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Details

Stereochemistry RACEMIC
Molecular Formula C4H10O2S2
Molecular Weight 154.251
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DITHIOTHREITOL

SMILES

O[C@@H](CS)[C@@H](O)CS

InChI

InChIKey=VHJLVAABSRFDPM-IMJSIDKUSA-N
InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1

HIDE SMILES / InChI

Molecular Formula C4H10O2S2
Molecular Weight 154.251
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Dithiothreitol is a chemical reagent with a wide actuation spectrum not only from a laboratorial view but also from a therapeutic standpoint, more clinical and practical. DTT (i) is frequently used in a variety of experiences that involve proteins or peptides, protecting sulfhydryl groups from oxidation and reducing disulfide bonds between cysteines; (ii) is also used in the study of disulfide exchange reactions of protein disulfides; (iii) is able to keep glutathione in the reduced state; (iv) acts as an "antidote" enabling the activity of detoxification systems; (v) participates in cellular mechanisms such as vesiculation, cell morphology, signal transduction pathways (hormone-'like' role), etc.; (vi) can be used in the treatment approach of diseases like cystinosis or medical conditions resulting from ion or metal toxicity. DTT is as a reducing or "deprotecting" agent. DTT protects notably enzyme activity loss by the oxidation of sulfhydryl groups. The DTT removal is performed by standard desalting.procedures (dialysis, gelfiltration). As an antioxidant, it is used as a protective agent against ionizing radiations in living cells. It has been used to enhance or inhibit enzymes or receptors activity.

