26289-39-4

Basic information

• Product Name: S-(2,4-Dinitrophenyl)-Glutathione
• Synonyms: 2,4-Dinitrophenyl-S-glutathione;Dinitrophenylglutathione;L-γGlu-S-(2,4-Dinitrophenyl)-L-Cys-Gly-OH;N-[L-γ-Glutamyl-S-(2,4-dinitrophenyl)-L-cysteinyl]glycine;γGlu-S-(2,4-Dinitrophenyl)-L-Cys-Gly-OH
• CAS NO: 26289-39-4
• Molecular Formula: C₁₆H₁₉N₅O₁₀S
• Molecular Weight: 473.41
• Product Categories: Glutathione S-Transferase Agents
• Mol File: 26289-39-4.mol
• Article Data: 42

Chemical Properties

• Melting Point: 210-212° dec.
• Boiling Point: 895.1°C at 760 mmHg
• Flash Point: 495.1°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 1.96E-34mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: -20°C Freezer
• PKA: 2.21±0.10(Predicted)
• CAS DataBase Reference: S-(2,4-Dinitrophenyl)-Glutathione(CAS DataBase Reference)
• NIST Chemistry Reference: S-(2,4-Dinitrophenyl)-Glutathione(26289-39-4)
• EPA Substance Registry System: S-(2,4-Dinitrophenyl)-Glutathione(26289-39-4)

Safety Data

• Hazardous Substances Data: 26289-39-4(Hazardous Substances Data)

Usage

Description

S-(2,4-Dinitrophenyl)-glutathione is a substrate for glutathione-S-transferase with a kinetic dissociation constant of 7 μM. In vitro, it is transported by multidrug resistance protein 1 (MDR1) and MDR3, which are transporters that confer resistance to some chemotherapeutics.

Chemical Properties

Light Yellow Solid

Uses

Different sources of media describe the Uses of 26289-39-4 differently. You can refer to the following data:
1. A substrate for Glutathione-S-Transferase, with a kinetically determined dissociation constant of 7uM
2. A substrate for Glutathione-S-Transferase, with a kinetically determined dissociation constant of 7uM.

Definition

ChEBI: A Glu-Cys-Gly tripeptide glutathione conjugate containing a 2,4-dinitrophenyl substituent on the S of Cys.

InChI:InChI=1/C16H19N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)

Upstream product

• 70-18-8 GLUTATHIONE 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 27025-41-8 Oxidized glutathione 
• 31283-98-4 4-phenyl 2,4-dinitrobenzenesulfonate 
• 54436-53-2 O,O-diethyl (2,4-dinitrophenyl) phosphate triester 
• 763114-26-7 2-fluoro-5-[(4’-oxo-3’H-phthalazin-1’-yl)methyl]benzoic acid 
• 420846-72-6 3-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid 
• 1431328-64-1 2,4-dinitrophenyl 4-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]-benzoyl]piperazine-1-yl-1-ium-1,2-diolate 
• 1431328-63-0 2,4-dinitrophenyl 4-[5-[(4-oxo-3H-phthalazin-1-yl)methyl]-benzoyl]piperazine-1-yl-1-ium-1,2-diolate 
• 1432473-79-4 N-(4-methyl-2-oxo-2H-chromen-7-yl)-2,4-dinitrobenzenesulfonamide 
• 1656-44-6 2,4-dinitrobenzenesulfonyl chloride 
• 1373156-67-2 2-(benzo[d]thiazol-2-yl)phenyl 2,4-dinitrobenzenesulfonate 
• 205432-08-2 O²-(2,4-dinitrophenyl) 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate 
• 584-48-5 2,4-dinitrobromobenzene 

Downstream Products

• 2217-55-2 bis(2,4-dinitrophenyl) disulphide 

Relevant articles and documents

Chemoselective bioconjugation based on modular click chemistry with 4-halocoumarins and aryl sulfonates

We report chemoselective and modular peptide bioconjugation using stoichiometric amounts of 4-halocoumarin and arylsulfonate agents that undergo metal-free C(sp2)-heteroatom bond formation at micromolar concentrations. The underlyingipso-substi

Metal complexes with biologically important ligands, CLXI [1]. Halfsandwich complexes with tert-leucine, dipeptides, pentaglycine and glutathione

Reactions of L-tert-Leucine (tert-butylglycine), tert-leucine methyl ester, GlyValOMe, and Leu-AlaOMe with the chloro-bridged complexes [Cp*IrCl 2]2, [(p-cymene)RuCl2]2 or [(C 6Me6)RuCl2]2 in the presence of NaOMe give the complexes [Cp*Ir(Cl)NH2CH(R)CO2] (1), [(p-cymene)Ru(Cl)-NH2CH(R)CO2] (2), Cp*Ir(Cl 2)[NH2CH(R)CO2Me] (5), {(C6Me 6)Ru(Cl)[NH2CH2CONHCH(R)-CO2Me]} +Cl- (6), [Cp*Ir(Cl)NH2CH 2CONCH(R)CO2Me] (7), [Cp*Ir(Cl)NH 2CH(CH2CHMe2)-CONCH(R)CO2Me)] (8), and Cp*Ir(Cl2)[NH2CH2CONHCH(R)CO 2Me) (9). With pentaglycine the complexes [Cp*Ir(Cl 2)(pentaglycinate+Na+)] (10) and [(C 6Me6)Ru(pentaglycineOMe-H+)] (11) could be isolated. Coordination of one equivalent of the S-protected tripeptide glutathione to [Cp*Ir(Cl)] and to [(C6Me6)Ru(Cl)] was observed. Some in situ prepared (p-cymene)Ru complexes with deprotonated dipeptide esters were tested as catalysts and the complex [(p-cymene)Ru(Cl) (NH2CH(CHMeEt)NCH (CHMe2)CO2tert-Bu)] gave a yield of 73% and moderate entantiomeric excess (36% ee) in the transfer hydrogenation of acetophenone to 2-propanol.

