Chemical properties of fatty acid derivatives as inhibitors of DNA polymerases

Organic and Biomolecular Chemistry

Volumn 5, Issue 24, 2007, Pages 3912-3921

  Nakamura, Ryoichi ^a   Takeuchi, Ryo ^a   Kuramochi, Kouji ^a   Mizushina, Yoshiyuki ^b   Ishimaru, Chisato ^b   Takakusagi, Yoichi ^a   Takemura, Masaharu ^a   Kobayashi, Susumu ^a   Yoshida, Hiromi ^b   Sugawara, Fumio ^a   Sakaguchi, Kengo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; DERIVATIVES; DNA; ENZYME ACTIVITY; ENZYME INHIBITION;

MONOPROTIC ACIDS; PERFLUOROOCTADECANOIC ACID; POLYMERASE ACTIVITY;

FATTY ACIDS;

EID: 36749034742     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b710944j     Document Type: Article

References (65)

1. U. Hübscher G. Maga S. Spadari Eukaryotic DNA polymerases Annu. Rev. Biochem. 2002 71 133 163
2. K. Benek T. A. Kunkel Functions of DNA polymerases Adv. Protein Chem. 2004 69 137 165
3. L. A. Loeb S. S. Agarwal D. K. Dube K. P. Gopinathan E. C. Travaglini G. Seal M. A. Sirover Inhibitors of mammalian DNA polymerases: possible chemotherapeutic approaches Pharmacol. Ther., Part A: 1977 2 171 193
4. S. Miura S. Izuta DNA polymerases as targets of anti-cancer nucleotides Curr. Drug Targets 2004 5 191 195
5. Y. Mizushina N. Kasai H. Iijima F. Sugawara H. Yoshida K. Sakaguchi Sulfo-quinovosyl-acyl-glycerol (SQAG), a eukaryotic DNA polymerase inhibitor and anticancer agent Curr. Med. Chem.: Anti-Cancer Agents 2005 5 613 625
6. M. R. Albertella A. Lau M. J. O'Connor The overexpression of specialized DNA polymerases in cancer DNA Repair 2005 4 583 592
7. 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 K. Sakaguchi J. Antibiot. 1996 49 491 492
8. Y. Mizushina N. Tanaka H. Yagi T. Kurosawa M. Onoue H. Seto T. Horie N. Aoyagi M. Yamaoka A. Matsukage S. Yoshida K. Sakaguchi Fatty acids selectively inhibit eukaryotic DNA polymerase activities in vitro Biochim. Biophys. Acta 1996 1308 256 262
9. Y. Mizushina S. Yoshida A. Matsukage K. Sakaguchi The inhibitory action of fatty acids on DNA polymerase β Biochim. Biophys. Acta 1997 1336 509 521
10. Y. Mizushina T. Ohkubo T. Date T. Yamaguchi M. Saneyoshi F. Sugawara 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. 1999 274 25599 25607
11. Y. Mizushina F. Sugawara A. Iida K. Sakaguchi Structural homology between DNA binding sites of DNA polymerase β and DNA topoisomerase II J. Mol. Biol. 2000 304 385 395
12. M. Oda T. Ueno N. Kasai H. Takahashi H. Yoshida H. Sugawara K. Sakaguchi H. Hayashi Y. Mizushina Inhibition of telomerase by linear-chain fatty acids: a structural analysis Biochem. J. 2002 367 329 334
13. N. Kasai Y. Mizushina F. Sugawara K. Sakaguchi Three-dimensional structural mode analysis of the binding site of an inhibitor, nervonic acid, of both DNA polymerase β and HIV-1 reverse transcriptase J. Biochem. 2002 132 819 828
14. J. Giesy K. Kannan Perfluorochemical surfactants in the environment Environ. Sci. Technol. 2002 36 146A 152A
15. K. Prevedouros I. T. Cousins R. C. Buck S. H. Korzeniowski Sources, fate and transport of perfluorocarboxylates Environ. Sci. Technol. 2006 40 32 44
16. J. Verreault M. Houde G. W. Gabrielsen U. Berger M. Haukas R. J. Letcher D. C. G. Muir Perfluorinated alkyl substances in plasma, liver, brain and eggs of glaucous gulls (Larus hyperboreus) from the Norwegian Arctic Environ. Sci. Technol. 2005 39 7439 7445
