2-Aminoethanethiosulfonic S-Acid

Alias: Thiotaurine; 2-hydroxysulfonothioylethanamine; 2-Aminoethanethiosulfonic acid; NQZ2D7AO62
Cat No.:V76337 Purity: = 99.64%
Thiotaurine (2-Aminoethanethiosulfonic S-Acid), a metabolic product of cystine, contains a sulfane sulfur atom that can be released as H(2)S, a gaseous molecule with a regulatory activity on inflammatory responses.
2-Aminoethanethiosulfonic S-Acid Chemical Structure CAS No.: 2937-54-4
Product category: Others 8
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg
1g
Official Supplier of:
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Purity & Quality Control Documentation

Purity: = 99.64%

Purity: ≥98%

Product Description
Thiotaurine (2-Aminoethanethiosulfonic S-Acid), a metabolic product of cystine, contains a sulfane sulfur atom that can be released as H(2)S, a gaseous molecule with a regulatory activity on inflammatory responses. In the last decade thiotaurine, 2-aminoethane thiosulfonate, has been investigated as an inflammatory modulating agent as a result of its ability to release hydrogen sulfide (H2S) known to play regulatory roles in inflammation. Thiotaurine can be included in the "taurine family" due to structural similarity to taurine and hypotaurine, and is characterized by the presence of a sulfane sulfur moiety. Thiotaurine can be produced by different pathways, such as the spontaneous transsulfuration between thiocysteine - a persulfide analogue of cysteine - and hypotaurine as well as in vivo from cystine. Moreover, the enzymatic oxidation of cysteamine to hypotaurine and thiotaurine in the presence of inorganic sulfur can occur in animal tissues and last but not least thiotaurine can be generated by the transfer of sulfur from mercaptopyruvate to hypotaurine catalyzed by a sulfurtransferase. Thiotaurine is an effective antioxidant agent as demonstrated by its ability to counteract the damage caused by pro-oxidants in the rat. Recently, we observed the influence of thiotaurine on human neutrophils functional responses. In particular, thiotaurine has been found to prevent human neutrophil spontaneous apoptosis suggesting an alternative or additional role to its antioxidant activity. It is likely that the sulfane sulfur of thiotaurine may modulate neutrophil activation via persulfidation of target proteins. In conclusion, thiotaurine can represent a biologically relevant sulfur donor acting as a biological intermediate in the transport, storage and release of sulfide.
Biological Activity I Assay Protocols (From Reference)
Targets
Metabolic product of cystine
ln Vitro
Thiotaurine, a metabolic product of cystine, contains a sulfane sulfur atom that can be released as H(2)S, a gaseous molecule with a regulatory activity on inflammatory responses. The influence of thiotaurine on human leukocyte spontaneous apoptosis has been evaluated by measuring caspase-3 activity in human neutrophils. Addition of 100 μM thiotaurine induced a 55% inhibition of caspase-3 activity similar to that exerted by 100 μM H(2)S. Interestingly, in the presence of 1 mM GSH, an increase of the inhibition of apoptosis by thiotaurine has been observed. These results indicate that the bioactivity of thiotaurine can be modulated by GSH, which promotes the reductive breakdown of the thiosulfonate generating H(2)S and hypotaurine. As thiotaurine is able to incorporate reversibly reduced sulfur, it is suggested that the biosynthesis of this thiosulfonate could be a means to transport and store H(2)S [1].
ln Vivo
Thiotaurine is an effective antioxidant agent as demonstrated by its ability to counteract the damage caused by pro-oxidants in the rat [2].
Enzyme Assay
Thiotaurine is a thiosulfonate compound bearing a sulfane sulfur atom metabolically generated in body fluids and tissues. Thiotaurine constitutes an interconnection molecule between aerobic and anaerobic pathways of cysteine metabolism. Thiotaurine formed as a result of the reaction between hypotaurine and sulfide may be converted back to H2S and hypotaurine. Thus, thiotaurine may be considered as a safe, non-toxic storage form of H2S and an important key intermediate in the biochemical routes of transport, storage and release of sulfide. Sulfane sulfur-containing compounds efficiently regulate the activity of enzymes and exhibit antioxidative properties. Interestingly, thiotaurine influences inflammatory processes modulating functional responses of human neutrophils and exhibits a protective effect against oxidative damage [2].
References
[1]. Adv Exp Med Biol. 2013:775:227-36. doi: 10.1007/978-1-4614-6130-2_19.
[2]. Adv Exp Med Biol. 2019:1155:755-771. doi: 10.1007/978-981-13-8023-5_66.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C2H7NO2S2
Molecular Weight
141.21248
Exact Mass
140.992
Elemental Analysis
Solid
CAS #
2937-54-4
Appearance
Solid
LogP
0.89
tPSA
93.35
SMILES
NCCS(=S)(O)=O
InChi Key
SHWIJIJNPFXOFS-UHFFFAOYSA-N
InChi Code
InChI=1S/C2H7NO2S2/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
Chemical Name
2-hydroxysulfonothioylethanamine
Synonyms
Thiotaurine; 2-hydroxysulfonothioylethanamine; 2-Aminoethanethiosulfonic acid; NQZ2D7AO62
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.0817 mL 35.4083 mL 70.8165 mL
5 mM 1.4163 mL 7.0817 mL 14.1633 mL
10 mM 0.7082 mL 3.5408 mL 7.0817 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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