Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1980, 45, 3039-3044

Inhibition of S-adenosyl-L-homocysteine hydrolase by the aliphatic nucleoside analogue - 9-(S)-(2,3-dihydroxypropyl)adenine

Ivan Votruba and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6

Crossref Cited-by Linking

  • De Clercq Erik: A 40-Year Journey in Search of Selective Antiviral Chemotherapy*. Annu. Rev. Pharmacol. Toxicol. 2011, 51, 1. <>
  • Čtrnáctá Vlasta, Fritzler Jason M., Šurinová Mária, Hrdý Ivan, Zhu Guan, Stejskal František: Efficacy of S-adenosylhomocysteine hydrolase inhibitors, D-eritadenine and (S)-DHPA, against the growth of Cryptosporidium parvum in vitro. Experimental Parasitology 2010, 126, 113. <>
  • Holý Antonin: Synthesis of Acyclic Analogs of Adenosine. Current Protocols in Nucleic Acid Chemistry 2005, 22. <>
  • Yamada Taro, Takata Yoshimi, Komoto Junichi, Gomi Tomoharu, Ogawa Hirofumi, Fujioka Motoji, Takusagawa Fusao: Catalytic mechanism of S-adenosylhomocysteine hydrolase: Roles of His 54, Asp130, Glu155, Lys185, and Aspl89. The International Journal of Biochemistry & Cell Biology 2005, 37, 2417. <>
  • Clercq Erik De, Holý Antonín: Acyclic nucleoside phosphonates: a key class of antiviral drugs. Nat Rev Drug Discov 2005, 4, 928. <>
  • El-Essawy Farag A., Khattab Ahmed F.: Alkylation of 2-pyridinones: Synthesis of novel acyclonucleosides. Journal of Heterocyclic Chemistry 2004, 41, 311. <>
  • Česnek Michal, Holý Antonín, Masojídková Milena: New 2-Alkynyl Derivatives of the Acyclic Nucleoside 9-(2,3-Dihydroxypropyl)adenine and Their 6-Guanidinopurine Counterparts as Potential Effectors of Adenosine Receptors. Collect. Czech. Chem. Commun. 2003, 68, 2201. <>
  • Česnek Michal, Holý Antonı́n, Masojı́dková Milena: 6-Guanidinopurine nucleosides and their analogues. Tetrahedron 2002, 58, 2985. <>
  • Huang Yafei, Komoto Junichi, Takata Yoshimi, Powell Douglas R., Gomi Tomoharu, Ogawa Hirofumi, Fujioka Motoji, Takusagawa Fusao: Inhibition ofS-Adenosylhomocysteine Hydrolase by Acyclic Sugar Adenosine Analogue d-Eritadenine. J. Biol. Chem. 2002, 277, 7477. <>
  • Meszárosová Kateřina, Holý Antonín, Masojídková Milena: Synthesis of Acyclic Adenine 8,N-Anhydronucleosides. Collect. Czech. Chem. Commun. 2000, 65, 1109. <>
  • Gelbič I., Soldán T.: Changes in fecundity ofRhodnius prolixusSål (Het., Reduviidae) caused by three nucleoside derivatives. Journal of Applied Entomology 1997, 121, 465. <>
  • Tzeng Cherng-Chyi, Hwang Long-Chih, Chen Chien-Chi, Wei Dau-Chang: Synthesis of Racemic 5-Substituted 1-(2,3-Dihydroxypropyl)-6-azauracils and Their Isosteric Isomers. Nucleosides and Nucleotides 1995, 14, 1425. <>
  • Marec František, Gelbič Ivan: High recombinagenic activities of three antiviral agents, adenine derivatives, in the Drosophila wing spot test. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis 1994, 311, 305. <>
  • Tukhtaev F. K., Bukin Yu. V.: Influence of cis-2,5-bis[aminooxymethyl]piperazine-3,6-dione on the anaphylactic shock reaction and resynthesis of S-adenosylmethionine in the pulmonary tissue of guinea pigs. Pharm Chem J 1993, 27, 12. <>
  • Liu Siming, Wolfe Michael S., Borchardt Ronald T.: Rational approaches to the design of antiviral agents based on S-adenosyl-l-homocysteine hydrolase as a molecular target. Antiviral Research 1992, 19, 247. <>
  • Azymah Muhammad, Chavis Claude, Lucas Marc, Morvan François, Imbach Jean-Louis: Isotactic Glycero Oligothymidylate. a Convenient Preparation of (R) and (S) 1′, 2′-Seco 2′-Nor Thymidine. Nucleosides and Nucleotides 1992, 11, 1241. <>
  • Baud Marie-V., Chavis Claude, Lucas Marc, Imbach Jean-L.: SnCl4 versus TiCl4-mediated coupling between N-6-benzoyladenine and perbenzoylated 2-deoxypyranose: Application to the synthesis of certain homochiral acyclo and carboacyclonucleosides. Tetrahedron 1991, 47, 9993. <>
