5-Substituted N4-hydoxy-2'-deoxycytidines and their 5'-monophosphates: Synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity

Journal of Medicinal Chemistry

Volumn 43, Issue 24, 2000, Pages 4647-4656

  Felczak, K ^a   Miazga, A ^a   Poznanski, J ^a   Bretner, M ^a   Kulikowski, T ^a   Dzik, J M ^b   Golos, B ^b   Zielinski, Z ^b   Ciesla, J ^b   Rode, W ^b  

^a INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

^b NENCKI INSTITUTE OF EXPERIMENTAL BIOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; N4 HYDROXY 2' DEOXYCYTIDINE 5' PHOSPHATE DERIVATIVE; THYMIDYLATE SYNTHASE; THYMIDYLATE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL CULTURE; DRUG CONFORMATION; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; LEUKEMIA CELL; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ANTINEOPLASTIC AGENTS; BROMODEOXYURIDINE; CATALYSIS; CELL DIVISION; DEOXYCYTIDINE; DEOXYCYTIDINE MONOPHOSPHATE; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; IDOXURIDINE; KINETICS; MICE; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THYMIDYLATE SYNTHASE; TUMOR CELLS, CULTURED;

EID: 0034736090     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000975u     Document Type: Article

References (44)

1. The catalytic mechanism and structure of thymidylate synthase
2. Molecular mechanism of thymidylate synthase-catalyzed reaction and interaction of the enzyme with 2- and/or 4-substituted analogues of dUMP and 5-fluoro-dUMP
3. Thymidylate synthetase - A target enzyme in cancer chemotherapy
4. Fluorinated pyrimidines and their nucleosides
5. Thymidylate synthetase inhibitors: Experimental and clinical aspects
6. Pharmacologically relevant proteins
7. Perspectives on the design and biochemical pharmacology of inhibitors of thymidylate synthetase
8. Thymidylate synthase and its interaction with 5-fluoro-2'-deoxyuridylate
9. Thymidylate synthetase as target enzyme for the inhibitory activity of 5-substituted 2'-deoxyuridines on mouse leukemia L1210 cell growth
10. The purification and properties of thymidylate synthetase from chick embryo extracts
11. 4-hydroxy-2'-deoxycytidylic acid with thymidylate synthetase
12. 4-hydroxy-5-fluoro-dCMP, and related analogues
13. The reaction of hydroxylamine with cytosine and related compounds
14. Nucleosides part XLVIII. The reaction of hydroxylamine with cytosine and related compounds
15. The purification and properties of deoxycytidylate deaminase from chick embryo extracts
16. Studies on possible mechanisms of hydroxylamine mutagenesis
17. Thiation of nucleosides. II. Synthesis of 5-methyl-2'-deoxycytidine and related pyrimidine nucleosides
18. 4-substituted derivatives of 1-β-D-arabinofuranosylcytosine and -5-fluorocytosine
19. 4-hydroxy-6-azacytidine 5'phosphate and 5'-diphosphate
20. Synthesis and anti HIV activity of different sugar modified pyrimidine and purine nucleosides
21. Nucleic acid related compounds. 38. Smooth and high-yield iodination and chlorination at C-5 of uracil bases and p-tolyl-protected nucleosides
22. Cerium (IV)-mediated halogenation at C-5 of uracil derivatives
23. Nucleic acid related compounds. 21. Direct fluorination of uracil and cytosine bases and nucleosides using trifluoromethyl hypofluorite. Mechanism, stereochemistry, and synthetic applications
24. 4-(1,2,4-Triazol-1-yl)- and 4-(3-nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyr imidin-2(1H)-ones. Valuable intermediates in the synthesis of derivatives of 1-(β-D-arabinofuranosyl)cytosine (Ara-C)
25. Reaction of uracil nucleosides with 1-methylimidazole in the presence of phosphoryl chloride. A convenient method for the synthesis of 4-substituted pyrimidin-2(1H)-one. Nucleosides
26. Enzymatic phosphorylation of nucleosides to the 5'-phosphates
27. Validation of the general purpose tripos 5.2 force field
28. 4-hydroxy-5-fluorocytosine. A theoretical Ab initio study
29. Thermodynamic cycle between DNA and RNA constituents for conformation of the sugar ring from nuclear magnetic resonance study
30. Conformation analysis of β-D-ribo, β-D-deoxyribo, β-D-arabino, β-D-xylo, β-D-lyxo-nucleosides from proton-proton coupling constant
31. Thymidylate synthase. Catalysis of dehalogenation of 5-bromo- and 5-iodo-2'-deoxyuridylate
32. Inhibition of the biosynthesis of thymidylic acid by 4-N-hydroxy-2'-deoxycytidine in L5178Y leukemic cells
33. Analogues of 1-β-D-arabinofuranosylcytosine. Studies on mechanisms of action in Burkitt's cell culture and mouse leukemia, and in vitro deamination studies
34. Modelling of reaction steps relevant to deoxyuridylate (dUMP) enzymatic methylation and thymidylate synthase mechanism-based inhibition
35. Inhibition of Loctobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship
36. Microdetermination of phosphorus
37. Synthesis and interactions with thymidylate synthase of 2,4-dithio- analogues of dUMP and 5-fluoro-dUMP
38. 4-hydroxy-5-FdCMP with L1210 thymidylate synthase differing in sensitivity towards 5-FdUMP inhibition
39. Isolation and expression of rat thymidylate synthase cDNA: Phylogenetic comparison with human and mouse thymidylate synthases
40. Trichinella spiralis thymidylate synthase: Developmental pattern, isolation, molecular properties and inhibition by substrate and cofactor analogues
41. 5-(α-bromoacetyl)-2'-deoxyuridine 5'-phosphate: An affinity label for thymidylate synthetase
42. Introduction of an immunochemical label in a cytidine analogue
43. 1H NMR conformational study of antiherpetic C5-substituted 2'-deoxyuridines: Insight into the nature of structure-activity relationships