Self-crosslinking smart hydrogels through direct complexation between benzoxaborole derivatives and diols from hyaluronic acid was written by Figueiredo, Tamiris;Ogawa, Yu;Jing, Jing;Cosenza, Vanina;Jeacomine, Isabelle;Olsson, Johan D. M.;Gerfaud, Thibaud;Boiteau, Jean-Guy;Harris, Craig;Auzely-Velty, Rachel. And the article was included in Polymer Chemistry in 2020.Recommanded Product: 7-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol The following contents are mentioned in the article:
Boronate ester cross-linked hydrogels have emerged as promising injectable scaffolds for biomedical applications given their rapid self-healing ability. For a rational design of such networks, all variables influencing their dynamic rheol. properties, especially the boronic acid and the diol-containing mol. selected as mol. crosslinkers have to be carefully considered. Herein, by tailoring the structure of benzoxaborole (BOR), self-crosslinking hydrogels based on hyaluronic acid (HA) modified with BOR derivatives are obtained for the first time through the direct BOR-HA diol complexation at physiol. pH. Among the different HA-BOR conjugates investigated, those prepared from 6-amino-7-fluoro-3,3-dimethyl benzoxaborole (HA-DMF6ABOR) and 7-amino-3,3-dimethyl benzoxaborole (HA-DM7ABOR) show unprecedented self-crosslinking properties, leading to the formation of self-healing hydrogels with extremely slow dynamics. These networks also exhibit remarkable pH- and glucose-responsive behaviors. These properties are related to the peculiar structure of these two BOR moieties, having as the common feature, a gem-di-Me group in the oxaborole ring and an ortho-substituent in the Ph ring. Mol. dynamic simulations are used to provide insight in the role of these substituents in the outstanding capability of DMF6ABOR and DM7ABOR to crosslink HA. They show that BOR complexation induces changes in conformation of HA favoring formation of a highly entangled 3D network. This study involved multiple reactions and reactants, such as 7-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol (cas: 174671-93-3Recommanded Product: 7-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol).
7-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol (cas: 174671-93-3) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Recommanded Product: 7-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol
Referemce:
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Alcohols – Chemistry LibreTexts