DL-Homocysteinethiolactone HCl | CAS#6038-19-3 | cysteine derivative

MedKoo Cat#: 540198 | Name: DL-Homocysteinethiolactone HCl

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

DL-Homocysteinethiolactone HCl is a cysteine derivative that binds to and induces conformational changes in various plasma proteins, slowing coagulation and inducing oxidative stress. It decreases left ventricular systolic blood pressure and cardiac force and induces seizures in vivo.

Chemical Structure

DL-Homocysteinethiolactone HCl

CAS#6038-19-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 540198

Name: DL-Homocysteinethiolactone HCl

CAS#: 6038-19-3 (HCl)

Chemical Formula: C4H8ClNOS

Exact Mass: 0.0000

Molecular Weight: 153.62

Elemental Analysis: C, 31.27; H, 5.25; Cl, 23.08; N, 9.12; O, 10.41; S, 20.87

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 weeks
25g	USD 450.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

D,L-Homocysteine thiolactone hydrochloride; HCTL hydrochloride; DL-Hcy thiolactone; DL-Hcy TLHC; NSC 22879; NSC22879; NSC-22879;

IUPAC/Chemical Name

3-aminodihydrothiophen-2(3H)-one hydrochloride

InChi Key

ZSEGSUBKDDEALH-UHFFFAOYSA-N

InChi Code

InChI=1S/C4H7NOS.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H

SMILES Code

O=C1C(N)CCS1.[H]Cl

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

DL-Homocysteine thiolactone hydrochloride is a cyclic amino acid derivative that exhibits root-growth inhibitory activity.

In vitro activity:

In order to assess the effects of HTL (homocysteine thiolactone) on plasma fibrin networks, a pool of normal plasma incubated with HTL (100, 500 and 1,000 μmol/L, respectively) was evaluated by global coagulation tests and fibrin formation kinetic assays, and the resulting fibrin was observed by scanning electron microscopy. HTL significantly prolonged global coagulation tests in a concentration-dependent manner with respect to control, and increases were up to 14.5%. Fibrin formation kinetic parameters displayed statistically significant differences between HTL-treated plasma and control in a concentration-dependent way, showing higher lag phase and lower maximum reaction velocity and final network optical density. Reference: J Thromb Thrombolysis. 2014 Nov;38(4):540-5. https://pubmed.ncbi.nlm.nih.gov/24659173/

In vivo activity:

The mice in the experimental groups were subjected to intravitreal injections of Hcy-T (homocysteine thiolactone) to reach final estimated intravitreal concentrations at 5, 25, and 200 μM, respectively. Dose-dependent retinal homocysteinylation after Hcy-T injection was confirmed. Excessive retinal homocysteinylation by Hcy-T, a condition of hyperhomocysteinemia, could lead to degeneration of photoreceptors, which might lead to retinopathies associated with severe hyperhomocysteinemia or diabetes mellitus. Reference: Biomed Res Int. 2013;2013:318471. https://pubmed.ncbi.nlm.nih.gov/24350259/

	Solvent	mg/mL	mM
Solubility
	DMSO	65.0	423.11
	PBS (pH 7.2)	10.0	0.65

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 153.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Genoud V, Lauricella AM, Kordich LC, Quintana I. Impact of homocysteine-thiolactone on plasma fibrin networks. J Thromb Thrombolysis. 2014 Nov;38(4):540-5. doi: 10.1007/s11239-014-1063-8. PMID: 24659173. 2. Mercié P, Garnier O, Lascoste L, Renard M, Closse C, Durrieu F, Marit G, Boisseau RM, Belloc F. Homocysteine-thiolactone induces caspase-independent vascular endothelial cell death with apoptotic features. Apoptosis. 2000 Nov;5(5):403-11. doi: 10.1023/a:1009652011466. PMID: 11256881. 3. Zivkovic V, Jakovljevic V, Pechanova O, Srejovic I, Joksimovic J, Selakovic D, Barudzic N, Djuric DM. Effects of DL-homocysteine thiolactone on cardiac contractility, coronary flow, and oxidative stress markers in the isolated rat heart: the role of different gasotransmitters. Biomed Res Int. 2013;2013:318471. doi: 10.1155/2013/318471. Epub 2013 Nov 24. PMID: 24350259; PMCID: PMC3857920. 4. Chang HH, Lin DP, Chen YS, Liu HJ, Lin W, Tsao ZJ, Teng MC, Chen BY. Intravitreal homocysteine-thiolactone injection leads to the degeneration of multiple retinal cells, including photoreceptors. Mol Vis. 2011;17:1946-56. Epub 2011 Jul 19. PMID: 21850169; PMCID: PMC3156793.

