PX-12

Specifications / Handling

More Information
Product Details
Synonyms	IV-2; 2-[(1-Methylpropyl)dithio]-1H-imidazole
Product Type	Chemical
Properties
Formula	C₇H₁₂N₂S₂
MW	188.3
CAS	141400-58-0
Purity Chemicals	≥98% (HPLC)
Appearance	White to off-white powder.
Solubility	Soluble in DMSO, ethanol or DMF (all 15mg/ml). Slightly soluble in water (~1mg/ml).
Identity	Determined by ¹H-NMR.
InChi Key	BPBPYQWMFCTCNG-UHFFFAOYSA-N
Smiles	CC(CC)SSC1=NC=CN1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

PX-12 is a competitive, irreversible inhibitor of thioredoxin 1 (Trx1), acting by binding to Cys73 of this enzyme.
High levels of Trx-1 have been associated with colorectal, gastric and lung cancers. PX-12 stimulates apoptosis, down-regulates HIF-1α, vascular endothelial growth factor (VEGF) and iNOS, and consequently inhibits proliferation and tumor growth in animal models. It has also been reported to inhibit tubulin polymerization in vitro, induce cell cycle arrest at G2/M phase and inhibit growth, migration and invasion of several cancer cell lines.
PX-12 shows antiviral activity against HIV-1, by inhibiting the enzymatic activity of Trx1 and the Trx1-dependent disulfide reduction of gp120. Microtubule polymerization and formation of acetylated microtubules are inhibited as well, activities shown to be required for HIV-1 life cycle propagation.
PX-12 has broad spectrum antimicrobial activity targeting the thioredoxin system of bacterial, fungal, protozoan and helminth pathogens without significant toxicity to the host.
PX-12 potentially inhibits the 33.8-kDa Main protease (Mpro)/3C-like protease of SARS-CoV-2, consequently inhibiting viral transcription and replication and possibly inhibiting spread of COVID-19.

Product References

Reversible inhibition of human thioredoxin reductase activity by cytotoxic alkyl 2-imidazolyl disulfide analogues: J.E. Oblong, et al.; Cancer Chemother. Pharmacol. 34, 434 (1994)
The thioredoxin redox inhibitors 1-methylpropyl 2-imidazolyl disulfide and pleurotin inhibit hypoxia-induced factor 1alpha and vascular endothelial growth factor formation: S.J. Welsh, et al.; Mol. Cancer Ther. 2, 235 (2003)
The antitumor thioredoxin-1 inhibitor PX-12 (1-methylpropyl 2-imidazolyl disulfide) decreases thioredoxin-1 and VEGF levels in cancer patient plasma: A.F. Baker, et al.; J. Lab. Clin. Med. 147, 83 (2006)
Drug evaluation: the thioredoxin inhibitor PX-12 in the treatment of cancer: C.M. Galmarini; Curr. Opin. Investig. Drugs 7, 1108 (2006) (Review)
2-[(1-methylpropyl)dithio]-1H-imidazole inhibits tubulin polymerization through cysteine oxidation: K. Huber, et al.; Mol. Cancer Ther. 7, 143 (2008)
PX-12 inhibits the growth of A549 lung cancer cells via G2/M phase arrest and ROS-dependent apoptosis: B.R. You, et al.; Int. J. Oncol. 44, 301 (2014)
PX-12 induces apoptosis in Calu-6 cells in an oxidative stress-dependent manner: B.R. You, et al.; Tumour Biol. 36, 2087 (2015)
Thioredoxin-1 inhibitor, 1-methylpropyl 2-imidazolyl disulfide, inhibits the growth, migration and invasion of colorectal cancer cell lines: F. Wang, et al.; Oncol. Rep. 33, 967 (2015)
Repurposing Auranofin, Ebselen, and PX-12 as Antimicrobial Agents Targeting the Thioredoxin System: H.C. May, et al.; Front. Microbiol. 9, 336 (2018)
Inhibition of the thioredoxin system by PX-12 (1-methylpropyl 2-imidazolyl disulfide) impedes HIV-1 infection in TZM-bl cells: M. Lundberg, et al.; Sci. Rep. 9, 5656 (2019)
Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors: Z. Jin, et al.; Nature 582, 289 (2020)

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