Inactivation of S-adenosyl-L-homocysteine hydrolase with novel 5′-thioadenosine derivatives.: Antiviral effects

被引：7
|
作者：
Guillerm, G
Guillerm, D
Vandenplas-Vitkowski, C
Glapski, C
De Clercq, E
机构：
[1] UFR Sci, Chim Bioorgan Lab, UMR 6519, F-51687 Reims 2, France
[2] Katholieke Univ Leuven, Rega Inst Med Res, Louvain, Belgium
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 10期
关键词：
D O I：
10.1016/S0960-894X(03)00279-8
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Synthesis of 5'-S-vinyl-5'-thioadenosine 5, 5'-S-ethynyl-5'-thioadenosine 7 and 5'-S-cyano-5'-thioadenosine 9 is described. Incubation of AdoHcy hydrolase with 5, 7 and 9 resulted in time- and concentration-dependent inactivation of the enzyme and partial depletion of its NAD(+) content. From these results and characterisation of metabolites released during the inactivation process, hypothetical mechanisms are suggested. The antiviral activity of 5, 7 and 9 was examined. Significant activities were noted with 5 against Vaccinia, Junin and Taccaribe viruses. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1649 / 1652
页数：4
相关论文
共 50 条
  • [31] EFFECTS OF AN S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE INHIBITOR ON MURINE MACROPHAGE ACTIVATION AND FUNCTION
    LAMBERT, LE
    FRONDORF, KA
    BERLING, JS
    WOLOS, JA
    IMMUNOPHARMACOLOGY, 1995, 29 (02): : 121 - 127
  • [32] Unexpected inhibition of S-adenosyl-L-homocysteine hydrolase by a guanosine nucleoside
    Seley, KL
    Quirk, S
    Salim, S
    Zhang, L
    Hagos, A
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (12) : 1985 - 1988
  • [33] Binding of Cu2+ to S-adenosyl-L-homocysteine hydrolase
    Li, YJ
    Chen, JJ
    Liu, J
    Yang, XD
    Wang, K
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2004, 98 (06) : 977 - 983
  • [34] Structural insights into the reaction mechanism of S-adenosyl-L-homocysteine hydrolase
    Yoshio Kusakabe
    Masaaki Ishihara
    Tomonobu Umeda
    Daisuke Kuroda
    Masayuki Nakanishi
    Yukio Kitade
    Hiroaki Gouda
    Kazuo T. Nakamura
    Nobutada Tanaka
    Scientific Reports, 5
  • [35] S-Adenosyl-L-homocysteine hydrolase as an attractive target for antimicrobial drugs
    Nakanishi, Masayuki
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2007, 127 (06): : 977 - 982
  • [36] The antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi
    Cai, Sumin
    Li, Qing-Shan
    Borchardt, Ronald T.
    Kuczera, Krzysztof
    Schowen, Richard L.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (23) : 7281 - 7287
  • [37] Antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi
    Cai, Sumin
    Li, Qing-shan
    Schowen, Richard L.
    Kuczera, Krzysztof
    Borchardt, Ronald T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [38] Antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi
    Cai, SM
    Li, QS
    Schowen, RL
    Kuczera, K
    Borchardt, RT
    FASEB JOURNAL, 2006, 20 (05): : A896 - A896
  • [39] Structural insights into the reaction mechanism of S-adenosyl-L-homocysteine hydrolase
    Kusakabe, Yoshio
    Ishihara, Masaaki
    Umeda, Tomonobu
    Kuroda, Daisuke
    Nakanishi, Masayuki
    Kitade, Yukio
    Gouda, Hiroaki
    Nakamura, Kazuo T.
    Tanaka, Nobutada
    SCIENTIFIC REPORTS, 2015, 5
  • [40] S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE FROM RAT-LIVER
    TREWYN, RW
    KERR, SJ
    FEDERATION PROCEEDINGS, 1977, 36 (03) : 718 - 718
12345