Modified substrates of DNA polymerases and design of antivirals

• Autorzy: Krayevsky A. A. , Alexandrova L. , Dyatkina N.B. , Kukhanova M.K. , Shirokova E.A.
• Języki publikacji: EN

Abstrakty

EN

The results obtained in our laboratory on investigating of substrate properties of a large number of compounds towards different DNA polymerases have been summarized. On the basis of systematic analysis a directed synthesis of nucleotides with antiviral properties was performed.

Słowa kluczowe

EN

modified nucleoside; DNA polymerase; antiviral drug; anticancer drug; deoxynucleoside 5'-triphosphate; antifungal drug; AIDS; HIV; DNA biosynthesis; antibacterial drug

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 1996
• Tom: 43
• Numer: 1
• Opis fizyczny: p.125-132

Twórcy

autor

Krayevsky A. A.

• Russian Academy of Sciences, 32 Vavilov str., Moscov, 117984, Russia

autor

Alexandrova L.

autor

Dyatkina N.B.

autor

Kukhanova M.K.

autor

Shirokova E.A.

Bibliografia

• 1. Krayevsky, A.A., Kukhanova, M.K., Atrazhev, A.M., Dvatkins, N.B., Papchikhin, A.V., Chidgeavadze, /..G. & Beabealashvilli, R.Sh. (1988) Selective inhibitors of DNA chain elongation catalyzed by DNA polymerases. Nucleosides & Nucleotides1.613-617.
• 2. Krayevsky, A.A. & Kukhanova, M.K. (1990) Physicochemical aspects of functioning of DNA polymerases. Sov. Sci. Rev. D. Physicochem. Biol. 9,179-242.
• 3. Krayevsky, A.A. (1992) Modified nucleosides and nucleotides, inhibiting HIV reproduction: analysis of situation and probable perspective. Mol. Biol. Russian 26, 725-744.
• 4. Chidgeavadze, Z.G., Beabealashvilli, R.Sh., Krayevsky. A.A. & Kukhanova, M.K. (1986) Nucleoside 5'-triphosphates with modified sugars as substrates for DNA polymerases. Biochim. Biophys. Acta 868,145-152.
• 5. Jasko, M.V., Fedorov, 1.1., Atrazhev, A.M., Mozzherin, D.G., Victorova, L.S., Bochkarev, A.V., Plavec, J., Gurskaya, G.V. & Krayevsky, A.A. (1995) Synthesis, molecular and crystal structure of 3'-N-alkylamino-3'-deoxythymi- dines and some biochemical properties of their phosphorus esters. Nucleosides & Nucleotides 14, 23-38.
• 6. Juzhakov, A.A., Chidgeavadze, Z.G., Beabealashvilli, R.Sh., Krayevsky, A.A.. Galegov, G.A., Korneyeva, M.A., Nosik, D.N. & Kilesso, T.Ju. (1991) 3'-Mercapto-.T-deoxythy­midine 5'-triphosphate as a terminator DNA synthesis catalyzed by RNA dependent DNA polymerases. Bioorg. Chem. Russian 17, .504-509.
• 7. Ku/netsova, h'.V., Kukhanova, M.K., Gurskaya, G.V., Fedorov, I.I., Jasko, M.V., Chattopadhaya, J. & Krayevsky, A.A. (1995) Conformation of 3'-nitro-2',3'-dideoxy thymidine in crystal and properties of its 5'-tri phosphate as terminating substrate for DNA polymerases. Mol. Biol. Russian 29, 407-414.
• 8. Dvatkina, N.B., Minassyan,Sh.Kh., Kukhanova, M.K., Krayevsky, A.A., von Janta-Lipinski, M., Chidgeavadze, Z.G. & Beabealashvilli, R.Sh. (1987) Properties of 2',3'-dideoxy-2\3'-dehydro- thymidine 5'-triphosphate in terminating DNA synthesis catalyzed by several different DNA polymerases. FEBS Lett. 219,151-155.