17. C. Lau J. L. Butenhoff J. M. Rogers The developmental toxicity of perfluoroalkyl acids and their derivatives Toxicol. Appl. Pharmacol. 2004 198 231 241
18. CIBA Ltd., Polyglycol ethers, GB 779829 19570724, 1957
19. K. Yutaka T. Ashizawa K. Kawashima S. Ikeda T. Tamaoki Bioorg. Med. Chem. Lett. 2003 13 455 458
20. D. H. Hunter R. A. Perry Synthetic application of crown ethers; the malonic ester synthesis Synthesis 1977 37 39
21. P. Bühlmann M. Badertscher W. Simon Molecular recognition of creatinine Tetrahedron 1993 49 595 598
22. T. Kawai, M. Shimamura, K. Obata, Preparation of hydroxamic acids and elastase inhibitors containing them, Jpn. Kokai Tokkyo Koho, Appl. JP 93-345168, 1995. See also ref. 47
23. P. Geneste A. Guida C. Reminiac G. Amblard C. Gavach Transport des cations a travers des membranes lipidiques biomoleculaires par des nouveaux macrocyles di et tetraesters polyetheres hydrophobes Tetrahedron Lett. 1981 22 1397 1398
24. K. Neimert-Anderson E. Blomberg P. Somfai Stereoselective synthesis of polyhydroxyl surfactants. Stereochemical influence on Langmuir monolayers J. Org. Chem. 2004 69 3746 3752
25. S. Fürmeier J. O. Metzger Synthesis of new heterocyclic fatty compounds Eur. J. Org. Chem. 2003 885 893
26. M. Akiyama, H. Akashi, T. Shiga, T. Matsui, Y. Hayashi, T. Kimura, H. Kobayashi, Jpn. Kokai Tokkyo Koho, Appl. JP 78-76988, 1980
27. C. Fruit P. Müller Intramolecular asymmetric amidations of sulfonamides and sulfamates catalyzed by chiral dirhodium (ii) complex Helv. Chim. Acta 2004 87 1607 1615
28. S. Junno T. Okita Synthesis and structure-activity relationships of phaffiaol and related antioxidant Chem. Pharm. Bull. 1998 46 1688 1694
29. F. Bergel A. Jacob R. Todd T. S. Work Vitamin E. IV. Synthetic experiments in the coumaran and chroman series. The structure of tocopherol J. Chem. Soc. 1938 1375 1382
30. T. Kamino K. Kuramochi K. Kobayashi A concise approach to 5-substituted-4-pyrones from kojic acid Tetrahedron Lett. 2003 44 7349 7351
31. R. F. Keyes W. M. Golebiewski M. Cushman Correlation of anti-HIV potency with lipophilicity in a series of cosalane analogs having normal alkenyl and phosphodiester chains as cholestane replacements J. Med. Chem. 1996 39 508 514
32. K. Tamai T. Kojima T. Hanaichi S. Masaki M. Suzuki H. Uekawa S. Yoshida Structural study of immunoaffinity-purified DNA polymerase α-DNA primase complex from calf thymus Biochim. Biophys. Acta 1988 950 263 273
33. Y. Uchiyama J. Tagami S. Kamisuki N. Kasai M. Oshige H. Chiku S. Ibe O. Koiwai F. Sugawara K. Sakaguchi Selective inhibitors of terminal deoxyribonucleotidyltransferase (TdT): baicalin and genistin Biochim. Biophys. Acta 2005 1725 298 304
34. K. Kuramochi F. Saito R. Takeuchi T. Era M. Takemura J. Kobayashi K. Sakaguchi S. Kobayashi F. Sugawara Synthesis of plakevulin A and structure-activity relationships of its related compounds against DNA polymerases Tetrahedron 2006 62 8006 8015
35. A. F. Thüneman H. Schnablegger Monodisperse disk-shaped micelles of perfluorooctadecanoic acid Langmuir 1999 15 5426 5428
36. K. Murakami-Murofushi M. Shioda K. Kaji S. Yoshida H. Murofushi Inhibition of eukaryotic DNA polymerase α with a novel lysophosphatidic acid (PHYLPA) isolated from myxoamoebae of Physarum polycephalum J. Biol. Chem. 1992 267 21512 21517
