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US 12,746,277 B2Granted
Dynamic-covalent hydrogels with glucose-specific and glucose-responsive diboronate crosslinking
AssigneeUniversity of Notre Dame du Lac
InventorsMatthew Webber, Yuanhui Xiang, Sijie Xian
Life of this patent
Estimating the term…
Abstract
Described herein are di-phenylboronic acid (DiPBA) motifs that bind glucose with high affinity and improved specificity. The compounds can be used to prepare dynamic injectable materials with improved encapsulation and glucose-triggered release of insulin in vitro and in vivo.
Claims21
A hydrogel, the hydrogel comprising:
- (i) a diboronate compound of formula (I):
- wherein:
- wherein:
- R1, at each occurrence, is independently C1-4alkyl, cyclopropyl, C1-2fluoroalkyl, —F, —CN, or —NO2;
- R2, at each occurrence, is independently C1-4alkyl, cyclopropyl, C1-2fluoroalkyl, —F, —CN, or —NO2;
- X⊖ is an anion having a net charge of −1;
- is a linking moiety;
- and
- is a first moiety comprising a hydrophilic polymer, a hyperbranched macromolecule, or a combination thereof;
- and
- (ii) a diol compound of formula (II):
- wherein:
- is a second moiety comprising a hydrophilic polymer, a hyperbranched macromolecule, or a combination thereof;
- wherein the diboronate compound of formula (I) and the diol compound of formula (II) form crosslinks by dynamic-covalent bonds.
11 more elements
A method of delivering insulin to a subject in need thereof, the method comprising:
- administering a pharmaceutical composition to a subject in need thereof, the pharmaceutical composition comprising insulin encapsulated within a hydrogel, the hydrogel comprising:
- (i) a diboronate compound of formula (I):
- wherein:
- wherein:
- R1, at each occurrence, is independently C1-4alkyl, cyclopropyl, C1-2fluoroalkyl, —F, —CN, or —NO2;
- R2, at each occurrence, is independently C1-4alkyl, cyclopropyl, C1-2fluoroalkyl, —F, —CN, or —NO2;
- and
- X⊖ is an anion having a net charge of −1;
- is a linking moiety;
- and
- is a first moiety comprising a hydrophilic polymer, a hyperbranched macromolecule, or a combination thereof;
- and
- (ii) a diol compound of formula (II):
- wherein:
- is a second moiety comprising a hydrophilic polymer, a hyperbranched macromolecule, or a combination thereof;
- wherein the diboronate compound of formula (I) and the diol compound of formula (II) form crosslinks by dynamic-covalent bonds.
13 more elements
Dependencies are inferred from the claim text.