Page last updated: 2024-12-07

s-(2,4-dinitrophenyl)glutathione

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

S-(2,4-dinitrophenyl)glutathione (DNP-GSH) is a hapten, a small molecule that can bind to a larger molecule (such as a protein) and elicit an immune response. DNP-GSH is formed by the conjugation of glutathione with 2,4-dinitrochlorobenzene (DNCB), a common environmental allergen. It plays an important role in the detoxification of DNCB and other electrophilic compounds. The study of DNP-GSH provides insight into the mechanisms of detoxification and immune responses to haptens. It has been used extensively as a model system to study hapten-specific antibody responses and to investigate the role of the major histocompatibility complex (MHC) in antigen presentation. DNP-GSH also has potential applications in the development of immunotherapies for allergic diseases.'

S-(2,4-dinitrophenyl)glutathione : A glutathione conjugate in which the thiol hydrogen of glutathione has been replaced by a 2,4-dinitrophenyl group. [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 CID97535
CHEMBL ID1232997
CHEBI ID8927
SCHEMBL ID1524589
MeSH IDM0095728

Synonyms (36)

Synonym
CHEMBL1232997
nsc-131112
glutathione s-(2,4 dinitrobenzene)
GDN ,
26289-39-4
s-(2,4-dinitrophenyl)glutathione
1-(s-glutathionyl)-2,4-dinitrobenzene
dnp-sgc
dnp-s-glutathione
DB02458
dinitrophenyl-s-glutathione
nsc 131112
ccris 1806
glycine, n-(s-(2,4-dinitrophenyl)-n-l-gamma-glutamyl-l-cysteinyl)-
gs-dnp
gsh-s-dnp
(2s)-2-amino-5-[[(2r)-1-(carboxymethylamino)-3-(2,4-dinitrophenyl)sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
l-gamma-glutamyl-s-(2,4-dinitrophenyl)-l-cysteinylglycine
CHEBI:8927 ,
hl4g8d2c8t ,
unii-hl4g8d2c8t
FXEUKVKGTKDDIQ-UWVGGRQHSA-N
SCHEMBL1524589
s-(2,4-dinitrophenyl)-glutathione
AKOS030254251
(2s)-2-amino-4-{[(1r)-1-[(carboxymethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoic acid
AS-70062
Q27108192
glycine, l-.gamma.-glutamyl-s-(2,4-dinitrophenyl)-l-cysteinyl-
glycine, l-|a-glutamyl-s-(2,4-dinitrophenyl)-l-cysteinyl-
D92971
glycine, l-gamma-glutamyl-s-(2,4-dinitrophenyl)-l-cysteinyl-
CS-0137775
HY-137330
DTXSID001043700
glycine,l-g-glutamyl-s-(2,4-dinitrophenyl)-l-cysteinyl-

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Rhei Rhizoma extract (100 microg/ml) significantly suppressed the CYP3A-mediated 6beta-hydroxylation of testosterone in hepatic microsomes, and increased the extent of bioavailability of midazolam, a typical CYP3A substrate, in rats."( Interaction of Rhei Rhizoma extract with cytochrome P450 3A and efflux transporters in rats.
Akashi, H; Kida, M; Mori, M; Mori, N; Murakami, T; Yokooji, T; Yoshihara, S, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
glutathione conjugateAny bioconjugate in which glutathione is one of the components
[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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1339473Antitrypanosomal activity against Trypanosoma cruzi MHOM/BR/OO/Y trypomastigotes infected in CD1 mouse peritoneal macrophages after 3 days2017Bioorganic & medicinal chemistry, 02-15, Volume: 25, Issue:4
Antiprotozoal glutathione derivatives with flagellar membrane binding activity against T. brucei rhodesiense.
AID1339471Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB900 bloodstream trypomastigote forms measured on day 3 post treatment by alamar blue assay2017Bioorganic & medicinal chemistry, 02-15, Volume: 25, Issue:4
Antiprotozoal glutathione derivatives with flagellar membrane binding activity against T. brucei rhodesiense.
AID1339472Antileishmanial activity against Leishmania donovani MHOM/ET/67/HU3 amastigotes infected in CD1 mouse peritoneal macrophages after 5 days2017Bioorganic & medicinal chemistry, 02-15, Volume: 25, Issue:4
Antiprotozoal glutathione derivatives with flagellar membrane binding activity against T. brucei rhodesiense.
AID1128174Drug level in aqueous phosphate buffer at pH 7.4 treated with 2-(2,4-dinitrophenoxy)-1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)diazene oxide measured after 2 half-lives by LC/MS analysis in presence of GSH2014Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6
Nitric oxide (NO) releasing poly ADP-ribose polymerase 1 (PARP-1) inhibitors targeted to glutathione S-transferase P1-overexpressing cancer cells.
AID1128196Retention time of the compound in human A549 cells treated with 2-(2,4-dinitrophenoxy)-1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)diazene oxide at 10 uM by LC/MS/MS analysis2014Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6
Nitric oxide (NO) releasing poly ADP-ribose polymerase 1 (PARP-1) inhibitors targeted to glutathione S-transferase P1-overexpressing cancer cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (149)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (11.41)18.7374
1990's78 (52.35)18.2507
2000's43 (28.86)29.6817
2010's10 (6.71)24.3611
2020's1 (0.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.84

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index9.84 (24.57)
Research Supply Index5.02 (2.92)
Research Growth Index4.86 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (2.65%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other147 (97.35%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]