1461648-55-4

Basic information

• Product Name: C₃₀H₃₇N₃O₇S
• CAS NO: 1461648-55-4
• Molecular Weight: 583.706
• Mol File: 1461648-55-4.mol

Chemical Properties

• CAS DataBase Reference: C₃₀H₃₇N₃O₇S(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₀H₃₇N₃O₇S(1461648-55-4)
• EPA Substance Registry System: C₃₀H₃₇N₃O₇S(1461648-55-4)

Safety Data

• Hazardous Substances Data: 1461648-55-4(Hazardous Substances Data)

Usage

Uses

P1 is a starting material and useful building block of various pharmaceuticals.

Enzyme inhibitor

This cell-permeable PDI inhibitor (FW = 583.70 g/mol; CAS 1461648-55- 4; Soluble to 100 mM in DMSO; N-[(1,1-dimethylethoxy)carbonyl]-Lphenylalanyl-O-(ethenyl-sulfonyl)-N-4-pentyn-1-yl-L-tyrosinamide) targets protein disulfide isomerase (IC50 = 1.7 μM), an enzyme that assists in the folding of cellular proteins within the endoplasmic reticulum of mammalian cells. P1 reduces the proliferation of numerous cancer cell lines, with nominal GI50 values of ～4 μM. PDI binds to the axonal microtubuleassociated protein known as Tau, mainly through its thioredoxin-like catalytic domain, by forming a one-to-one complex that prevents Tau misfolding.

Upstream product

• 1622-32-8 2-Chloroethanesulfonyl chloride 

Relevant articles and documents

Small molecule probe suitable for in situ profiling and inhibition of protein disulfide isomerase

Proper folding of cellular proteins is assisted by protein disulfide isomerases (PDIs) in the endoplasmic reticulum of mammalian cells. Of the at least 21 PDI family members known in humans, the 57-kDa PDI has been found to be a potential therapeutic target for a variety of human diseases including cancer and neurodegenerative diseases. Consequently, small molecule PDI-targeting inhibitors have been actively pursued in recent years, and thus far, compounds possessing moderate inhibitory activities (IC50 between 0.1 and 100 μM against recombinant PDI) have been discovered. In this article, by using in situ proteome profiling experiments in combination with in vitro PDI enzymatic inhibition assays, we have discovered a phenyl vinyl sulfonate-containing small molecule (P1; shown) as a relatively potent and specific inhibitor of endogenous human PDI in several mammalian cancer cells (e.g., GI50 ～ 4 μM). It also possesses an IC50 value of 1.7 ± 0.4 μM in an in vitro insulin aggregation assay. Our results indicate P1 is indeed a novel, cell-permeable small molecule PDI inhibitor, and the electrophilic vinyl sulfonate scaffold might serve as a starting point for future development of next-generation PDI inhibitors and probes.