Page last updated: 2024-09-24

selenodiglutathione

Description

selenodiglutathione : A thioselenide in which a selenium atom is attached to the sulfur atoms of two molecules of glutathione. It is an initial metabolite of selenite, SeO3(2-). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID108069
CHEBI ID26634
MeSH IDM0068687

Synonyms (17)

Synonym
selenodiglutathione
l-glutamine, n,n'-(selenobis(thio(1-(((carboxymethyl)amino)carbonyl)-2,1-ethanediyl)))bis-
glutamine, n,n'-((selenodithio)bis(1-((carboxymethyl)carbamoyl)ethylene))di-, l-
33944-90-0
gssesg
C18870
seleno-di-glutathione
bis(glutathione) selenide
CHEBI:26634
n,n'-((selenodithio)bis(1-((carboxymethyl)carbamoyl)ethylene))di-l-glutamine
n,n'-[(selenodithio)bis{1-[(carboxymethyl)carbamoyl]ethylene}]di-l-glutamine
gs-se-sg
seleno-diglutathione
AKOS025214052
(2s)-2-amino-5-[[(2r)-3-[(2r)-2-[[(4s)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]sulfanylselanylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Q27109906
DTXSID701315520

Research Excerpts

Overview

ExcerptReference
"Selenodiglutathione (GSSeSG) is a primary Se metabolite conjugated with two glutathione (GSH) moieties."( Ando, M; Kojima, N; Okamoto, Y; Tobe, T; Ueda, K, 2015)

Effects

ExcerptReference
"Selenodiglutathione has been shown to exert more cytotoxic effect than selenite in both assay systems."( Cho, DY; Chung, AS; Jung, U, 1999)

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
thioselenideA sulfur molecular entity containing a selenium-sulfur bond.
glutathione derivativeAny organonitrogen compound derived from the Glu-Cys-Gly tripeptide glutathione.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

selenodiglutathione is involved in 1 pathway(s), involving a total of 13 unique proteins and 17 unique compounds

PathwayProteinsCompounds
Selenium Metabolism1317

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (11.76)18.7374
1990's13 (38.24)18.2507
2000's7 (20.59)29.6817
2010's6 (17.65)24.3611
2020's4 (11.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (8.82%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other31 (91.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (6)

ArticleYear
Thiol-mediated multiple mechanisms centered on selenodiglutathione determine selenium cytotoxicity against MCF-7 cancer cells.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, Volume: 20, Issue: 4
2015
Comparison of different selenocompounds with respect to nutritional value vs. toxicity using liver cells in culture.
The Journal of nutritional biochemistry, Volume: 22, Issue: 10
2011
Extracellular thiol-assisted selenium uptake dependent on the x(c)- cystine transporter explains the cancer-specific cytotoxicity of selenite.
Proceedings of the National Academy of Sciences of the United States of America, Jul-07, Volume: 106, Issue: 27
2009
Induction of apoptosis by selenite and selenodiglutathione in HL-60 cells: correlation with cytotoxicity.
Biochemistry and molecular biology international, Volume: 47, Issue: 5
1999
The selenium metabolite selenodiglutathione induces cell death by a mechanism distinct from H2O2 toxicity.
Carcinogenesis, Volume: 16, Issue: 7
1995
Toxic effects of selenodiglutathione on pregnant mice.
Toxicology letters, Volume: 21, Issue: 1
1984
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (2)

ArticleYear
Induction of apoptosis by selenite and selenodiglutathione in HL-60 cells: correlation with cytotoxicity.
Biochemistry and molecular biology international, Volume: 47, Issue: 5
1999
Toxic effects of selenodiglutathione on pregnant mice.
Toxicology letters, Volume: 21, Issue: 1
1984
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]