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1993 | 40 | 3 |

Tytuł artykułu

Specifity of thymidylate synthase inactivation by 4,5-bisubstituted dUMP analogues

Autorzy

Warianty tytułu

Języki publikacji

EN

Abstrakty

Słowa kluczowe

Wydawca

-

Rocznik

Tom

40

Numer

3

Opis fizyczny

p.363-368,fig.

Twórcy

autor
  • Nencki Institute of Experimental Biology, Pasteura 3, 02-093 Warszawa, Poland

Bibliografia

  • 1. Santi, D.V. & Danenberg, P.V. (1984) Folates in pyrimidine nucleotide biosynthesis; in Folates and Pterines (Blakley, R. L. & Benkovic, S. J., eds.) vol. 1, pp 345 - 398, Wiley, New York.
  • 2. Rode, W. (1986) Thymidylate biosynthesis: biological role and regulation in animal cells. Post. Biochem. 32,401 - 420.
  • 3. Danenberg, P.V. (1977) Thymidylate synthetase - a target enzyme in cancer chemotherapy. Biochim. Biophys. Acta 473,73 - 92.
  • 4. Heidelberger, C, Danenberg, P.V. & Moran, R.G. (1983) Fluorinated pyrimidines and their nucleosides. Adv. Enzymol. 54,57-119.
  • 5. Jackman, A.L., Jones, T.R. & Calvert, A .H. (1985) Thymidylate synthetase inhibitors: experimen­tal and clinical aspects; in Experimetital and Clinical Progress in Cancer Chemotherapy (Muggia, F.M., ed.) pp. 155 - 210, Martinus Nijhoff Publishers, Boston.
  • 6. Douglas, K.T. (1987) The thymidylate synthesis cycle and anticancer drugs. Med. Res. Rev. 7,441 -475.
  • 7. Rathod, P.K., Leffers, N.P. & Young, R.D. (1992) Molecular targets of 5-fluoroorotate in the human malaria parasite, Plasmodium-falcipa- rum. Antimicrob. Agents Chemother. 36,704 - 711.
  • 8. Heidelberger, C., Kaldor, G., Mukherjee, K.L. & Danncberg, P.B. (1960) Studies on fluorinated pyrimidines. XI. In vitro studies on tumor resistance. Cancer Res. 20,903 - 909.
  • 9. Bapat, A.R., Zarow, C. & Danenberg, P.V. (1983) Human leukemic cells resistant to 5-fluoro- -2'-deoxyuridine contain a thymidylate synthe­tase with lower affinity for nucleotides. J. Biol. Chem. 258,4130 - 4136.
  • 10. Jastreboff, M.M., Kedzierska, B. & Rode, W. (1983) Altered thymidylate synthetase in 5-fluorodeoxyuridine-resistant Ehrlich ascites carcinoma cells. Biochem. Pharmacol. 32, 2259 - 2267.
  • 11. Berger, S.H., Barbour, K.W. & Berber, F.G. (1988) A naturally occurring variation in thymidylate synthase structure is associated with a reduced response to 5-fluoro-2'-deoxyuridine in a human colon tumor cell line. Mol. Pharmacol. 34, 480 - 484.
  • 12. Zieliński, Z., Dzik, J.M., Rode, W., Kulikowski, T., Bretner, M., Kierdaszuk, B. & Shugar, D. (1990) Pteridines and folic acid derivatives; in Chemistry and Biology of Pteridines 1989 (Curtius, H.-Ch., Ghisla, S. & Blau, N., eds.) pp. 817 - 820, Walter de Gruyter.
  • 13. De Clercq, E., Balzarini, J., Torrence, P.F., Mertes, M.P., Schmidt, L.C., Shugar, D., Barr, P.J., Jones, A.S., Verhelst, G. & Walker, R.T. (1981) Thymidylate synthetase as target enzyme for the inhibitory activity of 5-substituted 2'-deo- xyuridines on mouse leukemia L1210 cell growth. Mol. Pharmacol. 19,321 - 330.
