Details
| 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 |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11516523 | https://www.ncbi.nlm.nih.gov/pubmed/26500720 | https://www.ncbi.nlm.nih.gov/pubmed/26231081 | https://www.ncbi.nlm.nih.gov/pubmed/16543668
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11516523 | https://www.ncbi.nlm.nih.gov/pubmed/26500720 | https://www.ncbi.nlm.nih.gov/pubmed/26231081 | https://www.ncbi.nlm.nih.gov/pubmed/16543668
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
| Title | Date | PubMed |
|---|---|---|
| Inhibitory effect of snake venom toxin on NF-κB activity prevents human cervical cancer cell growth via increase of death receptor 3 and 5 expression. | 2016-02 |
|
| The metalloid arsenite induces nuclear export of Id3 possibly via binding to the N-terminal cysteine residues. | 2013-04-19 |
|
| PML/RARA oxidation and arsenic binding initiate the antileukemia response of As2O3. | 2010-07-13 |
|
| Enhanced IL-12p40 production by phenylarsine oxide is mediated by cAMP response element in macrophages. | 2010-05 |
|
| Critical cysteine residues of Kelch-like ECH-associated protein 1 in arsenic sensing and suppression of nuclear factor erythroid 2-related factor 2. | 2010-01 |
|
| Dual action of phenylarsine oxide on the glucose transport activity of GLUT1. | 2009-12-10 |
|
| NRF2 cysteine residues are critical for oxidant/electrophile-sensing, Kelch-like ECH-associated protein-1-dependent ubiquitination-proteasomal degradation, and transcription activation. | 2009-12 |
|
| Differential cytotoxic effects of arsenic compounds in human acute promyelocytic leukemia cells. | 2009-08-15 |
|
| Induction of metallothionein I by arsenic via metal-activated transcription factor 1: critical role of C-terminal cysteine residues in arsenic sensing. | 2009-05-08 |
|
| The mitochondrial phosphate carrier interacts with cyclophilin D and may play a key role in the permeability transition. | 2008-09-26 |
|
| COX-2 expression stimulated by Angiotensin II depends upon AT1 receptor internalization in vascular smooth muscle cells. | 2008-06 |
|
| Regulation of CA(v)3.2 Ca2+ channel activity by protein tyrosine phosphorylation. | 2008-02 |
|
| The vanilloid receptor TRPV1 is activated and sensitized by local anesthetics in rodent sensory neurons. | 2008-02 |
|
| Phenylarsine oxide inhibited beta-adrenergic receptor-mediated IL-6 secretion: inhibition of cAMP accumulation and CREB activation in cardiac fibroblasts. | 2007-01-19 |
|
| Redox regulation of RhoA. | 2006-12-05 |
|
| Redox regulation of the nutrient-sensitive raptor-mTOR pathway and complex. | 2005-11-25 |
|
| Dephosphorylation of the Rieske iron-sulfur protein after induction of the mitochondrial permeability transition. | 2005-09-02 |
|
| Accumulation and toxicity of monophenyl arsenicals in rat endothelial cells. | 2005-01 |
|
| Oxidative and calcium stress regulate DSCR1 (Adapt78/MCIP1) protein. | 2003-09-01 |
|
| Tyrosine phosphorylation and proteolysis. Pervanadate-induced, metalloprotease-dependent cleavage of the ErbB-4 receptor and amphiregulin. | 1998-08-07 |
|
| Tyrosine phosphatase-dependent/tyrosine kinase-independent induction of nuclear factor-kappa B by tumor necrosis factor-alpha: effects on prostaglandin endoperoxide synthase-2 mRNA accumulation. | 1998-05 |
|
| Ca2+-independent activation of the endothelial nitric oxide synthase in response to tyrosine phosphatase inhibitors and fluid shear stress. | 1998-04-06 |
|
| Tumour necrosis factor-alpha-dependent regulation of prostaglandin endoperoxide synthase-2. | 1998-03 |
|
| Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds. | 1997-12-24 |
|
| A new function for phospholipase C-gamma1: coupling to the adaptor protein GRB2. | 1997-09-01 |
|
| Evidence for involvement of NF-kappaB in the transcriptional control of COX-2 gene expression by IL-1beta. | 1997-08-08 |
|
| Presence and differential internalization of two distinct insulin-like growth factor receptors in rat hippocampal neurons. | 1997-05 |
|
| Phenylarsine oxide inhibits ex vivo HIV-1 expression. | 1997 |
|
| Phenylarsine oxide and vanadate: apparent paradox of inhibition of protein phosphotyrosine phosphatases in rat adipocytes. | 1996-07-24 |
|
| Mechanisms of manganese transport in rabbit erythroid cells. | 1996-05-15 |
|
| Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (ARE). | 1995-11 |
|
| Manipulation of B cell antigen receptor tyrosine phosphorylation using aluminum fluoride and sodium orthovanadate. | 1995-11 |
|
| Electrophile and antioxidant regulation of enzymes that detoxify carcinogens. | 1995-09-12 |
|
| Agonist-induced internalization of the substance P (NK1) receptor expressed in epithelial cells. | 1994-10-01 |
|
| Phenylarsine oxide inhibits insulin-stimulated protein phosphatase 1 activity and GLUT-4 translocation. | 1994-07 |
|
| Evidence for two distinct phosphorylation pathways activated by high affinity immunoglobulin E receptors. | 1992-09-05 |
|
| Iodophenylarsine oxide and arsenical affinity chromatography: new probes for dithiol proteins. Application to tubulins and to components of the insulin receptor-glucose transporter signal transduction pathway. | 1992-07-15 |
|
| Trafficking of glucose transporters in 3T3-L1 cells. Inhibition of trafficking by phenylarsine oxide implicates a slow dissociation of transporters from trafficking proteins. | 1992-02-01 |
|
| Effects of phenylarsine oxide on insulin-stimulated system A amino acid uptake in skeletal muscle. | 1991-10 |
|
| Angiotensin II-induced phosphatidylcholine hydrolysis in cultured vascular smooth-muscle cells. Regulation and localization. | 1991-05-15 |
|
| Effects of insulin and phospholipase C in control and denervated rat skeletal muscle. | 1991-02 |
|
| Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes. | 1990-08-01 |
|
| Effects of phenylarsine oxide on stimulation of glucose transport in rat skeletal muscle. | 1990-04 |
|
| The role of insulin receptor sulphydryl groups in insulin binding and cellular response in rat adipocytes. | 1990 |
|
| A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes. | 1989-08 |
|
| Insulin processing and signal transduction in rat adipocytes. | 1989-03-06 |
|
| Phenylarsine oxide stimulates hexose transport in 3T3-L1 adipocytes by a mechanism other than an increase in surface transporters. | 1989-01 |
|
| Effect of vanadate on the cellular accumulation of pp15, an apparent product of insulin receptor tyrosine kinase action. | 1988-09-25 |
|
| Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes. | 1985-03-10 |
|
| Inhibition of coupling factor B activity by cadmium ion, arsenite-2,3-dimercaptopropanol, and phenylarsine oxide, and preferential reactivation by dithiols. | 1981-11-10 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:48:06 GMT 2025
by
admin
on
Mon Mar 31 17:48:06 GMT 2025
|
| Record UNII |
0HUR2WY345
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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Preferred Name | English | ||
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Systematic Name | English | ||
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Systematic Name | English |
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EPA PESTICIDE CODE |
7101
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Phenylarsine oxide
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42470
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DTXSID5042249
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C029341
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0HUR2WY345
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m8318
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