Boronic acids are amongst the most useful synthetic intermediates, frequently used by modern drug design. However, their access and fast synthesis of libraries are often problematic. We present a methodology on the synthesis of drug-like scaffolds via IMCRs with unprotected phenylboronic acids. To demonstrate an application of our approach, we also performed one-pot Suzuki couplings on the primary MCR scaffolds. Moreover, we performed a thorough data-mining of the Cambridge Structural Database, revealing interesting geometrical features.
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http://dx.doi.org/10.1002/ejoc.201901187 | DOI Listing |
Carbohydr Polym
March 2025
Department of Orthopedics Trauma and Microsurgery, Zhongnan Hospital, Wuhan University, Wuhan 430000, China; Hubei Clinical Medical Research Center of Trauma and Microsurgery, Wuhan 430000, China. Electronic address:
Functional injectable hydrogel (IH) is promising for infected bone defects (IBDs) repair, but how to endow it with desired antibacterial/immunoregulatory functions as well as avoid mechanical failures during its manipulation has posed as main challenges. Herein, rosmarinic acid (RosA), a natural product with antibacterial/immunoregulatory activities, was utilized to develop a FCR IH through forming phenylboronic acid ester bonds with 4-formylphenyl phenylboronic acid (4-FPBA) grafted chitosan (CS) (FC). After being applied to the IBD site, the FCR IH was then injected with tobramycin (Tob) solution, another alkaline antibacterial drug, to induce in situ crystallization of the FC, endowing the resultant FCRT hydrogel with adaptively enhanced mechanical strength and structural stability.
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
Department of Gastroenterology, Changhai Hospital, Naval Medical University, No. 168 Changhai Road, Shanghai 200433, PR China. Electronic address:
In this paper, a pH-sensitive chitosan-grafted phenylboronic acid (CS-BA)/polyvinyl alcohol (PVA) hydrogel was constructed based on dynamic borate bonding for loading chemotherapeutic drug cisplatin (CDDP) and divalent Cu (CS-BA/PVA-Cu-CDDP). The hydrogel can respond and degrade specifically in the simulative acidic tumor microenvironment (TME), and the released Cu can deplete glutathione (GSH) in tumor cells and generate Cu. It is worth noting that, Cu can further catalyze the Fenton-like reaction to generate cancer cell-toxic hydroxyl radicals (OH•).
View Article and Find Full Text PDFAdv Healthc Mater
January 2025
Shanghai Key Laboratory of Hydrogen Science & Center of Hydrogen Science, School of Materials Science and Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Poor tumor penetration is the major predicament of nanomedicines that limits their anticancer efficacy. The dense extracellular matrix (ECM) in the tumor is one of the major barriers against the deep penetration of nanomedicines. In this work, a slimming/excavating strategy is proposed for enhanced intratumoral penetration based on an acid-disassemblable nanomicelles-assembled nanomedicine and the NO-mediated degradation of ECM.
View Article and Find Full Text PDFACS Biomater Sci Eng
January 2025
Henan International Joint Laboratory of Medicinal Plants Utilization, College of Chemistry and Molecular Sciences, Henan Key Laboratory of Natural Medicine Innovation and Transformation, State Key Laboratory of Antiviral Drugs, Henan University, Kaifeng 475004, China.
J Biomed Mater Res A
January 2025
Department of Chemical & Biomolecular Engineering, University of Notre Dame, Notre Dame, USA.
Precise blood glucose control continues to be a critical challenge in the treatment and management of type 1 diabetes in order to mitigate both acute and chronic complications. This study investigates the development of a supramolecular peptide amphiphile (PA) material functionalized with phenylboronic acid (PBA) for glucose-responsive glucagon delivery. The PA-PBA system self-assembles into nanofibrillar hydrogels in the presence of physiological glucose levels, resulting in stable hydrogels capable of releasing glucagon under hypoglycemic conditions.
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