Journal
CARBOHYDRATE POLYMERS
Volume 98, Issue 2, Pages 1288-1296Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carbpol.2013.08.014
Keywords
Alginate; Derivatization; Chemoselective; Modification; DS; Esters; Drug delivery; Naringenin; Solubility; Enhancement
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Funding
- Critical Technologies and Applied Science (ICTAS) at Virginia Tech
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1126534] Funding Source: National Science Foundation
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Alginates are (1 -> 4) linked linear copolysaccharides composed of beta-p-mannuronic acid (M) and its C-5 epimer, alpha-L-guluronic acid (G). Several strategies for synthesis of carboxyl modified alginate derivatives exist in the literature. Most of these however employ aqueous chemistries, such as carbodiimide coupling reactions. Based on our recently discovered method for homogeneous dissolution of tetrabutylammonium (TBA)-alginate, we now describe use of tetrabutylammonium fluoride (TBAF)-based two component solvent systems as media for synthesis of carboxyl-modified alginate esters. Partially and fully esterified benzyl, butyl, ethyl, and methyl alginates were synthesized via reaction with the corresponding alkyl halides. The newly synthesized derivatives were soluble in polar aprotic solvents without the addition of TBAF. Saponification was performed to demonstrate that allcylation was completely regioselective for carboxylate groups in preference to hydroxyl groups to form esters. We demonstrate the utility of these alginate esters to enhance aqueous solubility of the flavonoid naringenin by formation of solid dispersions. (C) 2013 Elsevier Ltd. All rights reserved.
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