Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H8N2O8S2 |
| Molecular Weight | 396.352 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC(SSC2=CC=C(C(=C2)C(O)=O)[N+]([O-])=O)=CC=C1[N+]([O-])=O
InChI
InChIKey=KIUMMUBSPKGMOY-UHFFFAOYSA-N
InChI=1S/C14H8N2O8S2/c17-13(18)9-5-7(1-3-11(9)15(21)22)25-26-8-2-4-12(16(23)24)10(6-8)14(19)20/h1-6H,(H,17,18)(H,19,20)
| Molecular Formula | C14H8N2O8S2 |
| Molecular Weight | 396.352 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Ellman's reagent 5,5'-dithio-bis-(2-nitrobenzoic acid), also known as DTNB, was introduced in 1959 as a versatile water-soluble compound for quantitating free sulfhydryl groups in solution. In this procedure, DTNB, a symmetric aryl disulfide, reacts with the free thiol to give a mixed disulfide plus 2-nitro-5-thiobenzoic acid (TNB) which is quantified by its absorbance at 412 nm. Determination of SH groups in proteins by Ellman's reagent after or in the presence of NO treatment is complicated since the reduced form of DTNB, TNB, can be reoxidized by NO back to DTNB, with subsequent loss of absorbance at 412 nm.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structure of the (113)Cd(3)beta domains from Homarus americanus metallothionein-1: hydrogen bonding and solvent accessibility of sulfur atoms. | 2002-09 |
|
| Surplus zinc is handled by Zym1 metallothionein and Zhf endoplasmic reticulum transporter in Schizosaccharomyces pombe. | 2002-08-16 |
|
| Antioxidative properties of cardoon (Cynara cardunculus L.) infusion against superoxide radical, hydroxyl radical, and hypochlorous acid. | 2002-08-14 |
|
| The roles of thiols in the bacterial organomercurial lyase (MerB). | 2002-08-13 |
|
| Role of cysteine 306 in the catalytic mechanism of Ascaris suum phosphoenolpyruvate carboxykinase. | 2002-08-01 |
|
| Identification of a peroxide-sensitive redox switch at the CXXC motif in the human mitochondrial branched chain aminotransferase. | 2002-07-23 |
|
| Redox-based control of the gamma heavy chain ATPase from Chlamydomonas outer arm dynein. | 2002-07 |
|
| Quick measurement of protein sulfhydryls with Ellman's reagent and with 4,4'-dithiodipyridine. | 2002-07 |
|
| Enhancement of lysosomal proton permeability induced by photooxidation of membrane thiol groups. | 2002-06-15 |
|
| S-nitrosation of Ca(2+)-loaded and Ca(2+)-free recombinant calbindin D(28K) from human brain. | 2002-05-14 |
|
| Involvement of amino-acid side chains of membrane proteins in the binding of glutathione to pig cerebral cortical membranes. | 2002-05 |
|
| Evaluation of peracid activated organophosphates in studies of insecticide resistance conferred by insensitive acetylcholinesterases. | 2002-04 |
|
| Sulfite induces adherence of polymorphonuclear neutrophils to immobilized fibrinogen through activation of Mac-1 beta2-integrin (CD11b/CD18). | 2002-03-29 |
|
| Conformational change of the E-F interhelical loop in the M photointermediate of bacteriorhodopsin. | 2002-03-29 |
|
| Molecular umbrella-assisted transport of thiolated AMP and ATP across phospholipid bilayers. | 2002-03-22 |
|
| Methylseleninate is a substrate rather than an inhibitor of mammalian thioredoxin reductase. Implications for the antitumor effects of selenium. | 2002-03-22 |
|
| Fluorescence studies of pyrene maleimide-labeled translin: excimer fluorescence indicates subunits associate in a tail-to-tail configuration to form octamer. | 2002-03-12 |
|
| Expression, characterization, and reaction of recombinant monkey metallothionein-1 and its C33M mutant. | 2002-03 |
|
| Crystallization, preliminary X-ray analysis and biophysical characterization of HPr kinase/phosphatase of Mycoplasma pneumoniae. | 2002-03 |
|
| Ca(2+)-activated K+ channel inhibition by reactive oxygen species. | 2002-03 |
|
| Electron spin resonance investigation of semiquinone radicals formed from the reaction of ubiquinone 0 with human oxyhemoglobin. | 2002-02-22 |
|
| Testing of the portal hypothesis: analysis of a V32G, F57G, K58G mutant of the fatty acid binding protein of the murine adipocyte. | 2002-02-12 |
|
| An NADH-dependent bacterial thioredoxin reductase-like protein in conjunction with a glutaredoxin homologue form a unique peroxiredoxin (AhpC) reducing system in Clostridium pasteurianum. | 2002-02-12 |
|
| Recombinant lysine:N(6)-hydroxylase: effect of cysteine-->alanine replacements on structural integrity and catalytic competence. | 2002-02-11 |
|
| Unfolding rates of barstar determined in native and low denaturant conditions indicate the presence of intermediates. | 2002-02-05 |
|
| The peroxisome proliferator-induced cytosolic type I acyl-CoA thioesterase (CTE-I) is a serine-histidine-aspartic acid alpha /beta hydrolase. | 2002-02-01 |
|
| [Modification of redox sites of N-methyl-D-aspartate receptors affects changes in bioelectrical activity of olfactory cortex slices induced by anoxia in rats]. | 2002-02 |
