Glutathione arsenoxide

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MedKoo CAT#: 527517

CAS#: 1271726-51-2

Description: Glutathione arsenoxide is a hydrophilic derivative of the protein tyrosine phosphatase inhibitor phenylarsine oxide (PAO). It inhibits angiogenesis and tumour growth. Glutathione arsenoxide has potential anti-angiogenic capability with application in cancer where tumour metastasis relies on neo-vascularisation. As GSAO arsenic is trivalent, the arsenoxide moiety reacts with appropriately spaced cysteine residues on adenine nucleotide translocase mitochondrial membrane protein.

Chemical Structure

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Glutathione arsenoxide
CAS# 1271726-51-2
Instruction

Theoretical Analysis

MedKoo Cat#: 527517
Name: Glutathione arsenoxide
CAS#: 1271726-51-2
Chemical Formula: C18H25AsN4O9S
Exact Mass: 548.06
Molecular Weight: 548.399
Elemental Analysis: C, 39.42; H, 4.60; As, 13.66; N, 10.22; O, 26.26; S, 5.85

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Glutathione arsenoxide; GSAO;

IUPAC/Chemical Name: N5-((R)-1-((carboxymethyl)amino)-3-((2-((4-(dihydroxyarsanyl)phenyl)amino)-2-oxoethyl)thio)-1-oxopropan-2-yl)-L-glutamine

InChi Key: ADJQAKCDADMLPP-STQMWFEESA-N

InChi Code: InChI=1S/C18H25AsN4O9S/c20-12(18(29)30)5-6-14(24)23-13(17(28)21-7-16(26)27)8-33-9-15(25)22-11-3-1-10(2-4-11)19(31)32/h1-4,12-13,31-32H,5-9,20H2,(H,21,28)(H,22,25)(H,23,24)(H,26,27)(H,29,30)/t12-,13-/m0/s1

SMILES Code: O=C(O)CNC([C@H](CSCC(NC1=CC=C([As](O)O)C=C1)=O)NC(CC[C@@H](C(O)=O)N)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 548.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Horsley L, Cummings J, Middleton M, Ward T, Backen A, Clamp A, Dawson M, Farmer H, Fisher N, Halbert G, Halford S, Harris A, Hasan J, Hogg P, Kumaran G, Little R, Parker GJ, Potter P, Saunders M, Roberts C, Shaw D, Smith N, Smythe J, Taylor A, Turner H, Watson Y, Dive C, Jayson GC; Cancer Research UK Drug Development Office Phase I clinical trial.. A phase 1 trial of intravenous 4-(N-(S-glutathionylacetyl)amino) phenylarsenoxide (GSAO) in patients with advanced solid tumours. Cancer Chemother Pharmacol. 2013 Dec;72(6):1343-52. doi: 10.1007/s00280-013-2320-9. PubMed PMID: 24141375.

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8: Xie BW, Park D, Van Beek ER, Blankevoort V, Orabi Y, Que I, Kaijzel EL, Chan A, Hogg PJ, Löwik CW. Optical imaging of cell death in traumatic brain injury using a heat shock protein-90 alkylator. Cell Death Dis. 2013 Jan 24;4:e473. doi: 10.1038/cddis.2012.207. PubMed PMID: 23348587; PubMed Central PMCID: PMC3563995.

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13: Dick LJ, Gray A, Ram A, Hume A, Parris C, Hogg PJ, Elliott MA, Ford SJ, Halbert GW. Elimination of the antimicrobial action of the organoarsenical cancer therapeutic, 4-(N-(S-glutathionylacetyl)amino) phenylarsonous acid, before finished product sterility testing. J Pharm Pharmacol. 2013 Nov;65(11):1664-9. doi: 10.1111/jphp.12143. PubMed PMID: 24102542.

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