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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Coordinate regulation of RARgamma2, TBP, and TAFII135 by targeted proteolysis during retinoic acid-induced differentiation of F9 embryonal carcinoma cells. | 2001 |
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| Inhibition of ryanodine binding to sarcoplasmic reticulum vesicles of cardiac muscle by Zn(2+) ions. | 2001 |
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| Nicotinamide-mononucleotide adenylyltransferase from Sulfolobus solfataricus. | 2001 |
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| Estrogen protects against the synergistic toxicity by HIV proteins, methamphetamine and cocaine. | 2001 |
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| [(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 Apr |
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| Comparing flow cytometry of sputum, bronchoalveolar lavage, and peripheral blood cells in healthy individuals. | 2001 Apr |
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| Hut1 proteins identified in Saccharomyces cerevisiae and Schizosaccharomyces pombe are functional homologues involved in the protein-folding process at the endoplasmic reticulum. | 2001 Apr |
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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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| Purification and characterization of thiol-reagent-sensitive glycerol-3-phosphate acyltransferase from the membrane fraction of an oleaginous fungus. | 2001 Apr 15 |
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| Purification and characterization of a Ca2+-independent endoprotease activity from peripheral blood lymphocytes: involvement in HIV-1 gp160 maturation. | 2001 Apr 17 |
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| 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 Apr 27 |
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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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| Two-phase unfolding pathway of ribonuclease A during denaturation induced by dithiothreitol. | 2001 Feb |
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| Molecular confinement influences protein structure and enhances thermal protein stability. | 2001 Feb |
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| The mechanism of type IA topoisomerase-mediated DNA topological transformations. | 2001 Feb |
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| Protein aggregation mediated by cysteine oxidation during the stacking phase of discontinuous buffer SDS-PAGE. | 2001 Feb |
|
| Purification and characterization of superoxide dismutase from chicken liver. | 2001 Feb |
|
| Sodium nitroprusside-induced seizures and adenosine release in rat hippocampus. | 2001 Feb 16 |
|
| Selenoxides inhibit delta-aminolevulinic acid dehydratase. | 2001 Feb 3 |
|
| Mechanisms underlying the induction of vasorelaxation in rat thoracic aorta by sanguinarine. | 2001 Jan |
|
| Oxidative insult in sheep red blood cells induced by T-butyl hydroperoxide: the roles of glutathione and glutathione peroxidase. | 2001 Jan |
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| Effects of ascorbate on membrane phospholipids and tocopherols of intact erythrocytes during peroxidation by t-butylhydroperoxide: comparison with effects of dithiothreitol. | 2001 Jan |
|
| The properties of the secretagogue-evoked chloride current in mouse pancreatic acinar cells. | 2001 Jan |
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| Nitric oxide-mediated inhibition of DNA repair potentiates oxidative DNA damage in cholangiocytes. | 2001 Jan |
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| Decreased oxidant buffering impairs NF-kappaB activation and ICAM-1 transcription in endothelial cells. | 2001 Jan |
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| 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 Jun 1 |
|
| Characterization of hepatic low-K(m) outer-ring deiodination in red drum (Sciaenops ocellatus). | 2001 Mar |
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| 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 Mar |
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| Thioredoxin peroxidases of the malarial parasite Plasmodium falciparum. | 2001 Mar |
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| Characterization of the maturation of human pro-apolipoprotein A-I in an in vitro model. | 2001 Mar 13 |
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| Triapsin, an unusual activatable serine protease from the saliva of the hematophagous vector of Chagas' disease Triatoma infestans (Hemiptera: Reduviidae). | 2001 Mar 15 |
|
| Metabolic fate of 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine by human spermatozoa: biosynthesis and biodegradation. | 2001 Mar 2 |
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| Activation of class III ribonucleotide reductase by flavodoxin: a protein radical-driven electron transfer to the iron-sulfur center. | 2001 Mar 27 |
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| Activation of class III ribonucleotide reductase by thioredoxin. | 2001 Mar 30 |
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| 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 Mar 5 |
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| Structural changes of mitochondrial creatine kinase upon binding of ADP, ATP, or Pi, observed by reaction-induced infrared difference spectra. | 2001 Mar 6 |
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| Activation of phosphatidylinositol transfer protein alpha and beta isoforms from inclusion bodies. | 2001 Mar 9 |
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| 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 Mar 9 |
|
| Phenylarsine oxide induces mitochondrial permeability transition, hypercontracture, and cardiac cell death. | 2001 May |
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| Discrimination between native and non-native disulfides by protein-disulfide isomerase. | 2001 May 11 |
|
| A GTP-dependent vertebrate-type phosphoenolpyruvate carboxykinase from Mycobacterium smegmatis. | 2001 May 11 |
|
| Regulation of macrophage migration inhibitory factor and thiol-specific antioxidant protein PAG by direct interaction. | 2001 May 4 |
|
| Conserved cysteines in the sialyltransferase sialylmotifs form an essential disulfide bond. | 2001 May 4 |
|
| S-nitrosation controls gating and conductance of the alpha 1 subunit of class C L-type Ca(2+) channels. | 2001 May 4 |
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
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NCI_THESAURUS |
C802
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C76286
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T8ID5YZU6Y
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3483-12-3
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m4689
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DITHIOTHREITOL
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DTXSID5041017
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100000076188
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ACTIVE MOIETY
