Impact of stereochemistry on the biological activity of novel oleandomycin derivatives (CROSBI ID 208665)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Bauer, Jurica ; Vine, Mark ; Čorić, Ilija ; Bosnar, Martina ; Pašalić, Ivanka ; Turkalj, Gordana ; Lazarevski, Gorjana ; Čulić, Ognjen ; Kragol, Goran
engleski
Impact of stereochemistry on the biological activity of novel oleandomycin derivatives
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.
Macrolide; Configuration determination; Biological activity; Inflammation
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Podaci o izdanju
20 (7)
2012.
2274-2281
objavljeno
0968-0896
10.1016/j.bmc.2012.02.013
Povezanost rada
Temeljne medicinske znanosti