  • Votruba Ivan, Hasobe Masahide, Holý Antonin, Borchardt Ronald T.: 2-methylpropyl ester of 3-(adenin-9-YL)-2-hydroxypropanoic acid. Biochemical Pharmacology 1990, 39, 1573. <>
  • Gelbič I., Šula J.: Ovicidal and biochemical effects of hempa and a nucleoside analogue onPyrrhocoris apterus(L.) (Het., Pyrrhocoridae). Journal of Applied Entomology 1990, 109, 401. <>
  • Němec V., Sláma K.: Inhibition of phosphatase by open-chain nucleoside analogues in insects. Experientia 1989, 45, 148. <>
  • Cools Marina, De Clercq Erik: Correlation between the antiviral activity of acyclic and carbocyclic adenosine analogues in murine L929 cells and their inhibitory effect on L929 cell S-adenosylhomocysteine hydrolase. Biochemical Pharmacology 1989, 38, 1061. <>
  • Sessler Jonathan L., Magda Darren J., Lynch Vincent, Schiff Gilbert M., Bernstein David I.: The Synthesis of 2-Amino 7-Substituted Purines. Nucleosides and Nucleotides 1989, 8, 431. <>
  • Schuster Gottfried, Holy Antonin: Inhibitory effects of 9-(2,3-dihydroxypropyl) adenine and 3-(adenin-9-yl)-2-hydroxypropanoic acid 2-methylpropylester on potato virus X replication. Antiviral Research 1988, 9, 329. <>
  • Jelínek R., Doskočil M., Holý A.: Microscopic-anatomical changes in the chick embryo after administration of 9-(RS)-(2,3-dihydroxypropyl) adenine. Teratology 1987, 35, 379. <>
  • De Clercq Erik: S-adenosylhomocysteine hydrolase inhibitors as broad-spectrum antiviral agents. Biochemical Pharmacology 1987, 36, 2567. <>
  • Chu Chung K., Cutler Stephen J.: Chemistry and antiviral activities of acyclonucleosides. Journal of Heterocyclic Chemistry 1986, 23, 289. <>
  • Kitaoka Setsuko, Konno Tasuke, De Clercq Erik: Comparative efficacy of broad-spectrum antiviral agents as inhibitors of rotavirus replication in vitro. Antiviral Research 1986, 6, 57. <>
  • De Clercq Erik, Cools Marina: Antiviral potency of adenosine analogues: Correlation with inhibition of S-adenosylhomocysteine hydrolase. Biochemical and Biophysical Research Communications 1985, 129, 306. <>
  • Votruba Ivan, Holý Antonín, Rosenberg Ivan, Sláma Karel: Inhibition of ovarian SAH-hydrolase in Pyrrhocoris apterus, sterilized with (S)-9-(2,3-dihydroxypropyl)adenine. Insect Biochemistry 1985, 15, 631. <>
  • De Clercq Erik: Recent trends and development in antiviral chemotherapy. Antiviral Research 1985, 5, 11. <>
  • Remy Richard J., Secrist John A.: Acyclic Nucleosides other than Acyclovir as Potential Antiviral Agents. Nucleosides and Nucleotides 1985, 4, 411. <>
  • Clercq Erik De: Targets for the Antiviral and Antitumor Activities of Nucleoside, Nucleotide and Oligonucleotide Analogues. Nucleosides and Nucleotides 1985, 4, 3. <>
  • Bailey Stuart, Shanks Colin T., Harnden Michael R.: Novel Acyclonucleosides. Part I. 2,3-Dihydroxy-1-Methoxypropyl-and 3-Hydroxy-1-Methoxypropyl-Substituted Pyrimidines. Nucleosides and Nucleotides 1985, 4, 565. <>
  • Benes K., Holý A., Melichar O.: The effect of 9-(2,3-dihydroxypropyl) adenine (DHPA) on seedling roots ofVicia faba L. in comparison with adenine, adenosine and some cytokinins. Biol Plant 1984, 26, 144. <>
  • De Clercq Erik, Bergstrom Donald E., John Antonin Holy, Montgomery A.: Broad-spectrum antiviral activity of adenosine analogues. Antiviral Research 1984, 4, 119. <>
  • Jelínek R., Holý A., Votruba I.: Embryotoxicity of 9-(s)-(2,3-dihydroxypropyl)adenine. Teratology 1981, 24, 267. <>
  • Holy Antonin, Čihák Alois: Metabolism of 9-(S)-(2,3-dihydroxypropyl)adenine, an antiviral agent, in mice. Biochemical Pharmacology 1981, 30, 2359. <>
  • De Clercq E., Leyten R., Sobis H., Matousek J., Holý A., De Somer P.: Inhibitory effect of a broad-spectrum antiviral egent, (S)-9-(2,3-dihydroxypropyl)adenine, on spermatogenesis in mice. Toxicology and Applied Pharmacology 1981, 59, 441. <>