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L-高半胱氨酸硫代内酯盐酸盐

L-高半胱氨酸硫代内酯盐酸盐用途

L-Homocysteine thiolactone hydrochloride是同型半胱氨酸的分子内硫酯; 防止同型半胱氨酸转化成蛋白质。

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L-高半胱氨酸硫代内酯盐酸盐名称

[ CAS 号 ]:
31828-68-9

[ 中文名 ]:
L-高半胱氨酸硫代内酯盐酸盐

[ 英文名 ]:
L-Homocysteine thiolactone hydrochloride

[中文别名 ]:

[英文别名 ]:

MFCD00065494
L-Homocysteine thiolactone hydrochloride
(3S)-3-aminothiolan-2-one,hydrochloride
EINECS 250-824-1
L-Homocysteine thiolactone (hydrochloride)

L-高半胱氨酸硫代内酯盐酸盐生物活性

[ 描述 ]:

L-Homocysteine thiolactone hydrochloride是同型半胱氨酸的分子内硫酯; 防止同型半胱氨酸转化成蛋白质。

[ 相关类别 ]:

信号通路 >> 其他 >> 其他

研究领域 >> 心血管疾病

[体外研究]

在所有细胞类型中,从细菌到人,同型半胱氨酸通过甲硫氨酰-tRNA合成酶代谢成同型半胱氨酸硫代内酯。同型半胱氨酸水平升高是人类心血管疾病的独立危险因素。同型半胱氨酸可能对人体细胞有害,因为它的代谢转化为同型半胱氨酸硫代内酯,一种活性硫代酯。这种转化发生在所有人类细胞类型中,包括内皮细胞[1]。同型半胱氨酸硫代内酯诱导细胞死亡和细胞凋亡的特征,包括增加膜表面的磷酸丝氨酸暴露,增加具有亚倍体DNA含量的凋亡细胞,以及HL-60细胞中的核小体间DNA片段化[2]。通过胱天蛋白酶-3激活和DNA片段化测量,同型半胱氨酸硫代内酯具有细胞毒性并且能够促进细胞死亡。 HcyT强烈激活IL-8释放[3]。

[体内研究]

同型半胱氨酸硫代内酯是有毒的,在啮齿动物中诱发癫痫发作,并且与阿尔茨海默病有关[4]。同型半胱氨酸硫代内酯诱导两种类型的癫痫发作,即惊厥和非惊厥性癫痫的共存。癫痫发作的等级是剂量依赖的[5]。

[细胞实验]

用同型半胱氨酸（1,5,10mM）或高半胱氨酸硫代内酯（0.25,0.5,1mM）处理HUVEC 3,6,12和24小时。细胞存活通过MTT方法确定。光密度在570nm处测量，630nm作为参考[3]。

[动物实验]

大鼠：同型半胱氨酸硫代内酯在盐水中新鲜制备，并以1.0mL / 100g体重的体积给药。将大鼠分成对照（注射盐水）组和同型半胱氨酸硫代内酯治疗组。后一组分别接受5.5mM / kg，8.0mM / kg和11.0mM / kg的不同剂量。每只大鼠只使用一次[5]。

[参考文献]

[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.

[相关活性小分子]

L-高半胱氨酸硫代内酯盐酸盐物理化学性质

[ 沸点 ]:
253.8ºC at 760mmHg

[ 熔点 ]:
185-191ºC

[ 分子式 ]:
C₄H₈ClNOS

[ 分子量 ]:
153.630

[ 闪点 ]:
107.3ºC

[ 精确质量 ]:
153.001511

[ PSA ]:
68.39000

[ LogP ]:
1.47950

[ 储存条件 ]:
2-8℃

L-高半胱氨酸硫代内酯盐酸盐MSDS

详细MSDS(安全技术说明书)

L-高半胱氨酸硫代内酯盐酸盐安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 安全声明 (欧洲) ]:
S22-S24/25

[ 危险品运输编码 ]:
NONH for all modes of transport

[ 海关编码 ]:
2934999090

L-高半胱氨酸硫代内酯盐酸盐合成路线

详细合成路线

L-高半胱氨酸硫代内酯盐酸盐上下游产品

L-高半胱氨酸硫代内酯盐酸盐上游产品

L-高半胱氨酸硫代内酯盐酸盐下游产品

L-高半胱氨酸硫代内酯盐酸盐海关

[ 海关编码 ]: 2934999090

[ 中文概述 ]:
2934999090. 其他杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途

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

L-高半胱氨酸硫代内酯盐酸盐文献

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...

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