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
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
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28242353 |
0.4 mM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Nicotinamide-mononucleotide adenylyltransferase from Sulfolobus solfataricus. | 2001 |
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Formation and properties of hybrid photosynthetic F1-ATPases. Demonstration of different structural requirements for stimulation and inhibition by tentoxin. | 2001 Apr |
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Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin. | 2001 Apr |
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Study of the chaperoning mechanism of bovine lens alpha-crystallin, a member of the alpha-small heat shock superfamily. | 2001 Apr |
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Decrease in Ca2+-ATPase activity in the brain plasma membrane of rats with increasing age: involvement of brain calcium accumulation. | 2001 Apr |
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Protein thiol oxidation by haloperidol results in inhibition of mitochondrial complex I in brain regions: comparison with atypical antipsychotics. | 2001 Apr |
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Preferential induction of a 9-lipoxygenase by salt in salt-tolerant cells of Citrus sinensis L. Osbeck. | 2001 Feb |
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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 |
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Antioxidants, vitamin C and dithiothreitol, activate membrane-bound guanylate cyclase in PC12 cells. | 2001 Feb |
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Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery. | 2001 Feb 2 |
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Characterization of a naturally occurring trans-splicing intein from Synechocystis sp. PCC6803. | 2001 Feb 6 |
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Mercuric chloride, but not methylmercury, inhibits glutamine synthetase activity in primary cultures of cortical astrocytes. | 2001 Feb 9 |
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Mechanisms underlying the induction of vasorelaxation in rat thoracic aorta by sanguinarine. | 2001 Jan |
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On the equilibrium between monomeric alpha-lactalbumin and the chaperoning complex of alpha-crystallin. | 2001 Jan 12 |
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Thioredoxin converts the Syrian hamster (29-231) recombinant prion protein to an insoluble form. | 2001 Jan 15 |
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Effect of cigarette smoke extract on neonatal porcine vascular smooth muscle cells. | 2001 Jan 15 |
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Three pairs of cysteine residues mediate both redox and zn2+ modulation of the nmda receptor. | 2001 Jan 15 |
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Reduced glutathione, dithiothreitol and cytochrome P-450 inhibitors do not influence hypoxic chemosensory responses in the rat carotid body. | 2001 Jan 19 |
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The integrity of renal cortical brush-border and basolateral membrane vesicles is damaged in vitro by nephrotoxic heavy metals. | 2001 Jan 2 |
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Interaction of metals and thiols in cell damage and glutathione distribution: potentiation of mercury toxicity by dithiothreitol. | 2001 Jan 2 |
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Biochemical properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
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Characterization of hepatic low-K(m) outer-ring deiodination in red drum (Sciaenops ocellatus). | 2001 Mar |
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Characterization and signaling of the AT(4) receptor in human proximal tubule epithelial (HK-2) cells. | 2001 Mar |
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Binding of levosimendan, a calcium sensitizer, to cardiac troponin C. | 2001 Mar 23 |
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Activation of phosphatidylinositol transfer protein alpha and beta isoforms from inclusion bodies. | 2001 Mar 9 |
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A GTP-dependent vertebrate-type phosphoenolpyruvate carboxykinase from Mycobacterium smegmatis. | 2001 May 11 |
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Conserved cysteines in the sialyltransferase sialylmotifs form an essential disulfide bond. | 2001 May 4 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2090033
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9788771
Treatment with 5 mM dithiothreitol significantly (P < 0.01) reduced the angiotensin II-induced contractile response to 1.2% in the rabbit aorta.
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NCI_THESAURUS |
C802
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ACTIVE MOIETY