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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
Buck, L.L., Pfau, C.J.: Inhibition of lymphocytic choriomeningitis virus replication by actinomycin D and 6-azauridine. Virology 37, 698–701 (1969).
Bukrinskaya, A.G., Asadullaev, T. A.: Comparative effect of histon and 6-azauridine on myxovirus reproduction. Vop. virus. 13, 549–554 (1968) (in Russian).
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).
Calabresi, P., Turner, R.W.: Beneficial effects of triacetyl azauridine in psoriasis and mycosis fungoides. Ann. intern. Med. 64, 352–371 (1966).
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).
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).
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).
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).
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).
Čihák, A., Šorm, F.: Biochemical effects and metabolic transformations of 5-azacytidine in Escherichia coli. Coll. Czech. Chem. Commun. 30, 2091–2102 (1965).
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).
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).
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).
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).
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).
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).
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).
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).
Deconti, R. C., Calabresi, P.: Treatment of polycythemia vera with azauridine and azaribine. Ann. intern. Med. 73, 575–579 (1970).
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).
Doskočil, J.: The kinetics of metabolic transformations of nucleosides by whole cells of Escherichia coli. Coll. Czech. Chem. Commun. 35, 2656–2672 (1970).
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).
Doskočil, J., Pačes, V., Šorm, F.: Inhibition of protein synthesis by 5-azacytidine in Escherichia coli. Biochim. biophys. Acta (Amst.) 145, 771–779 (1967).
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).
Doskočil, J., Šorm, F.: The inhibitory effects of 5-azacytidine and 5-azauridine in Escherichia coli. Coll. Czech. Chem. Commun. 35, 1880–1891 (1970b).
Doskočil, J., Šorm, F.: The mode of action of 5-aza-2’-deoxycytidine in Escherichia coli. Europ. J. Biochem. 13, 180–187 (1970c).
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).
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).
Elis, J., Rašková, H.: La toxicité foetale de l’azacytidine. J. Physiol. (Paris) 56, 559–560 (1964).
Elis, J., Rašková, H.: Controlled clinical trials with new cytostatic preparations produced in Czechoslovakia. Rev. Czech. Med. 12, 9–19 (1966).
Elis, J., Rašková, H.: New indications for 6-azauridine treatment in man. A review. Europ. J. Clin. Pharm. 4, 77–81 (1971).
Elis, J., Slavik, M., Raskovä, H.: Side effects of 6-azauridine triacetate in rheumatoid arthritis. Clin. Pharmacol. Ther. 11, 404–407 (1970).
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).
Ennis, H.L., Lubin, M.: Capacity for synthesis of a pyrimidine biosynthetic enzyme in mammalian cells. Biochem. biophys. Acta (Amst.) 68, 78–83 (1963).
Erukhimov, L.S., Vermel, E.M.: The use of azauridine in cancer of the bladder. Vop. onkol. 15, 91 (1969) (in Russian).
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).
Falke, D., Rada, B.: 6-Azauridine as an inhibitor of the synthesis of herpesvirus hominis. Acta virol. 14, 115–123 (1970).
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).
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).
Fischer, D.S., Cassidy, E.P., Welch, A. D.: Immunosuppression by pyrimidine nucleoside analogs. Biochem. Pharmacol. 15, 1013–1022 (1966).
Flanagan, J. F., Ginsberg, H.S.: Role of ribonucleic acid biosynthesis in multiplication of type 5 adenovirus. J. Bact. 87, 977–987 (1964).
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).
Fučík, V., ŠOrmova, Z., Šorm, F.: The effect of 5-azacytidine on the root meristem of VICIA
Faba. Biol, plant. (Prague) 7, 58 — 64 (1965).
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).
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).
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).
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).
Gershon, D., Sachs, L.: The early synthesis of RNA in polyoma virus (PV) development. Virology 29, 44–48 (1966).
Goldberg, I. H., Rabinowitz, M.: Inhibition of RNA nucleotidyltransferase by 6-azauridine triphosphate. Biochim. biophys. Acta (Amst.) 72, 116–119 (1963).
Grafnetter, D., Grafnetterová, J.: Effect of 6-azauridine on lipid metabolism in the rat. Neoplasma (Bratisl.) 14, 145–153 (1967).
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).
Grafnetterová, J., Grafnetter, D.: 6-Azauridine in brain tissue during chick embryonal development. Experientia (Basel) 24, 53 (1968).
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.
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).
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).
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).
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
Gutová, M., Elis, J., Rašková, H.: Teratogenic effect of 6-azauridine in rats. Teratology 4, 287–292 (1971).