Contributions of Thiolate "Desolvation" to Catalysis by Glutathione S-Transferase Isozymes 1-1 and 2-2: Evidence from Kinetic Solvent Isotope Effects

Kinetic solvent isotope effects on the reaction of glutathione with 1-chloro-2,4-dinitrobenzene catalyzed by rat liver glutathione S-transferase isozymes 1-1 and 2-2 (as expressed in Escherichia coli) have been measured. At pH (and pD) = 8.0, the isotope

Enhanced liver-targeting via coadministration of 10-Hydroxycamptothecin polymeric micelles with vinegar baked Radix Bupleuri

Background: Vinegar baked Radix Bupleuri (VBRB) is a wildly used traditional Chinese medicine, it could be used as a meridian guided drug to enhance liver targeting efficiency of the delivered drug in addition to its therapeutic effect. Purpose: To invest

GLUTATHIONE S-TRANSFERASE FROM OXADIAZON TREATED CHICKPEA

Glutathione S-transferase was purified more than 150-fold with ca 70 percent recovery from chickpea shoots after treatment with 10 ppm of the herbicide oxadiazon.The purification steps involved ammonium sulphate precipitation, gel filtration and affinity

Structure-based design and application of an engineered glutathione transferase for the development of an optical biosensor for pesticides determination

In the present work, a structure-based design approach was used for the generation of a novel variant of synthetic glutathione transferase (PvGmGSTU) with higher sensitivity towards pesticides. Molecular modelling studies revealed Phe117 as a key residue

Glutathione S-transferase catalysed dehalogenation of haloaromatic compounds which lack nitro groups near the reaction centre

A comparative kinetic study of the rat-liver glutathione S-transferase catalysed dehalogenation of fluoro- and chloroaromatic compounds showed no significant decrease of the F/Cl mobility ratio on going from substrates that carry an ortho-nitro group to t

A highly sensitive two-photon fluorescent probe for glutathione with near-infrared emission at 719?nm and intracellular glutathione imaging

A near-infrared turn-on two-photon fluorescent probe ST-BODIPY for glutathione-specific detection was designed and synthesized by attaching triphenylamine to BODIPY skeleton through the Knoevenagel condensation to prolong the maximum emission wavelength t

Twisted intramolecular charge transfer and aggregation-enhanced emission characteristics based quinoxaline luminogen: photophysical properties and a turn-on fluorescent probe for glutathione

Developing solid and aggregate state emitters with large Stokes shifts has long been a significant challenge in the detection and bioimaging fields. In this study, a novel quinoxaline-based luminogen (QUPY) with twisted intramolecular charge transfer (TICT) and aggregation-enhanced emission (AEE) characteristics has been designed and synthesized. Its pyridine salt derivative (QUPY-S) was also AEE-active and could be utilized as a fluorescent “turn-on” probe for the specific detection of glutathione (GSH). The cleavage of dinitrophenyl ether from QUPY-S by GSH generated AEE-active and less water-soluble QUPY, which exhibited a “turn-on” fluorescence response at around 516 nm. This reaction-based probe showed a large Stokes shift (131 nm), low detection limit (434 nM), fast response time, and low toxicity. QUPY-S was successfully applied for the detection of GSH in bovine serum samples with recoveries ranging from 91.9% to 100.7%. Additionally, QUPY-S could detect GSH in HeLa cells by confocal laser scanning microscopy.

Analysis of Arabidopsis glutathione-transferases in yeast

The genome of Arabidopsis thaliana encodes 54 functional glutathione transferases (GSTs), classified in seven clades. Although plant GSTs have been implicated in the detoxification of xenobiotics, such as herbicides, extensive redundancy within this large

Compared reactivites of trypanothione and glutathione in conjugation reactions

In order to compare the non-enzymatic capacities of the xenobiotic conjugation of trypanothione (a spermidine-glutathione conjugate unique to kinetoplastidae) and glutathione, the reactivity of their respective thiols was investigated. The acido-basic properties of both compounds and their nucleophilicity toward Ellman's reagent and 1-chloro-2,4-dinitrobenzene were studied. Our results show that although glutathione is a better nucleophile than trypanothione, the latter is more reactive because it is more ionized in a large pH range. This pH range likely includes the pH to which such conjugation reactions are expected to happen in vivo. Thus, the better conjugation capacity of trypanothione could make it the cornerstone for the xenobiotic detoxication of trypanosomatidae.

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A PET-based turn-on fluorescent probe for sensitive detection of thiols and H2S and its bioimaging application in living cells, tissues and zebrafish

A turn-on fluorescent probe, containing a naphthalimide platform and benzothiazole modified by the 2,4-dinitrobenzenesulfonyl (DNBS) group, was designed as an efficient fluorescent probe for sensitive detection of biological thiols and H2S spec