OBI-3424 - ≥99% , DNA cross-linking agent, CAS No.2097713-68-1, DNA cross-linking agent

CAS: 2097713-68-1 Cat. No.: O650664 Molecular Weight: 460.42 PubChem CID: 126961329

GRADE & PURITY ≥99%

Synonyms

2097713-68-1 | Obi 3424 | Phosphinic acid, P,P-bis(1-aziridinyl)-, (1R)-1-(3-(3-((dimethylamino)carbonyl)phenoxy)-4-nitrophenyl)ethyl ester | TH3424 | TH-3424 | 3-(5-((1R)-1-(Bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-N,N-dimethylbenzamide | G

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

OBI-3424 (TH-3424) is a proagent that is selectively converted by AKR1C3 (aldo-keto reductase 1C3) to a potent DNA-alkylating agent. OBI-3424 can be used for hepatocellular carcinoma, castrate-resistant prostate cancer , and acute lymphoblastic leukemia (ALL) research.

In Vitro

OBI-3424 exerts potent cytotoxicity against the H460 lung cancer cell line (IC 50 of 4.0 nM). OBI-3424 exhibits potent cytotoxicity, in particular against cell lines derived from T-ALL with high AKR1C3 expression, with IC 50 values in the low nM range. OBI-3424 also exerts potent cell killing against ALL PDXs, and the median IC 50 values were 60.3 nM for B-ALL, 9.7 nM for T-ALL and 31.5 nM for ETP-ALL. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

OBI-3424 (0.5-2.5 mg/kg; i.p.; once weekly; for 3 weeks) treatment induces regressions in PDXs mice and results in prolongation of mouse event-free survival . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female NSG mice (20-25 g) bearing patient-derived xenografts (PDX) Dosage: 0.5 mg/kg, 1 mg/kg, 2.5 mg/kg Administration: Intraperitoneal injection; once weekly; for 3 weeks Result: Resulted in prolongation of mouse event-free survival.

Form:-20°C Solid,>-20°C Oil

Specifications

Synonyms

2097713-68-1 | Obi 3424 | Phosphinic acid, P, P-bis(1-aziridinyl)-, (1R)-1-(3-(3-((dimethylamino)carbonyl)phenoxy)-4-nitrophenyl)ethyl ester | TH3424 | TH-3424 | 3-(5-((1R)-1-(Bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-N, N-dimethylbenzamide | G

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

OBI-3424 (TH-3424) is a proagent that is selectively converted by AKR1C3 (aldo-keto reductase 1C3) to a potent DNA-alkylating agent. OBI-3424 can be used for hepatocellular carcinoma, castrate-resistant prostate cancer , and acute lymphoblastic leukemia (

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

CROSS-LINKING AGENT

Mechanism of action

DNA cross-linking agent

Purity

≥99%

Product Properties

• ALogP: 2.2

Names and Identifiers

• Canonical Smiles: CC(C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4
• IUPAC Name: 3-[5-[(1R)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide
• InChIKey: NWGZZGNICQFUHV-OAHLLOKOSA-N
• INCHI: 1S/C21H25N4O6P/c1-15(31-32(29,23-9-10-23)24-11-12-24)16-7-8-19(25(27)28)20(14-16)30-18-6-4-5-17(13-18)21(26)22(2)3/h4-8,13-15H,9-12H2,1-3H3/t15-/m1/s1
• Isomeric SMILES: C[C@H](C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4
• Alternate CAS: 2097713-68-1
• PubChem CID: 126961329
• Molecular Weight: 460.42

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Diphenylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Diphenylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylethers
• Alternative Parents: Diarylethers Nitrobenzenes Benzamides Phenoxy compounds Phenol ethers Nitroaromatic compounds Benzoyl derivatives Phosphoric monoester diamides Phosphate esters Tertiary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Aziridines Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Diphenylether - Diaryl ether - Nitrobenzene - Benzoic acid or derivatives - Benzamide - Phenoxy compound - Nitroaromatic compound - Phenol ether - Benzoyl - Phosphoric monoester diamide - Organic phosphoric acid amide - Phosphoric acid ester - Organic phosphoric acid derivative - Tertiary carboxylic acid amide - Organic nitro compound - C-nitro compound - Carboxamide group - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic oxoazanium - Ether - Carboxylic acid derivative - Aziridine - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 50 mg/mL (108.60 mM; Need ultrasonic)