51146-91-9

Basic information

• Product Name: N-(bromoacetyl)-4-arsanilic acid
• Synonyms: N-(bromoacetyl)-4-arsanilic acid;(4-(2-bromoacetamido)phenyl)arsonic acid
• CAS NO: 51146-91-9
• Molecular Formula: C₈H₉AsBrNO₄
• Molecular Weight: 337.99
• Mol File: 51146-91-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(bromoacetyl)-4-arsanilic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-(bromoacetyl)-4-arsanilic acid(51146-91-9)
• EPA Substance Registry System: N-(bromoacetyl)-4-arsanilic acid(51146-91-9)

Safety Data

• Hazardous Substances Data: 51146-91-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H9AsBrNO4/c10-5-8(12)11-7-3-1-6(2-4-7)9(13,14)15/h1-4H,5H2,(H,11,12)(H2,13,14,15)

Upstream product

• 598-21-0 2-Bromoacetyl bromide 
• 98-50-0 p-aminophenylarsonic acid 

Downstream Products

• 1022085-60-4 4-(N-(S-penicillaminylacetyl)amino) phenylarsenic acid 
• 1310048-28-2 C₃₂H₄₆AsN₇O₁₈S 
• 1070872-42-2 4-(N-(bromoacetyl)amino)phenylarsonous acid 
• 67278-31-3 4-(N-(bromoacetyl)amino)phenylarsenoxide 

Relevant articles and documents

Direct Polymerization of the Arsenic Drug PENAO to Obtain Nanoparticles with High Thiol-Reactivity and Anti-Cancer Efficiency

PENAO (4-(N-(S-penicillaminylacetyl)amino) phenylarsonous acid), which is a mitochondria inhibitor that reacts with adenine nucleotide translocator (ANT), is currently being trialed in patients with solid tumors. To increase the stability of the drug, the formation of nanoparticles has been proposed. Herein, the direct synthesis of polymeric micelles based on the anticancer drug PENAO is presented. PENAO is readily available for amidation reaction to form PENAO MA (4-(N-(S-penicillaminylacetyl) amino) phenylarsonous acid methacrylamide) which undergoes RAFT (reversible addition-fragmentation chain transfer) polymerization with poly(ethylene glycol methyl ether methacrylate) as comonomer and poly(methyl methacrylate) (pMMA) as chain transfer agent, resulting in p(MMA)-b-p(PEG-co-PENAO) block copolymers with 3-15 wt % of PENAO MA. The different block copolymers self-assembled into micelle structures, varying in size and stability (Dh = 84-234 nm, cmc = 0.5-82 μg mol-1) depending on the hydrophilic to hydrophobic ratio of the polymer blocks and the amount of drug in the corona of the particle. The more stable micelle structures were investigated toward 143B human osteosarcoma cells, showing an enhanced cytotoxicity and cellular uptake compared to the free drug PENAO (IC50 (PENAO) = 2.7 ± 0.3 μM; IC50 (micelle M4) = 0.8 ± 0.02 μM). Furthermore, PENAOs arsonous acid residue remains active when incorporated into a polymer matrix and conjugates to small mono and closely spaced dithiols and is able to actively target the mitochondria, which is PENAO's main target to introduce growth inhibition in cancer cells. As a result, no cleavable linker between drug and polymer was necessary for the delivery of PENAO to osteosarcoma cells. These findings provide a rationale for in vivo studies of micelle M4 versus PENAO in an osteosarcoma animal model.

Optimization of the antitumor efficacy of a synthetic mitochondrial toxin by increasing the residence time in the cytosol

Plasma membrane drug efflux pumps of the multidrug resistance associated protein (MRP) family blunt the effectiveness of anticancer drugs and are often associated with drug resistance. GSAO, a tripeptide trivalent arsenical that targets a key mitochondria

Induction of the mitochondrial permeability transition

The present invention relates to process for identifying a compound which induces the mitochondrial permeability transition (MPT) in proliferating cells, wherein said process comprises contacting a cell or cell extract with a compound, determining whether