The role of sulfenic acids in cellular redox signaling: Reconciling chemical kinetics and molecular detection strategies.

Abstract:

:The reversible oxidation of protein cysteine residues is well recognized as an important regulatory mechanism in redox-dependent cell signaling. Cysteine oxidation is diverse in nature and involves various post-translational modifications (sulfenic acids, disulfides, etc.) and the specific functional or structural impact of these specific oxidative events is still poorly understood. The proximal product of protein cysteine oxidation by biological reactive oxygen species (ROS) is sulfenic acid (Cys-SOH), and experimental evidence is accruing for the formation of Cys-SOH as intermediate in protein cysteine oxidation in various biological settings. However, the plausibility of protein Cys-SH oxidation by ROS has often been put in question because of slow reaction kinetics compared to more favorable reactions with abundant thiol-based reductants such as peroxiredoxins (Prx) or glutathione (GSH). This commentary aims to address this controversy by highlighting the unique physical properties in cells that may restrict ROS diffusion and allow otherwise less favorable cysteine oxidation of proteins. Some limitations of analytical tools to assess Cys-SOH are also discussed. We conclude that formation of Cys-SOH in biological systems cannot always be predicted based on kinetic analyses in homogenous solution, and may be facilitated by unique structural and physical properties of Cys-containing proteins within e.g. signaling complexes.

journal_name

Arch Biochem Biophys

authors

Heppner DE,Janssen-Heininger YMW,van der Vliet A

doi

10.1016/j.abb.2017.01.008

subject

Has Abstract

pub_date

2017-02-15 00:00:00

pages

40-46

eissn

0003-9861

issn

1096-0384

pii

S0003-9861(16)30581-1

journal_volume

616

pub_type

杂志文章
  • Allene oxide cyclase: a new enzyme in plant lipid metabolism.

    abstract::The mechanism of the biosynthesis of 12-oxo-10,15(Z)-phytodienoic acid (12-oxo-PDA) from 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid in preparations of corn (Zea mays L.) was studied. In the initial reaction the hydroperoxide was converted into an unstable allene oxide, 12,13(S)-epoxy-9(Z),11,15(Z)-octade...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(90)90753-l

    authors: Hamberg M,Fahlstadius P

    更新日期:1990-02-01 00:00:00

  • Ontogeny of the murine glucose-6-phosphatase system.

    abstract::A deficiency in microsomal glucose-6-phosphatase (G6Pase) activity causes glycogen storage disease type 1 (GSD-1), a clinically and biochemically heterogeneous group of diseases. It has been suggested that catalysis by G6Pase involves multiple components, with defects in the G6Pase catalytic unit causing GSD-1a and de...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1998.0849

    authors: Pan CJ,Lei KJ,Chen H,Ward JM,Chou JY

    更新日期:1998-10-01 00:00:00

  • Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti.

    abstract::The sesquiterpene cyclase, aristolochene synthase, has been purified from Penicillium roqueforti by gel filtration and anion-exchange chromatography. Isolation was facilitated by a change in the elution behavior of the enzyme during gel filtration at different steps in the purification. The purified enzyme had a speci...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(89)90204-x

    authors: Hohn TM,Plattner RD

    更新日期:1989-07-01 00:00:00

  • Reaction of uric acid with peroxynitrite and implications for the mechanism of neuroprotection by uric acid.

    abstract::Peroxynitrite, a biological oxidant formed from the reaction of nitric oxide with the superoxide radical, is associated with many pathologies, including neurodegenerative diseases, such as multiple sclerosis (MS). Gout (hyperuricemic) and MS are almost mutually exclusive, and uric acid has therapeutic effects in mice ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.2000.1721

    authors: Squadrito GL,Cueto R,Splenser AE,Valavanidis A,Zhang H,Uppu RM,Pryor WA

    更新日期:2000-04-15 00:00:00

  • The chalcones cardamonin and flavokawain B inhibit the differentiation of preadipocytes to adipocytes by activating ERK.

    abstract:AIM:We searched for polyphenols capable of inhibiting the lipid accumulation in 3T3-L1 cells, and investigated the mechanisms of two effective chalcones cardamonin and flavokawain B on differentiation of preadipocytes. METHOD AND RESULTS:We treated 3T3-L1 cells with a panel of 46 polyphenols and measured intracellular...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2014.05.008

    authors: Zhang T,Yamamoto N,Yamashita Y,Ashida H

    更新日期:2014-07-15 00:00:00

  • Effect of D-amino acid substitution in a mucin 2 epitope on mucin-specific monoclonal antibody recognition.

    abstract::We have studied the influence of D-amino acid substitution in the flanking region on the antibody recognition of the 19TGTQ22 epitope core in the tandem repeat of mucin 2 (MUC2) glycoprotein. Analogue peptides corresponding to the optimal epitope sequence (16PTPTGTQ22) have been prepared by the replacement of single o...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.2000.1801

    authors: Uray K,Kajtár J,Vass E,Price MR,Hollósi M,Hudecz F

    更新日期:2000-06-01 00:00:00

  • The 85-kDa, arachidonic acid-specific phospholipase A2 is expressed as an activated phosphoprotein in Sf9 cells.

    abstract::A human, 85-kDa arachidonoyl-specific, cytosolic phospholipase A2 was expressed using the baculovirus-insect cell expression system. Expression resulted in the production of an active protein which consisted of approximately 3% of the total protein in the host Spodoptera frugiperda (Sf9) cells at 67 h after infection....

