Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the...
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Published in | Bioconjugate chemistry Vol. 25; no. 4; pp. 718 - 723 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society
16.04.2014
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Subjects | |
Online Access | Get full text |
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Summary: | Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1043-1802 1520-4812 |
DOI: | 10.1021/bc4005975 |