Document Detail

Immunosuppressive activity of chemically synthesized gangliosides.
MedLine Citation:
PMID:  7827069     Owner:  NLM     Status:  MEDLINE    
New chemical synthetic methods have permitted the synthesis of a spectrum of glycosphingolipid molecular species, some of which are not naturally occurring. Here we have studied a number of chemically synthesized gangliosides for immunosuppressive activity, using a human in vitro specific antigen (tetanus toxoid)-induced assay of the cellular immune response. Chemically synthesized GM3 and GM4 had the same high degree of immunosuppressive activity as did natural GM3 and GM4 gangliosides, verifying that inhibition is intrinsic to the ganglioside molecules and not caused by other molecules sometimes found in natural preparations (e.g., proteins). Studies of modified molecular species of GM3 and GM4, also prepared by chemical synthesis, have shown the influence of certain structural details upon the immunosuppressive activity of gangliosides: (i) the inverse relationship between fatty acyl chain length and immunosuppressive activity is extended to even shorter chain lengths, with the synthetic gangliosides d18:1-C2:0-GM3 and d18:1-C14:0-GM3 being more immunosuppressive than d18:1-C18:0-GM3 and d18:1-C24:0-GM3; (ii) hydroxylation of the fatty acyl group decreases immunosuppressive activity; (iii) substitution of an S-glycosidic bond for an O-glycosidic bond in the sialic acid ketosidic linkage in GM4 does not alter its activity; and (iv) modifications of the sialic acid group variably influence immunosuppressive activity, since KDN-GM3 and -GM4 ganglioside analogues, which contain a 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid in place of N-acetylneuraminic acid, retain activity, while other modifications such as 8-epi-GM3, and to a lesser extent 9-deoxy-GM3, reduce immunosuppressive activity.(ABSTRACT TRUNCATED AT 250 WORDS)
S Ladisch; A Hasegawa; R Li; M Kiso
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Biochemistry     Volume:  34     ISSN:  0006-2960     ISO Abbreviation:  Biochemistry     Publication Date:  1995 Jan 
Date Detail:
Created Date:  1995-02-23     Completed Date:  1995-02-23     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0370623     Medline TA:  Biochemistry     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1197-202     Citation Subset:  IM    
Center for Cancer and Transplantation Biology, Children's National Medical Center, Washington, DC.
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MeSH Terms
Brain Chemistry
Chromatography, Thin Layer
Gangliosides / chemical synthesis,  pharmacology*
Immunosuppressive Agents / chemistry*
Lymphocyte Activation / drug effects
Molecular Structure
Structure-Activity Relationship
Reg. No./Substance:
0/Gangliosides; 0/Immunosuppressive Agents

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