Darinaparsin

Base Information

• Chemical Name: Darinaparsin
• CAS No.: 69819-86-9
• Molecular Formula: C₁₂H₂₂AsN₃O₆S
• Molecular Weight: 411.311
• European Community (EC) Number: 684-606-6
• UNII: 9XX54M675G
• ChEMBL ID: CHEMBL3247378
• DSSTox Substance ID: DTXSID80220108
• NCI Thesaurus Code: C61490
• Nikkaji Number: J2.194.626E
• Wikidata: Q27166111
• Wikipedia: Darinaparsin
• Mol file: 69819-86-9.mol

Synonyms:clarinaparsin;darinaparsin;dimethylarsinous glutathione;DMAs(III)G;DMAs(III)SG;S-(dimethylarsino)-glutathione;S-(dimethylarsino)glutathione;S-dimethylarsino-glutathione;ZIO 101;ZIO-101;ZIO101

Chemical Property of Darinaparsin

Chemical Property:

• PKA: 2.21±0.10(Predicted)
• PSA: 191.10000
• LogP: 1.22930
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 411.044526
• Heavy Atom Count: 23
• Complexity: 449

Purity/Quality:

99%, ^*data from raw suppliers

Darinaparsin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[As](C)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
• Isomeric SMILES: C[As](C)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• Recent ClinicalTrials: A Phase-II Trial of ZIO 101 in Advanced Hepatocellular Carcinoma
• Recent NIPH Clinical Trials: None
• Description: Darinaparsin is a dimethylated arsenic linked to glutathione. It is cytotoxic to DU145, LNCaP, and PC3 prostate cancer cells (IC50s = 5-10 μM) and patient-derived primary prostate cancer cells (IC50s = 2.5-20 μM), as well as Jurkat T cell lymphoma and L540 Hodgkin lymphoma cells (IC50s = 2.7 and 1.3 μM, respectively). It decreases the tumor-initiating subpopulation in DU145 and PC3 cells and halts the cell cycle in the G2/M phase. Darinaparsin decreases transcription of Gli-2, a transcription factor that mediates Sonic hedgehog signaling, when used at a concentration of 1.5 but not 3 μM. It decreases SHP1 phosphatase activity and increases ERK phosphorylation. Darinaparsin reduces tumor growth in DU145 and PC3 prostate cancer mouse xenograft models when administered at a dose of 100 mg/kg every other day.

Technology Process of Darinaparsin

There total 7 articles about Darinaparsin 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: 75.0%

GLUTATHIONE (70-18-8) + Dimethylchloroarsine (557-89-1) → Darinaparsin (69819-86-9)

Guidance literature:

With pyridine; In 1,2-dimethoxyethane; at 20 ℃; for 4h; Heating / reflux;

Reference yield:

cysteinyldimethylthioarsenite (91919-78-7) + GLUTATHIONE (70-18-8) → L-Cysteine (52-90-4) + Darinaparsin (69819-86-9)

Guidance literature:

With water; at 25 ℃;

DOI:10.1039/c3ob40268a

Reference yield:

tetramethyldiarsine (471-35-2) → Darinaparsin (69819-86-9)

Guidance literature:

tetramethyldiarsine; In dichloromethane; at 20 ℃;

With oxygen; for 1h;

upstream raw materials:

GLUTATHIONE

sodium cacodylate

Dimethylchloroarsine

Dimethylarsinic acid

Refernces

• 1、 Cheng, Jinduo,Ji, Wenjuan,Ma, Suze,Ji, Xinjian,Deng, Zixin,Ding, Wei,Zhang, Qi. "Characterization and Mechanistic Study of the Radical SAM Enzyme ArsS Involved in Arsenosugar Biosynthesis". supporting information. p. 7570 - 7575. Retrieved 2021/03/01.
• 2、 Bohle, D. Scott,Gu, Yuxuan. "Facile dimethylarsenic exchange and pyramidal inversion in its cysteine and glutathione adducts". . p. 2578 - 2581. Retrieved 2013/06/05.