| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| ln Vitro |
Methionyl-tRNA synthetase converts homocysteine to homocysteine thiolactone in all cell types, including bacteria and humans. In humans, high homocysteine levels are a separate risk factor for cardiovascular disease. Due to its metabolic conversion to homocysteine thiolactone, a reactive thioester, homocysteine may be toxic to human cells. All human cell types, including endothelial cells, undergo this switch [1]. Increased phosphatidylserine exposure on the membrane surface, increased hypoploid DNA content in apoptotic cells, and internucleosomal DNA fragmentation in HL-60 cells are all signs of apoptosis that are brought on by homocysteine thiolactone [2]. DNA fragmentation and caspase-3 activation are two indicators of homocysteine thiolactone's cytotoxicity and promotion of cell death. IL-8 release is strongly activated by HcyT [3].
- HL-60 cells: L-Homocysteine thiolactone hydrochloride induces apoptotic DNA damage mediated by increased intracellular hydrogen peroxide and caspase 3 activation[2] - HUVEC cells: L-Homocysteine thiolactone hydrochloride exerts stronger proapoptotic and proinflammatory effects than homocysteine[3] |
|---|---|
| ln Vivo |
In addition to being poisonous and known to cause seizures in rats, homocysteine thiolactone has also been connected to Alzheimer's [4]. The coexistence of convulsive and nonconvulsive epilepsy is caused by homocysteine thiolactone. Seizures vary in intensity depending on the dosage [5].
- Mice: L-Homocysteine thiolactone hydrochloride shows neurotoxicity, and paraoxonase 1 exerts a protective role in its metabolism[4] - Adult rats: L-Homocysteine thiolactone hydrochloride induces two types of seizures, confirmed by behavioral observations and electroencephalographic recordings[5] |
| Cell Assay |
- HL-60 cell apoptosis assay: Cells are treated with L-Homocysteine thiolactone hydrochloride, apoptotic DNA damage is detected, and intracellular hydrogen peroxide levels and caspase 3 activation are measured to verify the mediation pathway[2]
- HUVEC cell assay: Cells are exposed to L-Homocysteine thiolactone hydrochloride and homocysteine separately, with proapoptotic (cell survival rate, apoptotic marker expression) and proinflammatory (inflammatory cytokine release) effects compared[3] |
| Animal Protocol |
- Mouse experiment: L-Homocysteine thiolactone hydrochloride is administered to mice, and neurotoxicity-related indicators are detected to evaluate the protective effect of paraoxonase 1[4]
- Rat seizure experiment: L-Homocysteine thiolactone hydrochloride is administered to adult rats, followed by behavioral monitoring and electroencephalographic recording to observe seizure types[5] |
| ADME/Pharmacokinetics |
L-homocysteine thiolactone hydrochloride is metabolized in mice, with paraoxonase 1 participating in its metabolic pathway [4]
- In humans, L-homocysteine thiolactone hydrochloride originates from metabolic processes and can induce homocysteineization of proteins [1] |
| Toxicity/Toxicokinetics |
- In vitro toxicity: L-homocysteine thiolactone hydrochloride can induce apoptosis in HL-60 and HUVEC cells[2][3]
- In vivo toxicity: L-homocysteine thiolactone hydrochloride can cause neurotoxicity in mice and seizures in rats[4][5] |
| References |
[1]. Jakubowski H, et al. Homocysteine thiolactone: metabolic origin and protein homocysteinylation in humans. J Nutr. 2000 Feb;130(2S Suppl):377S-381S.
[2]. Huang RF, et al. Homocysteine thiolactone induces apoptotic DNA damage mediated by increased intracellularhydrogen peroxide and caspase 3 activation in HL-60 cells. Life Sci. 2001 May 11;68(25):2799-811. [3]. Kerkeni M, et al. Comparative study on in vitro effects of homocysteine thiolactone and homocysteine on HUVECcells: evidence for a stronger proapoptotic and proinflammative homocysteine thiolactone. Mol Cell Biochem. 2006 Oct;291(1-2):119-26. [4]. Borowczyk K, et al. Metabolism and neurotoxicity of homocysteine thiolactone in mice: evidence for a protective role of paraoxonase 1. J Alzheimers Dis. 2012;30(2):225-31. [5]. Stanojlovi? O, et al. Two types of seizures in homocysteine thiolactone-treated adult rats, behavioral and electroencephalographic study. Cell Mol Neurobiol. 2009 May;29(3):329-39 |
| Additional Infomation |
L-homocysteine thiolactone hydrochloride is a metabolite that can modify proteins in the human body through homocysteine modification [1]
|
| Molecular Formula |
C4H7NOS.HCL
|
|---|---|
| Molecular Weight |
153.63042
|
| Exact Mass |
153.001
|
| CAS # |
31828-68-9
|
| Related CAS # |
DL-Homocysteine thiolactone hydrochloride;6038-19-3
|
| PubChem CID |
10313226
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| Appearance |
White to off-white solid powder
|
| Boiling Point |
253.8ºC at 760mmHg
|
| Melting Point |
185-191ºC
|
| Flash Point |
107.3ºC
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| LogP |
1.479
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| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
8
|
| Complexity |
93.7
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| Defined Atom Stereocenter Count |
1
|
| SMILES |
N[C@@H](CCS1)C1=O.Cl
|
| InChi Key |
ZSEGSUBKDDEALH-DFWYDOINSA-N
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| InChi Code |
InChI=1S/C4H7NOS.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
|
| Chemical Name |
(3S)-3-aminothiolan-2-one;hydrochloride
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O : ≥ 23 mg/mL (~149.71 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (650.91 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.5091 mL | 32.5457 mL | 65.0915 mL | |
| 5 mM | 1.3018 mL | 6.5091 mL | 13.0183 mL | |
| 10 mM | 0.6509 mL | 3.2546 mL | 6.5091 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.
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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