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Artículo

Alkyl esters of l-ascorbic acid: Stability, surface behaviour and interaction with phospholipid monolayers

Mottola, MilagroIcon ; Vico, Raquel VivianaIcon ; Villanueva, Martín EduardoIcon ; Fanani, Maria LauraIcon
Fecha de publicación: 11/2015
Editorial: Academic Press Inc Elsevier Science
Revista: Journal of Colloid and Interface Science
ISSN: 0021-9797
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Otras Ciencias Químicas

Resumen

l-ascorbic acid alkyl esters (ASCn) are molecules of pharmaceutical interest for their amphiphilic nature and proposed antioxidant power. In contrast to l-ascorbic acid, ASCn with different acyl chain lengths behaved stably upon oxidation and a tautomeric isomerization was observed. In Langmuir films, when the ascorbic ring has a negative charge, ASC14 and ASC16 form stable monolayers, contrary to ASC10 and ASC12. ASC16 films showed transition from liquid-expanded (LE) to liquid-condensed phase, whereas ASC14 showed only an LE phase. When ASCn are mainly neutral, ASC14 showed phase transition from LE to a crystalline phase, as previously reported for ASC16. The two-dimensional domains displayed crystal-like shapes with anisotropic optical activity when interacting with the polarized light under Brewster angle microscopy. The compounds with the longer acyl chain (ASC16, ASC14 and ASC12) exhibited good surface activity, forming Gibbs monolayers. They also were able to penetrate into phospholipid monolayers up to a critical point of 45-50mN/m. The 1-palmitoyl-2-oleoylphosphatidylcholine/ASCn films showed LC and/or crystalline domains only for ASC16. This study provides valuable evidence regarding the stability and surface properties of this drug family, and casts light into the differential interaction of these drugs with lipid membranes, which is important for understanding its differential pharmacological activity.
Palabras clave: Amphiphilic Vitamin C Derivatives , Ascorbic Acid Tautomerization , Chiral Crystalline Domains , Gibbs Adsorption Films , Langmuir Monolayers , Phospholipids Mixed Domains
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Atribución-NoComercial-SinDerivadas 2.5 Argentina (CC BY-NC-ND 2.5 AR)
Identificadores
URI: http://hdl.handle.net/11336/38411
URL: http://www.sciencedirect.com/science/article/pii/S0021979715300333
DOI: http://dx.doi.org/10.1016/j.jcis.2015.07.014
Colecciones
Articulos(IIBYT)
Articulos de INSTITUTO DE INVESTIGACIONES BIOLOGICAS Y TECNOLOGICAS
Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Mottola, Milagro; Vico, Raquel Viviana; Villanueva, Martín Eduardo; Fanani, Maria Laura; Alkyl esters of l-ascorbic acid: Stability, surface behaviour and interaction with phospholipid monolayers; Academic Press Inc Elsevier Science; Journal of Colloid and Interface Science; 457; 11-2015; 232-242
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