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Issue 9, 2008
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Carbohydrate-functionalized catanionic surfactantvesicles: preparation and lectin-binding studies

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Abstract

In this paper we describe the modification of anionic surfactant vesicles with surfactant-based glycoconjugates of glucose, lactose, maltose and maltotriose. Catanionic vesicles were prepared by mixing cetyltrimethylammonium tosylate and sodium dodecylbenzenesulfonate to obtain thermodynamically stable, spontaneously formed vesicles. Carbohydrate moieties were linked to a hydrocarbon chain via an N-glycosyl linkage to produce an amphiphilic glycoconjugate that undergoes hydrophobic insertion into the outer bilayer leaflet of the surfactant vesicle. Once inserted, the bioavailability of the surface-adsorbed carbohydrates was determined using agglutination of the modified vesicles through selective binding of the lectins concanavalin A and peanut agglutinin. In these studies, glycoconjugates were present in the vesicle bilayer at a carbohydrate-to-surfactant ratio of approximately 1 : 100. At this coverage, vesicle formation is uninhibited, the carbohydrate groups are displayed on the vesicle outer surface and bind selectively to lectins in solution. The preparation of stable, carbohydrate-functionalized, anionic surfactant vesicles may prove useful in the targeted delivery of molecular payloads such as dyes or drugs to cells with high selectivity for a wide range of biotechnological applications.

Graphical abstract: Carbohydrate-functionalized catanionic surfactant vesicles: preparation and lectin-binding studies

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Supplementary files

Article information


Submitted
11 Apr 2008
Accepted
04 Jun 2008
First published
16 Jul 2008

Soft Matter, 2008,4, 1916-1921
Article type
Paper

Carbohydrate-functionalized catanionic surfactant vesicles: preparation and lectin-binding studies

J. Park, L. H. Rader, G. B. Thomas, E. J. Danoff, D. S. English and P. DeShong, Soft Matter, 2008, 4, 1916
DOI: 10.1039/B806059B

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