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 |
|---|---|---|
| Inhibition of coupling factor B activity by cadmium ion, arsenite-2,3-dimercaptopropanol, and phenylarsine oxide, and preferential reactivation by dithiols. | 1981 Nov 10 |
|
| Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes. | 1985 Mar 10 |
|
| Effect of vanadate on the cellular accumulation of pp15, an apparent product of insulin receptor tyrosine kinase action. | 1988 Sep 25 |
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| A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes. | 1989 Aug |
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| Phenylarsine oxide stimulates hexose transport in 3T3-L1 adipocytes by a mechanism other than an increase in surface transporters. | 1989 Jan |
|
| Insulin processing and signal transduction in rat adipocytes. | 1989 Mar 6 |
|
| The role of insulin receptor sulphydryl groups in insulin binding and cellular response in rat adipocytes. | 1990 |
|
| Effects of phenylarsine oxide on stimulation of glucose transport in rat skeletal muscle. | 1990 Apr |
|
| Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes. | 1990 Aug 1 |
|
| Effects of insulin and phospholipase C in control and denervated rat skeletal muscle. | 1991 Feb |
|
| Angiotensin II-induced phosphatidylcholine hydrolysis in cultured vascular smooth-muscle cells. Regulation and localization. | 1991 May 15 |
|
| Effects of phenylarsine oxide on insulin-stimulated system A amino acid uptake in skeletal muscle. | 1991 Oct |
|
| Trafficking of glucose transporters in 3T3-L1 cells. Inhibition of trafficking by phenylarsine oxide implicates a slow dissociation of transporters from trafficking proteins. | 1992 Feb 1 |
|
| 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 Jul 15 |
|
| Evidence for two distinct phosphorylation pathways activated by high affinity immunoglobulin E receptors. | 1992 Sep 5 |
|
| Phenylarsine oxide inhibits insulin-stimulated protein phosphatase 1 activity and GLUT-4 translocation. | 1994 Jul |
|
| Agonist-induced internalization of the substance P (NK1) receptor expressed in epithelial cells. | 1994 Oct 1 |
|
| Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (ARE). | 1995 Nov |
|
| Manipulation of B cell antigen receptor tyrosine phosphorylation using aluminum fluoride and sodium orthovanadate. | 1995 Nov |
|
| Electrophile and antioxidant regulation of enzymes that detoxify carcinogens. | 1995 Sep 12 |
|
| Phenylarsine oxide and vanadate: apparent paradox of inhibition of protein phosphotyrosine phosphatases in rat adipocytes. | 1996 Jul 24 |
|
| Mechanisms of manganese transport in rabbit erythroid cells. | 1996 May 15 |
|
| Phenylarsine oxide inhibits ex vivo HIV-1 expression. | 1997 |
|
| Evidence for involvement of NF-kappaB in the transcriptional control of COX-2 gene expression by IL-1beta. | 1997 Aug 8 |
|
| Presence and differential internalization of two distinct insulin-like growth factor receptors in rat hippocampal neurons. | 1997 May |
|
| A new function for phospholipase C-gamma1: coupling to the adaptor protein GRB2. | 1997 Sep 1 |
|
| Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds. | 1997 Sep-Oct |
|
| Ca2+-independent activation of the endothelial nitric oxide synthase in response to tyrosine phosphatase inhibitors and fluid shear stress. | 1998 Apr 6 |
|
| Tyrosine phosphorylation and proteolysis. Pervanadate-induced, metalloprotease-dependent cleavage of the ErbB-4 receptor and amphiregulin. | 1998 Aug 7 |
|
| Tumour necrosis factor-alpha-dependent regulation of prostaglandin endoperoxide synthase-2. | 1998 Mar |
|
| 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 May |
|
| Oxidative and calcium stress regulate DSCR1 (Adapt78/MCIP1) protein. | 2003 Sep 1 |
|
| Accumulation and toxicity of monophenyl arsenicals in rat endothelial cells. | 2005 Jan |
|
| Redox regulation of the nutrient-sensitive raptor-mTOR pathway and complex. | 2005 Nov 25 |
|
| Dephosphorylation of the Rieske iron-sulfur protein after induction of the mitochondrial permeability transition. | 2005 Sep 2 |
|
| Redox regulation of RhoA. | 2006 Dec 5 |
|
| Phenylarsine oxide inhibited beta-adrenergic receptor-mediated IL-6 secretion: inhibition of cAMP accumulation and CREB activation in cardiac fibroblasts. | 2007 Jan 19 |
|
| Regulation of CA(v)3.2 Ca2+ channel activity by protein tyrosine phosphorylation. | 2008 Feb |
|
| The vanilloid receptor TRPV1 is activated and sensitized by local anesthetics in rodent sensory neurons. | 2008 Feb |
|
| COX-2 expression stimulated by Angiotensin II depends upon AT1 receptor internalization in vascular smooth muscle cells. | 2008 Jun |
|
| The mitochondrial phosphate carrier interacts with cyclophilin D and may play a key role in the permeability transition. | 2008 Sep 26 |
|
| Differential cytotoxic effects of arsenic compounds in human acute promyelocytic leukemia cells. | 2009 Aug 15 |
|
| NRF2 cysteine residues are critical for oxidant/electrophile-sensing, Kelch-like ECH-associated protein-1-dependent ubiquitination-proteasomal degradation, and transcription activation. | 2009 Dec |
|
| Dual action of phenylarsine oxide on the glucose transport activity of GLUT1. | 2009 Dec 10 |
|
| Induction of metallothionein I by arsenic via metal-activated transcription factor 1: critical role of C-terminal cysteine residues in arsenic sensing. | 2009 May 8 |
|
| Critical cysteine residues of Kelch-like ECH-associated protein 1 in arsenic sensing and suppression of nuclear factor erythroid 2-related factor 2. | 2010 Jan |
|
| PML/RARA oxidation and arsenic binding initiate the antileukemia response of As2O3. | 2010 Jul 13 |
|
| Enhanced IL-12p40 production by phenylarsine oxide is mediated by cAMP response element in macrophages. | 2010 May |
|
| The metalloid arsenite induces nuclear export of Id3 possibly via binding to the N-terminal cysteine residues. | 2013 Apr 19 |
|
| 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 Feb |
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
Fri Dec 15 15:08:54 GMT 2023
by
admin
on
Fri Dec 15 15:08:54 GMT 2023
|
| Record UNII |
0HUR2WY345
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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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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75253
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C029341
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0HUR2WY345
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4778
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211-275-3
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m8318
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637-03-6
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