• 9. Krayevsky, A.A. & Watanabe, K.A. (1993) Possibility for existence of a general conformational motif in active centers of enzymes which are involved in nucleic acids metabolism. Nucleosides & Nucleotides 12, 649-670.
• 10. Semizarov, D.G., Victorova, L.S., Krayevskv, A.A. & Kukhanova, M.K. (1993) Modified nucleoside 5'-triphosphates containing 2',3'- rused three-membered rings as substrates for different DNA polymerases. FEBS Lett. 327.45- -48.
• 11. Krayevskv, A.A., Victorova, L.S., Mozzherin, D.Ju. & kukhanova, M.K. (1993) Acyclic 2',3'- dideoxy-2',3'-didehydronucIeoside 5'-triphos- phates as termination substrates of broad set of DNA polymerases. Nucleosides & Nucleotides 12, 83-93.
• 12. Shirokova, E.A.,Tarussova,N.B.,Shipitsin, A.V., Semizarov, D.G. & Krayevskv, A.A. (1994) Novel acyclic nucleoside 5'-triphosphate ana­logs imitating 2',3'-dideoxy-2'3'-didehydro- nucleotides: synthesis and biological properties. /. Med. Chem. 37,3139-3148.
• 13. Kilesso, T.Ju., Tarussova, N.B., Atrazheva, E.D., Kukhanova, M.K., Shulenin, S.B., Bobkov, A.F., Garavev, M.M., Galegov, G.A. & Krayevsky, A.A. (1990) Inhibitory analysis of DNA biosynthesis catalyzed by retroviral reverse transcriptases. Bioorg. Chem. Russian 16, 524-530.
• 14. Rozovskaya, T.A., Mischenko. A.V., Tarussova, N.B., Kukhanova, M.K., Krayevsky, A.A. & Beabealashvilli, R.Sh. (1993) Reverse transcriptase of human immunodeficiency virus: isolation and substrate specificity. Mol. Biol. Russian 27,1051-1060.
• 15. Jie, L, Van Aerschot, A., Balzarini,).,Janssen,G., Bueson, R., Hoogmartens, J., De Clercq, F.. & Herde wjen, P. (1990) 5'-0-Phosphonylmethvl- 2',3'-dideoxynucleosides: synthesis and anti- H1V activity. /. Med. Chem. 33, 2481-2487.
• 16. Victorova, L.S., Dyatkina, N.B., Mozzherin, D.Ju., Atrazhev, A.M., Krayevsky, A.A. & Kukhanova. M.K. (1992) Formation of phosphonoester bonds catalyzed by DNA polymerases. Nucleic Acids Res. 20,783-789.
• 17. Dyatkina, N.B., Arzumanov, A.A., Victorova, L.S., Kukhanova, M.K.& Krayevsky, A.A. (1995) Synthesis and substrate properties of TTP analogs with large hydrophobic substituent groups at a-P atoms. Nucleosides & Nucleotides 14,91-104.
• 18. Ma,Q.-F., Bathurst,I.C.,Barr,F.J.&Kenyon.G.L. (1992) New thymidine triphosphate analogue inhibitors of human immunodeficiency virus type 1 reverse transcriptase. J. Med. Chem. 35, 1938-1941.
• 19. Balzarini, J., Herdewijn, P., Pauwels, R., Brodcr, S. & De Clercq, E. (1988) a,ß- and ^Methylene 5'-phosphonate derivatives of 3'-azido-2',3'- dideoxythymidine-5'-triphosphate. Biochem. Pharmacol. 37,2395-2403-
• 20. Jasko, M., Shipitsin, A., Shirokova, E., Kra­yevskv, A., Polsky, B., Baron, P., MacLow, C. Ostrander, M. & O'Hara, B. (1993) 5'-Phospho- nates of ribonucleosides and 2'-deoxyribo- -nucleosides: synthesis and antiviral activity. Nucleosides & Nucleotides 12, 879-892.
