Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway

被引：28

作者：

Dafik, Laila ^{[2
]}

d'Alarcao, Marc ^{[1
]}

Kumar, Krishna ^{[2
,3
]}

机构：

[1] San Jose State Univ, Dept Chem, San Jose, CA 95192 USA

[2] Tufts Univ, Dept Chem, Medford, MA 02155 USA

[3] Tufts Med Ctr, Ctr Canc, Boston, MA 02110 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2008年 / 18卷 / 22期

关键词：

Glycoengineering; Sialic acid; Fluorination; Cell adhesion;

D O I：

10.1016/j.bmcl.2008.09.010

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Metabolic oligosaccharide engineering has been employed to introduce fluorine-containing groups onto mammalian cell surfaces. Incubation of HeLa, Jurkat, and HL60 cells in culture with fluorinated sialic acid and mannosamine analogues resulted in cell-surface presentation of fluorinated glycans. Metabolic conversion of fluorinated precursors was detected and quantified by DMB-derivatization and HPLC ESI-MS analysis. Between 7% and 72% of total membrane-associated sialosides were fluorinated, depending on the precursor used and the cell type. Fluorination of mammalian cell surfaces provides a means for introducing a bioorthogonal surface for modulating noncovalent interactions such as those involved in cell adhesion. (C) 2008 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5945 / 5947

页数：3

相关论文

共 29 条

[1] Metabolic oligosaccharide engineering: perspectives, applications, and future directions [J].

Campbell, Christopher T. ;

Sampathkumar, Srinivasa-Gopalan ;

Yarema, Kevin J. .

MOLECULAR BIOSYSTEMS, 2007, 3 (03) :187-194

[2] Efficient metabolic engineering, of GM3 on tumor cells by N-phenylacetyl-D-mannosamine [J].

Chefalo, P ;

Pan, YB ;

Nagy, N ;

Guo, ZW ;

Harding, CV .

BIOCHEMISTRY, 2006, 45 (11) :3733-3739

[3]

DAFIK L, UNPUB

[4] Metabolic oligosaccharide engineering as a tool for glycobiology [J].

Dube, DH ;

Bertozzi, CR .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (05) :616-625

[5] Engineering the sialic acid in organs of mice using N-propanoylmannosamine [J].

Gagiannis, Daniel ;

Gossrau, Reinhart ;

Reutter, Werner ;

Zimmermann-Kordmann, Martin ;

Horstkorte, Ruediger .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2007, 1770 (02) :297-306

[6] FLUOROMETRIC HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY OF N-ACETYLNEURAMINIC AND N-GLYCOLYLNEURAMINIC ACIDS AND ITS APPLICATION TO THEIR MICRODETERMINATION IN HUMAN AND ANIMAL SERA, GLYCOPROTEINS, AND GLYCOLIPIDS [J].

HARA, S ;

TAKEMORI, Y ;

YAMAGUCHI, M ;

NAKAMURA, M ;

OHKURA, Y .

ANALYTICAL BIOCHEMISTRY, 1987, 164 (01) :138-145

[7] Increased expression of the selectin ligand sialyl-Lewisx by biochemical engineering of sialic acids [J].

Horstkorte, M ;

Rau, K ;

Reutter, W ;

Nöhring, S ;

Lucka, L .

EXPERIMENTAL CELL RESEARCH, 2004, 295 (02) :549-554

[8] Biochemical engineering of the N-acyl side chain of sialic acid leads to increased calcium influx from intracellular compartments and promotes differentiation of HL60 cells [J].

Horstkorte, R ;

Rau, K ;

Laabs, S ;

Danker, K ;

Reutter, W .

FEBS LETTERS, 2004, 571 (1-3) :99-102

[9] Substrate specificity of the sialic acid biosynthetic pathway [J].

Jacobs, CL ;

Goon, S ;

Yarema, KJ ;

Hinderlich, S ;

Hang, HC ;

Chai, DH ;

Bertozzi, CR .

BIOCHEMISTRY, 2001, 40 (43) :12864-12874

[10] Carbohydrate-mediated cell adhesion in cancer metastasis and angiogenesis [J].

Kannagi, R ;

Izawa, M ;

Koike, T ;

Miyazaki, K ;

Kimura, N .

CANCER SCIENCE, 2004, 95 (05) :377-384