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Lecturer: Prof. Remi Chauvin (University of Toulouse, France)
Topic: Tunable Lipidic Acetylenic Cytotoxics (LACs) against Cancers and Tuberculosis
Date: May 9th
Time: 16:00 (Kyiv)
Zoom link:
Join Zoom Meeting
https://us02web.zoom.us/j/4590042894?pwd=dEZzSjlMbEdkQnhNODZYYjJoekVPUT09
Meeting ID: 459 004 2894
Passcode: Ch24022022
Chairman: Prof. Valentyn Chebanov
Lecture abstract:
A long focus on acetylenic chemistry for organic materials science drew our attention to possible applications in biomedical sciences, as supported by literature reports revealing that after the discovery of the antituberculosis metabolite mycomycin in 1947, lipidic alkynylcarbinols (LACs) extracted from marine sponges were shown to exhibit potent antitumor cytotoxicity. Hence, structure-activity relationships studies from a natural alkenylalkynylcarbinol (AAC) led to the chiral dialkynylcarbinol (DAC or DACol) pharmacophore with a strong eudismic effect, whose prodrug mode of action was later elucidated. Further variation by installation of an allenyl group or insertion of an extra triple bond led to the corresponding AllenAC(diol)s or BACs, found to be active at the picomolar level. With the view to stabilizing the "pseudo-aromatic" BACs, the modulation was generalized through a pivotal "small synthon" strategy envisaged to be applicable in enantiopure series: PACs, DACdiols, and a unique ENAC on the way to DIENACs or TRIENACs will be presented. More basic structural variation from DACols to DACamines was inspired by isolobal analogy: OH <-0-> NH 2 . Remembering mycomycin, remarkable results on the cytotoxicity of artificial LACs against bacteria such as Mycobacterium tuberculosis will finally be disclosed.
Contact us: chebanov@gmail.com; info@isc.kh.ua
