An efficient synthesis of a 6"-BODIPY-α-Galactosylceramide probe for monitoring α-Galactosylceramide uptake by cells

被引：13

作者：

Cheng, Janice M. H. ^{[1
]}

Chee, Stephanie H. ^{[1
]}

Dolen, Yusuf ^{[2
]}

Verdoes, Martijn ^{[2
]}

Timmer, Mattie S. M. ^{[1
]}

Stocker, Bridget L. ^{[1
]}

机构：

[1] Victoria Univ Wellington, Sch Chem & Phys Sci, POB 600, Wellington 6140, New Zealand

[2] Radboud Univ Nijmegen, Radboud Inst Mol Life Sci, Dept Tumor Immunol, Med Ctr, Geert Grootepl 26, NL-6525 GA Nijmegen, Netherlands

来源：

CARBOHYDRATE RESEARCH | 2019年 / 486卷

基金：

欧洲研究理事会;

关键词：

ANTIGEN PRESENTATION; BIOLOGICAL EVALUATION; GALCER ANALOGS; CD1D; MOUSE; RECOGNITION; CHEMISTRY; RESIDUES; KRN7000;

D O I：

10.1016/j.carres.2019.107840

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Herein, an efficient synthesis of BODIPY-alpha-Galactosylceramide 3, which can be used to study the cellular uptake of the potent immunostimulatory parent compound alpha-Galactosylceramide, is reported. Key in our synthetic strategy is the six-step synthesis of the core BODIPY scaffold (64% yield overall) and its quantitative conversion to an N-hydroxysuccinimidyl ester to facilitate conjugation and purification of the target glycolipid. For the preparation of the core of the glycolipid, the solubility of the lipid acceptor proved to be critical. The ability of BODIPY-alpha GalCer 3 to activate invariant natural killer cells was then demonstrated in vitro.

引用

页数：9

共 44 条

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