Amide linkages of sugar moieties to amine terminated leashes attached to carbohydrate polymers
AssigneeNavidea Biopharmaceuticals, Inc.
InventorsJeffrey Scott Arnold, David A. Ralph
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Abstract
Provided are methods of attaching a mannose-binding C-type lectin receptor targeting moiety to a polymeric carbohydrate backbone using an amide linkage. The amide linkage may be found between a leash, such as an amine terminated leash, and the mannose-binding C-type lectin receptor targeting moieties. The compounds and compositions disclosed utilizing the amide linkage provide for highly stable compounds with a significant reduction in loss of mannose-binding C-type lectin receptor targeting moieties from the polymeric carbohydrate backbone.
Claims19
A compound comprising:
- a polymeric carbohydrate backbone comprising at least one amine terminated leash attached thereto, wherein the at least one amine terminated leash comprises a straight or branched chain having from about 1 to about 20 member atoms selected from the group consisting of carbon, oxygen, sulfur, nitrogen, and phosphorus;
- and
- one or more mannose-binding C-type lectin receptor targeting moieties,
- wherein the one or more mannose-binding C-type lectin receptor targeting moieties is attached to the at least one amine terminated leash as an amide linkage.
A method of attaching a mannose-binding C-type lectin receptor targeting moiety to a polymeric carbohydrate backbone, comprising:
- (a) synthesizing a mannose-binding C-type lectin receptor targeting moiety comprising an anomeric thio-carboxylate moiety;
- (b) converting the mannose-binding C-type lectin receptor targeting moiety comprising the anomeric thio-carboxylate moiety into an activated N-hydroxysuccinimide carboxylic acid ester;
- and
- (c) reacting the activated N-hydroxysuccinimide carboxylic acid ester with a polymeric carbohydrate backbone having one or more amine terminated leashes attached thereto, wherein the at least one amine terminated leash comprises a straight or branched chain having from about 1 to about 20 member atoms selected from the group consisting of carbon, oxygen, sulfur, nitrogen, and phosphorus,
- wherein the reacting of the activated N-hydroxysuccinimide carboxylic acid ester with the polymeric carbohydrate backbone having one or more amine terminated leashes attached thereto forms an amide linkage between the one or more amine terminated leashes and a carbonyl carbon of the activated N-hydroxysuccinimide carboxylic acid ester.
Dependencies are inferred from the claim text.