S-DNP-Glutathione

Base Information

• Chemical Name: S-DNP-Glutathione
• CAS No.: 26289-39-4
• Molecular Formula: C16H19 N5 O10 S
• Molecular Weight: 473.42
• NSC Number: 638615,131112
• DSSTox Substance ID: DTXSID00865277
• ChEMBL ID: CHEMBL176507
• Mol file: 26289-39-4.mol

Synonyms:S-DNP-Glutathione;NSC-638615;2-amino-5-[[1-(carboxymethylamino)-3-(2,4-dinitrophenyl)sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;NSC638615;NSC-131112;S-dinitrophenyl glutathione;CHEMBL176507;SCHEMBL1524585;DTXSID00865277;NSC131112;FT-0667594;A818428;J-016365;gamma-Glutamyl-S-(2,4-dinitrophenyl)cysteinylglycine;2-amino-5-[[1-(carboxymethylamino)-3-[(2,4-dinitrophenyl)thio]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;2-azanyl-5-[[3-(2,4-dinitrophenyl)sulfanyl-1-(2-hydroxy-2-oxoethylamino)-1-oxidanylidene-propan-2-yl]amino]-5-oxidanylidene-pentanoic acid

Chemical Property of S-DNP-Glutathione

Chemical Property:

• Vapor Pressure: 1.96E-34mmHg at 25°C
• Melting Point: 210-212° dec.
• Boiling Point: 895.1°C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 495.1°C
• PSA: 275.76000
• Density: 1.61g/cm³
• LogP: 2.00130
• Storage Temp.: -20°C Freezer
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 473.08526299
• Heavy Atom Count: 32
• Complexity: 740

Purity/Quality:

99%, ^*data from raw suppliers

S-(2,4-Dinitrophenyl)-Glutathione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
• 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.
• Uses: A substrate for Glutathione-S-Transferase, with a kinetically determined dissociation constant of 7uM A substrate for Glutathione-S-Transferase, with a kinetically determined dissociation constant of 7uM.

Technology Process of S-DNP-Glutathione

There total 24 articles about S-DNP-Glutathione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

GLUTATHIONE (70-18-8) + 4-phenyl 2,4-dinitrobenzenesulfonate (31283-98-4) → S-(2,4-dinitrophenyl)glutathione (26289-39-4,32728-50-0)

Guidance literature:

In acetonitrile; at 25 ℃; for 2h; chemoselective reaction;

DOI:10.1039/d1ra03271b

Reference yield: 99.0%

Oxidized glutathione (27025-41-8,121-24-4,87140-29-2) + 4-phenyl 2,4-dinitrobenzenesulfonate (31283-98-4) → S-(2,4-dinitrophenyl)glutathione (26289-39-4,32728-50-0)

Guidance literature:

In acetonitrile; for 24h; chemoselective reaction;

DOI:10.1039/d1ra03271b

Reference yield: 64.0%

GLUTATHIONE (70-18-8) + C29H20N4O9S2 → S-(2,4-dinitrophenyl)glutathione (26289-39-4,32728-50-0) + C23H18N2O3S

Guidance literature:

In ethanol; at 20 ℃; for 6h; Solvent; Kinetics;

DOI:10.1039/c8nj04926b

upstream raw materials:

glutathion

2,4-Dinitrofluorobenzene

1-chloro-2,4-dinitro-benzene

O²-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate

Refernces

• 1、 Cao, Wenbing,Qin, Xuewen,Wang, Yong,Dai, Zhen,Dai, Xianyin,Wang, Haoyu,Xuan, Weimin,Zhang, Yingming,Liu, Yu,Liu, Tao. "A General Supramolecular Approach to Regulate Protein Functions by Cucurbit[7]uril and Unnatural Amino Acid Recognition". . p. 11196 - 11200. Retrieved 2021.
• 2、 Yamamoto, Kohji,Usuda, Kazuhiro,Kakuta, Yoshimitsu,Kimura, Makoto,Higashiura, Akifumi,Nakagawa, Atsushi,Aso, Yoichi,Suzuki, Mamoru. "Structural basis for catalytic activity of a silkworm Delta-class glutathione transferase". . p. 1469 - 1474. Retrieved 2012.
• 3、 Van Der Aar, Ellen M.,De Groot, Marcel J.,Bijloo, Greetje J.,Van Der Goot, Henk,Vermeulen, Nico P. E.. "Structure-activity relationships for the glutathione conjugation of 2-substituted 1-chloro-4-nitrobenzenes by rat glutathione S-transferase 4-4". . p. 527 - 534. Retrieved 1996.
• 4、 Tang, Shiao-Shek,Chang, Gu-Gang. "Nucleophilic Aromatic Substitution of Glutathione and 1-Chloro-2,4-dinitrobenzene in Reverse Micelles. A Model System To Assess the Transition-State Stabilization in Glutathione Transferase Catalyzed Conjugation". . p. 6183 - 6185. Retrieved 1995.
• 5、 Pezzola, Silvia,Antonini, Giovanni,Geroni, Cristina,Beria, Italo,Colombo, Maristella,Broggini, Massimo,Mongelli, Nicola,Leboffe, Loris,MacArthur, Robert,Mozzi, Alessia Francesca,Federici, Giorgio,Caccuri, Anna Maria. "Role of glutathione transferases in the mechanism of brostallicin activation". . p. 226 - 235. Retrieved 2010.
• 6、 Bolton,Ahokas. "Purification and characterization of hepatic glutathione transferases from an insectivorous marsupial, the brown antechinus (Antechinus stuartii)". . p. 573 - 586. Retrieved 1997.
• 7、 Wang, Bing,Peng, Yingjie,Zhang, Tianlong,Ding, Jianping. "Crystal structures and kinetic studies of human Kappa class glutathione transferase provide insights into the catalytic mechanism". . p. 215 - 225. Retrieved 2011.
• 8、 Matsushima, Aoi,Oda, Keisuke,Mori, Nobuhiro,Murakami, Teruo. "Modulation of multidrug resistance-associated proteins function in erythrocytes in glycerol-induced acute renal failure rats". . p. 172 - 181. Retrieved 2017.
• 9、 Labrou, Nikolaos E.,Muharram, Magdy Mohamed,Abdelkader, Maged Saad. "Delineation of the structural and functional role of Arg111 in GSTU4-4 from Glycine max by chemical modification and site-directed mutagenesis". . p. 1315 - 1321. Retrieved 2016.
• 10、 Liou, Jong-Yan,Huang, Ter-Mei,Chang, Gu-Gang. "Reverse micelles as a catalyst for the nucleophilic aromatic substitution between glutathione and 2,4-dinitrochlorobenzene". . p. 2171 - 2176. Retrieved 1999.