| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H5AsO |
| Molecular Weight | 168.0249 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=[As]C1=CC=CC=C1
InChI
InChIKey=BQVCCPGCDUSGOE-UHFFFAOYSA-N
InChI=1S/C6H5AsO/c8-7-6-4-2-1-3-5-6/h1-5H
| Molecular Formula | C6H5AsO |
| Molecular Weight | 168.0249 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Oxophenylarsine (Phenylarsine oxide, PAO, PhAsO) is an organometallic compound with the phenyl group and an oxygen atom bonded to an arsenic atom. The arsenic atom in PAO has a high affinity for the sulfur atom of thiols inorganic compounds, in particular, forming stable complexes with vicinal cysteine residues in protein structures. This effect makes it the useful tool to investigate the interaction of peptides such as insulin with their receptors and the signal transduction from the receptor to the cell interior. Oxophenylarsine is commonly used in cell biological research as an inhibitor of phosphotyrosine phosphatases (PTPases); in particular, PTPases HA1, HA2, and SH-PTP2 have been identified as substrates for Oxophenylarsine. Covalent binding of Oxophenylarsine to cysteinyl residues residing in the catalytic sites causes inactivation of PTPases. Oxophenylarsine also acts on other phosphatases that harbor vicinal thiol groups [i.e., inositol 1,2,3,5,6-pentakisphosphate 5-phosphatase or calcineurin, a Ca2+/calmodulin-dependent serine/threonine phosphatase. Also, NADPH oxidase and mitochondrial adenine nucleotide transporter were reported to be inhibited by Oxophenylarsine. Furthermore, steric inhibition of Oxophenylarsine-linked NFκB was suggested to be responsible for its decreased binding to DNA.
Approval Year
PubMed
Patents
Sample Use Guides
Human embryonic kidney cells (HEK 293T) were maintained and used for Alamar Blue drug sensitivity assays. Wells of a 96- well microtiter plate were each seeded with 3 x10^4 cells in 100 mL DMEM and allowed to adhere for 24 h. Doubling drug dilutions were then added (100 mL per well), resulting in a maximum concentration of 200 mkM test compound (oxophenylarsine), and after 30 h incubation 10 mL resazurin solution (125 mg/mL in PBS) was added; the plate was read and analysed after another 24 h incubation as described above for trypanocidal activity.