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141400-58-0

141400-58-0 structure
141400-58-0 structure
  • Name: PX-12
  • Chemical Name: 2-(butan-2-yldisulfanyl)-1H-imidazole
  • CAS Number: 141400-58-0
  • Molecular Formula: C7H12N2S2
  • Molecular Weight: 188.314
  • Catalog: Research Areas Cancer
  • Create Date: 2017-06-02 12:25:10
  • Modify Date: 2025-08-20 19:24:58
  • PX-12(IV-2) is an irreversible inhibitor of Thioredoxin-1 (Trx-1); inhibits the growth of MCF-7 and HT-29 cells with IC50 values of 1.9 and 2.9 μM, respectively.
Name 2-(butan-2-yldisulfanyl)-1H-imidazole
Synonyms 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]-
PX-12
Description PX-12(IV-2) is an irreversible inhibitor of Thioredoxin-1 (Trx-1); inhibits the growth of MCF-7 and HT-29 cells with IC50 values of 1.9 and 2.9 μM, respectively.
Related Catalog
Target

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

In Vitro PX-12 inhibits the growth of MCF-7 and HT-29 cells with IC50 values of 1.9 and 2.9 μM, respectively[1]. PX-12 particularly reduces the activity of Trx-1 by means of thio-alkylating critical cysteine residue (Cys73) which is located in the outside the conserved redox catalytic site of Trx-1. PX-12 affects the oxidation state of thiols in a number of cell surface proteins. Key surface receptors for platelet adhesion and activation are affected, including the collagen receptor GPVI and the von Willebrand factor receptor, GPIb. PX-12 inhibits thrombus formation over Type I collagen in whole blood under flow conditions[2]. Thioredoxin-1 (Trx-1) is a cellular redox protein that promotes tumor growth, inhibits apoptosis, and up-regulates hypoxia-inducible factor-1α and vascular endothelial growth factor[3]. PX-12 inhibits the growth of colorectal cancer DLD-1 and SW620 cells in a dose- and time-dependent manner. PX-12 reduces cell colony formation and induced a G2/M phase arrest of the cell cycle. PX-12 treatment induces apoptosis. PX-12 inhibits colorectal cancer cell migration and invasion. Treatment of cancer cells with PX-12 reduces NOX1, CDH17 and S100A4 mRNA expression, and increases KLF17 mRNA expression. PX-12 decreases S100A4 protein expression in the colorectal cancer cells[4].
In Vivo PX-12 has been shown to have in vivo antitumor activity against human tumor xenografts including HT-29 colon cancer in SCID mice and has been tested in a phase I clinical trial in patients[3].
References

[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.
Density 1.2±0.1 g/cm3
Boiling Point 330.0±25.0 °C at 760 mmHg
Molecular Formula C7H12N2S2
Molecular Weight 188.314
Flash Point 153.4±23.2 °C
Exact Mass 188.044189
PSA 79.28000
LogP 3.40
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.590
Storage condition -20℃
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
RIDADR NONH for all modes of transport
HS Code 2933290090
HS Code 2933290090
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%
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