37. Y. Takahashi Y. Shimada M. Shioda S. Yoshida H. Murofushi K. Murofushi-Murakami Isolation of a new species of Physarum lysophosphatidic acid, PHLPA, and its effect on DNA polymerase activity Cell Struct. Funct. 1993 18 135 138
38. W. Schorr H. Hoffmann Electric birefringence measurements on micellar solutions of ionic surfactants J. Phys. Chem. 1981 85 3160 3167
39. D. P. Bossev M. Matsumoto M. Nakahara 1H and 19F NMR study of the counterion effect on the micellar structures formed by tetraethylammonium and lithium perfluorooctylsulfonate. 1. Neat systems J. Phys. Chem. B 1999 103 8251 8258
40. S. Hanashima Y. Mizushina K. Ohta T. Yamazaki F. Sugawara K. Sakaguchi Structure-activity relationship of a novel group of mammalian DNA polymerase inhibitors, synthetic sulfoquinovosylacylglycerols Jpn. J. Cancer Res. 2000 91 1073 1083
41. Y. Mizushina S. Miyazaki K. Ohta M. Hirota K. Sakaguchi Novel anti-inflammatory compounds from Myrsine seguinii, terpeno-benzoic acids, are inhibitors of mammalian DNA polymerases Biochim. Biophys. Acta 2000 1475 1 4
42. F. Saito R. Takeuchi T. Kamino K. Kuramochi F. Sugawara K. Sakaguchi S. Kobayashi Structure-activity relationships of untenone A and its derivatives for inhibition of DNA polymerases Bioorg. Med. Chem. Lett. 2004 14 1975 1977
43. Y. Mizushina C. Murakami H. Takikawa N. Kasai X. Xu K. Mori M. Oshige T. Yamaguchi M. Saneyoshi N. Shimazaki O. Koiwai H. Yoshida F. Sugawara K. Sakaguchi Molecular action mode of hippospongic acid A, an inhibitor of gastrulation of starfish embryos J. Biochem. 2003 133 541 552
44. Y. Mizushina C. Murakami K. Ohta H. Takikawa M. Mori H. Yoshida F. Sugawara K. Sakaguchi Selective inhibition of the activities of both eukaryotic DNA polymerases and DNA topoisomerases by elenic acid Biochem. Pharmcol. 2002 63 399 407
45. Y. Mizushina A. Iida K. Ohta F. Sugawara K. Sakaguchi Novel triterpenoids inhibit both DNA polymerase and DNA topoisomerase Biochem. J. 2000 350 757 763
46. J. Z. Deng S. R. Starck S. M. Hecht DNA polymerase β inhibitors from Baeckea gunniana J. Nat. Prod. 1999 62 1624 1626
47. Y. Mizushina C. Murakami K. Yogi K. Ueda T. Ishidoh M. Takemura M. Perpelescu M. Suzuki M. Oshige T. Yamaguchi M. Saneyoshi H. Yoshida K. Sakaguchi Kohamaic acid A, a novel sesterterpenic acid, inhibits activities of DNA polymerases from deuterostomes Biochim. Biophys. Acta 2003 1648 56 61
48. M. Oshige K. Kuramochi K. Ohta A. Ogawa H. Kuriyama F. Sugawara S. Kobayashi K. Sakaguchi Molecular design of cholesterols as inhibitors of DNA polymerase α J. Med. Chem. 2004 47 4971 4974
49. Y. Mizushina T. Ueno M. Oda T. Yamaguchi M. Saneyoshi K. Sakaguchi The biochemical mode of inhibition of DNA polymerase β by α-rubromycin Biochim. Biophys. Acta 2000 1523 172 181
50. Y. Mizushina S. Kamisuki T. Mizuno M. Takemura H. Asahara S. Linn T. Yamaguchi A. Matsukage F. Hanaoka S. Yoshida M. Saneyoshi F. Sugawara K. Sakaguchi Dehydroaltenusin, a mammalian DNA polymerase α inhibitor J. Biol. Chem. 2000 275 33957 33961
51. Y. Mizushina S. Kamisuki N. Kasai N. Shimazaki M. Takemura H. Asahara S. Linn S. Yoshida A. Matsukage O. Koiwai F. Sugawara H. Yoshida K. Sakaguchi A plant phytotoxin, solanapyrone A, is an inhibitor of DNA polymerase β and λ J. Biol. Chem. 2002 277 630 638