In vitro protocol:

In vivo protocol:

1. Zivkovic V, Jakovljevic V, Pechanova O, Srejovic I, Joksimovic J, Selakovic D, Barudzic N, Djuric DM. Effects of DL-homocysteine thiolactone on cardiac contractility, coronary flow, and oxidative stress markers in the isolated rat heart: the role of different gasotransmitters. Biomed Res Int. 2013;2013:318471. doi: 10.1155/2013/318471. Epub 2013 Nov 24. PMID: 24350259; PMCID: PMC3857920. 2. Chang HH, Lin DP, Chen YS, Liu HJ, Lin W, Tsao ZJ, Teng MC, Chen BY. Intravitreal homocysteine-thiolactone injection leads to the degeneration of multiple retinal cells, including photoreceptors. Mol Vis. 2011;17:1946-56. Epub 2011 Jul 19. PMID: 21850169; PMCID: PMC3156793.

1: Zivkovic V, Jakovljevic V, Pechanova O, Srejovic I, Joksimovic J, Selakovic D, Barudzic N, Djuric DM. Effects of DL-homocysteine thiolactone on cardiac contractility, coronary flow, and oxidative stress markers in the isolated rat heart: the role of different gasotransmitters. Biomed Res Int. 2013;2013:318471. doi: 10.1155/2013/318471. Epub 2013 Nov 24. PubMed PMID: 24350259; PubMed Central PMCID: PMC3857920. 2: Srejovic I, Jakovljevic V, Zivkovic V, Barudzic N, Radovanovic A, Stanojlovic O, Djuric DM. The effects of the modulation of NMDA receptors by homocysteine thiolactone and dizocilpine on cardiodynamics and oxidative stress in isolated rat heart. Mol Cell Biochem. 2015 Mar;401(1-2):97-105. doi: 10.1007/s11010-014-2296-8. Epub 2014 Dec 3. PubMed PMID: 25467376. 3: Marković AR, Hrnčić D, Macut D, Stanojlović O, Djuric D. Anticonvulsive effect of folic acid in homocysteine thiolactone-induced seizures. Cell Mol Neurobiol. 2011 Nov;31(8):1221-8. doi: 10.1007/s10571-011-9724-z. Epub 2011 Jun 22. PubMed PMID: 21695479. 4: Zaichko NV. [Effect of thiolactone homocysteine loading on adenosine metabolism in rats: relationship with platelet hyper-reactivity, correction of this metabolism disorders by vitamin-microelement complex]. Ukr Biokhim Zh (1999). 2010 Mar-Apr;82(2):59-66. Ukrainian. PubMed PMID: 20684246. 5: Desmet GB, D'hooge DR, Sabbe MK, Marin GB, Du Prez FE, Espeel P, Reyniers MF. Computational Study and Kinetic Analysis of the Aminolysis of Thiolactones. J Org Chem. 2015 Sep 4;80(17):8520-9. doi: 10.1021/acs.joc.5b01446. Epub 2015 Aug 21. PubMed PMID: 26280542. 6: Amos HE, Little CO, Digenis GA, Schelling GT, Tucker RE, Mitchell GE Jr. Methionine, DL-homocysteine thiolactone and n-acetyl-DL-methionine for ruminants. J Anim Sci. 1974 Sep;39(3):612-7. PubMed PMID: 4414655. 7: de Andrade CR, Tirapelli CR, Haddad R, Eberlin MN, Ramalho LN, Iyomasa MM, Uyemura SA, de Oliveira AM. Hyperhomocysteinemia induced by feeding rats diets rich in DL-homocysteine thiolactone promotes alterations on carotid reactivity independent of arterial structure. Vascul Pharmacol. 2009 Oct;51(4):291-8. doi: 10.1016/j.vph.2009.07.004. Epub 2009 Aug 4. PubMed PMID: 19660577. 8: Stangl GI, Weisse K, Dinger C, Hirche F, Brandsch C, Eder K. Homocysteine thiolactone-induced hyperhomocysteinemia does not alter concentrations of cholesterol and SREBP-2 target gene mRNAS in rats. Exp Biol Med (Maywood). 