HYDROPHOBICALLY MODIFIED POLYELECTROLYTES AS POTENTIAL DRUGS RESERVOIRS OF N-ALKYL-NITROIMIDAZOLES

The solubilization of three commercial drugs (ornindazole, metronidazole and tinidazole) and model compounds (N-alkyl-2-methyl-4-nitroimidazoles) on aggregates formed by anionic polyelectrolytes, carrying alkyl side chains of different length, have been investigated in aqueous solution at pH 3.0, 7....

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Autores principales: SALAMANCA,CONSTAIN H, BARRAZA,RAÚL G, ACEVEDO,BETSABÉ, OLEA,ANDRÉS F
Lenguaje:English
Publicado: Sociedad Chilena de Química 2007
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Acceso en línea:http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072007000100014
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Sumario:The solubilization of three commercial drugs (ornindazole, metronidazole and tinidazole) and model compounds (N-alkyl-2-methyl-4-nitroimidazoles) on aggregates formed by anionic polyelectrolytes, carrying alkyl side chains of different length, have been investigated in aqueous solution at pH 3.0, 7.0 and 11.0. Potassium salts of poly(maleic acid-co-1-olefins), PA-nK2 with n ranging from 8 to 18, were used as micelle-forming polymers. The partition of these drugs between water and the hydrophobic microdomains provided by PA-nK2 was studied by the pseudo-phase model to determinate the distribution coefficient K S, and the standard free energy of transfer Δμºt. The results indicate that solubility of alkyl-nitroimidazoles on these polymer micelles depends moderately on the length of the alkyl chain, and therefore is mainly determined by the heterocyclic group. On the other hand, the solubilization of 1-hexyl-2-methyl-4-nitroimidazole increase with decreasing length of the side alkyl chain; i.e. K S follows the order PA-8K2 > PA-10K2 > PA-12K2 > PA-14K2 > PA-16K2 >PA-18K2