52. Y. Mizushina S. Kamisuki N. Kasai T. Ishidoh N. Shimazaki M. Takemura H. Asahara S. Linn S. Yoshida O. Koiwai F. Sugawara H. Yoshida K. Sakaguchi Petasiphenol: a DNA polymerase λ inhibitor Biochemistry 2002 41 14463 14471
53. Y. Mizushina M. Hirota C. Murakami T. Ishidoh S. Kamisuki N. Shimazaki M. Takemura M. Perpelescu M. Suzuki H. Yoshida F. Sugawara O. Koiwai K. Sakaguchi Some anti-chronic inflammatory compounds are DNA polymerase λ-specific inhibitors Biochem. Pharmacol. 2003 66 1935 1944
54. Y. Mizushina L. Hanashima T. Yamaguchi M. Takemura F. Sugawara M. Saneyoshi A. Matsukage S. Yoshida K. Sakaguchi A mushroom fruiting body-inducing substance inhibits activities of replicative DNA polymerases Biochem. Biophys. Res. Commun. 1998 249 17 22
55. Y. Mizushina N. Takahashi A. Ogawa K. Tsurugaya H. Koshino M. Takemura S. Yoshida A. Matsukage F. Sugawara K. Sakaguchi The cyanogenic glucoside, prunasin (d-mandelonitrile-beta-d-glucoside), is a novel inhibitor of DNA polymerase β J. Biochem. 1999 126 430 436
56. Y. Mizushina Y. Sugiyama H. Yoshida S. Hanashima T. Yamazaki S. Kamisuki K. Ohta M. Takemura T. Yamaguchi A. Matsukage S. Yoshida M. Saneyoshi F. Sugawara K. Sakaguchi Galactosyldiacylglycerol, a mammalian DNA polymerase α-specific inhibitor from a sea alga, Petalonia bingbamiae Biol. Pharm. Bull. 2001 24 982 987
57. Y. Mizushina N. Tanaka A. Kitamura K. Tamai M. Ikeda M. Takemura F. Sugawara T. Arai A. Matsukage S. Yoshida K. Sakaguchi The inhibitory effect of novel triterpenoid compounds, fomitellic acids, on DNA polymerase β Biochem. J. 1998 330 1325 1332
58. N. Tanaka A. Kitamura Y. Mizushina F. Sugawara K. Sakaguchi Fomitellic acids, triterpenoid inhibitors of eukaryotic DNA polymerases from a basidiomycete, Fomitella fraxinea J. Nat. Prod. 1998 61 193 197
59. Y. Mizushina T. Ohkubo F. Sugawara K. Sakaguchi Structure of lithocholic acid binding to the N-terminal 8 kDa domain of DNA polymerase β Biochemistry 2000 39 12606 12613
60. Y. Mizushina N. Kasai F. Sugawara A. Iida H. Yoshida 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. 2001 130 657 664
61. Y. Mizushina N. Kasai K. Miura S. Hanashima M. Takemura H. Yoshida F. Sugawara K. Sakaguchi Structural relationship of lithocholic acid derivatives binding to the N-terminal 8 kDa domain of DNA polymerase β Biochemistry 2004 43 10669 10677
62. C. Murakami M. Takemura Y. Sugiyama S. Kamisuki H. Asahara M. Kawasaki T. Ishidoh S. Linn S. Yoshida F. Sugawra H. Yoshida K. Sakaguchi Y. Mizushina Vitamin A-related compounds, all-trans retinal and retinoic acids, selectively inhibit activities of mammalian replicative DNA polymerases Biochim. Biophys. Acta 2002 1574 85 92
63. C. Murakami K. Ishijima M. Hirota K. Sakaguchi S. Yoshida Y. Mizushina Novel anti-inflammatory compounds from Rubus sieboldii, triterpenoids, are inhibitors of mammalian DNA polymerases Biochim. Biophys. Acta 2002 1596 193 200
64. A. Kumar S. G. Widen K. R. Williams P. Kedar R. L. Karpel S. H. Wilson Studies of the domain structure of mammalian DNA polymerase β. Identification of a discrete template binding domain J. Biol. Chem. 1990 265 2124 2134
65. A. Kumar J. Abbotts E. M. Karawya S. H. Wilson Identification and properties of the catalytic domain of mammalian DNA polymerase β Biochemistry 1990 29 7156 7159