2007 Jan;232(1):81-7. PubMed PMID: 17202588. 9: Gobetti M, Pedrazzoli A, Bradamante S. DL-S-(2-[N-3-(2-oxo-tetrahydrothienyl)acetamido])-thioglycolic acid: a novel mucolytic agent of the class of homocysteine thiolactone derivatives. Farmaco Sci. 1986 Jan;41(1):69-79. PubMed PMID: 3956722. 10: Aaseth J, Wannag A, Norseth T. The effect of N-acetylated DL-penicillamine and DL-homocysteine thiolactone on the mercury distribution in adult rats, rat foetuses and macaca monkeys after exposure to methyl mercuric chloride. Acta Pharmacol Toxicol (Copenh). 1976 Sep;39(3):302-11. PubMed PMID: 823797. 11: Rasic-Markovic A, Rankov-Petrovic B, Hrncic D, Krstic D, Colovic M, Macut Dj, Djuric D, Stanojlovic O. The effect of subchronic supplementation with folic acid on homocysteine induced seizures. Acta Physiol Hung. 2015 Jun;102(2):151-62. doi: 10.1556/036.102.2015.2.6. PubMed PMID: 26100305. 12: Sood PP, Unnikumar KR. Effect of N-acetyl-DL-homocysteine thiolactone and 2,3-dimercaptosuccinic acid on the restoration of alkaline phosphatase in the nervous system of rat during methylmercury toxication. J Environ Pathol Toxicol Oncol. 1987 Jan-Feb;7(3):21-8. PubMed PMID: 3031268. 13: VIRUPAKSHA TK, TARVER H. THE REACTION OF INSULIN WITH N-ACETYL-DL-HOMOCYSTEINE THIOLACTONE: SOME CHEMICAL AND BIOLOGICAL PROPERTIES OF THE PRODUCTS. Biochemistry. 1964 Oct;3:1507-11. PubMed PMID: 14230802. 14: ABADI DM, WILCOX PE. Chemical derivatives of alpha-chymotrypsinogen. III. Reaction with N-acetyl-Dl-homocysteine thiolactone. J Biol Chem. 1960 Feb;235:396-404. PubMed PMID: 13791351. 15: Zivkovic V, Jakovljevic V, Djordjevic D, Vuletic M, Barudzic N, Djuric D. The effects of homocysteine-related compounds on cardiac contractility, coronary flow, and oxidative stress markers in isolated rat heart. Mol Cell Biochem. 2012 Nov;370(1-2):59-67. doi: 10.1007/s11010-012-1398-4. Epub 2012 Jul 22. PubMed PMID: 22821198. 16: Schatz RA, Wilens TE, Tatter SB, Gregor P, Sellinger OZ. Possible role of increased brain methylation in methionine sulfoximine epileptogenesis: effects of administration of adenosine and homocysteine thiolactone. J Neurosci Res. 1983;10(4):437-47. PubMed PMID: 6663652. 17: Mommer S, Keul H, Möller M. Tailored thiol-functional polyamides: synthesis and functionalization. Macromol Rapid Commun. 2014 Dec;35(23):1986-93. doi: 10.1002/marc.201400377. Epub 2014 Sep 25. PubMed PMID: 25257791. 18: Lisker N, Paster N, Chet I. Effects of cysteine and structurally related compounds on ochratoxin production by Aspergillus ochraceus. Can J Microbiol. 1985 Nov;31(11):973-6. PubMed PMID: 4092177. 19: Blennow G, Folbergrova J, Nilsson B, Siesjö BK. Cerebral metabolic and circulatory changes in the rat during sustained seizures induced by DL-homocysteine. Brain Res. 1979 Dec 21;179(1):129-46. PubMed PMID: 509226. 20: Karolczak K, Kamysz W, Karafova A, Drzewoski J, Watala C. Homocysteine is a novel risk factor for suboptimal response of blood platelets to acetylsalicylic acid in coronary artery disease: a randomized multicenter study. Pharmacol Res. 2013 Aug;74:7-22. doi: 10.1016/j.phrs.2013.04.010. Epub 2013 May 7. PubMed PMID: 23665469.