Habermann, V., Šorm, F.: Mechanism of the cancerostatic action of 6-azauracil and its riboside. Coll. Czech. Chem. Commun. 23, 2201–2206 (1958).
Halle, S.: 5-Azacytidine as a mutagen for arboviruses. J. Virol. 2, 1228–1229 (1968).
Handschfmacher, R.E.: Studies of bacterial resistance to 6-azauracil and its riboside. Biochim. biophys. Acta (Amst.) 23, 428–430 (1957).
Handschumacher, R.E.: Bacterial preparation of orotidine-5’-phosphate and uridine-5’-phosphate. Nature (Lond.) 182, 1090–1091 (1958).
Handschumacher, R.E.: Azauracil ribonucleoside and ribonucleotides: isolation and chemical synthesis. J. biol. Chem. 235, 764–768 (1960a).
Handschumacher, R.E.: Orotidylic acid decarboxylase: inhibition studies with azauridine 5’-phosphate. J. biol. Chem. 235, 2917–2919 (1960b).
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).
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).
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).
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).
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).
Hrodek, O., Veselý, J.: 5-Azacytidine in childhood leukemia. Neoplasma (Bratisl.) 18, 493–503 (1971).
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).
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).
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).
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).
Jelínek, R., Rychter, Z., Klika, E.: Syndrome of caudal regression and dystrophic malformations of the spinal cord. Folia morphol. (Prague) 19, 58–70 (1971).
Jelínek, R., Rychter, Z., Seichert, V.: Syndrome of caudal regression in the chick embryo. Folia Morphol. (Prague) 18, 125–137 (1970).
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).
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).
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).
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).
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).
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.
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).
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).
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).
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).
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).
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).
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).
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).
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).
Lisý, V., Škoda, J.: Deamination of some cytosine and cytidine analogues by an Escherichia coli extract. Coll. Czech. Chem. Commun. 31, 3020–3022 (1966).
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).
Loh, P.C.: The role of RNA in the synthesis of vaccinia virus. Proc. Soc. exp. Biol. (N.Y.) 116, 789–792 (1964).
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).
Magdon, E., Konopatzky, R.: Untersuchungen zur Wirkung von 6-Azaurazilribosid bei der Bestrahlung von experimentellen Tiertumoren. Arch. Geschwulstforsch. 29, 259–245 (1967).
Misařovä, Z., Elis, J.: Azauracilriboside and azauracilribosidetriacetate in the therapy of leukemia in children. Čs. Pediat. 19, 161–165 (1964) (in Czech).
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).
Myška, V., Elis, J., Plevová, J., Rašková, H.: Azauridine in viral eye infections. Lancet I, 1230–1231 (1967).
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).
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).
Nouza, K., Pokorná, Z., Slavík, M., Gottwaldová, A.: The immunosuppressive effects of 6-azauridine. Folia Biol. (Prague) 16, 188–195 (1970).
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).
Pačes, V., Doskočil, J., ŠOrm, F.: Incorporation of 5-azacytidine into nucleic acids of Escherichia coli. Biochim. biophys. Acta (Amst.) 161, 352–360 (1968a).
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).
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).
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).
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).
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).
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).
Plevová, J., Janků, I., Šeda, M.: Toxicity of 6-azauridine triacetate. Toxicol. Appl. Pharmacol. 17, 511–518 (1970a).
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).
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).
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).
Pliml, J., Šorm, F.: Synthesis of a 2-deoxy-D-ribofuranosyl-5-azacytosine. Coll. Czech. Chem. Commun. 29, 2576–2578 (1964).
Pontis, H., Degerstedt, G., Reichard, P.: Uridine and deoxyuridine phosphorylase from Ehrlich ascites tumor. Biochim. biophys. Acta (Amst.) 51, 138–147 (1961).
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).
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).
Prusoff, W.H.: Studies on mechanism of action of 6-azathymine. I. Biosynthesis of the deoxyriboside. J. biol. Chem. 215, 809–821 (1955).
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).
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).
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).
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).
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).
Rada, B., Blaškovič, D.: Inhibition of vaccinia virus multiplication In vitro by 6-azauracil riboside. Acta virol. (Bratisl.) 5, 308–316 (1961).
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).
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).
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).
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).
Rada, B., Shatxin, A. J.: The inhibitory effect of 6-azauridine on reovirus multiplication. Acta virol. (Bratisl.) 11, 551–553 (1967).
Rada, B., Smidova, V., Zavada, J.: The inhibitory effect of some antimetabolites and antibiotics on Rous sarcoma growth. Neoplasma (Bratisl.) 11, 553–559 (1964).
