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Azapyrimidine Nucleosides

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Abstract

Azapyrimidine analogs are derived from pyrimidine compounds through the replacement of one of the methine groups with an atom of nitrogen.

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References

  • Altanerova, V.: Virus production induced by various chemical carcinogens in a virogenic hamster cell line transformed by Rous sarcoma virus. J. Natl. Cancer Inst. 49, 1375–1380 (1972).

    PubMed  CAS  Google Scholar 

  • Bauer, V., Č, R.: The effects of 6-azauridine on the peripheral nervous system. I. The action on ganglionic transmission. Int. J. Neuropharmacol. 8, 263–269 (1969a).

    Google Scholar 

  • Bauer, V., Čapek, R.: The effects of 6-azauridine on the peripheral nervous system. II. The action on neuromuscular transmission and on striated muscle. Int. J. Neuropharmacol. 8, 721–727 (1969b).

    Google Scholar 

  • Beránek, J.: Nucleic acid components and their analogues. CXIX. Synthesis of l-β-D-lyxo- furanosyl-6-azauracil. Coll. Czech. Chem. Commun. 34, 618–629 (1969).

    Google Scholar 

  • Beránek, J., Pitha, J.: Nucleic acid components and their analogues. XLVI. Some derivatives of 6-azacytidine and 6-azauridine. Coll. Czech. Chem. Commun. 29, 625–634 (1964).

    Google Scholar 

  • Beránek, J., Šorm, F.: Nucleic acid components and their analogues. CVIII. Synthesis of 3’-deoxy-6-azauridine. Coll. Czechoslov. Chem. Commun. 33, 901–912 (1968a).

    Google Scholar 

  • Beránek, J., Šorm, F.: Nucleic acid components and their analogues. CIX. Synthesis of l-β-D-arabinofuranosyl-6-azaisocytosine.Coll.Czech. Chem. Commun. 33, 913–923 (1968b).

    Google Scholar 

  • Bobek, M., Farkaš, J., Šorm, F.: Nucleic acid components and their analogues. XCVII. Synthesis of 5-hydroxymethyl-6-aza-2’-deoxyuridine and 5-hydroxymethyl-6-aza-2’-deoxy- cytidine. Coll. Czech. Chem. Commun. 32, 3581–3586 (1967).

    CAS  Google Scholar 

  • Bobek, M., Farkaš, J., Šorm, F.: Nucleic acid components and their analogues. CXXIV. Synthesis of 5-β-D-ribofuranosyl-6-azauracil (6-azapseudouridine). Coll. Czech. Chem. Commun. 34, 1690–1695 (1969).

    CAS  Google Scholar 

  • Bono, V. H., Weissman, S. M., Frei, E. III.: The effect of 6-azauridine administration on de novo pyrimidine production in chronic myelogenous leukemia. J. clin. Invest. 43, 1486–1494 (1964).

    PubMed  CAS  Google Scholar 

  • Buck, L.L., Pfau, C.J.: Inhibition of lymphocytic choriomeningitis virus replication by actinomycin D and 6-azauridine. Virology 37, 698–701 (1969).

    PubMed  CAS  Google Scholar 

  • Bukrinskaya, A.G., Asadullaev, T. A.: Comparative effect of histon and 6-azauridine on myxovirus reproduction. Vop. virus. 13, 549–554 (1968) (in Russian).

    CAS  Google Scholar 

  • Buttoo, A.S., Israëls, M.C.G., Wilkinson, J. F.: Hypocholesterolaemia and orotic aciduria during treatment with 6-azauridine. Brit. med. J. 1, 552–554 (1965).

    PubMed  CAS  Google Scholar 

  • Calabresi, P., Turner, R.W.: Beneficial effects of triacetyl azauridine in psoriasis and mycosis fungoides. Ann. intern. Med. 64, 352–371 (1966).

    PubMed  CAS  Google Scholar 

  • Čerey, K., Elis, J., Rašková, H.: Studies on 6-azauridine and 6-azacytidine. V. Influence of 6-azacytidine on prenatal development in mice. Biochem. Pharmacol. 14, 1549–1556 (1965).

    PubMed  Google Scholar 

  • Černeckij, V., Chladek, S., Šorm, F., Smrt, J.: Nucleic acid components and their analogues. XIV. 6-Azacytidine and some of its N4-derivatives. Coll. Czech. Chem. Commun. 27, 87–93 (1962).

    Google Scholar 

  • Čihák, A., Broucek, J.: Dual effect of 5-azacytidine on the synthesis of liver ribonucleic acids. Lack of the relationship between metabolic transformation of orotic acid In vitro and its incorporation in vivo. Biochem. Pharmacol. 21, 2497–2507 (1972).

    PubMed  Google Scholar 

  • Čihák, A., Seifertova, M., Veselý, J.: Enhanced uridine kinase and RNA synthesis in regenerating rat liver after 5-azacytidine administration. Arch. Biochem. Biophys. 148, 400–406 (1972).

    PubMed  Google Scholar 

  • Čihák, A., Škoda, J., Norm, F.: Formation of 5-azauridine, ribosyl N-formylbiuret, ribosyl biuret, and their 5’-phosphates in Escherichia coli culture from 5-azauracil. Coll. Czech. Chem. Commun. 29, 300–308 (1964).

    Google Scholar 

  • Čihák, A., Šorm, F.: Biochemical effects and metabolic transformations of 5-azacytidine in Escherichia coli. Coll. Czech. Chem. Commun. 30, 2091–2102 (1965).

    Google Scholar 

  • Čihák, A., Veselý, J., Inoue, H., Pitot, H.C.: Effect of 5-azacytidine on dietary and hormone induction of serine dehydratase and tyrosine aminotransferase in rat liver. Biochem. Pharmacol. 21, 2545–2553 (1972).

    PubMed  Google Scholar 

  • Čihák, A., Veselý, J., Šorm, F.: Incorporation of 5-azacytidine into liver ribonucleic acids of leukemic mice sensitive and resistant to 5-azacytidine. Biochim. biophys. Acta (Amst.) 108, 516–518 (1965).

    Google Scholar 

  • Čihák, A., Veselý, J., ŠOrm, F.: Complete inhibition by 5-azacytidine of hormonal induction of tryptophan pyrrolase. Biochim. biophys. Acta (Amst.) 134, 486–489 (1967).

    Google Scholar 

  • Čihák, A., Veselý, J., Šorm, F.: Thymidine kinase and polyribosome distribution in regenerating rat liver following 5-azacytidine. Biochim. biophys. Acta (Amst.) 166, 277–279 (1968).

    Google Scholar 

  • Conn, H.O., Creasey, W.A., Calabresi, P.: Effect of 6-azauridine on plasma cell tumors of mice: correlation of antitumor effect with inhibition of orotic acid metabolism. Cancer Res. 27, 618–625 (1967).

    PubMed  CAS  Google Scholar 

  • Creasey, W.A., Fink, M.E., Handschumacher, R.E., Calabresi, P.: Clinical and pharmacological studies with 2’, 3’, 5’-triacetyl-6-azauridine. Cancer Res. 23, 444–453 (1963).