Originator

Curator's Comment: The reducing potential of Dithiothreitol was first described by Cleland in 1964.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.4 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pyridoxal phosphate binding sites are similar in human heme-dependent and yeast heme-independent cystathionine beta-synthases. Evidence from 31P NMR and pulsed EPR spectroscopy that heme and PLP cofactors are not proximal in the human enzyme.
2001-06-01
Discrimination between native and non-native disulfides by protein-disulfide isomerase.
2001-05-11
A GTP-dependent vertebrate-type phosphoenolpyruvate carboxykinase from Mycobacterium smegmatis.
2001-05-11
Regulation of macrophage migration inhibitory factor and thiol-specific antioxidant protein PAG by direct interaction.
2001-05-04
Conserved cysteines in the sialyltransferase sialylmotifs form an essential disulfide bond.
2001-05-04
S-nitrosation controls gating and conductance of the alpha 1 subunit of class C L-type Ca(2+) channels.
2001-05-04
Phenylarsine oxide induces mitochondrial permeability transition, hypercontracture, and cardiac cell death.
2001-05
RGD-containing peptides inhibit fibrinogen binding to platelet alpha(IIb)beta3 by inducing an allosteric change in the amino-terminal portion of alpha(IIb).
2001-04-27
Purification and characterization of a Ca2+-independent endoprotease activity from peripheral blood lymphocytes: involvement in HIV-1 gp160 maturation.
2001-04-17
Purification and characterization of thiol-reagent-sensitive glycerol-3-phosphate acyltransferase from the membrane fraction of an oleaginous fungus.
2001-04-15
[(35)S]GTPgammaS autoradiography reveals a wide distribution of G(i/o)-linked ADP receptors in the nervous system: close similarities with the platelet P2Y(ADP) receptor.
2001-04
Comparing flow cytometry of sputum, bronchoalveolar lavage, and peripheral blood cells in healthy individuals.
2001-04
Hut1 proteins identified in Saccharomyces cerevisiae and Schizosaccharomyces pombe are functional homologues involved in the protein-folding process at the endoplasmic reticulum.
2001-04
Formation and properties of hybrid photosynthetic F1-ATPases. Demonstration of different structural requirements for stimulation and inhibition by tentoxin.
2001-04
Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin.
2001-04
Study of the chaperoning mechanism of bovine lens alpha-crystallin, a member of the alpha-small heat shock superfamily.
2001-04
Decrease in Ca2+-ATPase activity in the brain plasma membrane of rats with increasing age: involvement of brain calcium accumulation.
2001-04
Protein thiol oxidation by haloperidol results in inhibition of mitochondrial complex I in brain regions: comparison with atypical antipsychotics.
2001-04
Activation of class III ribonucleotide reductase by thioredoxin.
2001-03-30
Activation of class III ribonucleotide reductase by flavodoxin: a protein radical-driven electron transfer to the iron-sulfur center.
2001-03-27
Triapsin, an unusual activatable serine protease from the saliva of the hematophagous vector of Chagas' disease Triatoma infestans (Hemiptera: Reduviidae).
2001-03-15
Characterization of the maturation of human pro-apolipoprotein A-I in an in vitro model.
2001-03-13
Activation of phosphatidylinositol transfer protein alpha and beta isoforms from inclusion bodies.
2001-03-09
Cysteine residues are involved in structure and function of melanocortin 1 receptor: Substitution of a cysteine residue in transmembrane segment two converts an agonist to antagonist.
2001-03-09
Structural changes of mitochondrial creatine kinase upon binding of ADP, ATP, or Pi, observed by reaction-induced infrared difference spectra.
2001-03-06
Quantitation of reduced and total glutathione at the femtomole level by high-performance liquid chromatography with fluorescence detection: application to red blood cells and cultured fibroblasts.
2001-03-05
Metabolic fate of 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine by human spermatozoa: biosynthesis and biodegradation.
2001-03-02
Characterization of hepatic low-K(m) outer-ring deiodination in red drum (Sciaenops ocellatus).
2001-03
Determination of reduced, protein-unbound, and total concentrations of N-acetyl-L-cysteine and L-cysteine in rat plasma by postcolumn ligand substitution high-performance liquid chromatography.
2001-03
Thioredoxin peroxidases of the malarial parasite Plasmodium falciparum.
2001-03
Sodium nitroprusside-induced seizures and adenosine release in rat hippocampus.
2001-02-16
Selenoxides inhibit delta-aminolevulinic acid dehydratase.
2001-02-03
Preferential induction of a 9-lipoxygenase by salt in salt-tolerant cells of Citrus sinensis L. Osbeck.
2001-02
Human recombinant interferon-inducible protein-10: intact disulfide bridges are not required for inhibition of hematopoietic progenitors and chemotaxis of T lymphocytes and monocytes.
2001-02
Antioxidants, vitamin C and dithiothreitol, activate membrane-bound guanylate cyclase in PC12 cells.
2001-02
Two-phase unfolding pathway of ribonuclease A during denaturation induced by dithiothreitol.
2001-02
Molecular confinement influences protein structure and enhances thermal protein stability.
2001-02
The mechanism of type IA topoisomerase-mediated DNA topological transformations.
2001-02
Protein aggregation mediated by cysteine oxidation during the stacking phase of discontinuous buffer SDS-PAGE.
2001-02
Purification and characterization of superoxide dismutase from chicken liver.
2001-02
Mechanisms underlying the induction of vasorelaxation in rat thoracic aorta by sanguinarine.
2001-01
Oxidative insult in sheep red blood cells induced by T-butyl hydroperoxide: the roles of glutathione and glutathione peroxidase.
2001-01
Effects of ascorbate on membrane phospholipids and tocopherols of intact erythrocytes during peroxidation by t-butylhydroperoxide: comparison with effects of dithiothreitol.
2001-01
The properties of the secretagogue-evoked chloride current in mouse pancreatic acinar cells.
2001-01
Nitric oxide-mediated inhibition of DNA repair potentiates oxidative DNA damage in cholangiocytes.
2001-01
Decreased oxidant buffering impairs NF-kappaB activation and ICAM-1 transcription in endothelial cells.
2001-01
Coordinate regulation of RARgamma2, TBP, and TAFII135 by targeted proteolysis during retinoic acid-induced differentiation of F9 embryonal carcinoma cells.
2001
Inhibition of ryanodine binding to sarcoplasmic reticulum vesicles of cardiac muscle by Zn(2+) ions.
2001
Nicotinamide-mononucleotide adenylyltransferase from Sulfolobus solfataricus.
2001
Estrogen protects against the synergistic toxicity by HIV proteins, methamphetamine and cocaine.
2001
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Was used in humans orally: Two male patients with late stage (uremic) infantile nephropathic cystinosis (INC) were treated by mouth with dithiothreitol (DTT), at doses not exceeding 25 mg-kg-1 body weight three times per day. https://www.ncbi.nlm.nih.gov/pubmed/840501
Rats were pretreated 20 min before NaSH injection with 100 mg/kg Dithiothreitol (DTI) (i.p.). The DTT dose used for rats was calculated from mouse LDs0 data using the differential ratio between mouse and rat sulfide LDs0 data (Reiffenstein and Warenycia 1987) as the comparison basis. A dose of 100 mg/kg Dql" was thus calculated by this method to be equivalent to an LD40.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Treatment with 5 mM dithiothreitol significantly (P < 0.01) reduced the angiotensin II-induced contractile response to 1.2% in the rabbit aorta.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:04 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:04 GMT 2025
Record UNII
T8ID5YZU6Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DITHIOTHREITOL
INCI  
INCI  
Official Name English
1,4-DITHIOTHREITOL
MI  
Preferred Name English
1,4-DIMERCAPTO-2,3-BUTANEDIOL, DL-
Common Name English
CLELAND REAGENT RACEMIC
Common Name English
2,3-BUTANEDIOL, 1,4-DIMERCAPTO-, DL-THREO-
Common Name English
THREITOL, 1,4-DITHIO-
Common Name English
SPUTOLYSIN
Brand Name English
2,3-BUTANEDIOL, 1,4-DIMERCAPTO-, (R*,R*)- (±)-
Systematic Name English
2,3-BUTANEDIOL, 1,4-DIMERCAPTO-, (2R,3R)-REL-
Common Name English
DTT
Common Name English
WR-34678
Code English
1,4-DITHIOTHREITOL [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C802
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C76286
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
FDA UNII
T8ID5YZU6Y
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
CAS
3483-12-3
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
MERCK INDEX
m4689
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
DITHIOTHREITOL
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID5041017
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
SMS_ID
100000076188
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
CHEBI
42106
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
PUBCHEM
439196
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
MESH
D004229
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
EVMPD
SUB16087MIG
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
ECHA (EC/EINECS)
222-468-7
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
CHEBI
18320
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
DRUG BANK
DB04447
Created by admin on Mon Mar 31 17:45:04 GMT 2025 , Edited by admin on Mon Mar 31 17:45:04 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY