Chemical synthesis and biological activities of 6,6'-di-O-mycoloyl-beta,beta- and -alpha,beta-trehalose.
6,6'Di-O-mycoloyl-beta,beta-trehalose (beta,beta-TDM) and 6,6'-di-O-mycoloyl-alpha,beta-trehalose (alpha,beta-TDM) were synthesized and their toxicity and ability to activate peritoneal macrophages in situ were examined in mice, in comparison with 6,6'-di-O-mycoloyl-alpha,alpha-trehalose (TDM). Both beta,beta-TDM and alpha,beta-TDM caused a decrease in body weight two days after injection, however the weights reverted to a normal level. No deaths were caused by either analog. On the other hand, TDM showed potent toxicity, causing decrease in body weight and death of all animals injected. Beta,beta-TDM and alpha,beta-TDM were effective in the in situ activation of mouse peritoneal macrophages.
Azuma
I
I
Institute of Immunological Science, Hokkaido University, Sapporo, Japan.
Sakurai
T
T
Ishida
H
H
Kitajima
T
T
Yamazaki
M
M
D000818:Animals; D001835:Body Weight / Q000187:drug effects; D002240:Carbohydrate Sequence; D003311:Cord Factors / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D008969:Molecular Sequence Data; D010529:Peritoneal Cavity / Q000166:cytology; D013329:Structure-Activity Relationship
C071847:6,6'-di-O-mycoloyltrehalose; C063099:6-deoxy-6-mycoloylamino-alpha,alpha-trehalose; D003311:Cord Factors