    PubMed  CAS  Google Scholar 

  • Cristescu, C.: 6-Azauracil derivatives with potential cytostatic activity. VI. An improved synthesis of 2-β-D-ribofuranosyl-as-triazine-3, 5(2H, 4H)dione (6-azauridine). Rev. Roumaine Chim. 12, 365–369 (1968).

    Google Scholar 

  • Crkvenjakov, R., Bajkovič, N., Glišin, V.: The effect of 5-azacytidine on development, nucleic acid and protein metabolism in sea urchin embryos. Biochem. biophys. Res. Commun. 39, 655–660 (1970).

    CAS  Google Scholar 

  • Deconti, R. C., Calabresi, P.: Treatment of polycythemia vera with azauridine and azaribine. Ann. intern. Med. 73, 575–579 (1970).

    PubMed  CAS  Google Scholar 

  • Demidova, S.A., Azadova, N.B., Martynova, V.N., Galegov, G.A., Zhdanov, V.M.: The injurious effect of 6-azauridine on the multiplication of cytomegalovirus in man. Dokl. Akad. Nauk SSSR 186, 709–710 (1969) (in Russian).

    PubMed  CAS  Google Scholar 

  • Doskočil, J.: The kinetics of metabolic transformations of nucleosides by whole cells of Escherichia coli. Coll. Czech. Chem. Commun. 35, 2656–2672 (1970).

    Google Scholar 

  • Doskočil, J., Pačes, V.: The effect of azapyrimidine nucleosides and deoxynucleosides on the metabolism of thymidine and thymine in cultures of Escherichia coli. Coll. Czech. Chem. Commun. 33, 4369–4378 (1968).

    Google Scholar 

  • Doskočil, J., Pačes, V., Šorm, F.: Inhibition of protein synthesis by 5-azacytidine in Escherichia coli. Biochim. biophys. Acta (Amst.) 145, 771–779 (1967).

    Google Scholar 

  • Doskočil, J., Šorm, F.: The effects of 5-azacytidine and 5-azauridine on protein synthesis in Escherichia coli. Biochem. biophys. Res. Commun. 38, 569–574 (1970a).

    Google Scholar 

  • Doskočil, J., Šorm, F.: The inhibitory effects of 5-azacytidine and 5-azauridine in Escherichia coli. Coll. Czech. Chem. Commun. 35, 1880–1891 (1970b).

    Google Scholar 

  • Doskočil, J., Šorm, F.: The mode of action of 5-aza-2’-deoxycytidine in Escherichia coli. Europ. J. Biochem. 13, 180–187 (1970c).

    PubMed  Google Scholar 

  • Durr, G.J., Hammond, S.: The synthesis of l-(2-deoxy-D-arabinohexopyranosyl)-5-bromo-6- azauracil(l). J. heterocycl. Chem. 7, 743–745 (1970).

    CAS  Google Scholar 

  • Durr, G.J., Keiser, J.F., Ierardi, P.A.: The 6-azauracil and 6-azathymine nucleosides of 2-deoxy-D-arabinohexopyranose(l). J. heterocycl. Chem. 4, 291–294 (1967).

    CAS  Google Scholar 

  • Elis, J., Rašková, H.: La toxicité foetale de l’azacytidine. J. Physiol. (Paris) 56, 559–560 (1964).

    Google Scholar 

  • Elis, J., Rašková, H.: Controlled clinical trials with new cytostatic preparations produced in Czechoslovakia. Rev. Czech. Med. 12, 9–19 (1966).

    PubMed  CAS  Google Scholar 

  • Elis, J., Rašková, H.: New indications for 6-azauridine treatment in man. A review. Europ. J. Clin. Pharm. 4, 77–81 (1971).

    Google Scholar 

  • Elis, J., Slavik, M., Raskovä, H.: Side effects of 6-azauridine triacetate in rheumatoid arthritis. Clin. Pharmacol. Ther. 11, 404–407 (1970).

    PubMed  CAS  Google Scholar 

  • Elves, M.W., Buttoo, A.S., Israels, M.C.G., Wilkinson, J.F.: Chromosome changes caused by 6-azauridine during treatment of acute myeloblasts leukemia. Brit. med. J. 1, 156–159 (1963).

    PubMed  CAS  Google Scholar 

  • Ennis, H.L., Lubin, M.: Capacity for synthesis of a pyrimidine biosynthetic enzyme in mammalian cells. Biochem. biophys. Acta (Amst.) 68, 78–83 (1963).

    CAS  Google Scholar 

  • Erukhimov, L.S., Vermel, E.M.: The use of azauridine in cancer of the bladder. Vop. onkol. 15, 91 (1969) (in Russian).

    CAS  Google Scholar 

  • Evans, J.S., Haňka, L. J.: The in vivo activity of combinations of 5-azacytidine and cytidine on leukemia L-1210. Experientia (Basel) 24, 922–923 (1968).

    CAS  Google Scholar 

  • Falke, D., Rada, B.: 6-Azauridine as an inhibitor of the synthesis of herpesvirus hominis. Acta virol. 14, 115–123 (1970).

    PubMed  CAS  Google Scholar 

  • Fallon, H.J., Frei, E., III, Block, J., Seegmiller, J.E.: The uricosuria and orotic aciduria induced by 6-azauridine. J. clin. Invest. 40, 1906–1914 (1961).

    PubMed  CAS  Google Scholar 

  • Farkaš, J., Beránek, J., Šorm, F.: Nucleic acid components and their analogues. LXXXVI. Synthesis of l-β-D-arabinofuranosyI-6-azacytosine. Coll. Czech. Chem. Commun. 31. 4002–4008 (1966).

    Google Scholar 

  • Fischer, D.S., Cassidy, E.P., Welch, A. D.: Immunosuppression by pyrimidine nucleoside analogs. Biochem. Pharmacol. 15, 1013–1022 (1966).

    PubMed  CAS  Google Scholar 

  • Flanagan, J. F., Ginsberg, H.S.: Role of ribonucleic acid biosynthesis in multiplication of type 5 adenovirus. J. Bact. 87, 977–987 (1964).

    PubMed  CAS  Google Scholar 

  • Fučík, V., Michaelis, A., Rieger, R.: On the induction of segment extension and chromatid structural changes in Vicia Faba chromosomes after treatment with 5-azacytidine and 5-aza- deoxycytidine. Mutation Res. 9, 599–606 (1970).

    PubMed  Google Scholar 

  • Fučík, V., ŠOrmova, Z., Šorm, F.: The effect of 5-azacytidine on the root meristem of VICIA

    Google Scholar 

  • Faba. Biol, plant. (Prague) 7, 58 — 64 (1965).

    Google Scholar 

  • Fučík, V., Zadrazil, S., Jurovcik, M., Sormova, Z.: Mechanism of resistance to 5-azacytidine in Bacillus Subtilis. I. Isolation and properties of mutants resistant to 5-azacytidine and (1966) aza-2’-deoxycytidine. Folia Microbiol. (Prague) 17, 517–521 (1972).

