2-[(1-Methylpropyl)dithio]-1H-imidazole Chemical Properties

Boiling point:

330.0±25.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: >25mg/mL

pka

11.88±0.10(Predicted)

form 

powder

color 

off-white to tan

InChI

InChI=1S/C7H12N2S2/c1-3-6(2)10-11-7-8-4-5-9-7/h4-6H,3H2,1-2H3,(H,8,9)

InChIKey

BPBPYQWMFCTCNG-UHFFFAOYSA-N

SMILES

C1(SSC(C)CC)NC=CN=1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29332900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

2-[(1-Methylpropyl)dithio]-1H-imidazole Usage And Synthesis

Uses

PX 12 is an irreversible and competitive inhibitor of thioredoxin-1.

Definition

ChEBI: 2-(butan-2-yldisulfanyl)-1H-imidazole is a member of imidazoles.

Biological Activity

px 12 is an inhibitor of thioredoxin-1 [1].thioredoxin-1 (trx-1) is a small redox protein with a conserved catalytic site and plays an important role in cells that includes the regulation of trans-activating activity and the dna binding of redox-sensitive transcription factors [1].in ht-29 human colon carcinoma cells and mcf-7 human breast cancer, px 12 prevented the hypoxia-induced increase in hif-1 protein. also, px 12 decreased inducible nitric oxide synthase, hif-1-trans-activating activity and vegf formation [2].in immunodeficient mice bearing ht-29 human colon xenografts, px 12 decreased the average tumor blood vessel permeability by 63% within 2 hours and returned to pretreatment values after 48 hours. px 12 reduced tumor-derived vegf and tumor after 24 hours. also, trx-1 showed a rapid decrease within 2 hours and maintained for 24 hours [1]. in mice bearing mcf-7 tumor xenografts, px 12 reduced hif-1ɑ and vegf protein levels [2]. in cancer patients, px-12 treatment significantly reduced the levels of trx-1 and vegf in plasma [3].

Biochem/physiol Actions

PX-12 inhibits the thioredoxin redox system and HIF-1a activity. PX 12 inhibits hypoxia-induced HIF-1a transcriptional activity (IC50 11 nM) and proliferation of HT29 and MCF-7 tumor cells (IC50 1.9 and 0.9 uM, respectively).

storage

Store at +4°C

References

[1]. jordan bf, runquist m, raghunand n, et al. the thioredoxin-1 inhibitor 1-methylpropyl 2-imidazolyl disulfide (px-12) decreases vascular permeability in tumor xenografts monitored by dynamic contrast enhanced magnetic resonance imaging. clin cancer res, 2005, 11(2 pt 1): 529-536.
[2]. welsh sj, williams rr, birmingham a, 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, 2(3): 235-243.
[3]. baker af, dragovich t, tate wr, et al. the antitumor thioredoxin-1 inhibitor px-12 (1-methylpropyl 2-imidazolyl disulfide) decreases thioredoxin-1 and vegf levels in cancer patient plasma. j lab clin med, 2006, 147(2): 83-90.

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