Telomerase inhibitors from cyanobacteria: isolation and synthesis of sulfoquinovosyl diacylglycerols from Microcystis aeruguinosa PCC 7806.

Authors :: Makhlouf Brahmi M
Portmann C
D'Ambrosio D
Woods TM
Banfi D
Reichenbach P
Da Silva L
Baudat E
Turcatti G
Lingner J
Gademann K
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2013 Apr 02; Vol. 19 (14), pp. 4596-601. Date of Electronic Publication: 2013 Jan 31.
Publication Year :: 2013
Abstract: By using the Telospot assay, 27 different extracts of cyanobacteria were evaluated for telomerase inhibition. All extracts showed varying, but significant activity. We selected Microcystis aeruguinosa PCC 7806 to identify the active compound and a bioassay guided fractionation led us to isolate mixtures of sulfoquinovosyl diacylglycerols (SQDGs), which were identified by 2D NMR and MS/MS experiments. Pure SQDG derivatives were then synthesized. The IC(50) values of pure synthetic sulfoquinovosyl dipalmitoylglycerol and the monopalmitoylated derivative against telomerase were determined to be 17 and 40 μM, respectively. A structure-activity relationship study allowed the identification of compounds with modified lipophilic acyl groups that display improved activity.<br /> (Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Diglycerides chemistry
Enzyme Inhibitors chemical synthesis
Enzyme Inhibitors chemistry
Enzyme Inhibitors pharmacology
Glycolipids chemistry
Phencyclidine analogs & derivatives
Structure-Activity Relationship
Tandem Mass Spectrometry
Telomerase metabolism
Diglycerides chemical synthesis
Glycolipids chemical synthesis
Microcystis metabolism
Telomerase antagonists & inhibitors

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