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Dendritic Catanionic Assemblies: In vitro Anti‐HIV Activity of Phosphorus‐Containing Dendrimers Bearing Galβ 1 cer Analogues
Author(s) -
Blanzat Muriel,
Turrin CédricOlivier,
Aubertin AnneMarie,
CouturierVidal Christiane,
Caminade AnneMarie,
Majoral JeanPierre,
RicoLattes Isabelle,
Lattes Armand
Publication year - 2005
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200500203
Subject(s) - dendrimer , supramolecular chemistry , in vitro , chemistry , lipophilicity , combinatorial chemistry , human immunodeficiency virus (hiv) , stereochemistry , organic chemistry , polymer chemistry , biochemistry , molecule , biology , immunology
Two series of water‐soluble dendritic catanionic assemblies, acting as multisite analogues of galactosylceramide (Galβ 1 cer), have been prepared with the goal of blocking HIV infection prior to the entry of the virus into human cells. Trifunctional and hexafunctional cinnamic acid‐terminated dendrimers have been synthesized from phosphorus‐containing dendrimers bearing aldehyde end groups. A classical acid–base reaction performed in water between acid‐terminated dendrimers and stoichiometric amounts of N ‐hexadecylamino‐1‐deoxylactitol ( 3 ) provided the expected catanionic assemblies. Antiviral assays on these supramolecular entities confirmed the crucial roles both of multivalency effects and of lipophilicity on the biological activity of Galβ 1 cer analogues. Moreover, correlation between in vitro tests and molecular modeling highlights the specific influence of the assembly shape on the anti‐HIV efficiency, with the tri‐ and hexafunctional cored dendrimers, both decorated with 12 sugar moieties, exhibiting IC 50 values of 1.1 and 0.12 μ M , respectively.