• 21. Tarussova, N.B., Khorlin, A.A., Krayevsky, A.A.. Korneyeva, M.N., Nosik, D.N., Kruglov, N.B., Galegov, G.A. & Beabealashvilli, R.Sh. (1989) Inhibition of human immunodeficiency virus reproduction in cell culture by 3'-azido-2',3'- -dideoxynucleoside 5'-phosphonates. Mol. Biol. Russian 23,1716-1723.
• 22. Karamov, E.V., Lukashov, V.V., Tarussova, N.B., Kornilaveva, G.V., Rodina, M.A., Kukhanova, M.K. & Krayevsky, A.A. (1990) Inhibition of immunodeficiency virus in cell cultures by 3'- azido-2',3'-dideoxynucIeosides 5'-phosphites. Mol. Biol. Russian 24, 1695-1701.
• 23. Karamov, E.V., Lukashov, V.V., Gorbachova, A.L., Makarova, T.V., Kornilayeva, G.V., Taru­ssova, N.B. & Krayevsky, A.A. (1992) Inhibition of human immunodeficiency virus repro­duction in cell cultures by 2',3'-dideoxv- nucleoside 5'-phosphites. Mol. Biol. Russian 26, 201-207.
• 24. Krayevsky, A.A., Tarussova, N.B., Zhu, Q.-Y., Vidal, P., Chou, T.-C., Baron, P., Polsky, B.,Jiang, X.-Y., Matulic-Adamic, J., Rosenberg, I. & Watanabe, K.A. (1992) 5'-Hydrogen-phospho- nates and 5'-methylphosphonates of sugar modified pyrimidine nucleosides as potential anti-HIV agents. Nucleosides & Nucleotides 11, 177-1%.
• 25. Dyatkina, N., Arzumanov, A., Krayevsky, A., O'Hara, B., Gluzman, Ja., Baron, P., MacLow, C. & Polsky, B. (1994) Synthesis and antiviral activity of some fluorinated nucleotide derivatives. Nucleosides & Nucleotides 13, 325-337.
• 26. Matulic-Adamic, J., Rosenberg, I., Arzumanov, A.A., Dyatkina, N.B., Shirokova, E.A., Kra­yevsky, A.A. & Watanabe, K.A. (1993) A simple multigram synthesis of 5'-hydrogenphospho- nates and 5'-phosphorofluoridates of sugar modified nucleosides. Nucleosides & Nucleotides 12,1085-1092.
• 27. Krayevsky, A.A., Tarussova, N.B., Kukhanova, M.K., Balzarini, J., De Clercq, E., Karamov, F..V. & Lukashov, V.V. (1991) Investigation of DNA biosynthesis catalyzed by DNA polymerases: approach of synthesis of compounds with anti-HIV activity. Nucleic Acids Res., Symp. Series, 24,13-16.
• 28. Atrazheva, E.D., Lukin, M.A., Jasko, M.V.. Shushkova, T.V., Tarussova, N.B., Kravevsky, A.A., Balzarini, ]. & DeClercq. E. (1991) 2',3'-0- Cyclic derivatives of ribonucleosides and their 5'-phosphonates: synthesis and anti-HIV activity. Med. Chem. Res. 1,155-165.
• 29. Shirokova, E.A. (1992) Synthesis of new 5'-hydrogenthio phoshonates of pyrimidine nucleosides. Bioorg.Chem. 18,1255-1257.
• 30. Kukhanova, M.K., Tarussova, N.B., jasko, M.V., Arzumanov, A.A., Gudima, S.O., Krayevsky, A.A., Chidgeavadze, Z.G. & Beabealashvilli, R.Sh. (1992) Hydrolysis of nucleoside 5'-phosphonates and ^'-phosphates by phos­phatases of different origin and by human and calf blood sera. Mol. Biol. Russian 26, 1142-1154.
• 31. Kuznetsova, E.V., Kukhanova, M.K., Arzumanov, A.A. & Krayevsky, A.A. (1995) Reaction of 5'-hydrogenphosphonates, 5'-phos- phorofluoridates and 5'-phosphates of modi­fied nucleosides in blood serum. Mo/. Biol. Ru­ssian 29, in press.
