Formation and Reactions of Sulfenic Acid in Human Serum Albumin

Álvarez, Beatriz; Carballal, Sebastián; Turell, Lucía; Radí, Rafael

doi:10.1016/s0076-6879(10)73005-6

Cited by 50 publications

(36 citation statements)

References 34 publications

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“…Gas-tight Hamilton syringes were used throughout the study. 5-Thio-2-nitrobenzoic acid (TNB) solutions were prepared as reported previously (26). LMW disulfides were purchased from Sigma or AppliChem.…”

Section: Methodsmentioning

confidence: 99%

“…Preparation of HSA Derivatives-HSA (Sigma) was delipidated; its thiol was reduced with ␤-mercaptoethanol, and the concentrations of protein and thiol were quantified as described previously (26). Mixed disulfides were prepared by incubating reduced HSA (ϳ1 mM) overnight with the disulfide of interest (up to 20 mM) in acetate buffer (100 mM, pH 4.5, 0.1 mM diethylenetriaminepentaacetic acid (DTPA), 4°C) or tris buffer (100 mM, pH 7.4, 0.1 mM DTPA, 4°C).…”

Section: Methodsmentioning

confidence: 99%

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Reaction of Hydrogen Sulfide with Disulfide and Sulfenic Acid to Form the Strongly Nucleophilic Persulfide

Cuevasanta

Lange

Bonanata

et al. 2015

Journal of Biological Chemistry

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284

344

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Background:Hydrogen sulfide (H 2 S) modulates physiological processes in mammals. Results: The reactivity of H 2 S toward disulfides (RSSR) and albumin sulfenic acid (RSOH) to form persulfides (RSSH) was assessed. Conclusion: H 2 S is less reactive than thiols. Persulfides have enhanced nucleophilicity. Significance: This kinetic study helps rationalize the contribution of the reactions with oxidized thiol derivatives to H 2 S biology.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Reaction of Hydrogen Sulfide with Disulfide and Sulfenic Acid to Form the Strongly Nucleophilic Persulfide

Cuevasanta

Lange

Bonanata

et al. 2015

Journal of Biological Chemistry

Self Cite

284

344

View full text Add to dashboard Cite

show abstract

“…Free thiol content was determined by measuring an increase in absorbance at 250 nm that occurs upon mercaptide formation between free thiols and p-chloromercuribenzoate (p-CMB) (25,26). The p-CMB titration results showed that the air-oxidized RegBЉ contains ϳ0.1 free thiol per monomer (Fig.…”

Section: Sulfenic Acid Formation At Cys-265 In Vitro-mentioning

confidence: 99%

RegB Kinase Activity Is Repressed by Oxidative Formation of Cysteine Sulfenic Acid

Cheng

Reddie

et al. 2013

Journal of Biological Chemistry

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Background: Activity of the redox responsive global sensor kinase RegB is repressed under aerobic conditions. Results: Stable and reversible sulfenic acid modification forms at cysteine 265 to repress kinase activity. Conclusion: Cysteine 265 functions as a redox switch that regulates kinase activity in response to aerobic conditions. Significance: This study discloses additional regulatory details of the redox-sensing sensor kinase RegB.

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“…As a relatively stable label, SA can be spontaneously formed in HSA, 19 and the control sample (without H 2 O 2 addition) indicated some minor labelling percentage for SA. A similar percentage for SA labelling with Nd-DOTA-KE was detected for the 2-fold excess of H 2 O 2 , which might indicate that this concentration is too low for any further formation of SA above the spontaneously existing amount.…”

Section: Quantication For Labelled Sa With Isotopic Dilution Analysimentioning

confidence: 94%

“…Albumin contains 35 cysteines forming 17 disulde bridges (-S-S-) with only one free thiol, Cys-34, which comprises 80% of the total free thiols in plasma and can follow the smallest change in the redox environment of a biological system. [18][19][20] Ln-DOTA-KE was used to label the free cysteine (Cys-34) in albumin using Nd as metal to follow with ICP-MS. The use of isotope dilution analysis in conjunction with liquid chromatography-ICP-MS permits quantifying the evolution of the oxidative process in the albumin aer a suitable purication process.…”

mentioning

confidence: 99%

Detection of sulfenic acid in intact proteins by mass spectrometric techniques: application to serum samples

et al. 2017

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Formation of cysteine sulfenic acid (SA) is considered a transient state of thiol oxidation in living organisms that can be either reduced back or continue to result in the formation of sulfinic and sulfonic acids. As any disturbance in oxidation is correlated to age-related diseases such as cancer and Alzheimer's disease, the detection of SA transient state formed a sensor for such redox-mediated events. Thus, detection of low amounts of SA is critical in order to prevent further oxidative damage of cells and tissues and for this aim specific strategies have to be developed. In this work, detection and quantification of induced SA in human serum albumin is reported by specific capture using alkyne bketoester (KE) previously linked to a lanthanide (Ln)-containing chelator (Ln-DOTA, where DOTA is 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid). SA formation was induced by hydrogen peroxide to mimic oxidative conditions produced in living cells by ROS and was detected using molecular and elemental mass spectrometric (MS) techniques. The developed strategy has been further applied to the determination of SA-induced formation in human serum by using affinity chromatography for purification of albumin followed by inductively coupled plasma mass spectrometry (ICP-MS) to monitor the formed SA linked to Ln-DOTA-KE in combination with isotope dilution analysis (IDA) for absolute quantification. Quantitative results showed levels of oxidative damage regarding SA formation in up to 40% of the albumin present.

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Formation and Reactions of Sulfenic Acid in Human Serum Albumin

Cited by 50 publications

References 34 publications

Reaction of Hydrogen Sulfide with Disulfide and Sulfenic Acid to Form the Strongly Nucleophilic Persulfide

Reaction of Hydrogen Sulfide with Disulfide and Sulfenic Acid to Form the Strongly Nucleophilic Persulfide

RegB Kinase Activity Is Repressed by Oxidative Formation of Cysteine Sulfenic Acid

Detection of sulfenic acid in intact proteins by mass spectrometric techniques: application to serum samples

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