MedKoo Cat#: 597279 | Name: Selenodiglutathione

Description:

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

Selenodiglutathione is a primary Se metabolite conjugated with two glutathione (GSH) moieties.

Chemical Structure

Selenodiglutathione
CAS#33944-90-0

Theoretical Analysis

MedKoo Cat#: 597279

Name: Selenodiglutathione

CAS#: 33944-90-0

Chemical Formula: C20H32N6O12S2Se

Exact Mass: 692.0685

Molecular Weight: 691.58

Elemental Analysis: C, 34.73; H, 4.66; N, 12.15; O, 27.76; S, 9.27; Se, 11.42

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 #
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Synonym
Selenodiglutathione; Bis(glutathione) selenide; Seleno-di-glutathione;
IUPAC/Chemical Name
(2S)-9-((((S)-4-amino-1-carboxy-4-oxobutyl)amino)methyl)-2-(3-amino-3-oxopropyl)-5-((carboxymethyl)carbamoyl)-10-oxo-6,8-dithia-7-selena-3,11-diazatridecanedioic acid
InChi Key
BOCWNWYDWDFXLM-JYBOHDQNSA-N
InChi Code
InChI=1S/C20H32N6O12S2Se/c21-13(27)3-1-9(19(35)36)23-5-11(17(33)25-7-15(29)30)39-41-40-12(18(34)26-8-16(31)32)6-24-10(20(37)38)2-4-14(22)28/h9-12,23-24H,1-8H2,(H2,21,27)(H2,22,28)(H,25,33)(H,26,34)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11?,12?/m0/s1
SMILES Code
O=C(C(S[Se]SC(C(NCC(O)=O)=O)CN[C@@H](CCC(N)=O)C(O)=O)CN[C@@H](CCC(N)=O)C(O)=O)NCC(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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 691.58 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
1: Qiao Y, Huang X, Chen B, He M, Hu B. In vitro study on antagonism mechanism of glutathione, sodium selenite and mercuric chloride. Talanta. 2017 Aug 15;171:262-269. doi: 10.1016/j.talanta.2017.04.074. Epub 2017 May 5. PubMed PMID: 28551139. 2: Tobe T, Ueda K, Aoki A, Okamoto Y, Kojima N, Jinno H. Selenium uptake through cystine transporter mediated by glutathione conjugation. J Toxicol Sci. 2017;42(1):85-91. doi: 10.2131/jts.42.85. PubMed PMID: 28070112. 3: Fisher B, Yarmolinsky D, Abdel-Ghany S, Pilon M, Pilon-Smits EA, Sagi M, Van Hoewyk D. Superoxide generated from the glutathione-mediated reduction of selenite damages the iron-sulfur cluster of chloroplastic ferredoxin. Plant Physiol Biochem. 2016 Sep;106:228-35. doi: 10.1016/j.plaphy.2016.05.004. Epub 2016 May 9. PubMed PMID: 27182957. 4: Tobe T, Ueda K, Ando M, Okamoto Y, Kojima N. Thiol-mediated multiple mechanisms centered on selenodiglutathione determine selenium cytotoxicity against MCF-7 cancer cells. J Biol Inorg Chem. 2015 Jun;20(4):687-94. doi: 10.1007/s00775-015-1254-6. Epub 2015 Mar 18. PubMed PMID: 25783495. 5: Imai T, Kurihara T, Esaki N, Mihara H. Glutathione contributes to the efflux of selenium from hepatoma cells. Biosci Biotechnol Biochem. 2014;78(8):1376-80. doi: 10.1080/09168451.2014.918487. Epub 2014 Jun 17. PubMed PMID: 25130740. 6: Wallenberg M, Misra S, Wasik AM, Marzano C, Björnstedt M, Gandin V, Fernandes AP. Selenium induces a multi-targeted cell death process in addition to ROS formation. J Cell Mol Med. 2014 Apr;18(4):671-84. doi: 10.1111/jcmm.12214. Epub 2014 Jan 8. PubMed PMID: 24400844; PubMed Central PMCID: PMC4000118. 7: Freeman JL, Marcus MA, Fakra SC, Devonshire J, McGrath SP, Quinn CF, Pilon-Smits EA. Selenium hyperaccumulator plants Stanleya pinnata and Astragalus bisulcatus are colonized by Se-resistant, Se-excluding wasp and beetle seed herbivores. PLoS One. 2012;7(12):e50516. doi: 10.1371/journal.pone.0050516. Epub 2012 Dec 3. PubMed PMID: 23226523; PubMed Central PMCID: PMC3513300. 8: Fernandes AP, Wallenberg M, Gandin V, Misra S, Tisato F, Marzano C, Rigobello MP, Kumar S, Björnstedt M. Methylselenol formed by spontaneous methylation of selenide is a superior selenium substrate to the thioredoxin and glutaredoxin systems. PLoS One. 2012;7(11):e50727. doi: 10.1371/journal.pone.0050727. Epub 2012 Nov 30. PubMed PMID: 23226364; PubMed Central PMCID: PMC3511371. 