L-Homocysteine thiolactone hydrochloride

Modify Date: 2024-01-03 08:48:37

L-Homocysteine thiolactone hydrochloride Structure
L-Homocysteine thiolactone hydrochloride structure
Common Name L-Homocysteine thiolactone hydrochloride
CAS Number 31828-68-9 Molecular Weight 153.630
Density N/A Boiling Point 253.8ºC at 760mmHg
Molecular Formula C4H8ClNOS Melting Point 185-191ºC
MSDS USA Flash Point 107.3ºC

 Use of L-Homocysteine thiolactone hydrochloride


L-Homocysteine thiolactone hydrochloride is an intramolecular thioester of homocysteine; prevents translational incorporation of homocysteine into proteins.

 Names

Name L-2-Amino-4-mercaptobutyric acid 1,4-thiolactone hydrochloride
Synonym More Synonyms

 L-Homocysteine thiolactone hydrochloride Biological Activity

Description L-Homocysteine thiolactone hydrochloride is an intramolecular thioester of homocysteine; prevents translational incorporation of homocysteine into proteins.
Related Catalog
In Vitro In all cell types, from bacterial to human, homocysteine is metabolized to homocysteine thiolactone by methionyl-tRNA synthetase. Elevated levels of homocysteine are an independent risk factor for cardiovascular disease in humans. Homocysteine can be harmful to human cells because of its metabolic conversion to homocysteine thiolactone, a reactive thioester. This conversion occurs in all human cell types, including endothelial cells[1]. Homocysteine thiolactone induces cell death and features of apoptosis including increased phosphotidylserine exposure on the membrane surface, increased apoptotic cells with hypoploid DNA contents, and internucleosomal DNA fragmentation in HL-60 cells[2]. Homocysteine thiolactone is cytotoxic and capable of promoting cell death, as measured by caspase-3 activation and DNA fragmentation. HcyT strongly activates IL-8 release[3].
In Vivo Homocysteine thiolactone is toxic, induces epileptic seizures in rodents, and has been implicated in Alzheimer’s disease[4]. Homocysteine thiolactone induces two types of seizures, the coexistence of convulsive and nonconvulsive epilepsy. The grade of seizures is dose dependent[5].
Cell Assay HUVEC are treated with homocysteine (1, 5, 10 mM) or homocysteine thiolactone (0.25, 0.5, 1 mM) for 3, 6, 12 and 24 h. Cell survival is determined by the MTT method. The optical density is measured at 570 nm with 630 nm as a reference[3].
Animal Admin Rats: Homocysteine thiolactone is freshly prepared in saline and administered in a volume of 1.0 mL/100 g body weight. Rats are divided into control (saline-injected) group and homocysteine thiolactone-treated group. The latter group receives different doses 5.5 mM/kg, 8.0 mM/kg, and 11.0 mM/kg, respectively. Each rat is used only once[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]. Stanojlović 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.

 Chemical & Physical Properties

Boiling Point 253.8ºC at 760mmHg
Melting Point 185-191ºC
Molecular Formula C4H8ClNOS
Molecular Weight 153.630
Flash Point 107.3ºC
Exact Mass 153.001511
PSA 68.39000
LogP 1.47950
Storage condition 2-8℃

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
HS Code 2934999090

 Synthetic Route

~%

L-Homocysteine thiolactone hydrochloride Structure

L-Homocysteine ...

CAS#:31828-68-9

Literature: EP1964838 A1, ; Page/Page column 5 ;

~%

L-Homocysteine thiolactone hydrochloride Structure

L-Homocysteine ...

CAS#:31828-68-9

Literature: EP1964838 A1, ; Page/Page column 5 ;

~%

L-Homocysteine thiolactone hydrochloride Structure

L-Homocysteine ...

CAS#:31828-68-9

Literature: WO2010/148191 A2, ; Page/Page column 45-49; 63 ;

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles7

More Articles
Quality control in tRNA charging -- editing of homocysteine.

Acta Biochim. Pol. 58 , 149-163, (2011)

All living organisms conduct protein synthesis with a high degree of accuracy maintained in the transmission and flow of information from a gene to protein product. One crucial 'quality control' point...

Homocysteine and its thiolactone-mediated modification of fibrinogen affect blood platelet adhesion.

Platelets 23(5) , 409-12, (2011)

Homocysteine (Hcys) and homocysteine thiolactone (HTL) concentrations in organism are correlated with a number of serious pathologies. In the literature, there are few papers describing studies on the...

Effect of homocysteine thiolactone on structure and aggregation propensity of bovine pancreatic insulin.

Protein J. 30 , 299-307, (2011)

Homocysteine thiolactone (HCTL) is a cyclic thioester of homocysteine, showing high reactivity toward lysine residues of proteins. In the present study the structural properties and aggregation propen...

 Synonyms

MFCD00065494
(3S)-3-Aminodihydro-2(3H)-thiophenone hydrochloride (1:1)
L-Homocysteine thiolactone hydrochloride
(3S)-3-Aminodihydrothiophen-2(3H)-one hydrochloride (1:1)
2(3H)-Thiophenone, 3-aminodihydro-, (3S)-, hydrochloride (1:1)
(3S)-3-aminothiolan-2-one,hydrochloride
EINECS 250-824-1
L-Homocysteine thiolactone (hydrochloride)