• 32. Jasko, M.V., Semizarov, D.G., Victorova, L.S., Mozzherin, D.Ju., Krayevsky, A.A. & Kukhanova, M.K. (1995) New modified subs­trates for discriminating between human DNA polymerases a and e. FEBS Lett. 357,23-26.
• 33. Kukhanova, M.K., Kuznetsova, E.V., Jasko, M.V., O'Hara, B., Bekker, J., Morin, J. & Gluzman, Ya. (1994) Inhibitory analysis of DNA polymerase of herpes simplex virus type 1. Mol. Biol. Russian 28,875-886.
• 34. Kukhanova,M.K., Kuznetsova, F..V., Krayevsky. A.A., O'Hara, B., Bekker, J., Morin, J. & Gluz­man, Ya. (1994) Inhibitory analysis of human DNA polymerases by modified substrates. Mol. Biol. Russian 28,530-541.
• 35. Sharkin,J.A., Alexandrova, L.A., Victorova, L.S., Kuznetsova, F..V. & Krayevsky, A.A. (1995) Purine arabinonucleotide 5'-lriphosphates with substilucnts at 2'-position as substrates for DNA polymerases. Biochem. Mol. Biol. Int. 35, 1041-104«.
• 36. Semizarov, D.G., Victorova, L.S., Dvatkina, N.B., von Janta I.ipinski, M. & Krayevsky, A.A. (1994) Selectivity of DNA polymerases toward «and p nucleotide substrates of D and L. series. FEBS Lett. 354, 187-190.
• 37. Krayevsky, A.A., Dyatkina, N.B. & Kukhanova, M.K. (1995) Does interaction of dNTP glvcone with an active center of reverse transcriptases takes place? A model for a binding site. Nucleosides & Nucleotides 14. in press.
• 38. Langen, P.R., Waldrop, A.A. & Ward, D.C. (1981) Enzymatic synthesis of biotin-labeled poly­nucleotides: novel nucleic acids affinity probes. Proc. Natl. Acad. Sei. U.S.A. 78,6633-6637.
• 39. Alexandrova, I..A., Atrazhev, A.M., Kukha­nova, M.K. & Krayevsky, A.A. (1987) Incor­poration of fluorescent derivatives of 3'-dcoxy- uridine 5'-tri phosphate into DNA chain with E. coli DNA polymerase catalysis. Bioorg. Cheni. Russian 13, 643-647.
• 40. I.eary, J.J., Brigati, D.J. & Ward, D.C. (1983) Rapid and sensitive colorimetric method for visualizing biotin-labeled DNA probes hybridized to DNA or RNA immobilized on nitrocellulose: Bio-blots. Proc. Natl. Acad. Sei. U.S.A. 80,4045-4049.
• 41. Alexandrova, I..A., l.ukin, M.A., Rozovskava, T.A., Atrazhev, A.M., Kukhanova, M.K. & Kra­yevsky, A.A. (1990) Fluorescent analogues of nucleoside 5'-phosphonates for investigation of nucleic acids by radioactive methods. Mol. Biol. Russian 24,1100-1108.
• 42. D'yachenko, L.V., Chenchik, A.A., Lukin, M.A., Alexandrova, L.A., Krayevsky, A.A. & Beabe­alashvilli. R.Sh. (1994) ddUTP Derivatives modified in uridine 5-position as substrate terminators of reverse transcriptases; hydrolysis of oligonucleotides terminated by these analogues by phosphodiesterase 1. Mol. Biol. Russian 28,102-112.
• 43. Reardon, J.F.. (1992) Human immunodeficiency virus reverse transcriptase: steady-state and pre-steady-state kinetics of nucleotide incor­poration. Biochemistry 31,4473-1479.