Synthesis and anti-HIV activity of catanionic analogs of galactosylceramide

被引：29

作者：

Blanzat, M ^{[1
]}

Perez, E ^{[1
]}

Rico-Lattes, I ^{[1
]}

Lattes, A ^{[1
]}

机构：

[1] Univ Toulouse 3, Lab Interact Mol & React Chim & Photochim, CNRS, UMR 5623, F-31062 Toulouse, France

来源：

NEW JOURNAL OF CHEMISTRY | 1999年 / 23卷 / 11期

关键词：

D O I：

10.1039/a905417k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two-chain and gemini catanionic analogs of galactosylceramide were easily prepared in quantitative yields, affording high anti-HIV activities with low cytotoxicities on human cells (e.g. for gemini 4b an EC50 of 0.5 mu M with a CC50 of >100 mu M were obtained).

引用

收藏

页码：1063 / 1065

页数：3

相关论文

共 11 条

[1] Synthesis and vesicle formation from hybrid bolaphile/amphiphile ion-pairs. Evidence of membrane property modulation by molecular design [J].

Bhattacharya, S ;

De, SM ;

Subramanian, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7640-7651

[2] VESICLE FORMATION FROM DIMERIC SURFACTANTS THROUGH ION-PAIRING - ADJUSTMENT OF POLAR HEADGROUP SEPARATION LEADS TO CONTROL OVER VESICULAR THERMOTROPIC PROPERTIES [J].

BHATTACHARYA, S ;

DE, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (06) :651-652

[3] New catanionic glycolipids.: 1.: Synthesis, characterization, and biological activity of double-chain and gemini catanionic analogues of galactosylceramide (galβ1cer) [J].

Blanzat, M ;

Perez, E ;

Rico-Lattes, I ;

Prome, D ;

Prome, JC ;

Lattes, A .

LANGMUIR, 1999, 15 (19) :6163-6169

[4] Synthetic soluble analogs of galactosylceramide (GalCer) bind to the V3 domain of HIV-1 gp120 and inhibit HIV-1-induced fusion and entry [J].

Fantini, J ;

Hammache, D ;

Delezay, O ;

Yahi, N ;

AndreBarres, C ;

RicoLattes, I ;

Lattes, A .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (11) :7245-7252

[5] BILAYER-FORMING ION-PAIR AMPHIPHILES FROM SINGLE-CHAIN SURFACTANTS [J].

FUKUDA, H ;

KAWATA, K ;

OKUDA, H ;

REGEN, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (04) :1635-1637

[6] RHO-SIGMA-PI ANALYSIS . METHOD FOR CORRELATION OF BIOLOGICAL ACTIVITY + CHEMICAL STRUCTURE [J].

HANSCH, C ;

FUJITA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (08) :1616-&

[7] ANIMAL GLYCOSPHINGOLIPIDS AS MEMBRANE ATTACHMENT SITES FOR BACTERIA [J].

KARLSSON, KA .

ANNUAL REVIEW OF BIOCHEMISTRY, 1989, 58 :309-350

[8]

Mammen M, 1998, ANGEW CHEM INT EDIT, V37, P2755

[9]

RICOLATTES I, 1995, NEW J CHEM, V19, P341

[10] GALACTOSYL CERAMIDE (OR A CLOSELY RELATED MOLECULE) IS THE RECEPTOR FOR HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 ON HUMAN COLON EPITHELIAL HT29 CELLS [J].

YAHI, N ;

BAGHDIGUIAN, S ;

MOREAU, H ;

FANTINI, J .

JOURNAL OF VIROLOGY, 1992, 66 (08) :4848-4854