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1998 | 45 | 1 |

Tytuł artykułu

Unusual nucleoside triphosphate donors for nucleoside kinases: 3'-deoxyadenosine-2'-triphosphate and 2'-deoxyadenosine-3'-triphosphate

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Two non-conventional analogues of ATP, 3'-deoxyadenosine-2'-triphosphate (3'-d-2'-ATP) and 2'-deoxyadenosine-3'-triphosphate (2'-d-3'-ATP), the syntheses of which are described, were examined as potential phosphate donors for the nucleoside kinases: 2'-deoxycytidine kinase (dCK), cytosolic thymidine kinase (TK1) and mitochondrial thymidine kinase (TK2). The reactions were monitored by means of a mixture of [γ-32P]ATP and cold analogue, andór with the use of 3H-labelled acceptors and cold donor. With dCK, using equimolar mixtures of ATP with each analogue, and dC as acceptor, phosphate transfer from 3'-d-2'-ATP and 2'-d-3'-ATP amounted to 34% and 14%, respectively. With each analogue used alone (each at concentration of 100 μM), phosphate transfer from 3'-d-2'-ATP was 55% that from ATP, and from 2'-d-3'-ATP 16%. With human TK2, and equimolar mixtures of [γ-32P]ATP with each of the analogues, and 1 μM dT as acceptor, there was no detectable transfer from either analogue. But, when each analogue was used alone, phosphate transfer attained 11% and 5%, respectively, that for ATP alone. With the low affinity form of human TK1, and dT as acceptor, only low phosphate transfer occurred with either analogue used alone. Both compounds exhibited Michaelis-Menten kinetics (with significantly lower Vmax than ATP), while ATP exhibited cooperative kinetics with all three kinases.

Wydawca

-

Rocznik

Tom

45

Numer

1

Opis fizyczny

p.87-94

Twórcy

autor
  • University of Warsaw, F.Zwirki i S.Wigury 93, 02-089 Warsaw, Poland
autor

