Document Detail

Metabolic installation of thiols into sialic acid modulates adhesion and stem cell biology.
MedLine Citation:
PMID:  16474386     Owner:  NLM     Status:  MEDLINE    
Metabolic 'oligosaccharide engineering' methods based on N-acetyl-D-mannosamine (ManNAc) analogs allow the glycocalyx of living cells to be remodeled. Herein we report the analog Ac(5)ManNTGc (1) that enables thiols to be expressed in surface sialic acids. By locating this versatile functional group on the outer periphery of normally nonadhesive human Jurkat cells, we obtained spontaneous cell-cell clustering and attachment to complementary maleimide-derivatized substrates. When analyzed in human embryoid body-derived (hEBD) stem cells, Ac(5)ManNTGc induced beta-catenin expression and altered cell morphology, consistent with neuronal differentiation. Notably, these effects were modulated by the growth substrate of the cells, with a stronger response observed on a gold surface than on glass. Together, these results establish sugar analogs as small-molecule tools for tissue engineering by providing a method for attaching cells to scaffolds via their surface carbohydrates as well as offering a means to influence stem cell fates.
Srinivasa-Gopalan Sampathkumar; Adrienne V Li; Mark B Jones; Zhonghui Sun; Kevin J Yarema
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2006-02-12
Journal Detail:
Title:  Nature chemical biology     Volume:  2     ISSN:  1552-4450     ISO Abbreviation:  Nat. Chem. Biol.     Publication Date:  2006 Mar 
Date Detail:
Created Date:  2006-02-17     Completed Date:  2006-05-16     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  101231976     Medline TA:  Nat Chem Biol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  149-52     Citation Subset:  IM    
Department of Biomedical Engineering, The Johns Hopkins University, 3400 N. Charles Street, Clark Hall 106A, Baltimore, Maryland 21218, USA.
Data Bank Information
Bank Name/Acc. No.:
PubChem-Substance/8139825;  8139826
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MeSH Terms
Cell Adhesion / drug effects,  physiology
Cell Differentiation / physiology
Cell Membrane / physiology
Gold / chemistry
Hexosamines / chemistry,  metabolism*
Jurkat Cells
Molecular Conformation
N-Acetylneuraminic Acid / biosynthesis*,  chemistry
Stem Cells / chemistry,  physiology*
Sulfhydryl Compounds / chemistry,  metabolism*,  pharmacology
Surface Properties
beta Catenin / metabolism
Grant Support
1R01CA112314-01A1/CA/NCI NIH HHS
Reg. No./Substance:
0/Hexosamines; 0/Ligands; 0/Sulfhydryl Compounds; 0/beta Catenin; 131-48-6/N-Acetylneuraminic Acid; 4773-29-9/N-acetylmannosamine; 7440-57-5/Gold
Comment In:
Nat Chem Biol. 2006 Mar;2(3):127-8   [PMID:  16485002 ]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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