9: Mao X, Hu B, He M, Chen B. High polar organic-inorganic hybrid coating stir bar sorptive extraction combined with high performance liquid chromatography-inductively coupled plasma mass spectrometry for the speciation of seleno-amino acids and seleno-oligopeptides in biological samples. J Chromatogr A. 2012 Sep 21;1256:32-9. doi: 10.1016/j.chroma.2012.07.080. Epub 2012 Aug 1. PubMed PMID: 22885051. 10: Weekley CM, Aitken JB, Vogt S, Finney LA, Paterson DJ, de Jonge MD, Howard DL, Witting PK, Musgrave IF, Harris HH. Metabolism of selenite in human lung cancer cells: X-ray absorption and fluorescence studies. J Am Chem Soc. 2011 Nov 16;133(45):18272-9. doi: 10.1021/ja206203c. Epub 2011 Oct 20. PubMed PMID: 21957893; PubMed Central PMCID: PMC3237720. 11: Lazard M, Ha-Duong NT, Mounié S, Perrin R, Plateau P, Blanquet S. Selenodiglutathione uptake by the Saccharomyces cerevisiae vacuolar ATP-binding cassette transporter Ycf1p. FEBS J. 2011 Nov;278(21):4112-21. doi: 10.1111/j.1742-4658.2011.08318.x. Epub 2011 Sep 29. PubMed PMID: 21880115. 12: Gammelgaard B, Rasmussen LH, Gabel-Jensen C, Steffansen B. Estimating intestinal absorption of inorganic and organic selenium compounds by in vitro flux and biotransformation studies in Caco-2 cells and ICP-MS detection. Biol Trace Elem Res. 2012 Feb;145(2):248-56. doi: 10.1007/s12011-011-9174-y. Epub 2011 Aug 24. PubMed PMID: 21863324. 13: Hoefig CS, Renko K, Köhrle J, Birringer M, Schomburg L. Comparison of different selenocompounds with respect to nutritional value vs. toxicity using liver cells in culture. J Nutr Biochem. 2011 Oct;22(10):945-55. doi: 10.1016/j.jnutbio.2010.08.006. Epub 2010 Dec 28. PubMed PMID: 21190829. 14: Khan MA, Wang F. Chemical demethylation of methylmercury by selenoamino acids. Chem Res Toxicol. 2010 Jul 19;23(7):1202-6. doi: 10.1021/tx100080s. PubMed PMID: 20499893. 15: Wallenberg M, Olm E, Hebert C, Björnstedt M, Fernandes AP. Selenium compounds are substrates for glutaredoxins: a novel pathway for selenium metabolism and a potential mechanism for selenium-mediated cytotoxicity. Biochem J. 2010 Jul 1;429(1):85-93. doi: 10.1042/BJ20100368. PubMed PMID: 20408818. 16: Olm E, Fernandes AP, Hebert C, Rundlöf AK, Larsen EH, Danielsson O, Björnstedt M. Extracellular thiol-assisted selenium uptake dependent on the x(c)- cystine transporter explains the cancer-specific cytotoxicity of selenite. Proc Natl Acad Sci U S A. 2009 Jul 7;106(27):11400-5. doi: 10.1073/pnas.0902204106. Epub 2009 Jun 22. PubMed PMID: 19549867; PubMed Central PMCID: PMC2708693. 17: Lu J, Berndt C, Holmgren A. Metabolism of selenium compounds catalyzed by the mammalian selenoprotein thioredoxin reductase. Biochim Biophys Acta. 2009 Nov;1790(11):1513-9. doi: 10.1016/j.bbagen.2009.04.013. Epub 2009 May 3. Review. PubMed PMID: 19406206. 18: Lothrop AP, Ruggles EL, Hondal RJ. No selenium required: reactions catalyzed by mammalian thioredoxin reductase that are independent of a selenocysteine residue. Biochemistry. 2009 Jul 7;48(26):6213-23. doi: 10.1021/bi802146w. PubMed PMID: 19366212; PubMed Central PMCID: PMC2754045. 19: Cui SY, Jin H, Kim SJ, Kumar AP, Lee YI. Interaction of glutathione and sodium selenite in vitro investigated by electrospray ionization tandem mass spectrometry. J Biochem. 2008 May;143(5):685-93. doi: 10.1093/jb/mvn023. Epub 2008 Feb 22. PubMed PMID: 18296716. 20: Tarze A, Dauplais M, Grigoras I, Lazard M, Ha-Duong NT, Barbier F, Blanquet S, Plateau P. Extracellular production of hydrogen selenide accounts for thiol-assisted toxicity of selenite against Saccharomyces cerevisiae. J Biol Chem. 2007 Mar 23;282(12):8759-67. Epub 2007 Jan 29. PubMed PMID: 17261587.