Bibliografia

  • 1. Bohman, C. & Eriksson, S. (1988) Deoxycyti- dine kinase from human leukemic spleen: Preparation and characterization of the homo­geneous enzyme. Biochemistry 27,4258-4265.
  • 5. Kierdaszuk, B., Bohman, C., Ullman, B. & Eriksson, S. (1992) Substrate specificity of hu­man deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs. Biochem. Pharmacol. 43, 197-206.
  • 6. Bretner, M., Baliriska, M, Krawiec, K., Kier­daszuk, B., Shugar. D. & Kulikowski, T. (1995) Synthesis and biological activity of 5-fluoro-2- thiocytosine nucleosides. Nucleosides & Nu­cleotides 14, 657-660.
  • 7. Sherley, J.L. & Kelly, TJ. (1988) Human cyto- solic thymidine kinase. Purification and physi­cal characterization of the enzyme from HeLa cells. J. Biol Chem. 263, 375-382.
  • 8. Munch-Petersen, B., Cloos, L., Tyrsted, G. & Eriksson, S. (1991) Diverging substrate speci­ficity of pure human thymidine kinases 1 and 2 against antiviral dideoxynucleosides. J. Biol Chem. 266, 9032-9038.
  • 9. Kessel, D. (1968) Properties of deoxycytidine kinase partially purified from L1210 cells. J. Biol Chem. 243, 4739-4744.
  • 10. Durham. J.P. & Ives, D.H. (1970) Deoxycyti­dine kinase. II. Purification and general prop­erties of the calf thymus enzyme. J. Biol. Chem. 245, 2276-2284.
  • 11. Her, M.O. & Momparler, R.L. (1971) Mammal­ian deoxynucleoside kinases. IV. Deoxythy- midine kinase: Purification, properties and ki­netic studies. J. Biol Chem. 246,6152-6158.
  • 12. Cheng. Y.-C. & Prusoff, W.H. (1974) Mouse as­cites sarcoma 180 deoxythymidine kinase. General properties and inhibition studies. Bio­chemistry 13, 1179-1185.
  • 13. Lee, L.-S. & Cheng, Y-c. (1976) Human de­oxythymidine kinase II: Substrate specificity and kinetic behavior of the cytoplasmic and mitochondrial isozymes derived from blast cells of acute myelocytic leukemia. Biochemis­try 15, 3686-3690.
  • 14. Shugar, D. (1996) The NTP phosphate donor in kinase reactions: Is ATP a monopolist? Acta Biochim. Polon. 43, 9-24.
  • 15. Eriksson, S., Kierdaszuk, B., Munch-Peter- sen, B., 6berg, B. & Johansson, N.G. (1991) Comparison of the substrate specificities of human thymidine kinase 1 and 2 and de­oxycytidine kinase toward antiviral and cyto­static nucleoside analogs. Biochem. Biophys. Res. Commun. 176, 586-592.
  • 16. White. J.C. & Capizzi, R.L. (1991) A critical role for uridine nucleotides in the regulation of deoxycytidine kinase and the concentration dependence of l-^-D-arabinofuranosylcytosino phosphorylation in human leukemia cells. Cancer Res. 61, 2559-2565.
  • 17. Shewach, D.S., Reynolds, K.K. & Hertel, L. (1992) Nucleotide specificity of human de­oxycytidine kinase. Mol Pharmacol. 42, 518- 524.
  • 18. Krawiec, K., Kierdaszuk, B., Eriksson, S., Munch-Petersen, B. & Shugar, D. (1995) Nu­cleoside triphosphate donors for nucleoside ki­nases: Donor properties of UTP with human deoxycytidine kinase. Biochem. Riophys. Res. Commun. 216, 42-48.
  • 19. Hughes, T.L., Hahn, T.M., Reynolds, K.K. & Shewach, D.S. (1997) Kinetic analysis of hu­man deoxycytidine kinase with the true phos­phate donor uridine triphosphate. Biochemis­try 36, 7540-7547.
  • 20. Englund, P.T., Huberman, J.A., Jovin, T.M. & Kornberg, A. (1969) Enzymatic synthesis of deoxyribonucleic acid. XXX. Binding of tri­phosphates to deoxyribonucleic acid po­lymerase. J. Biol Chem. 244. 3038-3044.
  • 21. Desaubry, L., Shoshani, I. & Johnson, R.A. (1996) Inhibition of adenyl cyclase by a family of newly synthesized adenine nucleoside 3'- polyphospha:es. J. Biol Chem. 271, 14028- 14034.
  • 22. Munch-Petersen, B., Tyrsted, G. & Cloos, L. (1993) Reversible ATP-dependent transition between two forms of human cytosolic thymid­ine kinase with different enzymatic proper­ties. J. Biol Chem. 268, 15621-15625.
  • 22. Ives, D.H. & Wang, S.-M. (1978) Deoxycyti­dine kinase from calf thymus. Methods Enzy- mol 51, 337-345.
  • 23. Kierdaszuk, B. & Eriksson, S. (1990) Selective inactivation of the deoxyadenosine phosphory- lating activity of pure human deoxycytidine ki­nase: Stabilisation of different forms of the en- 93 zyme by substrates and biological detergents. Biochemistry 29, 4109-4114.
  • 24. Munch-Petersen, B. (1984) Differences in the kinetic properties of thymidine kinase isoen­zymes in unstimulated and phytohemagglu- tinin-stimulated human lymphocytes. MoL Cell. Biochem. 64, 173-185.
  • 25. Akherm, A.A., Zaitseva, G.V., Kalinichenko, E.N. & Mikhailopulo, I.A. (1976) Modified nu­cleosides. IX. The interaction of acetylsalicy- loyl chloride with adenosine, inosine, uridine and 5-bromouridine. Bioorg. Khim. (Moscow) 2, 1325-1336.
  • 26. Kvasyuk, E.I., Kulak. T.I., Kalinichenko, E.N., Podkopaeva, T.L., Mikhailopulo, I.A. & Pfleiderer, W. (1985) Chemical synthesis of some (2'-5 ^oligonucleotides, analogues of (2'- 5')oligoadenylic acid. Bioorg. Khim. (Moscow) 11, 1227-1238.
  • 27. Schaller, H., Weimann, G., Lerch, B. & Kho- rana, H.G. (1963) Studies on polynucleotides. XXIV. The stepwise synthesis of specific de- oxyribonucleotides. (4). Protected derivatives of deoxyribonucleosides and new synthesis of deoxyribonucleoside-3'-phosphates. J. Am. Chem. Soc. 85, 3821-3827.
  • 28.Sergeeva, N.V., Smirnov, V.D., Shabarova, Z.A., Prokofiev, M.A., Zarytova, V.F., Lebe- dev, A.V. & Knorre, D.G. (1976) Interaction of deoxyribonucleosides and dinucleoside phos­phates with phosphoryl chloroimidazolides and phosphoryl triimidazolide in pyridine so­lution. Bioorg. Khim. (Moscow) 2,1056- 1062.
  • 29. Moffatt, J.G. (1964) A general synthesis of nucleoside-5'-triphosphate. Can. J. Chem. 42, 599-604.
  • 30. Torrence, P.F., Brozda, D., Alster, D., Cha- rubala, R. & Pfleiderer, W. (1988) Only one 3'- hydroxyl group of ppp5'A2'p5'A2'p5'A (2-5A) is required for activation of the 2-5A- dependent endoribonuclease. J. Biol Chem. 263, 1131-1139.
  • 31. Munch-Petersen, B., Tyrsted, G., Closs, L., Beck, R.A. & Eger, K. (1995) Different affinity of the two forms of human cytosolic thymidine kinase towards pyrimidine analogs. Biochim. Biophys. Acta 1250, 158-162.
  • 32. Johnson, R.A., Desaubry, L., Bianchi, G., Shoshani. I., Lyons, E., Taussing, R., Watson, P.A., Cali, J.J., Krupiński, J., Pierom, J.P. & Iyenger, R. (1997) Isozyme-dependent sensiv- ity of adenylyl cyclases to P-site-mediated inhi­bition by adenine nucleosides and nucleoside 3'-polyphosphates. J. Biol Chem. 272, 8962- 8966.3. Krenitsky, T.A., Tuttle, J.V., Koszalka, G.W., Chen, I.S., Beacham III, L.M., Rideout, J.L. & Elion, G.B. (1976) Deoxycytidine kinase from calf thymus. Substrate and inhibitor specific­ity. J. Biol Chem. 251, 4055-4061.

Typ dokumentu

Bibliografia

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