L-Homocysteine thiolactone hydrochloride

Names

[ Name ]:
L-Homocysteine thiolactone hydrochloride

[Synonym ]:
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)

Biological Activity

[Description]:

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

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cardiovascular Disease

[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.

[Related Small Molecules]

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℃

MSDS

Click to get detail MSDS

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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...