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Comparison of Reductive Ligation‐Based Detection Strategies for Nitroxyl (HNO) and S‐Nitrosothiols

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abstract
Phosphine‐based detection strategies for both nitroxyl (HNO) and S‐nitrosothiols (RSNO) were investigated and compared. Phosphorus NMR studies show that azaylides derived from HNO or organic RSNO efficiently participate in subsequent reductive ligation required for fluorescence generation in properly substituted substrates. S‐Azaylides derived from biological RSNO containing free amine and carboxylic acid groups primarily yield phosphine oxides suggesting these groups facilitate nonligation pathways such as hydrolysis. The fluorescence response of a phosphine‐based fluorophore toward the same RSNO confirms these differences and indicates that these probes selectively react with HNO. Flow cytometry experiments in HeLa cells reinforce the reactivity difference and offer a potential fast screening approach for endogenous HNO sources.
subject
fluorescence
nitroxyl
phosphine
reductive ligation
S-nitrosothiol
contributor
Miao, Z. (author)
King, B. (author)
date
2020-02-04T14:46:45Z (accessioned)
2020-02-04T14:46:45Z (available)
1/13/16 (issued)
identifier
Miao, Z., & King, S. B. (2016). Comparison of Reductive Ligation‐Based Detection Strategies for Nitroxyl (HNO) and S‐Nitrosothiols. ChemistryOpen, 5(2), 110-114. (citation)
https://doi.org/10.1002/open.201500200 (doi)
http://hdl.handle.net/10339/95972 (uri)
language
en (iso)
publisher
Wiley
rights
https://creativecommons.org/licenses/by/4.0/ (uri)
source
ChemistryOpen
title
Comparison of Reductive Ligation‐Based Detection Strategies for Nitroxyl (HNO) and S‐Nitrosothiols
type
Article

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