    Google Scholar 

  • Galegov, G.A., Bikbulatova, T.M., Vanag, K.A., Shen, R.M.: Inhibiting effect of 6-aza- uridine upon reproduction of herpes simplex virus. Vop. Virus. 13, 18–21 (1968) (in Russian).

    PubMed  CAS  Google Scholar 

  • Galegov, G.A., Kukhar, E.E., Bikbulatov, R.M.: Treatment of keratitis in rabbits due to herpes simplex virus with 6-azauridine. Vop. Virus. 15, 351–354 (1970) (in Russian).

    PubMed  CAS  Google Scholar 

  • Gelbard, A.S., Kim, S.H., Eidinoff, M.L.: Nucleoside kinase activities in tissue infected with Rous sarcoma virus. Cancer Res. 26, 748–751 (1966).

    PubMed  CAS  Google Scholar 

  • Gershon, D., Sachs, L.: The early synthesis of RNA in polyoma virus (PV) development. Virology 29, 44–48 (1966).

    PubMed  CAS  Google Scholar 

  • Goldberg, I. H., Rabinowitz, M.: Inhibition of RNA nucleotidyltransferase by 6-azauridine triphosphate. Biochim. biophys. Acta (Amst.) 72, 116–119 (1963).

    CAS  Google Scholar 

  • Grafnetter, D., Grafnetterová, J.: Effect of 6-azauridine on lipid metabolism in the rat. Neoplasma (Bratisl.) 14, 145–153 (1967).

    CAS  Google Scholar 

  • Grafnetterová, J., Beránek, J., Konig, J., ŠMahel, O., Šorm, F.: Catabolism of 2’, 3’, 5’-tri- O-acetyl-6-azauridine in human organism. Neoplasma (Bratisl.) 13, 241–249 (1966b).

    Google Scholar 

  • Grafnetterová, J., Grafnetter, D.: 6-Azauridine in brain tissue during chick embryonal development. Experientia (Basel) 24, 53 (1968).

    Google Scholar 

  • Grafnetterová, J., Grafnetter, D., Poledne, R.: Lipid changes induced by 6-azauridine. Estratto dal Volume degli Atti del Congresso Internazionale su “Clinical evaluation of testing methods of vasoactive drug effects”. Roma, 1–4 maggio 1968a.

    Google Scholar 

  • Grafnetterová, J., Grossi, E., Fumagalli, R., Morganti, P., Grafnetter, D.: Effects of (1967) azauridine on the developing chick embryo. Neoplasma (Bratisl.) 13, 251–258 (1966a).

    Google Scholar 

  • Grafnetterová, J., Jedlicka, V., ŠMAHEL, O.: Influence of 6-azauridine on the calcium content of plasma and bones in new-born chicks. Experientia (Basel) 24, 1144–1145 (1968b).

    Google Scholar 

  • Grozdanovič, J., Vích, Z., Truxova, G.: The combined effect of 6-azauridine and irradiation In vivo and In vitro. I. The acute effect on the mouse Ehrlich ascites carcinoma. Neoplasma (Bratisl.) 15, 247–249 (1968).

    Google Scholar 

  • Grozdanovič, J., Vích, Z., Truxova, G., Kratochvil, J.: Combined effect of 6-azauridine and irradiation In vivo and In vitro. VI. Nuclear diameters of Ehrlich ascites carcinoma cells after repeated irradiation and 6-AzUR application. Neoplasma (Bratisl.) 17, 601–606 ( 1970

    Google Scholar 

  • Gutová, M., Elis, J., Rašková, H.: Teratogenic effect of 6-azauridine in rats. Teratology 4, 287–292 (1971).

    PubMed  Google Scholar 

  • Habermann, V., Šorm, F.: Mechanism of the cancerostatic action of 6-azauracil and its riboside. Coll. Czech. Chem. Commun. 23, 2201–2206 (1958).

    CAS  Google Scholar 

  • Halle, S.: 5-Azacytidine as a mutagen for arboviruses. J. Virol. 2, 1228–1229 (1968).

    PubMed  CAS  Google Scholar 

  • Handschfmacher, R.E.: Studies of bacterial resistance to 6-azauracil and its riboside. Biochim. biophys. Acta (Amst.) 23, 428–430 (1957).

    Google Scholar 

  • Handschumacher, R.E.: Bacterial preparation of orotidine-5’-phosphate and uridine-5’-phosphate. Nature (Lond.) 182, 1090–1091 (1958).

    CAS  Google Scholar 

  • Handschumacher, R.E.: Azauracil ribonucleoside and ribonucleotides: isolation and chemical synthesis. J. biol. Chem. 235, 764–768 (1960a).

    PubMed  CAS  Google Scholar 

  • Handschumacher, R.E.: Orotidylic acid decarboxylase: inhibition studies with azauridine 5’-phosphate. J. biol. Chem. 235, 2917–2919 (1960b).

    PubMed  CAS  Google Scholar 

  • Handschumacher, R.E., Calabresi, P., Welch, A.D., Bono, V.H. JR., Fallon, H. J., Frei, E. Ill: Summary of current information on 6-azauridine.Cancer Chemother.Rep.21, 1–18(1962).

    Google Scholar 

  • Handschumacher, R.E., Pasternak, C.A.: Inhibition of orotidylic acid decarboxylase, a primary site of carcinostasis by 6-azauracil. Biochim. biophys. Acta. (Amst.) 30, 451–452 (1958).

    CAS  Google Scholar 

  • Handschumacher, R.E., Škoda, J., 8orm, F.: Metabolic and biochemical effects of 6-aza- cytidine in mice with Ehrlich ascites carcinoma. Coll. Czech. Chem. Commun. 28, 2983– 2990 (1963).

    Google Scholar 

  • Hanka, L. J., Evans, J. S., Mason, D. J., Dietz, A.: Microbiological production of 5-azacytidine. I. Production and biological activity. Antimicrob. Agents Chemother. 619–624 (1966).

    Google Scholar 

  • Havelka, S., Pegrimova, E., Trnavsky, K., Slavik, M., Elis, J.: 6-Azauridin-Triacetat in der Therapie der chronischen Polyarthritis. Z. f. Rheumaforsch. 28, 29–35 (1969).

    CAS  Google Scholar 

  • Hrodek, O., Veselý, J.: 5-Azacytidine in childhood leukemia. Neoplasma (Bratisl.) 18, 493–503 (1971).

    CAS  Google Scholar 

  • Jaffe, J.J., Handschumacherjr.E., Welch, A.D.: Studies on the carcinostatic activity in mice of 6-azauracil riboside (6-azauridine), in comparison with that of 6-azauracil. Yale J. biol. Med. 30, 168–175 (1957).

