Sugawara, H. Yoshida, and K. Sakaguchi A plant phytotoxin, solanapyrone A, is an inhibitor of DNA polymerase β and λ J. Biol. Chem. 277 2002 630 638
9. Y. Mizushina, S. Kamisuki, N. Kasai, T. Ishidoh, N. Shimazaki, M. Takemura, H. Asahara, S. Linn, S. Yoshida, O. Koiwai, F. Sugawara, H. Yoshida, and K. Sakaguchi Petasiphenol: a DNA polymerase λ inhibitor Biochemistry 41 2002 14463 14471
10. Y. Mizushina, X. Xu, H. Asahara, R. Takeuchi, M. Oshige, N. Shimazaki, M. Takemura, T. Yamaguchi, K. Kuroda, S. Linn, H. Yoshida, O. Koiwai, M. Saneyoshi, F. Sugawara, and K. Sakaguchi A sulphoquinovosyl diacylglycerol is a DNA polymerase ε inhibitor Biochem. J. 370 2003 299 305
11. 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
12. 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
13. M. Garcia-Diaz, O. Dominguez, L.A. Lopez-Fernandez, L.T. de Lera, M.L. Saniger, J.F. Ruiz, M. Parraga, M.J. Garcia-Ortiz, T. Kirchhoff, J. del Mazo, A. Bernad, and L. Blanco DNA polymerase λ (Pol λ), a novel eukaryotic DNA polymerase with a potential role in meiosis J. Mol. Biol. 301 2000 851 867
14. P. Bork, K. Hofmann, P. Bucher, A.F. Neuwald, S.F. Altschul, and E.V. Koonin A superfamily of conserved domains in DNA damage-responsive cell cycle checkpoint proteins FASEB J. 11 1997 68 76
15. M. Garcia-Diaz, K. Bebenek, J.M. Krahn, T.A. Kunkel, and L.C. Pedersen A closed conformation for the Pol λ catalytic cycle Nat. Struct. Mol. Biol. 12 2005 97 98
16. P.J. Roughley, and D.A. Whiting Experiments in the biosynthesis of curcumin J. Chem. Soc. Perkin Trans. 1 1973 2379 2388
17. 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
18. 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
19. 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
20. 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
21. 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
22. 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
23. 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 2002 639 651
24. M. Tomikawa, K. Seno, C. Sato-Kiyotaki, T. Ohtsuki, T. Hirai, T. Yamaguchi, T. Kawaguchi, S. Yoshida, and M. Saneyoshi 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 Nucleosides Nucleotides 17 1998 487 501
25. N. Aoyagi, F. Matsuoka, A. Furunobu, A. Matsukage, and K. Sakaguchi Drosophila DNA polymerase δ: purification and characterization J. Biol. Chem. 269 1994 6045 6050
26. N. Aoyagi, M. Oshige, F. Hirose, K. Kuroda, A. Matsukage, and K. Sakaguchi DNA polymerase ε from Drosophila melanogaster Biochem. Biophys. Res. Commun. 230 1997 297 301
27. 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
28. K.T. Koizumi, T. Murate, M. Suzuki, C.G. Simbulan, M. Nakagawa, M. Takamura, 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 1997 1179 1189
29. 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
30. D.A. Soltis, and O.C. Uhlenbeck Isolation and characterization of two mutant forms of T4 polynucleotide kinase J. Biol. Chem. 257 1982 11332 11339
31. 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
32. N.W. Kim, M.A. Piatyszek, K.R. Prowse, C.B. Harley, M.D. West, P.L. Ho, G.M. Coviello, W.E. Wright, S.L. Weinrich, and J.W. Shay Specific association of human telomerase activity with immortal cells and cancer Science 266 1994 2011 2015
33. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248 254
34. R. Takada-Takayama, S. Tada, F. Hanaoka, and M. Ui Peptide mapping of the four subunits of the mouse DNA polymerase α-primase complex Biochem. Biophys. Res. Commun. 170 1990 589 595
35. C. Murakami-Nakai, N. Maeda, Y. Yonezawa, I. Kuriyama, S. Kamisuki, S. Takahashi, F. Sugawara, H. Yoshida, K. Sakaguchi, and Y. Mizushina The effects of dehydroaltenusin, a novel mammalian DNA polymerase α inhibitor, on cell proliferation and cell cycle progression Biochim. Biophys. Acta 1674 2004 193 199
36. R.A. Sharma, A.J. Gescher, and W.P. Steward Curcumin: the story so far Eur. J. Cancer 41 2005 1955 1968
37. C.H. Park, J.H. Lee, and C.H. Yang Curcumin derivatives inhibit the formation of Jun-Fos-DNA complex independently of their conserved cysteine residues J. Biochem. Mol. Biol. 38 2005 474 480