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2-(仲丁基二硫基)-1H-咪唑

2-(仲丁基二硫基)-1H-咪唑用途

PX-12(IV-2)是可逆的硫氧还蛋白-1(Trx-1)抑制剂; 抑制MCF-7 和HT-29 cells细胞生长的IC50值分别为1.9和2.9 μM。

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2-(仲丁基二硫基)-1H-咪唑名称

[ CAS 号 ]:
141400-58-0

[ 中文名 ]:
2-(仲丁基二硫基)-1H-咪唑

[ 英文名 ]:
PX-12

[英文别名 ]:

2-(butan-2-yldisulfanyl)-1H-imidazole
IV-2 compound
UNII:8PQ9CZ8BTJ
1-methylpropyl 2-imidazolyl disulfide
PX 12
1-methyl-1-propyl 2-imidazolyl disulfide
2-(sec-Butyldisulfanyl)-1H-imidazole
1-methylpropyl 2-mercaptoimidazolyl disulfide
2-[(1-Methylpropyl)dithio]-1H-imidazole
1H-Imidazole, 2-[(1-methylpropyl)dithio]-

2-(仲丁基二硫基)-1H-咪唑生物活性

[ 描述 ]:

PX-12(IV-2)是可逆的硫氧还蛋白-1(Trx-1)抑制剂; 抑制MCF-7 和HT-29 cells细胞生长的IC50值分别为1.9和2.9 μM。

[ 相关类别 ]:

信号通路 >> 其他 >> 其他

研究领域 >> 癌症

[ 靶点 ]

IC50: 1.9 (MCF-7), 2.9 μM (HT-29 cells)[1]

[体外研究]

PX-12抑制MCF-7和HT-29细胞的生长,IC50值分别为1.9和2.9μM[1]。 PX-12特别通过硫代烷基化关键半胱氨酸残基(Cys73)降低Trx-1的活性,所述半胱氨酸残基位于Trx-1的保守氧化还原催化位点的外部。 PX-12影响许多细胞表面蛋白中硫醇的氧化态。血小板粘附和活化的关键表面受体受到影响,包括胶原受体GPVI和冯维勒布兰德因子受体GPIb。在流动条件下,PX-12抑制全血中I型胶原的血栓形成[2]。硫氧还蛋白-1(Trx-1)是一种细胞氧化还原蛋白,可促进肿瘤生长,抑制细胞凋亡,并上调缺氧诱导因子-1α和血管内皮生长因子[3]。 PX-12以剂量和时间依赖性方式抑制结肠直肠癌DLD-1和SW620细胞的生长。 PX-12减少细胞集落形成并诱导细胞周期的G2/M期阻滞。 PX-12处理诱导细胞凋亡。 PX-12抑制结肠直肠癌细胞迁移和侵袭。用PX-12处理癌细胞减少NOX1,CDH17和S100A4 mRNA表达,并增加KLF17 mRNA表达。 PX-12降低结直肠癌细胞中S100A4蛋白的表达[4]。

[体内研究]

已经显示PX-12在SCID小鼠中具有针对人肿瘤异种移植物(包括HT-29结肠癌)的体内抗肿瘤活性,并且已经在患者的I期临床试验中进行了测试[3]。

[参考文献]

[1]. Welsh SJ, et al. The thioredoxin redox inhibitors 1-methylpropyl 2-imidazolyl disulfide and pleurotin inhibit hypoxia-induced factor 1alpha and vascular endothelial growth factor formation. Mol Cancer Ther. 2003 Mar;2(3):235-43.

[2]. Metcalfe C, et al. Thioredoxin Inhibitors Attenuate Platelet Function and Thrombus Formation.PLoS One. 2016 Oct 7;11(10):e0163006

[3]. Ramanathan RK, et al. A Phase I pharmacokinetic and pharmacodynamic study of PX-12, a novel inhibitor of thioredoxin-1, in patients with advanced solid tumors. Clin Cancer Res. 2007 Apr 1;13(7):2109-14.

[4]. Wang F, et al. Thioredoxin-1 inhibitor, 1-methylpropyl 2-imidazolyl disulfide, inhibits the growth, migration and invasion of colorectal cancer cell lines. Oncol Rep. 2015 Feb;33(2):967-73.

[5]. Lou M, et al. Physical interaction between human ribonucleotide reductase large subunit and thioredoxin increases colorectal cancer malignancy. J Biol Chem. 2017 Jun 2;292(22):9136-9149.

[相关活性小分子]

2-(仲丁基二硫基)-1H-咪唑物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
330.0±25.0 °C at 760 mmHg

[ 分子式 ]:
C₇H₁₂N₂S₂

[ 分子量 ]:
188.314

[ 闪点 ]:
153.4±23.2 °C

[ 精确质量 ]:
188.044189

[ PSA ]:
79.28000

[ LogP ]:
3.40

[ 外观性状 ]:
粉末

[ 蒸汽压 ]:
0.0±0.7 mmHg at 25°C

[ 折射率 ]:
1.590

[ 储存条件 ]:
-20℃

2-(仲丁基二硫基)-1H-咪唑MSDS

详细MSDS(安全技术说明书)

2-(仲丁基二硫基)-1H-咪唑安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319-H335

[ 警示性声明 ]:
P261-P305 + P351 + P338

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

[ 海关编码 ]:
2933290090

2-(仲丁基二硫基)-1H-咪唑海关

[ 海关编码 ]: 2933290090

[ 中文概述 ]:
2933290090. 其他结构含非稠合咪唑环的化合物. 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, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

2-(仲丁基二硫基)-1H-咪唑文献

The overexpression and nuclear translocation of Trx-1 during hypoxia confers on HepG2 cells resistance to DDP, and GL-V9 reverses the resistance by suppressing the Trx-1/Ref-1 axis.

Free Radic. Biol. Med. 82 , 29-41, (2015)

Microenvironmental hypoxia gives many tumor cells the capacity for drug resistance. Thioredoxin family members play critical roles in the regulation of cellular redox homeostasis in a stressed environ...

Inhibition of thioredoxin 1 leads to apoptosis in drug-resistant multiple myeloma.

Oncotarget 6 , 15410-24, (2015)

Multiple myeloma (MM) is a hematological malignancy characterized by the aberrant accumulation of clonal plasma cells in the bone marrow. Despite recent advancement in anti-myeloma treatment, MM remai...

Thioredoxin is involved in endothelial cell extracellular transglutaminase 2 activation mediated by celiac disease patient IgA.

PLoS ONE 8 , e77277, (2013)

To investigate the role of thioredoxin (TRX), a novel regulator of extracellular transglutaminase 2 (TG2), in celiac patients IgA (CD IgA) mediated TG2 enzymatic activation.TG2 enzymatic activity was ...

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