Document Detail

Adjuvant activity of 6-O-acyl-muramyldipeptides to enhance primary cellular and humoral immune responses in guinea pigs: adaptability to various vehicles and pyrogenicity.
MedLine Citation:
PMID:  3744548     Owner:  NLM     Status:  MEDLINE    
Thirteen 6-O-acyl-N-acetylmuramyl-L-alanyl-D-isoglutamines (6-O-acyl-MDPs), including four inactive D-isoasparagine and L-isoglutamine analogs, were tested for their pyrogenicity and immunopotentiating activity to stimulate primary humoral and cellular immune responses in guinea pigs to a model protein antigen, ovalbumin, when administered in various vehicles. Among them, derivatives whose muramic acid residue was substituted by alpha-branched (and beta-hydroxylated) higher fatty acids at the carbon-6 position, especially 6-O-(2-tetradecylhexadecanoyl)-MDP (B3O-MDP) and, to a lesser extent, 6-O-(3-hydroxy-2-docosylhexacosanoyl)-MDP (BH48-MDP) and its L-serine analog [BH48-MDP(L-Ser)], were found to exert strong adjuvant activity in both the induction of delayed-type hypersensitivity and the stimulation of circulating precipitating antibody levels when combined with nonirritating vehicles (liposomes, squalene-in-water emulsion, and phosphate-buffered saline). These vehicles did not efficiently support the adjuvant activity of MDP, the parent molecule of the above lipophilic derivatives. Pyrogenicity tests showed that introduction of alpha-branched higher fatty acid groups but not of straight, long-chain fatty acids at the 6-position of the muramic acid residue resulted in marked decrease of the pyrogenicity inherent to MDP via intravenous administration.
M Tsujimoto; S Kotani; F Kinoshita; S Kanoh; T Shiba; S Kusumoto
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Infection and immunity     Volume:  53     ISSN:  0019-9567     ISO Abbreviation:  Infect. Immun.     Publication Date:  1986 Sep 
Date Detail:
Created Date:  1986-10-15     Completed Date:  1986-10-15     Revised Date:  2009-11-18    
Medline Journal Info:
Nlm Unique ID:  0246127     Medline TA:  Infect Immun     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  511-6     Citation Subset:  IM    
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MeSH Terms
Acetylmuramyl-Alanyl-Isoglutamine / analogs & derivatives*,  pharmacology
Adjuvants, Immunologic / pharmacology*,  toxicity
Antibody Formation / drug effects*
Fever / chemically induced*
Guinea Pigs
Immunity, Cellular / drug effects*
Liposomes / administration & dosage
Structure-Activity Relationship
Reg. No./Substance:
0/Adjuvants, Immunologic; 0/Emulsions; 0/Liposomes; 0/Vehicles; 53678-77-6/Acetylmuramyl-Alanyl-Isoglutamine

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

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