Issue 10, 1999

New design of vesicle-forming potential anti-cancer agent

Abstract

A novel amphiphile derivative of the anti-cancer agent PALA (N-(phosphonoacetyl)-L-aspartate), has been synthesized: dioctadecyl N-(phosphonoacetyl)-L-aspartate (PALAmod). Its aptitude to form bilayers or vesicles has been investigated. The melting temperature Tm of the alkyl chains of PALAmod is comparable with those of the bilayers of distearoyl phosphatidylcholine (DSPC) or distearoyl phosphatidylglycerol (DSPG) which have fatty chains of the same length. Encapsulation of two different hydrophilic probes, carboxyfluorescein (CF) and glucose, was examined, demonstrating the likely existence of vesicular structures either in lecithin–PALAmod mixtures or in pure PALAmod, respectively. The size of the particles has been measured from quasielastic light scattering experiments. The particle diameter at fixed pH (6.9), goes from 74 nm at [PALAmod] 3.6 mM to 52 nm at 14.8 mM. Nouvelle conception d'un agent anticance′reux potentiel sous forme de ve′sicule. Le diester carboxylique ste′arique de l'acide N-(phosphonoacetyl)-L-aspartique (PALAmod) a e′te′ synthe′tise′ en vue d'examiner les capacite′s de ce tensioactif à s'autoorganiser en bicouches ou en ve′sicules. La tempe′rature de fusion Tm des chaı[> with combining circumflex]nes alkyles du PALAmod est comparable à celles des bicouches de la distearoyl phosphatidyl choline (DSPC) ou du distearoyl phosphatidyl glycerol (DSPG), qui possèdent des chaı[> with combining circumflex]nes grasses de même longueur. La formation de structures ve′siculaires constitue′es soit d'un me′lange le′cithine–PALAmod, soit de PALAmod pur a e′te′ e′tablie à partir de mesures d'encapsulation de sondes hydrophiles, carboxyfluoresce′ine (CF) ou glucose. La taille des particules a e′te′ e′value′e par des expe′riences de diffusion quasie′lastique de la lumière. Le diamètre des particules à pH fixe′ (6.9), varie de 74 nm, à une concentration en PALAmod de 3.6 mM, à 52 nm, à une concentration de 14.8 mM.

Article information

Article type
Paper

New J. Chem., 1999,23, 981-987

New design of vesicle-forming potential anti-cancer agent

P. Coutrot, P. Oliger, C. Grison, S. Joliez, M. He′brant and C. Tondre, New J. Chem., 1999, 23, 981 DOI: 10.1039/A904759J

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