Use of 1-fluoro-2,4-dinitrobenzene as a probe for the presence of hydrodisulfide groups in proteins

Sawahata, Tadashi; Neal, Robert A.

doi:10.1016/0003-2697(82)90528-0

Cited by 21 publications

(14 citation statements)

References 21 publications

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“…Neal and Sawahata used 1-fluoro-2,4-dinitrobenzene (145) as a probe for persulfides. 205 The persulfide reacts in a nucleophilic aromatic substitution with 145. The dinitrobenzene disulfide product (146) can then be reduced with DTT to release 2,4-dinitrothiophenol (147), which can be analysed spectroscopically (Fig.…”

Section: Chemical Methods For Detecting Rsshmentioning

confidence: 99%

Chemical methods for mapping cysteine oxidation

2018

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Cysteine residues in proteins are subject to diverse redox chemistry. Oxidation of cysteine to S-nitrosocysteine, cysteine sulfenic and sulfinic acids, disulfides and persulfides are a few prominent examples of these oxidative post-translational modifications. In living organisms, these modifications often play key roles in cell signalling and protein function, but a full account of this biochemistry is far from complete. It is therefore an important goal in chemical biology to identify what proteins are subjected to these modifications and understand their physiological function. This review provides an overview of these modifications, how they can be detected and quantified using chemical probes, and how this information provides insight into their role in biology. This survey also highlights future opportunities in the study of cysteine redox chemistry, the challenges that await chemists and biologists in this area of study, and how meeting such challenges might reveal valuable information for biomedical science.

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Section: Chemical Methods For Detecting Rsshmentioning

confidence: 99%

Chemical methods for mapping cysteine oxidation

2018

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“…[7a] Forthis study,we used dinitrofluorobenzene (DNFB,Compound 5), which was known to trap persulfides (Scheme 3b). [16] Specifically,w e incubated 100 mm of the prodrugs with 1UmL À1 PLE at 37 8 8C for 10 sa nd then added 4mm of DNFB to the mixture.T he resulting solution was further incubated for another 30 min. Then the formation of disulfide compound 6 was analyzed by HPLC ( Table 2).…”

Section: Angewandte Chemiementioning

confidence: 99%

“…[16] Specifically,w e incubated 100 mm of the prodrugs with 1UmL À1 PLE at 37 8 8C for 10 sa nd then added 4mm of DNFB to the mixture.T he resulting solution was further incubated for another 30 min. Next, it was important to demonstrate persulfide formation without the added the thiol species, 3.Inthe field of designing detection methods for protein S-sulfhydration, ak ey step is developing trapping reagents,which could efficiently trap the persulfide under physiological conditions.…”

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confidence: 99%

An Esterase‐Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species

Zheng

et al. 2017

Angew Chem Int Ed

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A strategy to deliver a well-defined persulfide species in a biological medium is described. Under near physiological conditions, the persulfide prodrug can be activated by an esterase to generate a "hydroxymethyl persulfide" intermediate, which rapidly collapses to form a defined persulfide. Such persulfide prodrugs can be used either as chemical tools to study persulfide chemistry and biology or for future development as H S-based therapeutic reagents. Using the persulfide prodrugs developed in this study, the reactivity between S-methyl methanethiosulfonate (MMTS) with persulfide was unambiguously demonstrated. Furthermore, a representative prodrug exhibited potent cardioprotective effects in a murine model of myocardial ischemia-reperfusion (MI/R) injury with a bell shape therapeutic profile.

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“…In the field of designing detection methods for protein S ‐sulfhydration, a key step is developing trapping reagents, which could efficiently trap the persulfide under physiological conditions . For this study, we used dinitrofluorobenzene (DNFB, Compound 5 ), which was known to trap persulfides (Scheme b) . Specifically, we incubated 100 μ m of the prodrugs with 1 U mL −1 PLE at 37 °C for 10 s and then added 4 m m of DNFB to the mixture.…”

Section: Methodsmentioning

confidence: 99%

An Esterase‐Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species

Zheng

et al. 2017

Angewandte Chemie

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A strategy to deliver a well‐defined persulfide species in a biological medium is described. Under near physiological conditions, the persulfide prodrug can be activated by an esterase to generate a “hydroxymethyl persulfide” intermediate, which rapidly collapses to form a defined persulfide. Such persulfide prodrugs can be used either as chemical tools to study persulfide chemistry and biology or for future development as H2S‐based therapeutic reagents. Using the persulfide prodrugs developed in this study, the reactivity between S‐methyl methanethiosulfonate (MMTS) with persulfide was unambiguously demonstrated. Furthermore, a representative prodrug exhibited potent cardioprotective effects in a murine model of myocardial ischemia‐reperfusion (MI/R) injury with a bell shape therapeutic profile.

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Use of 1-fluoro-2,4-dinitrobenzene as a probe for the presence of hydrodisulfide groups in proteins

Cited by 21 publications

References 21 publications

Chemical methods for mapping cysteine oxidation

Chemical methods for mapping cysteine oxidation

An Esterase‐Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species

An Esterase‐Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species

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