Synthesis, micellization and lectin binding of new glycosurfactants

Author(s)

Dal Bo, Alexandre G. ^{[1, 2, 3]} ; Soldi, Valdir ^[4] ; Giacomelli, Fernando C. ^[5] ; Travelet, Christophe ^{[1, 2]} ; Borsali, Redouane ^{[1, 2]} ; Fort, Sebastien ^{[1, 2]}

Affiliation

^[1] Univ Grenoble Alpes, CERMAV, F-38000 Grenoble - France

^[2] CNRS, CERMAV, F-38000 Grenoble - France

^[3] Univ Extremo Sul Catrinense UNESC, Postgrad Program Sci & Mat Engn, BR-88806000 Criciuma, SC - Brazil

^[4] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC - Brazil

^[5] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210170 Santo Andre, SP - Brazil

• Document type: Journal article
• Source: Carbohydrate Research; v. 397, p. 31-36, OCT 9 2014.
• Web of Science Citations: 8

Abstract

Here we report the preparation and physico-chemical characterization of carbohydrate-decorated micelles and their interaction with lectins. A library of biosourced amphiphiles was prepared by copper-catalyzed azide-alkyne cycloaddition (CuAAC) between alkynyl sugars (lactose, N-acetyl-D-glucosamine) and azido-functionalized poly(ethylene glycol) esters (N-3-PEG(900)-decanoate (C-10) and -dodecanoate (C-12)). In water, these glycoconjugates self-assemble into micelles of homogeneous nanometric size (11 nm) as evidenced by scattering techniques (DLS for light, and SAXS for X-ray). A comparative study with previously synthesized octadecanoate counterparts pointed out that that nature of the fatty acid has no significant influence on the particle size but only affects their compactness. These findings are in favor of a possible bulk preparation from lipid mixtures such as those encountered in renewable vegetable oils. The presence of the carbohydrate epitopes on the surface of the micelles and their bioavailability for lectin targeting were also evidenced by light scattering measurements using wheat germ agglutinin (WGA) and peanut (Arachis hypogaea) (PNA) lectins, supporting possible application as targeted drug nanocarriers. (C) 2014 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 10/06348-0 - Development of versatile supramolecular polymeric systems for controlled release of antitumoral agents
• Grantee: Fernando Carlos Giacomelli
• Support Opportunities: Regular Research Grants