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1993.1549

    authors: de Carvalho MS,McCormack FX,Leslie CC

    更新日期:1993-11-01 00:00:00

  • A model for hydropathy-based peptide interactions.

    abstract::Two peptides are specified when the noncoding DNA strand is read in the 5' to 3', or the 3' to 5' direction, and both peptides form strong complexes with the natural peptide, as found by J. E. Blalock and K. L. Bost with ACTH [1986) Biochem. J. 234, 679-683). We report here that strong hydropathic complementarity (pai...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(89)90237-3

    authors: Markus G,Tritsch GL,Parthasarathy R

    更新日期:1989-08-01 00:00:00

  • Cardiac transcription factor Nkx2.5 interacts with p53 and modulates its activity.

    abstract::Transcription factor Nkx2.5, essential for heart development, regulates cardiomyocyte-specific gene expression through combinatorial interactions with other cardiac-restricted (GATA4 and dHAND) or ubiquitous (p300) transcription regulators. Here we demonstrate that Nkx2.5 and p53 synergistically activate the promoter ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2015.02.001

    authors: Kojic S,Nestorovic A,Rakicevic L,Protic O,Jasnic-Savovic J,Faulkner G,Radojkovic D

    更新日期:2015-03-01 00:00:00

  • Insulin replacement therapy in diabetic rats using an osmotic pump normalizes expression of enzymes key to hepatic carbohydrate metabolism.

    abstract::Intensively treating type I diabetics with continuous subcutaneous insulin infusions or multiple daily insulin injections to normalize mean blood glucose concentrations significantly reduces the onset of secondary diabetic complications when compared to conventionally treated diabetics. Our studies focused on characte...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1999.1299

    authors: Kramer KL,Giffin BF,Fox JW,Drake RL

    更新日期:1999-08-15 00:00:00

  • Comparison of kinetic and molecular properties of two forms of amygdalin hydrolase from black cherry (Prunus serotina Ehrh.) seeds.

    abstract::Two forms of the beta-glucosidase amygdalin hydrolase (AH I and II), which catalyze the hydrolysis of (R)-amygdalin to (R)-prunasin and D-glucose, have been purified over 200-fold from mature black cherry (Prunus serotina Ehrh.) seeds. These proteins showed very similar molecular and kinetic properties but could be re...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(86)90603-x

    authors: Kuroki GW,Poulton JE

    更新日期:1986-06-01 00:00:00

  • Serum acetone and liver acetone monooxygenase activity in pregnant rats, fetuses, and neonates: reversible pretranslational reduction of cytochrome P450IIE1 (P450IIE1) during pregnancy.

    abstract::Serum acetone in neonates was found to increase from < 20 microM at 20 days gestation to 377 +/- 107 microM 1 day after birth. This increase in acetone occurs concurrently with the initial expression of liver P450IIE1 in rat (Song et al., 1986, J. Biol. Chem. 261:16689-16697). Treating pregnant rats with drinking wate...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1994.1092

    authors: Casazza JP,Sohn DH,Park KS,Song BJ

    更新日期:1994-02-15 00:00:00

  • A novel miR17/protein tyrosine phosphatase-oc/EphA4 regulatory axis of osteoclast activity.

    abstract::Information about the molecular mechanisms leading to the activation of the osteoclast is relatively limited. While there is compelling evidence that the signaling mechanisms of Src and integrin β3 are essential for osteoclast activation, the regulation of these two signaling mechanisms is not fully understood. In thi...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章,评审

    doi:10.1016/j.abb.2018.05.014

    authors: Lau KW,Sheng MH

    更新日期:2018-07-15 00:00:00

  • MicroRNA-130a has pro-fibroproliferative potential in hypertrophic scar by targeting CYLD.

    abstract::Hypertrophic scars are dermal fibrosis diseases that protrude from the surface of the skin and irregularly extend to the periphery, seriously affecting the appearance and limb function of the patient. In this study, we found that microRNA-130a (miR-130a) was increased in hypertrophic scar tissues and derived primary f...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2019.07.003

    authors: Zhang J,Zhou Q,Wang H,Huang M,Shi J,Han F,Cai W,Li Y,He T,Hu D

    更新日期:2019-08-15 00:00:00

  • Effects of sulfhydryl reagents, retinoids, and solubilization on the activity of microsomal retinol dehydrogenase.

