Faculty Collaboration Database

Evaluation of a novel pyridinium cation-linked styryl-based boronate probe for the detection of selected inflammation-related oxidants. Free Radic Biol Med 2024 Feb 20;212:255-270

Date

12/21/2023

Pubmed ID

38122872

DOI

10.1016/j.freeradbiomed.2023.12.003

Scopus ID

2-s2.0-85181830257 (requires institutional sign-in at Scopus site)

Abstract

Reactive oxygen and nitrogen species (RONS) are a range of chemical individuals produced by living cells that contribute to the proper functioning of organisms. Cells under oxidative and nitrative stress show excessive production of RONS (including hydrogen peroxide, H₂O₂, hypochlorous acid, HOCl, and peroxynitrite, ONOO^-) which may result in a damage proteins, lipids, and genetic material. Thus, the development of probes for in vivo detection of such oxidants is an active area of research, focusing on molecular redox sensors, including boronate-caged fluorophores. Here, we report a boronate-based styryl probe with a cationic pyridinium moiety (BANEP+) for the fluorescent detection of selected biological oxidants in vitro and in vivo. We compare the chemical reactivity of the BANEP+ probe toward H₂O₂, HOCl, and ONOO^- and examine the influence of the major intracellular non-enzymatic antioxidant molecule, glutathione (GSH). We demonstrate that, at the physiologically relevant GSH concentration, the BANEP+ probe is efficiently oxidized by peroxynitrite, forming its phenolic derivative HNEP+. GSH does not affect the fluorescence properties of the BANEP+ and HNEP+ dyes. Finally, we report the identification of a novel type of molecular marker, with the boronate moiety replaced by the iodine atom, formed from the probe in the presence of HOCl and iodide anion. We conclude that the reported chemical reactivity and structural features of the BANEP+ probe may be a basis for the development of new red fluorescent probes for in vitro and in vivo detection of ONOO^-.

Author List

Siarkiewicz P, Luzak B, Michalski R, Artelska A, Szala M, Przygodzki T, Sikora A, Zielonka J, Grzelakowska A, Podsiadły R

Author

Jacek M. Zielonka PhD Assistant Professor in the Biophysics department at Medical College of Wisconsin

MESH terms used to index this publication - Major topics in bold

Fluorescent Dyes
Humans
Hydrogen Peroxide
Hypochlorous Acid
Inflammation
Oxidants
Peroxynitrous Acid
Reactive Nitrogen Species