Design and synthesis of novel [60]fullerene derivatives as potential HIV aspartic protease inhibitors

被引:107
作者
Marcorin, GL
Da Ros, T
Castellano, S
Stefancich, G
Bonin, I
Miertus, S
Prato, M
机构
[1] Univ Trieste, Dipartimento Sci Farmaceut, I-34127 Trieste, Italy
[2] Int Ctr Sci & High Technol, ICS UNIDO, I-34012 Trieste, Italy
关键词
D O I
10.1021/ol000217y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two water-soluble fullerene derivatives have been computer designed and synthesized. They may exhibit interesting anti-HIV activity owing to the presence of two ammonium groups strategically located on the spheroid surface.
引用
收藏
页码:3955 / 3958
页数:4
相关论文
共 14 条
[1]  
Da Ros T, 1999, CHEM COMMUN, P663
[2]   Easy access to water-soluble fullerene derivatives via 1,3-dipolar cycloadditions of azomethine ylides to C-60 [J].
DaRos, T ;
Prato, M ;
Novello, F ;
Maggini, M ;
Banfi, E .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9070-9072
[3]   Templated regioselective and stereoselective synthesis in fullerene chemistry [J].
Diederich, F ;
Kessinger, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (06) :537-545
[4]   INHIBITION OF THE HIV-1 PROTEASE BY FULLERENE DERIVATIVES - MODEL-BUILDING STUDIES AND EXPERIMENTAL-VERIFICATION [J].
FRIEDMAN, SH ;
DECAMP, DL ;
SIJBESMA, RP ;
SRDANOV, G ;
WUDL, F ;
KENYON, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6506-6509
[5]   PREDICTION OF THE PROTONATION STATE OF THE ACTIVE-SITE ASPARTYL RESIDUES IN HIV-1 PROTEASE INHIBITOR COMPLEXES VIA MOLECULAR-DYNAMICS SIMULATION [J].
HARTE, WE ;
BEVERIDGE, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3883-3886
[6]  
HIRSCH A, 1999, FULLERENES RELATED S, V199
[7]   ADDITION OF AZOMETHINE YLIDES TO C-60 - SYNTHESIS, CHARACTERIZATION, AND FUNCTIONALIZATION OF FULLERENE PYRROLIDINES [J].
MAGGINI, M ;
SCORRANO, G ;
PRATO, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9798-9799
[8]   A computational study of the resistance of HIV-1 aspartic protease to the inhibitors ABT-538 and VX-478 and design of new analogues [J].
Nair, AC ;
Miertus, S ;
Tossi, A ;
Romeo, D .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1998, 242 (03) :545-551
[9]   Molecular dynamics study of HIV-1 protease-substrate complex: Roles of the water molecules at the loop structures of the active site [J].
Okimoto, N ;
Tsukui, T ;
Kitayama, K ;
Hata, M ;
Hoshino, T ;
Tsuda, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5613-5622
[10]   Synthesis of RNAse active site model systems using a steroid template [J].
Oost, T ;
Kalesse, M .
TETRAHEDRON, 1997, 53 (25) :8421-8438