Impact of stereochemistry on the biological activity of novel oleandomycin derivatives
2012
Bauer, Jurica | Vine, Mark | Čorić, Ilija | Bosnar, Martina | Pašalić, Ivanka | Turkalj, Gordana | Lazarevski, Gorjana | Čulić, Ognjen | Kragol, Goran
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.
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