Background: Phenylboronic acid-polymers (PBA-polymers) have attracted tremendous attention as potential stimuli-responsive materials with applications in drug-delivery depots, scaffolds for tissue engineering, HIV barriers, and biomolecule-detecting/sensing platforms. The unique aspect of PBA-polymers is their interactions with diols, which result in reversible, covalent bond formation. This very nature of reversible bonding between boronic acids and diols has been fundamental to their applications in the biomedical area.
Methods: We have searched peer-reviewed articles including reviews from Scopus, PubMed, and Google Scholar with a focus on the 1) chemistry of PBA, 2) synthesis of PBA-polymers, and 3) their biomedical applications.
Results: We have summarized approximately 179 papers in this review. Most of the applications described in this review are focused on the unique ability of PBA molecules to interact with diol molecules and the dynamic nature of the resulting boronate esters. The strong sensitivity of boronate ester groups towards the surrounding pH also makes these molecules stimuli-responsive. In addition, we also discuss how the re-arrangement of the dynamic boronate ester bonds renders PBA-based materials with other unique features such as self-healing and shear thinning.
Conclusion: The presence of PBA in the polymer chain can render it with diverse functions/ relativities without changing their intrinsic properties. In this review, we discuss the development of PBA polymers with diverse functions and their biomedical applications with a specific focus on the dynamic nature of boronate ester groups.
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http://dx.doi.org/10.2174/0929867325666181008144436 | DOI Listing |
Biomacromolecules
December 2024
Department of Chemical Engineering, University of Patras, Patras 26504, Greece.
We report on 3D-printable polymer networks based on the combination of modified alginate-based polymer blends; two alginate polymers were prepared, namely, a thermoresponsive polymer grafted with P(NIPAM--NtBAM)-NH copolymer chains and a second polymer modified with diol/pH-sensitive 3-aminophenylboronic acid. The gelation properties were determined by the hydrophobic association of the thermosensitive chains and the formation of boronate esters. At a mixing ratio of 70/30 wt % of the thermo/diol-responsive polymers, the semi-interpenetrating network exhibited an optimum storage modulus ranging from ca.
View Article and Find Full Text PDFBiomaterials
December 2024
Guangzhou Key Laboratory of Spine Disease Prevention and Treatment, Department of Orthopaedic Surgery, Guangdong Provincial Key Laboratory of Major Obstetric Diseases, Guangdong Provincial Clinical Research Center for Obstetrics and Gynecology, The Third Affiliated Hospital, Guangzhou Medical University, Guangzhou, 510150, PR China. Electronic address:
Diabetes is associated with excessive inflammation, which negatively impacts the fracture healing process and delays bone repair. Previously, growing evidence indicated that activation of the nod-like receptor (NLR) family, such as nod-like receptor thermal protein domain-associated protein 3 (NLRP3) inflammasome induces a vicious cycle of chronic low-grade inflammatory responses in diabetic fracture. Here, we describe the synthesis of a bone adhesive hydrogel that can be locally injected into the fracture site and releases a natural inhibitor of NLRP3 (rutin) in response to pathological cue reactive oxygen species activity (ROS).
View Article and Find Full Text PDFACS Biomater Sci Eng
December 2024
Future Industries Institute, University of South Australia, Mawson Lakes, South Australia 5095, Australia.
Polymer based nanoformulations offer substantial prospects for efficacious chemotherapy delivery. Here, we developed a pH-responsive polymeric nanoparticle based on acidosis-triggered breakdown of boronic ester linkers. A biocompatible hyaluronic acid (HA) matrix served as a substrate for carrying a doxorubicin (DOX) prodrug which also possesses natural affinity for CD44 cells.
View Article and Find Full Text PDFChemistry
December 2024
Centre National de la Recherche Scientifique, Institut des Sciences Moléculaires, 351 Cours de la libération - Bâtiment A12, 33405, TALENCE CEDEX, FRANCE.
Various protecting groups have been developed for boronic acids, mostly based on diols. Alternatives include trifluoroborates and amine complexes, which offer easier synthesis and release under milder conditions. We present here a new strategy involving photocleavable protecting groups for boronic and borinic acids, based on the 2-nitrobenzyl motif.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
The University of Edinburgh School of Chemistry, Chemistry, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
Arene borylation reactions provide direct access to aryl organoboranes, including aryl boronic esters. Precious metals, namely Ir, Rh, Pt, remain the go-to for metal-catalysed borylation reactions, however, significant efforts have been expended in developing Earth-abundant metal alternatives. The iron-catalysed borylation of 2-aryl pyridine derivatives with 9-borabicyclo[3.
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