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 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.
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain. rquesada@ubu.es.
Elsa
E
Hernando
Vanessa
V
Soto-Cerrato
Susana
S
Cortés-Arroyo
Ricardo
R
Pérez-Tomás
Roberto
R
Quesada
D000470:Alkaloids / Q000378:metabolism* / Q000633:toxicity; D000838:Anions / Q000378:metabolism*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D017136:Ion Transport; D009682:Magnetic Resonance Spectroscopy; D011758:Pyrroles / Q000378:metabolism* / Q000633:toxicity; D021241:Spectrometry, Mass, Electrospray Ionization
D000470:Alkaloids; D000838:Anions; D011758:Pyrroles