Anti-HIV properties of cationic fullerene derivatives

被引:115
作者
Marchesan, S
Da Ros, T
Spalluto, G
Balzarini, J
Prato, M
机构
[1] Univ Trieste, Dipartimento Sci Farmaceut, I-34127 Trieste, Italy
[2] Katholieke Univ Leuven, Rega Inst Med Res, Lab Virol & Chemotherapy, B-3000 Louvain, Belgium
关键词
fullerene; fulleropyrrolidine; bis-adducts; anti-HIV activity;
D O I
10.1016/j.bmcl.2005.05.069
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of regioisomeric bis-fulleropyrrolidines bearing two ammonium groups have been synthesized and their activities against HIV-1 and HIV-2 have been evaluated. Two trans isomers have been endowed with interesting antiviral properties, confirming the importance of the relative positions of the substituent on the C-60 cage. In addition, reduced amphiphilicity of molecules to other compounds previously reported decreases their cytotoxicity in CEM cell cultures. None of the compounds showed any inhibitory activity against a variety of DNA and RNA viruses other than HIV. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3615 / 3618
页数:4
相关论文
共 28 条
[1]   TREATMENT OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 (HIV-1)-INFECTED CELLS WITH COMBINATIONS OF HIV-1-SPECIFIC INHIBITORS RESULTS IN A DIFFERENT RESISTANCE PATTERN THAN DOES TREATMENT WITH SINGLE-DRUG THERAPY [J].
BALZARINI, J ;
KARLSSON, A ;
PEREZPEREZ, MJ ;
CAMARASA, MJ ;
TARPLEY, WG ;
DECLERCQ, E .
JOURNAL OF VIROLOGY, 1993, 67 (09) :5353-5359
[2]  
Bisaglia M, 2000, J NEUROCHEM, V74, P1197
[3]   Hemolytic effects of water-soluble fullerene derivatives [J].
Bosi, S ;
Feruglio, L ;
Da Ros, T ;
Spalluto, G ;
Gregoretti, B ;
Terdoslavich, M ;
Decorti, G ;
Passamonti, S ;
Moro, S ;
Prato, M .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (27) :6711-6715
[4]   Synthesis and water solubility of novel fullerene bisadduct derivatives [J].
Bosi, S ;
Feruglio, L ;
Milic, D ;
Prato, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) :4741-4747
[5]   Synthesis and anti-HIV properties of new water-soluble bis-functionalized[60]fullerene derivatives [J].
Bosi, S ;
Da Ros, T ;
Spalluto, G ;
Balzarini, J ;
Prato, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (24) :4437-4440
[6]  
BOUTORINE AS, 1994, ANGEW CHEM INT EDIT, V33, P2462
[7]   A highly water-soluble dendro[60]fullerene [J].
Brettreich, M ;
Hirsch, A .
TETRAHEDRON LETTERS, 1998, 39 (18) :2731-2734
[8]  
Cusan C, 2002, EUR J ORG CHEM, V2002, P2928
[9]  
DAROS T, 2002, J SUPRAMOL CHEM, P327
[10]   COMPARATIVE EFFICACY OF ANTIHERPES DRUGS AGAINST DIFFERENT STRAINS OF HERPES-SIMPLEX VIRUS [J].
DECLERCQ, E ;
DESCAMPS, J ;
VERHELST, G ;
WALKER, RT ;
JONES, AS ;
TORRENCE, PF ;
SHUGAR, D .
JOURNAL OF INFECTIOUS DISEASES, 1980, 141 (05) :563-574