Selenodiglutathione

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

MedKoo CAT#: 597279

CAS#: 33944-90-0

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

Chemical Structure

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Selenodiglutathione
CAS# 33944-90-0
Instruction

Theoretical Analysis

MedKoo Cat#: 597279
Name: Selenodiglutathione
CAS#: 33944-90-0
Chemical Formula: C20H32N6O12S2Se
Exact Mass: 692.07
Molecular Weight: 691.580
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 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.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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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.