    abstract::A microsomal retinol dehydrogenase (RoDH) that recognizes holo-cellular retinol binding protein (CRBP) as substrate is inhibited by phenylarsine oxide (IC50 = 3 microM) in the presence of 10 mM cysteine. Inhibition was reversible with dithiothreitol, indicating that two cysteine residues in close proximity are essenti...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1995.1415

    authors: Boerman MH,Napoli JL

    更新日期:1995-08-20 00:00:00

  • Stark absorption spectroscopy on the carotenoids bound to B800-820 and B800-850 type LH2 complexes from a purple photosynthetic bacterium, Phaeospirillum molischianum strain DSM120.

    abstract::Stark absorption spectroscopy was applied to clarify the structural differences between carotenoids bound to the B800-820 and B800-850 LH2 complexes from a purple photosynthetic bacterium Phaeospirillum (Phs.) molischianum DSM120. The former complex is produced when the bacteria are grown under stressed conditions of ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2014.12.015

    authors: Horibe T,Qian P,Hunter CN,Hashimoto H

    更新日期:2015-04-15 00:00:00

  • Myotoxin II from Bothrops asper (Terciopelo) venom is a lysine-49 phospholipase A2.

    abstract::A basic, dimeric myotoxic protein, myotoxin II, purified from Bothrops asper venom has a similar molecular weight and is immunologically cross-reactive with antibodies raised to previously isolated B. asper phospholipases A2, except that it shows only 0.1% of the phospholipase activity against L-alpha-phosphatidylchol...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(91)90307-5

    authors: Francis B,Gutierrez JM,Lomonte B,Kaiser II

    更新日期:1991-02-01 00:00:00

  • Glucose requirement for induction by sodium butyrate of the glycoprotein hormone alpha subunit in HeLa cells.

    abstract::Butyric acid produces multiple effects on mammalian cells in culture, including alterations in morphology, depression of growth rate, increased histone acetylation, and modified production of various proteins and enzymes. The latter effect is exemplified by the induction in HeLa cells of the glycoprotein hormone alpha...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(84)90605-2

    authors: McClure DS,Cox GS

    更新日期:1984-08-15 00:00:00

  • ATP, histidine or magnesium ions can protect DNA against sisomicin-induced damage, following stray Cu(II) binding.

    abstract::The oxidative DNA damage by the cupric complexes of sisomicin was investigated in the presence of varying amounts of histidine, ATP, Mg(II) ions or phosphates. We found that by very low concentrations, the amino acid is able to inhibit the cleavage totally. This occurs both by its competition with antibiotic for coppe...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2004.07.018

    authors: Szczepanik W,Swiatek M,Skała J,Jezowska-Bojczuk M

    更新日期:2004-11-01 00:00:00

  • Biochemical and functional insights on the triheme cytochrome PpcA from Geobacter metallireducens.

    abstract::G. metallireducens bacterium has highly versatile respiratory pathways that provide the microorganism an enormous potential for many biotechnological applications. However, little is known about the structural and functional properties of its electron transfer components. In this work, the periplasmic cytochrome PpcA ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2018.02.017

    authors: Portela PC,Fernandes TM,Dantas JM,Ferreira MR,Salgueiro CA

    更新日期:2018-04-15 00:00:00

  • Activation of calcium-sensing receptor by allosteric agonists cinacalcet and AC-265347 abolishes the 1,25(OH)2D3-induced Ca2+ transport: Evidence that explains how the intestine prevents excessive Ca2+ absorption.

    abstract::Long-term high-calcium intake and intestinal calcium hyperabsorption are hazardous to the body. It is hypothesized that enterocytes possess mechanisms for preventing superfluous calcium absorption, including secretion of negative regulators of calcium absorption and utilization of calcium-sensing receptor (CaSR) to de...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2018.09.004

    authors: Wongdee K,Rodrat M,Keadsai C,Jantarajit W,Teerapornpuntakit J,Thongbunchoo J,Charoenphandhu N

    更新日期:2018-11-01 00:00:00

  • Cancer chemopreventive oltipraz generates superoxide anion radical.

    abstract::The cancer chemopreventive actions of oltipraz, a member of a class of 1,2-dithiolethiones, have been primarily associated with the induction of phase 2 enzymes mediated by a 41bp enhancer element known as the anti-oxidant response element in the promoter regions of many phase 2 genes. It has been suggested that oxyge...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2004.11.028

    authors: Velayutham M,Villamena FA,Fishbein JC,Zweier JL

    更新日期:2005-03-01 00:00:00

  • Intramolecular cross-linking in the native JHBP molecule.

