Journal
MOLECULES
Volume 26, Issue 19, Pages -Publisher
MDPI
DOI: 10.3390/molecules26195940
Keywords
fluorescent probe; coumarin derivatives; peroxynitrite
Funding
- Polish National Science Centre within the SONATA BIS 6 program [2016/22/E/ST4/00549]
- American Cancer Society [16-183-31]
- MCW Cancer Center
Ask authors/readers for more resources
This study reports on the synthesis and characterization of a coumarin derivative containing an oxidant-sensitive boronate group as a fluorescent probe for the detection of peroxynitrite. The probe showed high stability and a fast response time, with the ability to detect peroxynitrite and hypochlorite in biological settings. HPLC-based identification of oxidant-specific products complements the fluorescence measurements for accurate detection of the oxidants.
Derivatives of coumarin, containing oxidant-sensitive boronate group, were recently developed for fluorescent detection of inflammatory oxidants. Here, we report the synthesis and the characterization of 3-(2-benzothiazolyl)-7-coumarin boronic acid pinacol ester (BC-BE) as a fluorescent probe for the detection of peroxynitrite (ONOO-), with high stability and a fast response time. The BC-BE probe hydrolyzes in phosphate buffer to 3-(2-benzothiazolyl)-7-coumarin boronic acid (BC-BA) which is stable in the solution even after a prolonged incubation time (24 h). BC-BA is slowly oxidized by H2O2 to form the phenolic product, 3-benzothiazol-2-yl-7-hydroxy-chromen-2-one (BC-OH). On the other hand, the BC-BA probe reacts rapidly with ONOO-. The ability of the BC-BA probe to detect ONOO- was measured using both authentic ONOO- and the system co-generating steady-state fluxes of O-2(center dot-) and (NO)-N-center dot;. BC-BA is oxidized by ONOO- to BC-OH. However, in this reaction 3-benzothiazol-2-yl-chromen-2-one (BC-H) is formed in the minor pathway, as a peroxynitrite-specific product. BC-OH is also formed in the reaction of BC-BA with HOCl, and subsequent reaction of BC-OH with HOCl leads to the formation of a chlorinated phenolic product, which could be used as a specific product for HOCl. We conclude that BC-BA shows potential as an improved fluorescent probe for the detection of peroxynitrite and hypochlorite in biological settings. Complementation of the fluorescence measurements by HPLC-based identification of oxidant-specific products will help to identify the oxidants detected.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available