Transmembrane anion transport and cytotoxicity of synthetic tambjamine analogs

Ten synthetic analogs of the marine alkaloids tambjamines, bearing aromatic enamine moieties, have been synthesized. These compounds proved to be highly efficient transmembrane anion transporters in model liposomes. Changes in the electronic nature of the substituents of the aromatic enamine or the...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-03, Vol.12 (11), p.1771-1778
Main Authors: Hernando, Elsa, Soto-Cerrato, Vanessa, Cortés-Arroyo, Susana, Pérez-Tomás, Ricardo, Quesada, Roberto
Format: Article
Language:English
Subjects:
Alkaloids - metabolism
Alkaloids - toxicity
Anions - metabolism
Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Ion Transport
Magnetic Resonance Spectroscopy
Pyrroles - metabolism
Pyrroles - toxicity
Spectrometry, Mass, Electrospray Ionization
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Summary:Ten synthetic analogs of the marine alkaloids tambjamines, bearing aromatic enamine moieties, have been synthesized. These compounds proved to be highly efficient transmembrane anion transporters in model liposomes. Changes in the electronic nature of the substituents of the aromatic enamine or the alkoxy group of the central pyrrole group did not affect this anionophore activity. The in vitro activity of these compounds has also been studied. They trigger apoptosis in several cancer cell lines with IC50 values in the low micromolar range as well as modify the intracellular pH, inducing the basification of acidic organelles.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob42341g