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Harnessing a bis-electrophilic boronic acid lynchpin for azaborolo thiazolidine (ABT) grafting in cyclic peptides.
Chem Sci
July 2024
Biomimetic Peptide Engineering Laboratory, Department of Chemistry, Indian Institute of Technology Ropar Rupnagar Punjab 140001 India
Chemical modifications of native peptides have significantly advanced modern drug discovery in recent decades. On this front, the installation of multitasking molecular grafts onto macrocyclic peptides offers numerous opportunities in biomedical applications. Here, we showcase a new class of borono-cyclic peptides featuring an azaborolo thiazolidine (ABT) graft, which can be readily assembled utilizing a bis-electrophilic boronic acid lynchpin while harnessing the inherent reactivity difference (>10 M s) between the N-terminal cysteine and backbone cysteine for rapid and highly regioselective macrocyclization (∼1 h) under physiological conditions.
View Article and Find Full Text PDFA Self-Assembled Nanoindicator from Alizarin Red S-Borono-Peptide for Potential Imaging of Cellular Copper(II) Ions.
ACS Biomater Sci Eng
July 2021
The Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, South-Central University for Nationalities, Wuhan 430074, P. R. China.
Recently, smart nanomaterials from peptide self-assembly have received extensive attention in the field of biological and medical applications. Through rationally designing the molecular structure, we constructed a borono-peptide that self-assembled into well-defined nanofibers. Relying on the specific recognition between the vicinal diol compound and boronic acid, a novel alizarin red S (ARS)-borono-peptide (BP) spherical nanoindicator was fabricated, accompanying with the emission of strong fluorescent signal.
View Article and Find Full Text PDFIn Vitro Studies to Define the Cell-Surface and Intracellular Targets of Polyarginine-Conjugated Sodium Borocaptate as a Potential Delivery Agent for Boron Neutron Capture Therapy.
Cells
September 2020
Neutron Therapy Research Center, Okayama University, 2-5-1 Shikata-cho, Kita-ku, Okayama 700-8558, Japan.
Boron neutron capture therapy (BNCT) requires pharmaceutical innovations and molecular-based evidence of effectiveness to become a standard cancer therapeutic in the future. Recently, in Japan, 4-borono-L-phenylalanine (BPA) was approved as a boron agent for BNCT against head and neck (H&N) cancers. H&N cancer appears to be a suitable target for BPA-BNCT, because the expression levels of L-type amino acid transporter 1 (LAT1), one of the amino acid transporters responsible for BPA uptake, are elevated in most cases of H&N cancer.
View Article and Find Full Text PDFDNA Condensation with a Boron-Containing Cationic Peptide for Modeling Boron Neutron Capture Therapy.
Radiat Phys Chem Oxf Engl 1993
January 2020
Department of Basic Sciences, School of Medicine, Loma Linda University, 11085 Campus Street, Loma Linda, CA 92350, USA.
The amino acid derivative 4-borono--phenylalanine (BPA) has been used in the radiation medicine technique boron neutron capture therapy (BNCT). Here we have characterized its interaction with DNA when incorporated into a positively charged hexa--arginine peptide. This ligand binds strongly to DNA and induces its condensation, an effect which is attenuated at higher ionic strengths.
View Article and Find Full Text PDFConformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction.
Chem Commun (Camb)
August 2019
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a powerful control element for conformationally homogenous peptide macrocycles.
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