In:
Proceedings of the National Academy of Sciences, Proceedings of the National Academy of Sciences, Vol. 118, No. 50 ( 2021-12-14)
Abstract:
Hydrogen peroxide (H 2 O 2 ) is responsible for numerous damages when overproduced, and its detection is crucial for a better understanding of H 2 O 2 -mediated signaling in physiological and pathological processes. For this purpose, various “off–on” small fluorescent probes relying on a boronate trigger have been prepared, and this design has also been involved in the development of H 2 O 2 -activated prodrugs or theranostic tools. However, this design suffers from slow kinetics, preventing activation by H 2 O 2 with a short response time. Therefore, faster H 2 O 2 -reactive groups are awaited. To address this issue, we have successfully developed and characterized a prototypic borinic-based fluorescent probe containing a coumarin scaffold. We determined its in vitro kinetic constants toward H 2 O 2 -promoted oxidation. We measured 1.9 × 10 4 m −1 ⋅s −1 as a second-order rate constant, which is 10,000-fold faster than its well-established boronic counterpart (1.8 m −1 ⋅s −1 ). This improved reactivity was also effective in a cellular context, rendering borinic acids an advantageous trigger for H 2 O 2 -mediated release of effectors such as fluorescent moieties.
Type of Medium:
Online Resource
ISSN:
0027-8424
,
1091-6490
DOI:
10.1073/pnas.2107503118
Language:
English
Publisher:
Proceedings of the National Academy of Sciences
Publication Date:
2021
detail.hit.zdb_id:
209104-5
detail.hit.zdb_id:
1461794-8
SSG:
11
SSG:
12
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