  • 14. Balzarini, J., Dc Clercq, E., Mertes, M.P., Shugar, D. & Torrence, P.F. (1982) 5-Substituted 2'-deo- xyuridines: correlation between inhibition of tumor cell growth and inhibition of thymidine kinase and thymidylate synthetase. Biochem. Pharmacol. 31,3673 - 3682.
  • 15. Rode, W., Zieliński, Z., Dzik, J.M., Kulikowski, T., Bretner, M., Kierdaszuk, B., Cieśla, J. & Shugar, D. (1990) Mechanism of inhibition of mammalian tumor and other thymidylate synthases by A^-hydroxy-dCMP, AT-hydroxy- -5-fluoro-dCMP, and related analogues. Biochemistry 29,10835 - 10842.
  • 16. Dzik, J.M., Zieliński, Z., Cieśla, J., Rode, W., Bretner, M., Kulikowski, T. & Shugar, D. (1993) Interaction with 2(4)-thio-5-fluoro-dUMP of thymidylate synthases with differing sensitivi­ties to 5-fluoro-dUMP; in Chemistry and Biology of Pteridines and Folates (Ayling, J.E., Nair, M.G. & Baugh, C.M., eds.) pp. 617 - 620, Plenum Publishing Corp.
  • 17. Kalman, T.I., Bloch, A., Szekenes, G.L. & Bardos, T.J. (1973) Methylation of 4-thio-2'-deoxyuri- dylate by thymidylate synthetase. Biochem. Biophys. Res. Commun. 55,210 - 217.
  • 18. Leś, A., Adamowicz, L. & Rode, W. (1993) Structure and conformation of N^hydroxycyto- sine and N^hydroxy-S-fluorocytosine. A theoretical ab initio study. Biochim. Biophys. Acta 1173,39 - 48.
  • 19. Leś, A., Adamowicz, L. & Rode, W. (1993) Mechanism of thymidylate synthase inhibition by N^hydroxy-iW^-hydroxy-S-fluoroJ-dCMP in view of the structure and conformation of N4-hydroxy-(N4-hydroxy-5-fluoro)-cytosine calculated by the ah initio quantum mechanical methods; in Chemistry and Biology of Pteridineand Folates (Ayling, J.E., Nair, M.C. & Baugh, C.M., eds.) Plenum Publishing Corp., in press.
  • 20. Hardy, L.W. & Nalivaika, E. (1992) Asn (177) in Escherichia-coli thymidylate synthase is a major determinant of pyrimidine specificity. Proc. Natl. Acad. Sci. U.S.A. 89,9725 - 9729.
  • 21. Liu, L. & Santi, D.V. (1992) Mutation of asparagine 229 to aspartate in thymidylate synthase converts the enzyme to a deoxycytidylate methylase. Biochemistry 31, 5100 - 5104.
  • 22. Matthews, D.A., Villafranca, J.E., Janson, C.A., Smith, W.W., Welsh, K. & Freer, S. (1990) Stereochemical mechanism of action for thymidylate synthase based on the X-ray structure of the covalent inhibitory ternary complex with 5-fluoro-2'-deoxyuridylate and 5,10-methylenetetrahydrofolate. J. Mol. Biol. 214,937-948.
  • 23. Dzik, J.M., Kulikowski, T., Zieliński, Z., Cieśla, J., Rode, W. & Shugar, D. (1987) Interaction of 5-fluoro-4-thio-2/-deoxyuridine 5'-phosphate with mammalian tumour thymidylate synthase: role of the pyrimidine N(3)-H dissociation. Biochern. Biophys. Res. Commun. 149,1200-1207.
  • 24. Bretner, M., Kulikowski,T., Dzik,J.M., Balińska, M., Rode, W. & Shugar, D. (1993) 2-Thio-deri- vatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumour thymidylate synthase and in vitro antitumour activity. /. Med. Chetti., in press.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

bwmeta1.element.agro-article-74bb7f7b-b2b4-4260-a08a-9be6b4c3e781
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