MedKoo Cat#: 527517 | Name: Glutathione arsenoxide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Glutathione arsenoxide
Glutathione arsenoxide
CAS#1271726-51-2

Theoretical Analysis

MedKoo Cat#: 527517

Name: Glutathione arsenoxide

CAS#: 1271726-51-2

Chemical Formula: C18H25AsN4O9S

Exact Mass: 548.0558

Molecular Weight: 548.40

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 currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Glutathione arsenoxide; GSAO; P-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

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
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Optical imaging of treatment-related tumor cell death using a heat shock protein-90 alkylator. Mol Pharm. 2013 Oct 7;10(10):3882-91. doi: 10.1021/mp4003464. PubMed PMID: 23968358. 7: Dilda PJ, Ramsay EE, Corti A, Pompella A, Hogg PJ. Metabolism of the tumor angiogenesis inhibitor 4-(N-(S-Glutathionylacetyl)amino)phenylarsonous acid. J Biol Chem. 2008 Dec 19;283(51):35428-34. doi: 10.1074/jbc.M804470200. PubMed PMID: 18723877. 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. 9: Ramsay EE, Decollogne S, Joshi S, Corti A, Apte M, Pompella A, Hogg PJ, Dilda PJ. Employing pancreatic tumor γ-glutamyltransferase for therapeutic delivery. Mol Pharm. 2014 May 5;11(5):1500-11. doi: 10.1021/mp400664t. PubMed PMID: 24654974. 10: Dilda PJ, Decollogne S, Rossiter-Thornton M, Hogg PJ. Para to ortho repositioning of the arsenical moiety of the angiogenesis inhibitor 4-(N-(S-glutathionylacetyl)amino)phenylarsenoxide results in a markedly increased cellular accumulation and antiproliferative activity. Cancer Res. 2005 Dec 15;65(24):11729-34. PubMed PMID: 16357185. 11: Dilda PJ, Don AS, Tanabe KM, Higgins VJ, Allen JD, Dawes IW, Hogg PJ. Mechanism of selectivity of an angiogenesis inhibitor from screening a genome-wide set of Saccharomyces cerevisiae deletion strains. J Natl Cancer Inst. 2005 Oct 19;97(20):1539-47. PubMed PMID: 16234568. 12: Hua VM, Abeynaike L, Glaros E, Campbell H, Pasalic L, Hogg PJ, Chen VM. Necrotic platelets provide a procoagulant surface during thrombosis. Blood. 2015 Dec 24;126(26):2852-62. doi: 10.1182/blood-2015-08-663005. PubMed PMID: 26474813; PubMed Central PMCID: PMC4692145. 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. 14: Donoghue N, Yam PT, Jiang XM, Hogg PJ. Presence of closely spaced protein thiols on the surface of mammalian cells. Protein Sci. 2000 Dec;9(12):2436-45. PubMed PMID: 11206065; PubMed Central PMCID: PMC2144521. 15: Don AS, Kisker O, Dilda P, Donoghue N, Zhao X, Decollogne S, Creighton B, Flynn E, Folkman J, Hogg PJ. A peptide trivalent arsenical inhibits tumor angiogenesis by perturbing mitochondrial function in angiogenic endothelial cells. Cancer Cell. 2003 May;3(5):497-509. PubMed PMID: 12781367. 16: Dilda PJ, Decollogne S, Weerakoon L, Norris MD, Haber M, Allen JD, Hogg PJ. Optimization of the antitumor efficacy of a synthetic mitochondrial toxin by increasing the residence time in the cytosol. J Med Chem. 2009 Oct 22;52(20):6209-16. doi: 10.1021/jm9008339. PubMed PMID: 19788237. 17: Harrington CF, Taylor A. Analytical approaches to investigating metal-containing drugs. J Pharm Biomed Anal. 2015 Mar 15;106:210-7. doi: 10.1016/j.jpba.2014.10.017. PubMed PMID: 25455724. 18: Ramsay EE, Dilda PJ. Glutathione S-conjugates as prodrugs to target drug-resistant tumors. Front Pharmacol. 2014 Aug 11;5:181. doi: 10.3389/fphar.2014.00181. Review. PubMed PMID: 25157234; PubMed Central PMCID: PMC4127970. 19: Citrin D, Scott T, Sproull M, Menard C, Tofilon PJ, Camphausen K. In vivo tumor imaging using a near-infrared-labeled endostatin molecule. Int J Radiat Oncol Biol Phys. 2004 Feb 1;58(2):536-41. PubMed PMID: 14751525.