    CAS  Google Scholar 

  • Janků, I., Kršiak, M., Novotný, J., Volicer, L., Čapek, R.: Studies on 6-azauridine and 6-azacytidine. IV. Correlations between metabolism and central nervous effects of 6-aza- cytidine. Biochem. Pharmacol. 14, 1545–1548 (1965a).

    PubMed  Google Scholar 

  • Janků, I., Kršiak, M., Volicer, L., Čapek, R., Smetana, R., Novotný, J.: Studies on 6-azauridine and 6-azacytidine. II. The effects of 6-azauridine on the central nervous system. Biochem. Pharmacol. 14, 1526–1535 (1965b).

    Google Scholar 

  • Jasińska, S., Link, F., Blaškovič, D., Rada, B.: Studies on the effect of antiviral substances on experimental virus infections. III. The effect of 6-azauracil riboside and urethane on vaccina virus infection in mice. Acta virol. (Bratisl.) 6, 17–23 (1962).

    Google Scholar 

  • Jelínek, R., Rychter, Z., Klika, E.: Syndrome of caudal regression and dystrophic malformations of the spinal cord. Folia morphol. (Prague) 19, 58–70 (1971).

    Google Scholar 

  • Jelínek, R., Rychter, Z., Seichert, V.: Syndrome of caudal regression in the chick embryo. Folia Morphol. (Prague) 18, 125–137 (1970).

    Google Scholar 

  • Jiřička, Z., Smetana, K., Janků, I., Elis, J., Novotný, J.: Studies on 6-azauridine and 6-azacytidine. I. Toxicity studies of 6-azauridine and 6-azacytidine. Biochem. Pharmacol. 14, 1517–1523 (1965).

    PubMed  Google Scholar 

  • Jurovčík, M., Raška, K., Šormová, Z., Šorm, F.: Anabolic transformation of a novel antimetabolite, 5-azacytidine, and evidence for its incorporation into ribonucleic acid. Coll. Czech. Chem. Commun. 30, 3370–3376 (1965).

    Google Scholar 

  • Jurovčík, M., Zadražil, S., FučiK, V., Šormová, Z.: Mechanism of resistance to 5-azacytidine in Bacillus Subtilis. II. Utilization of 5-azacytidine and of natural pyrimidines. Coll. Czech. Chem. Commun. 37, 299–308 (1972).

    Google Scholar 

  • Kafka, V., Musil, J., Padovec, J., ŠOrm, F.: Chemotherapie maligner Tumoren in der Gynäkologie. Bericht über eine Therapie mit Azauridin (6-Azauracilribosid). Gynaecologia 152, 191–197 (1971).

    Google Scholar 

  • Kára, J.: Activation of DNA biosynthesis in Ehrlich ascites cells in vivo following application of 6-aza-2’-deoxycytidine. Biochem. biophys. Res. Commun. 17, 377–382 (1964).

    Google Scholar 

  • Kára, J., Šorm, F.: Study of the substrate specificity of deoxynucleoside phosphokinases. Phosphorylation of 3H-thymidine, 6-azathymidine, deoxyuridine, 6-azadeoxyuridine and 5-hydroxymethyldeoxyuridine labelled with 14C, by enzymes from normal and malignant mammalian tissues In vitro . Coll.

    Google Scholar 

  • Kára, J., Šorm, F.: Activation of deoxycytidylate deaminase from Ehrlich ascites-tumor cells by 6-aza-2’-deoxycytidine 5’-phosphate. Biochim. biophys. Acta (Amst.) 80, 154–157 (1964).

    Google Scholar 

  • Karon, M., Sieger, L., Leimbrock, S., Finkelstein, J.Z., Nesbit, M.E., Swaney, J.J.: (1968) Azacytidine: a new active agent for the treatment of acute leukemia. Blood 42, 359–365 (1973).

    PubMed  CAS  Google Scholar 

  • Kaverin, N.V., Emeliyanov, B.A.: The effect of 6-azauridine on the course of latent period in RNA viruses. Vop. Virus. 12, 51–54 (1967) (in Russian).

    PubMed  CAS  Google Scholar 

  • Korbecki, M., Łuczak, M., Klimowitz, Z.: Influence of 6-azauridine on the multiplication of the parainfluenza 3 virus. Bull. Acad. Polonaise Sei. 16, 539–543 (1968).

    CAS  Google Scholar 

  • Korbecki, M., Plagemann, P. G. W.: Competitive inhibition of uridine incorporation by (1969) azauridine in uninfected and mengovirus-infected Novikoff hepatoma cells. Proc. Soc. exp. Biol. (N.Y.) 132, 587–595 (1969).

    CAS  Google Scholar 

  • Leonard, L.L., Meulen, V. Ter, Freeman, J. M.: In vitro sensitivity of measles virus to 6-azauridine. Proc. Soc. exp. Biol. (N.Y.) 136, 857–862 (1971).

    Google Scholar 

  • Levitan, I.B., Webb, T.E.: Effect of 5-azacytidine on polyribosomes and on the controls of tyrosine transaminase in rat liver. Biochim. biophys. Acta (Amst.) 182, 491–500 (1969).

    CAS  Google Scholar 

  • Li, L.H., Olin, E.J., Buskirk, H.H., Reineke, L.M.: Cytotoxicity and mode of action of 5-azacytidine on L 1210 leukemia. Cancer Res. 30, 2760–2769 (1970a).

    PubMed  CAS  Google Scholar 

  • Li, L.H., Olin, E.J., Fraser, T.J., Bhuyan, B.K.: Phase specificity of 5-azacytidine against mammalian cells in tissue culture. Cancer Res. 30, 2770–2775 (1970 b).

    Google Scholar 

  • Lisý, V., Škoda, J.: Deamination of some cytosine and cytidine analogues by an Escherichia coli extract. Coll. Czech. Chem. Commun. 31, 3020–3022 (1966).

    Google Scholar 

  • Lisý, V., Škoda, J., Rychlik, I., Smrt, J., Holý, A., Šorm, F.: Changes in coding properties of poly- and oligonucleotides containing 6-azapyrimidine ribonucleosides. Coll. Czech. Chem. Commun. 33, 4111–4119 (1968).

    Google Scholar 

  • Loh, P.C.: The role of RNA in the synthesis of vaccinia virus. Proc. Soc. exp. Biol. (N.Y.) 116, 789–792 (1964).

    CAS  Google Scholar 

  • Lowy, D.R., Rowe, W.P., Teich, N., Hartley, J. W.: Murine leukemia virus: high-frequency activation In vitro by 5-iododeoxyuridine and 5-bromodeoxyuridine. Science 174, 155–156 (1971).

    PubMed  CAS  Google Scholar 

  • Magdon, E., Konopatzky, R.: Untersuchungen zur Wirkung von 6-Azaurazilribosid bei der Bestrahlung von experimentellen Tiertumoren. Arch. Geschwulstforsch. 29, 259–245 (1967).

    PubMed  CAS  Google Scholar 

  • Misařovä, Z., Elis, J.: Azauracilriboside and azauracilribosidetriacetate in the therapy of leukemia in children. Čs. Pediat. 19, 161–165 (1964) (in Czech).

