Chemical synthesis and biological activities of 6,6′-di-O-mycoloyl-β,β- and -α,β-trehalose

Abstract 6,6′-Di- O -mycoloyl-β,β-trehalose (β,β-TDM) and 6,6′-di- O -mycoloyl-α,β-trehalose (α,β-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-α,α-trehalose (TDM). Both β,β-TDM and α,β-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. β,β-TDM and α,β-TDM were effective in the in situ activation of mouse peritoneal macrophages.