U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
Nicotinamide-mononucleotide adenylyltransferase from Sulfolobus solfataricus.
2001
Formation and properties of hybrid photosynthetic F1-ATPases. Demonstration of different structural requirements for stimulation and inhibition by tentoxin.
2001 Apr
Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin.
2001 Apr
Study of the chaperoning mechanism of bovine lens alpha-crystallin, a member of the alpha-small heat shock superfamily.
2001 Apr
Decrease in Ca2+-ATPase activity in the brain plasma membrane of rats with increasing age: involvement of brain calcium accumulation.
2001 Apr
Protein thiol oxidation by haloperidol results in inhibition of mitochondrial complex I in brain regions: comparison with atypical antipsychotics.
2001 Apr
Preferential induction of a 9-lipoxygenase by salt in salt-tolerant cells of Citrus sinensis L. Osbeck.
2001 Feb
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 Feb
Antioxidants, vitamin C and dithiothreitol, activate membrane-bound guanylate cyclase in PC12 cells.
2001 Feb
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.
2001 Feb 2
Characterization of a naturally occurring trans-splicing intein from Synechocystis sp. PCC6803.
2001 Feb 6
Mercuric chloride, but not methylmercury, inhibits glutamine synthetase activity in primary cultures of cortical astrocytes.
2001 Feb 9
Mechanisms underlying the induction of vasorelaxation in rat thoracic aorta by sanguinarine.
2001 Jan
On the equilibrium between monomeric alpha-lactalbumin and the chaperoning complex of alpha-crystallin.
2001 Jan 12
Thioredoxin converts the Syrian hamster (29-231) recombinant prion protein to an insoluble form.
2001 Jan 15
Effect of cigarette smoke extract on neonatal porcine vascular smooth muscle cells.
2001 Jan 15
Three pairs of cysteine residues mediate both redox and zn2+ modulation of the nmda receptor.
2001 Jan 15
Reduced glutathione, dithiothreitol and cytochrome P-450 inhibitors do not influence hypoxic chemosensory responses in the rat carotid body.
2001 Jan 19
The integrity of renal cortical brush-border and basolateral membrane vesicles is damaged in vitro by nephrotoxic heavy metals.
2001 Jan 2
Interaction of metals and thiols in cell damage and glutathione distribution: potentiation of mercury toxicity by dithiothreitol.
2001 Jan 2
Biochemical properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.
2001 Jan 5
Characterization of hepatic low-K(m) outer-ring deiodination in red drum (Sciaenops ocellatus).
2001 Mar
Characterization and signaling of the AT(4) receptor in human proximal tubule epithelial (HK-2) cells.
2001 Mar
Binding of levosimendan, a calcium sensitizer, to cardiac troponin C.
2001 Mar 23
Activation of phosphatidylinositol transfer protein alpha and beta isoforms from inclusion bodies.
2001 Mar 9
A GTP-dependent vertebrate-type phosphoenolpyruvate carboxykinase from Mycobacterium smegmatis.
2001 May 11
Conserved cysteines in the sialyltransferase sialylmotifs form an essential disulfide bond.
2001 May 4
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.
Name Type Language
DITHIOTHREITOL
INCI  
INCI  
Official Name English
1,4-DIMERCAPTO-2,3-BUTANEDIOL, DL-
Common Name English
CLELAND REAGENT RACEMIC
Common Name English
1,4-DITHIOTHREITOL
MI  
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
DITHIOTHREITOL [INCI]
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 Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C76286
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
FDA UNII
T8ID5YZU6Y
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
CAS
3483-12-3
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
MERCK INDEX
m4689
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
DITHIOTHREITOL
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID5041017
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
SMS_ID
100000076188
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
CHEBI
42106
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
PUBCHEM
439196
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
MESH
D004229
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
EVMPD
SUB16087MIG
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-468-7
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
CHEBI
18320
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY
DRUG BANK
DB04447
Created by admin on Fri Dec 15 15:03:42 GMT 2023 , Edited by admin on Fri Dec 15 15:03:42 GMT 2023
PRIMARY