    Google Scholar 

  • Morris, J.M., Van Wagenen, G., Hurteau, G.D., Johnston, D.W., Carlsen, R.A.: Compounds interfering with ovum implantation and development. Fertil. Steril. 18, 7–17 (1967).

    PubMed  CAS  Google Scholar 

  • Myška, V., Elis, J., Plevová, J., Rašková, H.: Azauridine in viral eye infections. Lancet I, 1230–1231 (1967).

    Google Scholar 

  • Nirenberg, M., Leder, P.: RNA codewords and protein synthesis. The effect of trinucleotides upon the binding of sRNA to ribosomes. Science 145, 1399–1407 (1964).

    PubMed  CAS  Google Scholar 

  • Nouza, K.: Screening of immunosuppressive drugs in the allotransplantation reaction between mice differing at the H-3 locus. Folia Biol. (Prague) 12, 266–277 (1966).

    CAS  Google Scholar 

  • Nouza, K., Pokorná, Z., Slavík, M., Gottwaldová, A.: The immunosuppressive effects of 6-azauridine. Folia Biol. (Prague) 16, 188–195 (1970).

    CAS  Google Scholar 

  • Novotný, J., Smetana, R., Raškova, H.: Studies on 6-azauridine and 6-azacytidine. III. The fate of 6-azacytidine in various animal species. Biochem. Pharmacol. 14, 1537–1544 (1965).

    PubMed  Google Scholar 

  • Pačes, V., Doskočil, J., ŠOrm, F.: Incorporation of 5-azacytidine into nucleic acids of Escherichia coli. Biochim. biophys. Acta (Amst.) 161, 352–360 (1968a).

    Google Scholar 

  • Pačes, V., Doskočil, J., Šorm, F.: The effect of 5-azacytidine on the synthesis of ribosomes in Escherichia coli. FEBS Let. 1, 55–58 (1968b).

    Google Scholar 

  • Pasternak, C. A., Fischer, G. A., Handschumacher, R. E.: Alteration in pyrimidine metabolism in L5178 Y leukemia cells resistant to 6-azauridine. Cancer Res. 21, 110–117 (1961).

    PubMed  CAS  Google Scholar 

  • Pasternak, C.A., Handschumacher, R.E.: The biochemical activity of 6-azauridine: interference with pyrimidine metabolism in transplantable mouse tumors. J. biol. Chem. 234, 2992–2997 (1959).

    PubMed  CAS  Google Scholar 

  • Pinsky, L., Krooth, R.S.: Studies on the control of pyrimidine biosynthesis in human diploid cell strains. I. Effect of 6-azauridine on cellular phenotype. Proc. nat. Acad. Sei. (Wash.) 57, 925–932 (1967a).

    CAS  Google Scholar 

  • Pinsky, L., Krooth, R.S.: Studies on the control of pyrimidine biosynthesis in human diploid cell strains. II. Effects of 5-azaorotic acid, barbituric acid, and pyrimidine precursors on cellular phenotype. Proc. nat. Acad. Sei. (Wash.) 57, 1267–1274 (1967b).

    CAS  Google Scholar 

  • Pískala, A., Šorm, F.: Nucleic acid components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine. Coll. Czech. Chem. Commun. 29, 2060–2076 (1964).

    Google Scholar 

  • Plevová, J., Janků, I., Šeda, M.: Toxicity of 6-azauridine triacetate. Toxicol. Appl. Pharmacol. 17, 511–518 (1970a).

    PubMed  Google Scholar 

  • Plevová, J., Šeda, M., Janků, I.: The deacetylation of 6-azauridine-triacetate in the plasma of various species correlated with toxicity. Proc. Europ. Soc. Study Drug Toxicity. 11, 240–241 (1970b).

    Google Scholar 

  • Pliml, J., Prystas, M., Šorm, F.: Nucleic acid components and their analogues. XXXIX. Synthesis of anomeric 2’-deoxy-6-azauridines and of 6-azathymidine. Coll. Czech. Chem. Commun. 28, 2588–2597 (1963).

    CAS  Google Scholar 

  • Pliml, J., Šorm, F.: Nucleic acid components and their analogues. XXVIII. Synthesis of 6-aza-2’-deoxycytidine. Coll. Czech. Chem. Commun. 28, 546–550 (1963).

    CAS  Google Scholar 

  • Pliml, J., Šorm, F.: Synthesis of a 2-deoxy-D-ribofuranosyl-5-azacytosine. Coll. Czech. Chem. Commun. 29, 2576–2578 (1964).

    CAS  Google Scholar 

  • Pontis, H., Degerstedt, G., Reichard, P.: Uridine and deoxyuridine phosphorylase from Ehrlich ascites tumor. Biochim. biophys. Acta (Amst.) 51, 138–147 (1961).

    CAS  Google Scholar 

  • Pravdina, N.F., Lysenko, A.M., Linevich, Yu.G., Galegov, G.A.: The action of 6-azauridine on reproduction of T2 phage. Mikrobiologija 38, 295–298 (1969) (in Russian).

    CAS  Google Scholar 

  • Pringle, C. R.: Genetic characteristics of conditional lethal mutants of vesicular stomatitis virus induced by 5-fluorouracil, 5-azacytidine, and ethyl methane sulfonate. J. Virol. 5, 559–567 (1970).

    PubMed  CAS  Google Scholar 

  • Prusoff, W.H.: Studies on mechanism of action of 6-azathymine. I. Biosynthesis of the deoxyriboside. J. biol. Chem. 215, 809–821 (1955).

    CAS  Google Scholar 

  • Prystaš, M., Gut, J., Šorm, F.: Nucleic acid components and their analogues. XXI. Synthesis of 3-methyl-6-azauridine. Structure proof and general approach to the synthesis of 6-aza- uridines. Coll. Czech. Chem. Commun. 27, 1572–1577 (1962).

    Google Scholar 

  • Prystaš, M., Šorm, F.: Nucleic acid components and their analogues. XXII. Synthesis of 6-azauridine and 5-methyl-6-azauridine. Coll. Czech. Chem. Commun. 27, 1578–1584 (1962).

    Google Scholar 

  • Prystaš, M., Šorm, F.: Nucleic acid components and their analogues. XL. Synthesis of 5- methyl-2’-deoxy-6-azacytidine. Coll. Czech. Chem. Commun. 28, 2598–2604 (1963).

    Google Scholar 

  • Rada, B.: The effect of cell-free extracts on the inhibition of virus multiplication by 6-azauridine. Ann. N.Y. Acad. Sci. 173, 176–184 (1970).

    CAS  Google Scholar 

  • Rada, B., Altanerová, V.: Virus-inhibitory activity of 6-azauridine dependent on cell-free extracts containing uridine kinase. I. Inhibition of plaque-formation. Acta virol. (Bratisl.) 14, 425–434 (1970).

    CAS  Google Scholar 

  • Rada, B., Blaškovič, D.: Inhibition of vaccinia virus multiplication In vitro by 6-azauracil riboside. Acta virol. (Bratisl.) 5, 308–316 (1961).

    Google Scholar 

  • Rada, B., Blaškovič, D.: Some characteristics of the effects of 6-azauridine on vaccinia virus multiplication in comparison with those of 5-iododeoxyuridine. Acta virol. (Bratisl.) 10, 1–9 (1966).

    CAS  Google Scholar 

  • Rada, B., BlašKovič, D., Šorm, f., Škoda, J.: The inhibitory effect of 6-azauracil riboside on the multiplication of vaccinia virus. Experientia (Basel) 16, 487–488 (1960).

    CAS  Google Scholar 

  • Rada, B., Gregusova, V.: Increase of uridine kinase activity after infection of cells with vaccinia and Rous sarcoma viruses. Biochem. biophys. Res. Commun. 15, 324–328 (1964).

    CAS  Google Scholar 

  • Rada, B., Hanusovska, T.: Virus-inhibitory activity of 6-azauridine dependent on cell-free extracts containing uridine kinase. II. Quantitative aspects, efficacy of pretreatment. Acta virol. (Bratisl.) 14, 435 - 444 (1970).

    CAS  Google Scholar 

  • Rada, B., Shatxin, A. J.: The inhibitory effect of 6-azauridine on reovirus multiplication. Acta virol. (Bratisl.) 11, 551–553 (1967).

    CAS  Google Scholar 

  • Rada, B., Smidova, V., Zavada, J.: The inhibitory effect of some antimetabolites and antibiotics on Rous sarcoma growth. Neoplasma (Bratisl.) 11, 553–559 (1964).

    CAS  Google Scholar 

  • Rada, B., Zavada, J.: Screening-test for cytostatic and virostatic substances. Neoplasma (Bratisl.) 9, 57–65 (1962).

    CAS  Google Scholar 

  • Raška, K., Jurovčík, M., Šormova, Z., Šorm, F.: On the metabolism of 5-azacytidine and (1970) aza-2’-deoxycytidine in mice. Coll. Czech. Chem. Commun. 30, 3001–3006 (1965).

    Google Scholar 

  • Raška, K., Zedeck, M.S., Welch, A. D.: Relationship between the metabolic effects and the pregnancy-interrupting property of 6-azauridine in mice. Biochem. Pharmacol. 15, 2136–2138 (1966).

    PubMed  Google Scholar 

  • Raškova, H., Elis, J., Gutová, M., Nižńanska, J., Mikulecký, Z., Kubíčkova, V., Borč, K., Přibíková, V, Hulínský, K., Kantner, V., Belsan, I., Kůtta, A., Erbertova, B., Kleibei, K., Seyček, V., Duchková, H.: Indications for 6-azauridine triacetate — psoriasis. Čs. 1ék. čes. 106,

    Google Scholar 

  • Rašková, H., Elis, J., PerlíK, F., Polanský, F., Slavík, M.: Unexpected sideeffects of 6-azauridine in rheumatoid arthritis and feedback in animal experiments. Proc. Europ. Soc. Study Drug Toxicity 12, 191–198 (1971).

    Google Scholar 

  • Rubin, R. J., Jaffe, J. J., Handschumacher, R.E.: Qualitative differences in the pyrimidine metabolism of Trypanosoma equiperdum and mammals as characterized by 6-azauracil and (1971) azauridine. Biochem. Pharmacol. 11, 563–572 (1962).

    PubMed  CAS  Google Scholar 

  • Rychter, Z., Jelínek, R.: Change in shape and location of non-vascularized area of ventricular myocardium in chick embryo during terminal phase of heart vascularization after administration of 6-azauridine in different doses. Folia morphologica (Prague) 21, 1–11 (1973).

    CAS  Google Scholar 

  • Rychter, Z., Ošťádal, B., Jelínek, R.: Weight analysis of development of the chick embryo myocardium during the terminal phase of its vascularization after administration of 6-azauridine. Physiologia Bohemoslovaca 21, 569–580 (1972).

    PubMed  CAS  Google Scholar 

  • Sagar, P., Kára, J.: Activation of deoxycytidylate deaminase from certain embryonal and tumor tissues by 6-aza-2’-deoxycytidine-5’-monophosphate and 2’-deoxycytidine-5’-tri- phosphate. Folia biol. (Prague) 12, 75–79 (1966).

    CAS  Google Scholar 

  • Saksena, S.K., Chaudhttry, R.R.: The antifertility effect of 2’, 3’, 5’-tri-0-acetyl-6-azauridine. Part II. In rabbits. Indian J. med. Ites. 58, 374–376 (1970).

    Google Scholar 

  • Sanders, M. A., Wiesner, B.P., Yudkin, J.: Control of fertility by 6-azauridine. Nature (Lond.) 189, 1015–1016 (1961).

    CAS  Google Scholar 

  • Schäfer, W., Pister, L., Schneider, R.: Analyse des Vermehrungsmechanismus des Newcastle disease Virus (NDV) mit Hilfe verschiedener Inhibitoren. Z. Naturforsch. 22 b, 1319–1330 (1967).

    Google Scholar 

  • Schindler, R., Welch, A.D.: Ribosidation as a means of activating 6-azauracil as an inhibitor of cell reproduction. Science 125, 548–549 (1957).

    PubMed  CAS  Google Scholar 

  • Šeferna, I., Loukomskaya, N., Kadlec, O., Janků, I.: The effect of 6-azauridine on the contractile responses of the isolated ileum of the guinea-pig to drugs and to coaxial stimulation. J. pharm. Pharmacol. 18, 501–506 (1966).

    PubMed  Google Scholar 

  • Seifertová M., Čihák, A., Veselý, JJ.: Effect of 5-azacytidine and 6-azauridine on the synthesis of DNA in embryonic mouse brain, mitotic activity and migration of ventricular cells. Neoplasma (Bratisl.) 20, 243–249 (1973).

    Google Scholar 

  • Seifertová, M., Veselý, J., Šorm, F.: Effect of 5-azacytidine on developing mouse embryo. Experientia (Basel) 24, 487–488 (1968).

    Google Scholar 

  • Škoda, J., Hess, V.F., Šorm, F.: The biosynthesis of 6-azauracil riboside by Escherichia coli growing in the presence of 6-azauracil. Experientia (Basel) 13, 150–151 (1957 a).

    Google Scholar 

  • Škoda, J., Hess, V.F., Šorm, F.: Production of 6-azauracil riboside by Escherichia coli growing in the presence of 6-azauracil. Coll. Czech. Chem. Commun. 22, 1330–1333 (1957b).

    Google Scholar 

  • Škoda, J., Kara, J., Cihak, A., Šorm, F.: Formation of the ribonucleoside of 5-azauracil by Escherichia coli and isolation of ribosyl biuret as the main decomposition product of 5-azauridine. Coll. Czech. Chem. Commun. 27, 1692–1694 (1962).

    Google Scholar 

  • Škoda, J., Kara, J., Sormova, Z.: Interaction of 6-azauridine-5’-diphosphate with Escherichia coli polynucleotide phosphorylase. Coll. Czech. Chem. Commun. 24, 3783–3789 (1959b).

    Google Scholar 

  • Škoda, J., Kara, J., Sormova, Z., Šorm, F.: Inhibition of Escherichia coli polynucleotide phosphorylase by 6-azauridine diphosphate. Biochim. biophys. Acta (Amst.) 33, 579–580 (1959a).

    Google Scholar 

  • Škoda, J., Listý, V., Smrt, J., Holý, A., Šorm, F.: Formation of a dead code triplet through replacement of the terminal ribonucleoside in guanylyl-uridylyl-uridine and guanylyl-uri- dylyl-cytidine by 6-azacytidine. Molec. Pharmacol. 2, 608–610 (1966).

    Google Scholar 

  • Škoda, J., Šorm, F.: Czechoslovak patent No. 88063 (1958a) (in Czech).

    Google Scholar 

  • Škoda, J., Šorm, F.: Accumulation of nucleic acid metabolites in Escherichia coli exposed to the action of 6-azauracil. Biochim. biophys. Acta (Amst.) 28, 659–660 (1958b).

    Google Scholar 

  • Škoda, J., Šorm, F.: The accumulation of orotic acid, uracil and hypoxanthine by Escherichia coli in the presence of 6-azauracil and the biosynthesis of 6-azauridylic acid. Coll. Czech. Chem. Commun. 24, 1331–1337 (1959).

    Google Scholar 

  • Škoda, J., Šorm, F.: Biosynthesis of co-polymers of uridylic and cytidylic acids with 6-aza- cytidylic acid. Biochim. biophys. Acta (Amst.) 91, 352–354 (1964).

    Google Scholar 

  • Sköld, O.: Uridine kinase from Ehrlich ascites tumor: purification and properties. J. biol. Chem. 235, 3273–3279 (1960).

    Google Scholar 

  • Slavík, M., Elis, J., Raškova, H., Gutová, M., Duchková, M., Kubíková, M., Seyček, V.: Therapeutic effects of 6-azauridine triacetate in psoriasis. Pharm. Clin. 2, 120–125 (1970).

    Google Scholar 

  • Slavík, M., Hýanek, J., Elis, J., Homolka, J.: Typical hyperaminoaciduria after high doses of 6-azauridine triacetate. Biochem. Pharmacol. 18, 1782–1784 (1969).

    PubMed  Google Scholar 

  • Šmahel, O., Öernoch, A., Šorm, F., König, J., Valenta, 0., Svehla, C., Svorc, J., Blaha, V., Uher, V., Gerberova, J.: An attempt to treat chorionepithelioma with 6-azauridine. Ös. lek. ces. 104, 1085–1087 (1965) (In Czech.).

    Google Scholar 

  • Šmahel, O., Grafnetterová, J., König, K., Schück, O.: Der Blutspiegel und die renale Ausscheidung von 6-Azauridin bei verschiedenem Applikations- und Dosierungsmodus. Internationale Zeitschrift für Klinische Pharmakologie. Therap. Toxikol. 2, 101–105 (1967).

    Google Scholar 

  • Šmejkal, F., Šorm, F.: The effect of 6-azauracil riboside against vaccinia virus in rabbits. Acta virol. (Bratisl.) 6, 282 (1962).

    Google Scholar 

  • Šorm, F., Keilova, H.: The anti-tumor activity of 6-azauracil riboside. Experientia (Basel) 14, 215 (1958).

    Google Scholar 

  • Šorm, F., Pískala, A., Číhák, A., Veselý, J.: 5-Azacytidine, a new, highly effective cancero- statie. Experientia (Basel) 20, 202–203 (1964).

    Google Scholar 

  • Šorm, F., Smrt, J., Černěckij, V.: 6-Azacytidine—a new antimetabolite. Experientia (Basel) 17, 64–65 (1961).

    Google Scholar 

  • Šorm, F., Šormová, Z., Raska, K., Jurovöik, M.: Comparison of the metabolism and inhibitory effects of 5-azacytidine and 5-aza-2’-deoxycytidine in mammalian tissues. Rev. Roumaine Biochim. 3, 139–147 (1966).

    Google Scholar 

  • Šorm, F., Veselý, J.: Potentiation of the cancerostatic effect of 6-azauridine and 6-azacytidine with 5-bis-(2-chloroethyl)-aminomethyluracil. Experientia (Basel) 17, 355 (1961).

    Google Scholar 

  • Šorm, F., Veselý, J.: The activity of a new antimetabolite, 5-azacytidine, against lymphoid leukemia in AK mice. Neoplasma (Bratisl.) 11, 123–130 (1964).

    Google Scholar 

  • Šorm, F., Veselý, J.: Partial reversal of toxic effects of 5-azacytidine by 6-azauridine in normal mice. Experientia (Basel) 21, 581–582 (1965).

    Google Scholar 

  • Šorm, J., Veselý, J.: Effect of 5-aza-2’-deoxycytidine against leukemic and hemopoietic tissues in AKR mice. Neoplasma (Bratisl.) 15, 339–343 (1968).

    Google Scholar 

  • Stollar, V., Stevens, T.M., Schlesinger, R. W.: Studies on the nature of dengue viruses. II. Characterization of viral RNA and effects of inhibitors of RNA synthesis. Virology 30, 303–312 (1966).

    PubMed  CAS  Google Scholar 

  • Stejskalová, V., Iványi, J., Kára, J.: Enhancement of antibody synthesis In vitro by 6- azauridine, uridine and actinomycin D. Folia Biol. (Prague) 16, 250–258 (1970).

    Google Scholar 

  • Šterzl, J.: Effect of some metabolic inhibitors on antibody formation. Nature (Lond.) 189, 1022–1023 (1961).

    Google Scholar 

  • Svatá, M., Raška, K., Šorm, F.: Interruption of pregnancy by 5-azacytidine. Experientia (Basel) 22, 53 (1966).

    Google Scholar 

  • Terskikh, I. I., Galegov, G.A., Chutkov, N.A., Bekleshova, A.Iu.: The inhibitory effect produced by 5-bromo-2’-deoxyuridine and 6-azauridine on the reproduction of the causative organism of ornithosis. Dokl. Akad. Nauk SSSR 180, 480–481 (1968) (in Russian).

    PubMed  CAS  Google Scholar 

  • Tkaczynski, T., Šmejkal, J., Šorm, F.: Nucleic acid components and their analogues. L. Synthesis of l-β-d-xylofuranosyl-6-azauracil. Coll. Czech. Chem. Commun. 29, 1736–1738 (1964).

    CAS  Google Scholar 

  • Tong, G.L., Lee, W.L., Goodman, L.: A Convenient Synthesis Of 6-AZA-2, -Deoxycytidine (1). J. Heterocycl. Chem. 3, 226–227 (1966).

