Inhibition of delayed hypersensitivity reactions by cinnamyl 1-thioglycosides

Cinnamyl 1-thio-alpha-D-manno(and L-rhamno)pyranosides have good inhibitory effects in an antigen-specific T cell proliferation assay. The beta anomers are slightly less effective than the alpha anomers. The 6-substituted analogues of cinnamyl 1-thio-alpha-D-mannopyranoside such as 6-deoxy and 6-O-m...

Full description

Saved in:
Bibliographic Details
Published in:Journal of medicinal chemistry 1987-04, Vol.30 (4), p.705-710
Main Authors: Ponpipom, Mitree M, Bugianesi, Robert L, Blake, Thomas J
Format: Article
Language:English
Subjects:
Animals
Carbohydrate Conformation
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Cinnamates - pharmacology
Depression, Chemical
Exact sciences and technology
Female
Guinea Pigs
Hypersensitivity, Delayed - immunology
Immunity, Cellular - drug effects
Lymphocyte Activation - drug effects
Macrophages - drug effects
Macrophages - immunology
Mice
Mice, Inbred BALB C
Organic chemistry
Ovalbumin - immunology
Preparations and properties
Structure-Activity Relationship
T-Lymphocytes - drug effects
T-Lymphocytes - immunology
Thioglycosides - pharmacology
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Cinnamyl 1-thio-alpha-D-manno(and L-rhamno)pyranosides have good inhibitory effects in an antigen-specific T cell proliferation assay. The beta anomers are slightly less effective than the alpha anomers. The 6-substituted analogues of cinnamyl 1-thio-alpha-D-mannopyranoside such as 6-deoxy and 6-O-methyl derivatives also block macrophages in presenting the antigen to T cells. D-Mannose and L-rhamnose, when tested by themselves with no modifications, did not block at concentrations up to 1 mM. These cinnamyl 1-thioglycosides when given ip or po at 3-30 mg/kg to mice significantly inhibited the delayed type hypersensitivity reaction as measured by footpad swelling.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00387a021