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A simple and effective biocompatible domino reaction triggered by a model protease and leading to the formation of strongly fluorescent quinoxalin-2(1)-one -heterocycles is described. Some positive attributes including versatility and the ability to provide outstanding fluorescence "OFF-ON" responses were revealed by this work. They open the way for practical applications of this novel type of "covalent-assembly"-based fluorescent probe in the fields of sensing and bioimaging.
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http://dx.doi.org/10.1021/acs.orglett.0c02287 | DOI Listing |
Anal Chim Acta
October 2025
College of Pharmacy, Xinjiang Key Laboratory of Biopharmaceuticals and Medical Devices, Xinjiang Medical University, Urumqi, 830017, China; Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China. Electronic address:
Background: Acid phosphatase (ACP) serves as a crucial clinical biomarker for early detection of various diseases, most notably prostate cancer (PCa), which ranks as the second most common cancer among men worldwide and remains typically asymptomatic in its initial developmental phase. Enzyme-triggered fluorescent reactions under mild conditions offer significant potential for advancing in-situ enzyme activity assays. Despite this promise, the development of acid phosphatase (ACP)-specific detection systems remains challenging due to the scarcity of efficient fluorescent response mechanisms and undesirable fluorescence under acidic conditions.
View Article and Find Full Text PDFChem Sci
November 2024
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, School of Chemistry and Materials Science, Nanjing Normal University Nanjing 210046 China
Amonafide (ANF), a topoisomerase II inhibitor and DNA intercalator, has exhibited promise in phase II trials but faces significant limitations due to adverse side effects. Here, we have developed a novel enzyme-triggered fluorogenic prodrug, AcKLP, that incorporates dual-locked enzyme activation, ensuring that the prodrug remains inactive until it confronts the unique enzymatic environment of glioblastoma cells. This approach minimizes premature activation and reduces toxicity to normal cells, with an IC > 100 μM for human umbilical vein endothelial cells (HUVEC) and ∼2.
View Article and Find Full Text PDFJ Agric Food Chem
October 2024
Université d'Orléans et CNRS, ICOA, UMR 7311, BP 6759, Orléans F-45067, France.
Myrosinase, a thioglucosidase, is a key enzyme in the mechanism of defense of plants that hydrolyzes glucosinolates (GSLs) into isothiocyanates. These isothiocyanates are the main bioactive molecules exerting protective effect in Brassicales plants. These plants that contain this specific enzyme-substrate couple belong to our daily human diet and have demonstrated health benefits, such as chemopreventive effects.
View Article and Find Full Text PDFJ Mater Chem B
March 2022
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India.
We describe herein the rational development of an organopolysulfide-based fluorogenic donor of hydrogen sulfide (HS) DCI-PS, which can be activated by the antioxidant selenoenzyme thioredoxin reductase (TrxR) with concomitant release of the dicyanoisophorone-based near-infrared (NIR) fluorophore. Along with the polysulfide probe DCI-PS capable of releasing the NIR fluorophore and HS, the corresponding disulfide-probe DCI-DS was also rationally designed and synthesized, which releases the fluorophore without donating HS. Detailed spectroscopic and kinetic studies in an aqueous medium revealed significantly higher reactivity of the probes towards DTT (for TrxR activity) over the well-known cellular abundant biothiol GSH.
View Article and Find Full Text PDFOrg Lett
August 2020
Institut de Chimie Moléculaire de l'Université de Bourgogne, UMR 6302, CNRS, Univ. Bourgogne Franche-Comté, 9, UMR 6302, CNRS, Univ. Bourgogne Franche-Comté, 9, Avenue Alain Savary, 21000 Dijon, France.
A simple and effective biocompatible domino reaction triggered by a model protease and leading to the formation of strongly fluorescent quinoxalin-2(1)-one -heterocycles is described. Some positive attributes including versatility and the ability to provide outstanding fluorescence "OFF-ON" responses were revealed by this work. They open the way for practical applications of this novel type of "covalent-assembly"-based fluorescent probe in the fields of sensing and bioimaging.
View Article and Find Full Text PDF