    CAS  Google Scholar 

  • Trnavsky, K., Laparova, V.: Anti-inflammatory activity of 6-azauridine. Med. Pharmacol. Exp. 16, 171–177 (1967).

    CAS  Google Scholar 

  • Turner, R.W., Calabresi, P.: The effect of triacetyl azauridine on psoriasis. J. Invest. Derm. 43, 551–557 (1964).

    PubMed  CAS  Google Scholar 

  • Vadlamttdi, S., Pajdarathsingh, M., Bonmassar, E., Goldin, A.: Reduction of antileukemic and imunosuppressive activities of 5-azacytidine in mice by concurrent treatment with uridine. Proc. Soc. exptl. Biol. (N. Y.) 133, 1232–1238 (1970).

    Google Scholar 

  • vanWagenen, G., DeConti, R.C., Handschumacher, R.E., Wade, M. E.: Abortifacient and teratogenic effects of triacetyl-6-azauridine in the monkey. Am. J. Obstet. Gynec. 108, 272–281 (1970).

    CAS  Google Scholar 

  • Veselý, J.: The effect of 6-azauridine and 6-azacytidine on the intracellular synthesis of RNA in fowl leukemic and normal myeloblasts IN VITRO. Acta biol. med. german. 12, 60–64 (1964).

    PubMed  Google Scholar 

  • Veselý, J., Číhak, A.: High-frequency induction in vivo of mouse leukemia in AKR strain by 5-azacytidine and 5-iodo-2’-deoxyuridine. Experientia (Basel) 29, 1132–1133 (1973).

    Google Scholar 

  • Veselý, J., Číhak, A., Šorm, F.: Characteristics of mouse leukemic cells resistant to 5-azacytidine and 5-aza-2’-deoxycytidine. Cancer Res. 28, 1995–2000 (1968 a).

    Google Scholar 

  • Veselý, J., Číhak, A., Šorm, F.: Biochemical mechanism of drug resistance. VII. Inhibition of orotic acid metabolism by 5-azacytidine in leukemic mice sensitive and resistant to 5-azacytidine. Biochem. Pharmacol. 17, 519–524 (1968b).

    PubMed  Google Scholar 

  • Veselý, J., Číhak, A., Šorm, F.: Enhanced triphosphatase activity of mouse leukemic cells resistant to 5-azacytidine. Coll. Czech. Chem. Commun. 33, 341–345 (1968 c).

    Google Scholar 

  • Veselý, J., Číhak, A., Šorm, F.: Biochemical mechanisms of drug resistance. IX. Metabolic alterations in leukemic mouse cells following 5-aza-2’-deoxycytidine. Coll. Czech. Chem. Commun. 34, 901–909 (1969a).

    Google Scholar 

  • Veselý, J., Číhak, A., Šorm, F.: Association of decreased uridine and deoxycytidine kinase with enhanced RNA and DNA polymerase in mouse leukemic cells resistant to 5-azacytidine and 5-aza-2’-deoxycytidine. Cancer Res. 30, 2180–2186 (1970).

    PubMed  Google Scholar 

  • Veselý, J., Gostof, R., Číhak, A., Šorm, F.: Radioprotective effect of 5-azacytidine in AKR mice. Z. Naturforsch. 24b, 318–320 (1969b).

    Google Scholar 

  • Vogler, W.R., Olansky, S.: A double-blind study of azaribine in the treatment of psoriasis. Ann. intern. Med. 73, 951–956 (1970).

    PubMed  CAS  Google Scholar 

  • Vojta, M., Jirasek, J.: 6-Azauridine-induced changes of the trophoblast in early human pregnancy. Clin. Pharmacol. Ther. 7, 162–165 (1966).

    CAS  Google Scholar 

  • Vorherr, H., Welch, A. D.: The mode of interruption of pregnancy by 6-azauridine in mice and rats. Biochem. Pharmacol. 19, 1001–1006 (1970).

    CAS  Google Scholar 

  • Vrba, M.: Titration of Rous sarcoma virus on the chick embryo chorioallantoic membrane. Acta virol. (Bratisl.) 7, 525–533 (1964).

    Google Scholar 

  • Wells, W., Gaines, D., Koenig, H.: Studies of pyrimidine nucleotide metabolism in the central nervous system. I. Metabolic effects and metabolism of 6-azauridine. J. Neurochem. 10, 709–723 (1963).

    PubMed  CAS  Google Scholar 

  • Wieczorkowski, J., Šorm, F., Beránek, J.: Nucleic acid components and their analogues. CX. Synthesis of l-(2’, 3’-epoxy-β-d-lyxofuranosyl)-6-azaisocytosine. Coll. Czech. Chem. Commun. 33, 924–930 (1968).

    CAS  Google Scholar 

  • Wilkinson, J.F.: Treatment of leukemias. Proc. roy. Soc. Med. 56, 644–648 (1963).

    CAS  Google Scholar 

  • Wilson, D.E., LoGerfo, P.: Inhibition of ribonucleic acid synthesis in Newcastle disease virus-infected cells by puromycin and 6-azauridine. J. Bact. 88, 1550–1555 (1964).

    PubMed  CAS  Google Scholar 

  • Winkler, A., Drahovský, D., Gregušová, V., Thurzo, V., Kára, J., Škoda, J., Šorm, F.: Determination of uridine kinase activity in some tumours and in leukaemic cells using 4, 5-14C-azauridine as substrate. Neoplasma (Bratisl.) 9, 101–103 (1962).

    CAS  Google Scholar 

  • Zaruba, F., kfrta, A., Elis, J.: Treatment of mycosis fungoides with 6-azauracilriboside. Lancet H, 275 (1963).

    Google Scholar 

  • Žemlička, J., Smrt, J., Šorm, F.: Nucleic acid components and their analogues. XLVIII. Synthesis and structure of nitrogen mustard derivatives of cytidine and 6-azacytidine. Coll. Czech. Chem. Commun. 29, 635–644 (1964).

    Google Scholar 

  • Žemlička, J., Šorm, F.: Nucleic acid components and their analogues. LXIII. The reaction of dimethylchloromethylenammonium chloride with 2’, 3’, 5’-tri-0-acyl derivatives of uridine and 6-azauridine; a new synthesis of 6-azacytidine. Coll. Czech. Chem. Commun. 30, 2052–206

    Google Scholar 

  • Žemlička, J., Šorm, F.: Nucleic acid components and their analogues. LXXXIX. Synthesis of 2’, 3’-0-isopropylidene-02, 5’-cyclo-6-azauridine and 2-(β-d-ribofuranosyl)-3-amino-4, 5- dihydro-l, 2, 4-triazine-3-one (6-azaisocytidine). Coll. Czech. Chem. Commun. 32, 576–590 (1967).

    Google Scholar 

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Škoda, J. (1975). Azapyrimidine Nucleosides. In: Sartorelli, A.C., Johns, D.G. (eds) Antineoplastic and Immunosuppressive Agents. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology, vol 38 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-65806-8_16

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