1384426-12-3

Basic information

• Product Name: (E)-3-(3-bromo-4,5-dihydroxyphenyl)-N-(3,4,5-trihydroxybenzyl)prop-2-enethioamide
• Synonyms: (E)-3-(3-bromo-4,5-dihydroxyphenyl)-N-(3,4,5-trihydroxybenzyl)prop-2-enethioamide;NT-157;(2E)-3-(3-Bromo-4,5-dihydroxyphenyl)-N-[(3,4,5-trihydroxyphenyl)methyl]-2-propenethioamide;AK174915;AKOS025404921;CS-5531
• CAS NO: 1384426-12-3
• Molecular Formula: C16H14BrNO5S
• Molecular Weight: 412.25506
• EINECS: -0
• Mol File: 1384426-12-3.mol

Chemical Properties

• Boiling Point: 660.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.794±0.06 g/cm3(Predicted)
• Solubility: insoluble in H2O; ≥21.5 mg/mL in EtOH; ≥50 mg/mL in DMSO
• PKA: 8.06±0.36(Predicted)
• CAS DataBase Reference: (E)-3-(3-bromo-4,5-dihydroxyphenyl)-N-(3,4,5-trihydroxybenzyl)prop-2-enethioamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(3-bromo-4,5-dihydroxyphenyl)-N-(3,4,5-trihydroxybenzyl)prop-2-enethioamide(1384426-12-3)
• EPA Substance Registry System: (E)-3-(3-bromo-4,5-dihydroxyphenyl)-N-(3,4,5-trihydroxybenzyl)prop-2-enethioamide(1384426-12-3)

Safety Data

• Hazardous Substances Data: 1384426-12-3(Hazardous Substances Data)

Usage

Biological Activity

nt157 is an irs-1/2 inhibitor.insulin receptor substrates 1 and 2 (irs1/2) mediate antiapoptotic and mitogenic signaling from insulin receptor (ir), insulin-like growth factor 1 receptor (igf-ir), and other oncoproteins. irs1 plays a critical role in cancer cell proliferation, and its expression is increased in many human malignancies.

in vitro

nt157 treatment was fonund to be able to lead to dose-dependent suppression of irs protein expression, inhibition of igf1r activation, inhibition of igf1-induced akt activation, but increased erk activation in nt157-treated cells. these effects were associated with decreased proliferation, increased apoptosis of lncap cells and increased g2-m arrest in pc3 cells. moreover, nt157 could significantly affect the cell migratory ability, as demonstrated by a wound-healing assay. in addition, the nt157 treatment was able to induce cell cycle arrest and inhibit igf system signaling [1].

in vivo

in previous animal study, nt157 was found to suppress androgen-responsive growth, delay crpc progression of lncap xenografts, and suppress pc3 tumor growth alone or in combination with docetaxel. this study reported the first preclinical proof-of-principle data that nt157 suppressed irs1/2 expression, delayed crpc progression, and suppressed growth of crpc tumors in vivo [1].

IC 50

0.3 to 0.8 μm

references

[1] ibuki n et al. the tyrphostin nt157 suppresses insulin receptor substrates and augments therapeutic response of prostate cancer. mol cancer ther. 2014 dec;13(12):2827-39.