Synonym
L-Cystine S,S-dioxide; Cystinedisulfoxide;
IUPAC/Chemical Name
S-(((R)-2-amino-2-carboxyethyl)sulfonyl)-D-cysteine
InChi Key
RXQXJZDPDXVIEN-DMTCNVIQSA-N
InChi Code
InChI=1S/C6H12N2O6S2/c7-3(5(9)10)1-15-16(13,14)2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4+/m1/s1
SMILES Code
N[C@@H](CS(SC[C@H](C(O)=O)N)(=O)=O)C(O)=O
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
Biological target:
L-Cystine S,S-dioxide is a metabolite of L-Cystine.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
272.29
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.
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:
TBD
1: Wang Y, Peng L, Bellamri M, Langouët S, Turesky RJ. Mass Spectrometric Characterization of Human Serum Albumin Adducts Formed with N-Oxidized Metabolites of 2-Amino-1-methylphenylimidazo[4,5-b]pyridine in Human Plasma and Hepatocytes. Chem Res Toxicol. 2015 May 18;28(5):1045-59. doi: 10.1021/acs.chemrestox.5b00075. Epub 2015 Apr 10. PubMed PMID: 25815793; PubMed Central PMCID: PMC4437839.
2: Peng L, Turesky RJ. Optimizing proteolytic digestion conditions for the analysis of serum albumin adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, a potential human carcinogen formed in cooked meat. J Proteomics. 2014 May 30;103:267-78. doi: 10.1016/j.jprot.2014.03.023. Epub 2014 Mar 31. PubMed PMID: 24698664; PubMed Central PMCID: PMC4277649.
3: Phillips RS. Structure, mechanism, and substrate specificity of kynureninase. Biochim Biophys Acta. 2011 Nov;1814(11):1481-8. doi: 10.1016/j.bbapap.2010.12.003. Epub 2010 Dec 15. Review. PubMed PMID: 21167323; PubMed Central PMCID: PMC3102132.
4: Tao L, English AM. Protein S-glutathiolation triggered by decomposed S-nitrosoglutathione. Biochemistry. 2004 Apr 6;43(13):4028-38. PubMed PMID: 15049710.
5: Heiss C, Anderson J, Phillips RS. Differential effects of bromination on substrates and inhibitors of kynureninase from Pseudomonas fluorescens. Org Biomol Chem. 2003 Jan 21;1(2):288-95. PubMed PMID: 12929424.
6: Li K, Horanyi PS, Collins R, Phillips RS, Eriksson KL. Investigation of the role of 3-hydroxyanthranilic acid in the degradation of lignin by white-rot fungus Pycnoporus cinnabarinus. Enzyme Microb Technol. 2001 Mar 8;28(4-5):301-307. PubMed PMID: 11240183.
7: Li J, Huang FL, Huang KP. Glutathiolation of proteins by glutathione disulfide S-oxide derived from S-nitrosoglutathione. Modifications of rat brain neurogranin/RC3 and neuromodulin/GAP-43. J Biol Chem. 2001 Feb 2;276(5):3098-105. Epub 2000 Nov 1. PubMed PMID: 11060308.
8: Drysdale MJ, Reinhard JF. S-aryl cysteine S,S-dioxides as inhibitors of mammalian kynureninase. Bioorg Med Chem Lett. 1998 Jan 20;8(2):133-8. PubMed PMID: 9871640.
9: Mann CJ, Hardies SC, Nishimura JS. Site-directed mutagenesis of Escherichia coli succinyl-CoA synthetase. beta-Cys325 is a nonessential active site residue. J Biol Chem. 1989 Jan 25;264(3):1457-60. PubMed PMID: 2643599.
10: Abo-Ghalia M, Flegel M, Blanot D, Van Heijenoort J. Synthesis of inhibitors of the meso-diaminopimelate-adding enzyme from Escherichia coli. Int J Pept Protein Res. 1988 Sep;32(3):208-22. PubMed PMID: 3072305.
11: Zarkadas CG, Rochemont JA, Zarkadas GC, Karatzas CN, Khalili AD. Determination of methylated basic, 5-hydroxylysine, elastin crosslinks, other amino acids, and the amino sugars in proteins and tissues. Anal Biochem. 1987 Feb 1;160(2):251-66. PubMed PMID: 3578753.
12: Carson JF, Boggs LE. Synthesis and cyclization of S-(2-propynyl)-L-cysteine S-oxide and S-dioxide. J Org Chem. 1971 Feb 26;36(4):611-3. PubMed PMID: 5546396.