Abstract：
:A set of 8-methylene-, 8-methyl-, and 8-methyl-9-dihydro-oleandomycin derivatives having different combinations of stereochemistries at positions C-8 and/or C-9 have been prepared in a chemoselective and stereoselective manner and tested in vitro for antibacterial activity and inhibition of IL-6 production. Configurations of the stereocenters at C-8 and C-9 were determined using 2D NMR techniques. We have shown that change of stereochemistry at these positions can exert a major influence on antibacterial activity as well as IL-6 inhibition, providing novel macrolide derivatives with diminished antibacterial and potent anti-inflammatory activity. In addition, the anti-inflammatory activity observed in vitro was confirmed in an in vivo model of lipopolysaccharide-induced inflammation.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Bauer J,Vine M,Corić I,Bosnar M,Pašalić I,Turkalj G,Lazarevski G,Culić O,Kragol Gdoi
10.1016/j.bmc.2012.02.013subject
Has Abstractpub_date
2012-04-01 00:00:00pages
2274-81issue
7eissn
0968-0896issn
1464-3391pii
S0968-0896(12)00106-Xjournal_volume
20pub_type
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