Rada, B., Zavada, J.: Screening-test for cytostatic and virostatic substances. Neoplasma (Bratisl.) 9, 57–65 (1962).
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).
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).
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,
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).
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).
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).
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).
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).
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).
Sanders, M. A., Wiesner, B.P., Yudkin, J.: Control of fertility by 6-azauridine. Nature (Lond.) 189, 1015–1016 (1961).
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).
Schindler, R., Welch, A.D.: Ribosidation as a means of activating 6-azauracil as an inhibitor of cell reproduction. Science 125, 548–549 (1957).
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).
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).
Seifertová, M., Veselý, J., Šorm, F.: Effect of 5-azacytidine on developing mouse embryo. Experientia (Basel) 24, 487–488 (1968).
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).
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).
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).
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).
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).
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).
Škoda, J., Šorm, F.: Czechoslovak patent No. 88063 (1958a) (in Czech).
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).
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).
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).
Sköld, O.: Uridine kinase from Ehrlich ascites tumor: purification and properties. J. biol. Chem. 235, 3273–3279 (1960).
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).
Slavík, M., Hýanek, J., Elis, J., Homolka, J.: Typical hyperaminoaciduria after high doses of 6-azauridine triacetate. Biochem. Pharmacol. 18, 1782–1784 (1969).
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.).
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).
Šmejkal, F., Šorm, F.: The effect of 6-azauracil riboside against vaccinia virus in rabbits. Acta virol. (Bratisl.) 6, 282 (1962).
Šorm, F., Keilova, H.: The anti-tumor activity of 6-azauracil riboside. Experientia (Basel) 14, 215 (1958).
Šorm, F., Pískala, A., Číhák, A., Veselý, J.: 5-Azacytidine, a new, highly effective cancero- statie. Experientia (Basel) 20, 202–203 (1964).
Šorm, F., Smrt, J., Černěckij, V.: 6-Azacytidine—a new antimetabolite. Experientia (Basel) 17, 64–65 (1961).
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).
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).
Šorm, F., Veselý, J.: The activity of a new antimetabolite, 5-azacytidine, against lymphoid leukemia in AK mice. Neoplasma (Bratisl.) 11, 123–130 (1964).
Šorm, F., Veselý, J.: Partial reversal of toxic effects of 5-azacytidine by 6-azauridine in normal mice. Experientia (Basel) 21, 581–582 (1965).
Šorm, J., Veselý, J.: Effect of 5-aza-2’-deoxycytidine against leukemic and hemopoietic tissues in AKR mice. Neoplasma (Bratisl.) 15, 339–343 (1968).
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).
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).
Šterzl, J.: Effect of some metabolic inhibitors on antibody formation. Nature (Lond.) 189, 1022–1023 (1961).
Svatá, M., Raška, K., Šorm, F.: Interruption of pregnancy by 5-azacytidine. Experientia (Basel) 22, 53 (1966).
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).
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).
Tong, G.L., Lee, W.L., Goodman, L.: A Convenient Synthesis Of 6-AZA-2, -Deoxycytidine (1). J. Heterocycl. Chem. 3, 226–227 (1966).
Trnavsky, K., Laparova, V.: Anti-inflammatory activity of 6-azauridine. Med. Pharmacol. Exp. 16, 171–177 (1967).
Turner, R.W., Calabresi, P.: The effect of triacetyl azauridine on psoriasis. J. Invest. Derm. 43, 551–557 (1964).
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).
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).
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).
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).
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).
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).
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).
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).
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).
Veselý, J., Gostof, R., Číhak, A., Šorm, F.: Radioprotective effect of 5-azacytidine in AKR mice. Z. Naturforsch. 24b, 318–320 (1969b).
Vogler, W.R., Olansky, S.: A double-blind study of azaribine in the treatment of psoriasis. Ann. intern. Med. 73, 951–956 (1970).
Vojta, M., Jirasek, J.: 6-Azauridine-induced changes of the trophoblast in early human pregnancy. Clin. Pharmacol. Ther. 7, 162–165 (1966).
Vorherr, H., Welch, A. D.: The mode of interruption of pregnancy by 6-azauridine in mice and rats. Biochem. Pharmacol. 19, 1001–1006 (1970).
Vrba, M.: Titration of Rous sarcoma virus on the chick embryo chorioallantoic membrane. Acta virol. (Bratisl.) 7, 525–533 (1964).
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).
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).
Wilkinson, J.F.: Treatment of leukemias. Proc. roy. Soc. Med. 56, 644–648 (1963).
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).
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).
Zaruba, F., kfrta, A., Elis, J.: Treatment of mycosis fungoides with 6-azauracilriboside. Lancet H, 275 (1963).
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).
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
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).
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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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