Synthesis and immunological evaluation of fluorinated α-C-galactosylceramide analogs

被引：6

作者：

Colombel, Sophie ^{[1
,2
]}

Van Hijfte, Nathalie ^{[1
,2
]}

Poisson, Thomas ^{[1
,2
]}

Pannecoucke, Xavier ^{[1
,2
]}

Monneaux, Fanny ^{[3
,4
]}

Leclerc, Eric ^{[5
]}

机构：

[1] Normandie Univ, COBRA, UMR 6014, F-76821 Mont St Aignan, France

[2] Univ Rouen, CNRS, INSA Rouen, FR 3038, F-76821 Mont St Aignan, France

[3] CNRS, Inst Biol Mol & Cellulaire, UPR3572, Immunopathol & Chim Therapeut, F-67084 Strasbourg, France

[4] FRC 1589, F-67084 Strasbourg, France

[5] CNRS, Inst Charles Gerhardt, UM2 UM1 ENSCM, UMR 5253, F-34296 Montpellier 5, France

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2015年 / 173卷

关键词：

Galactosylceramides; Glycomimetics; Fluorine; Immunoregulation; C-Glycosides; CONFORMATIONAL BEHAVIOR; GLYCOSIDES; CLEARANCE; CHEMISTRY; ANTITUMOR; RADICALS; CELLS;

D O I：

10.1016/j.jfluchem.2015.02.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A synthesis of difluorinated alpha-C-galactosylceramides analogs featuring an extra hydroxy group in 1'-position is reported. These compounds were prepared according to unprecedented and unusual methodologies that were previously reported by the authors on simpler substrates. Unfortunately, all four compounds, which feature different lipidic chain lengths, failed to activate iNKT cells. The question whether it is due to the anomeric oxygen/CF2 transposition or to the presence of the extra OH group remains unanswered. (C) 2015 Published by Elsevier B.V.

引用

收藏

页码：84 / 91

页数：8

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