    abstract::Juvenile hormone binding protein (JHBP) acts as a shuttle, carrying one of the most crucial hormones for insect development to target tissues. We have found that although the JHBP molecule does not contain tryptophan residues, it exhibits a weak fluorescence maximum near 420nm upon excitation at 315nm. Gel filtration ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2011.10.021

    authors: Bystranowska D,Szewczuk Z,Lisowski M,Sitkiewicz E,Dobryszycki P,Ożyhar A,Kochman M

    更新日期:2012-01-01 00:00:00

  • Vasodilatory effect of kaempferol-7-O-α-L-rhamnopyranoside via NO-cGMP-PKG signaling.

    abstract::Hypertension is one of the major causes of mortality. Though a host of drugs are available for the treatment of hypertension, majority have been linked to adverse side effects, necessitating the need for research into natural compounds with fewer side effects. Kaempferol-7-O-α-L-rhamnopyroside (KR) is a glycosylated f...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2019.04.001

    authors: Tettey CO,Yang IJ,Shin HM

    更新日期:2019-05-30 00:00:00

  • A novel acetyl-CoA carboxylase inhibitor reduces de novo fatty acid synthesis in HepG2 cells and rat primary hepatocytes.

    abstract::To identify the novel inhibitor of de novo lipogenesis in hepatocytes, we screened for inhibitory activity of triglyceride (TG) synthesis using [14C]acetate in the human hepatoma cell line, HepG2. Using this assay system we discovered the novel compound, benzofuranyl alpha-pyrone (TEI-B00422). TEI-B00422 also inhibite...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2007.09.012

    authors: Sugimoto Y,Naniwa Y,Nakamura T,Kato H,Yamamoto M,Tanabe H,Inoue K,Imaizumi A

    更新日期:2007-12-01 00:00:00

  • Chemiluminescent aerobic oxidation of protein adducts with glycolaldehyde catalyzed by horseradish peroxidase.

    abstract::Horseradish peroxidase (EC 1.11.1.7) is shown to catalyze the aerobic oxidation of lysozyme, bovine serum albumin, and protamine adducts with glycolaldehyde at physiological pH. This reaction is accompanied by light emission, which is attributed to the generation of triplet species. The intensity of chemiluminescence ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(86)90441-8

    authors: de Medeiros MH,Bechara EJ

    更新日期:1986-07-01 00:00:00

  • Characterization of the methionine S-oxidase activity of rat liver and kidney microsomes: immunochemical and kinetic evidence for FMO3 being the major catalyst.

    abstract::Methionine is oxidized to methionine sulfoxide by rat liver and kidney microsomes in an O2- and NADPH-dependent manner. In all microsomal assays, no methionine sulfone was detected. Use of a monoclonal antibody to rat liver cytochrome P-450 reductase, various cytochrome P-450 and peroxidase inhibitors, antioxidants, a...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1996.0370

    authors: Krause RJ,Ripp SL,Sausen PJ,Overby LH,Philpot RM,Elfarra AA

    更新日期:1996-09-01 00:00:00

  • Upregulation of α2-adrenoceptor synthesis in SHR cardiomyocytes: Recompense without sense - Increased amounts, impaired commands.

    abstract:AIMS:to investigate α2-AR subtype distribution and the relationship between receptor amounts and their functionality in normotensive and spontaneously hypertensive rats. METHODS:experiments were performed on left ventricular cardiomyocytes isolated from Wistar rats and SHR (2-2.5 months). Molecular routine tools (RT-P...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2019.108109

    authors: Kokoz YM,Evdokimovskii EV,Maltsev AV

    更新日期:2019-10-15 00:00:00

  • Infrared spectroscopic studies on interactions of water and carbohydrates with a biological membrane.

    abstract::Infrared spectroscopy was used to investigate the changes in bands assigned to phospholipids and proteins in dehydrated and rehydrated sarcoplasmic reticulum. The changes in CH2 and CH3 stretching bands, amide bands, and phosphate stretching bands are similar to shifts in frequency seen for those bands in phospholipid...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(84)90555-1

    authors: Crowe JH,Crowe LM,Chapman D

    更新日期:1984-07-01 00:00:00

  • 1,4-Benzoquinone reductase from basidiomycete Phanerochaete chrysosporium: spectral and kinetic analysis.

    abstract::The reaction mechanism of a 1,4-benzoquinone reductase from the wood-rotting basidiomycete Phanerochaete chrysosporium was investigated. The native, oxidized, FMN-containing enzyme was reduced quantitatively by NADH and the resulting reduced enzyme was reoxidized in the presence of one equivalent of 2,6-di-methoxy-1,4...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1996.0279

    authors: Brock BJ,Gold MH

    更新日期:1996-07-01 00:00:00