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
  • [41] SYNTHESIS OF 4'-FLUOROADENOSINE AS AN INHIBITOR OF S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE
    GUILLERM, D
    MUZARD, M
    ALLART, B
    GUILLERM, G
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (14) : 1455 - 1460
  • [42] PREPARATION AND PROPERTIES OF S-ADENOSYL-L-HOMOCYSTEINE S-ADENOSYL-L-HOMOCYSTEINE SULFOXIDE AND S-RIBOSYL-L-HOMOCYSTEINE
    DUERRE, JA
    ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1962, 96 (01) : 70 - &
  • [43] THE SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME NEW S-ADENOSYL-L-HOMOCYSTEINE DERIVATIVES AND THEIR NUCLEOSIDE PRECURSORS
    SERAFINOWSKI, P
    DORLAND, E
    BALZARINI, J
    DECLERCQ, E
    NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5): : 545 - 547
  • [44] DESIGN AND SYNTHESIS OF ARISTEROMYCIN 5'-CARBOXALDEHYDE AS A POTENTIAL INHIBITOR OF S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE
    LIU, SM
    YUAN, CS
    BORCHARDT, RT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 105 - MEDI
  • [45] Identification of S-adenosyl-L-homocysteine hydrolase from banana fruit as a novel plant panallergen
    Durasinovic, Tatjana
    Lopandic, Zorana
    Protic-Rosicb, Isidora
    Nesic, Andrijana
    Trbojevic-Ivic, Jovana
    Jappe, Uta
    Gavrovic-Jankulovic, Marija
    FOOD CHEMISTRY, 2024, 437
  • [46] Doubly homologated dihalovinyl and acetylene analogues of adenosine:: Synthesis, interaction with S-adenosyl-L-homocysteine hydrolase, and antiviral and cytostatic effects
    Wnuk, SF
    Valdez, CA
    Khan, J
    Moutinho, P
    Robins, MJ
    Yang, XD
    Borchardt, RT
    Balzarini, J
    De Clercq, E
    JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (06) : 1180 - 1186
  • [47] Synthesis and biological evaluation of substituted indazolyl amide derivatives as S-adenosyl-L-homocysteine hydrolase inhibitors
    Xiang-Duan Tan
    Li-Guang Mao
    Wei Wu
    Si-Yun Nian
    Guo-Ping Wang
    Chinese Chemical Letters, 2016, 27 (06) : 984 - 988
  • [48] Inhibitory effect of Epimedium extract on S-adenosyl-L-homocysteine hydrolase and biomethylation
    Zhang, XY
    Li, YJ
    Yang, XD
    Wang, K
    Ni, JZ
    Qu, XG
    LIFE SCIENCES, 2005, 78 (02) : 180 - 186
  • [49] Synthesis and biological evaluation of substituted indazolyl amide derivatives as S-adenosyl-L-homocysteine hydrolase inhibitors
    Tan, Xiang-Duan
    Mao, Li-Guang
    Wu, Wei
    Nian, Si-Yun
    Wang, Guo-Ping
    CHINESE CHEMICAL LETTERS, 2016, 27 (06) : 984 - 988
  • [50] S-Adenosyl-L-Homocysteine Hydrolase Inhibition by a Synthetic Nicotinamide Cofactor Biomimetic
    Kailing, Lyn L.
    Bertinetti, Daniela
    Paul, Caroline E.
    Manszewski, Tomasz
    Jaskolski, Mariusz
    Herberg, Friedrich W.
    Pavlidis, Ioannis V.
    FRONTIERS IN MICROBIOLOGY, 2018, 9
12345