|
| Purification and characterization of N-acetylneuraminic acid-9-phosphate synthase from rat liver. | 2002-02 |
|
| Transient forebrain ischemia induces persistent hyperactivity of large conductance Ca2+-activated potassium channels via oxidation modulation in rat hippocampal CA1 pyramidal neurons. | 2002-02 |
|
| Enhancement of lysosomal osmotic sensitivity induced by the photooxidation of membrane thiol groups. | 2002-02 |
|
| Folding pathway of apo-metallothionein induced by Zn2+, Cd2+ and Co2+. | 2002-01-15 |
|
| Preparation of irreversibly sickled cell beta-actin from normal red blood cell beta-actin. | 2002-01-08 |
|
| Simple shifts in redox/thiol balance that perturb blood coagulation. | 2002-01-02 |
|
| Lecithin: cholesterol acyltransferase is insufficient to prevent oxidative modification of low-density lipoprotein. | 2002-01 |
|
| Human placenta thioredoxin reductase: preparation and inhibitor studies. | 2002 |
|
| Thioredoxin, thioredoxin reductase, and thioredoxin peroxidase of malaria parasite Plasmodium falciparum. | 2002 |
|
| Mitochondrial thioredoxin reductase and thiol status. | 2002 |
|
| Reduced redox state allows prolonged survival of axotomized neonatal retinal ganglion cells. | 2002 |
|
| Allosteric behaviour of 1:5 hybrids of mutant subunits of Clostridium symbiosum glutamate dehydrogenase differing in their amino acid specificity. | 2001-12-15 |
|
| The influence of oxidation of membrane thiol groups on lysosomal proton permeability. | 2001-12-01 |
|
| Identification of a critical lysine residue at the active site in glyceraldehyde-3-phosphate dehydrogenase of Ehrlich ascites carcinoma cell. Comparison with the rabbit muscle enzyme. | 2001-12 |
|
| Calcium-dependent cysteine reactivities in the neuronal calcium sensor guanylate cyclase-activating protein 1. | 2001-11-23 |
|
| Anandamide amidohydrolase activity, released in the medium by Tetrahymena pyriformis. Identification and partial characterization. | 2001-11-23 |
|
| On the nature of conformational openings: native and unfolded-state hydrogen and thiol-disulfide exchange studies of ferric aquomyoglobin. | 2001-11-16 |
|
| Progress curves analysis as an alternative for exploration of activation-inhibition phenomena in cholinesterases. | 2001-11 |
|
| The importance of zinc-binding to the function of Rhodobacter sphaeroides ChrR as an anti-sigma factor. | 2001-10-26 |
|
| Conversion of a peroxiredoxin into a disulfide reductase by a triplet repeat expansion. | 2001-10-05 |
|
| Determination of whole blood cholinesterase in different animal species using specific substrates. | 2001-06 |
|
| Acetylcholinesterase assay for cerebrospinal fluid using bupivacaine to inhibit butyrylcholinesterase. | 2001 |
|
| Kinetics of inactivation of glutamate decarboxylase by cysteine-specific reagents. | 2001 |
Sample Use Guides
A sub-effective dose (0.01nmol/site, i.c.v.) of the oxidizing agent DTNB (5,5'-dithiobis(2-nitrobenzoic acid)) potentiated the effect of GSH (100nmol/site, i.c.v.), while the pretreatment (25-100mg/kg, i.p.) with the reducing agent DTT (dl-dithiothreitol) prevented the antidepressant-like effect of GSH (300nmol/site, i.c.v.). DTNB (0.1nmol/site, i.c.v.), produced an antidepressant-like effect, per se, which was abolished by DTT (25mg/kg, i.p.).
Route of Administration:
Other
In rat hippocampal slices, severe hypoxia caused a massive depolarization of CA1 neurons and a negative shift of the extracellular DC potential, the characteristic sign of hypoxia-induced spreading depression (HSD). Oxidizing SH groups by 5,5'-dithiobis 2-nitrobenzoic acid (DTNB, 2 mM) postponed HSD by 30%, whereas their reduction by 1,4-dithio-dl-threitol (DTT, 2 mM) or alkylation by N-ethylmaleimide (500 microM) hastened HSD onset. In CA1 neurons DTNB induced a moderate hyperpolarization, blocked spontaneous spike discharges and postponed the massive hypoxic depolarization.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:21:09 GMT 2025
by
admin
on
Mon Mar 31 21:21:09 GMT 2025
|
| Record UNII |
9BZQ3U62JX
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
86228
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | |||
|
9BZQ3U62JX
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | |||
|
D004228
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | |||
|
Ellman's reagent
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | |||
|
m4876
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | Merck Index | ||
|
200-714-4
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | |||
|
6254
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | |||
|
DTXSID5058779
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY | |||
|
69-78-3
Created by
admin on Mon Mar 31 21:21:09 GMT 2025 , Edited by admin on Mon Mar 31 21:21:09 GMT 2025
|
PRIMARY |