Synthesis and evaluation of 3"- and 4"-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000

被引：47

作者：

Raju, Ravinder ^{[1
]}

Castillo, Bernard F. ^{[1
]}

Richardson, Stewart K. ^{[1
]}

Thakur, Meena ^{[1
]}

Severins, Ryan ^{[2
]}

Kronenberg, Mitchell ^{[2
]}

Howell, Amy R. ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] La Jolla Inst Allergy & Immunol, Div Dev Immunol, La Jolla, CA 92037 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 15期

关键词：

Galactosyl ceramides; CD1d; NKT cells; KRN7000; analogs; KILLER T-CELLS; CD1D-RESTRICTED NKT CELLS; ALPHA-GALACTOSYLCERAMIDES; ANTIGEN PRESENTATION; DERIVATIVES; RECOGNITION; CD1; ACTIVATION; DISCOVERY; ANTITUMOR;

D O I：

10.1016/j.bmcl.2009.06.005

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Four 3 ''- and 4 ''-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4 ''-fluoro analog led to the production of significant levels of IL-2. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4122 / 4125

页数：4

相关论文

共 45 条

[1] The biology of NKT cells [J].

Bendelac, Albert ;

Savage, Paul B. ;

Teyton, Luc .

ANNUAL REVIEW OF IMMUNOLOGY, 2007, 25 :297-336

[2] NK cells and NKT cells in innate defense against viral infections [J].

Biron, CA ;

Brossay, L .

CURRENT OPINION IN IMMUNOLOGY, 2001, 13 (04) :458-464

[3] CD1d-lipid-antigen recognition by the semi-invariant NKT T-cell receptor [J].

Borg, Natalie A. ;

Wun, Kwok S. ;

Kjer-Nielsen, Lars ;

Wilce, Matthew C. J. ;

Pellicci, Daniel G. ;

Koh, Ruide ;

Besra, Gurdyal S. ;

Bharadwaj, Mandvi ;

Godfrey, Dale I. ;

McCluskey, James ;

Rossjohn, Jamie .

NATURE, 2007, 448 (7149) :44-49

[4] CD1: Antigen presentation and T cell function [J].

Brigl, M ;

Brenner, MB .

ANNUAL REVIEW OF IMMUNOLOGY, 2004, 22 :817-890

[5]

Brimacombe J.S., 1970, CAN J CHEM, V48, P3946

[6] Structural requirements for antigen presentation by mouse CD1 [J].

Burdin, N ;

Brossay, L ;

Degano, M ;

Iijima, H ;

Gui, M ;

Wilson, IA ;

Kronenberg, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (18) :10156-10161

[7]

Cerundolo V, 2007, CURR TOP MICROBIOL, V314, P325

[8] THE RAPID SYNTHESIS OF DEOXYFLUORO SUGARS USING TRIS(DIMETHYLAMINO)SULFONIUM DIFLUOROTRIMETHYLSILICATE (TASF) [J].

DOBOSZEWSKI, B ;

HAY, GW ;

SZAREK, WA .

CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (02) :412-419

[9] Synthesis of uridine 5′-[2-S-pyridy1-3-thio-α-D-galactopyranosyl diphosphate]:: Precursor of UDP-thiogal sugar nucleotide donor substrate for β-1,4-galactosyltransferase [J].

Elhalabi, J ;

Rice, KG .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (1-2) :195-205

[10] AN IMPROVEMENT IN THE PREPARATION OF SOME CARBOHYDRATE BENZYLIDENE ACETALS [J].

FERRO, V ;

MOCERINO, M ;

STICK, RV ;

TILBROOK, DMG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (05) :813-815

← 1 2 3 4 5 →