Apoptozole - ≥99% , CAS No.1054543-47-3

CAS: 1054543-47-3 Cat. No.: A345787 Molecular Weight: 625.56

GRADE & PURITY ≥99%

Synonyms

CCG-270274 | Apoptosis Activator VII, Apoptozole | 4-[[2-[3,5-bis(trifluoromethyl)phenyl]-4,5-bis(4-methoxyphenyl)-1H-imidazol-1-yl]methyl]benzamide | 1054543-47-3 | UNII-WD0EH16QCD | 4-((2-(3,5-bis(trifluoromethyl)phenyl)-4,5-bis(4-methoxyphenyl)-1H-imid

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Apoptosis Activator VII, Apoptozole is a cell-permeable imidazole compound that directly binds anti-apoptotic chaperone Hsc70 and its inducible homologue Hsp70 (K|d|= 210 and 140 nM, respectively). Apoptozole is shown to effectively inhibit the proliferation of SK-OV-3, HCT-15, and A549 cancer cell lines (IC|50|= 220, 250 and 130 nM, respectively) and induce 90% apoptotic cell death in P19 embryonic carcinoma and A549 lung cancer cultures after 12 hours drug treatment (1 μM).

Specifications

Synonyms

CCG-270274 | Apoptosis Activator VII, Apoptozole | 4-[[2-[3, 5-bis(trifluoromethyl)phenyl]-4, 5-bis(4-methoxyphenyl)-1H-imidazol-1-yl]methyl]benzamide | 1054543-47-3 | UNII-WD0EH16QCD | 4-((2-(3, 5-bis(trifluoromethyl)phenyl)-4, 5-bis(4-methoxyphenyl)-1H-imid

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Apoptozole induces caspase dependent apoptosis by blocking interaction of HSP70 with APAF-1, without affecting interactions of HSP70 with ASK1, JNK, BAX, and AIF. However, apoptozole may form aggregates under aqueous conditions that could interact with HS

Storage

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

INHIBITOR

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504769898
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504769898
• Canonical Smiles: COC1=CC=C(C=C1)C2=C(N(C(=N2)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)CC4=CC=C(C=C4)C(=O)N)C5=CC=C(C=C5)OC
• IUPAC Name: 4-[[2-[3,5-bis(trifluoromethyl)phenyl]-4,5-bis(4-methoxyphenyl)imidazol-1-yl]methyl]benzamide
• InChIKey: ZIMMTPFXOMAJTQ-UHFFFAOYSA-N
• INCHI: 1S/C33H25F6N3O3/c1-44-26-11-7-20(8-12-26)28-29(21-9-13-27(45-2)14-10-21)42(18-19-3-5-22(6-4-19)30(40)43)31(41-28)23-15-24(32(34,35)36)17-25(16-23)33(37,38)39/h3-17H,18H2,1-2H3,(H2,40,43)
• Isomeric SMILES: COC1=CC=C(C=C1)C2=C(N(C(=N2)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)CC4=CC=C(C=C4)C(=O)N)C5=CC=C(C=C5)OC
• Molecular Weight: 625.56
• Reaxy-Rn: 18476007
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=18476007&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azoles
      • Subclass Imidazoles
        • Level5 Substituted imidazoles
          • Level6 Phenylimidazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azoles
• Subclass: Imidazoles
• Intermediate Tree Nodes: Substituted imidazoles
• Direct Parent: Phenylimidazoles
• Alternative Parents: Trifluoromethylbenzenes 1,2,4,5-tetrasubstituted imidazoles Benzamides Phenoxy compounds Anisoles Methoxybenzenes Benzoyl derivatives Alkyl aryl ethers N-substituted imidazoles Heteroaromatic compounds Primary carboxylic acid amides Azacyclic compounds Hydrocarbon derivatives Organic oxides Alkyl fluorides Organofluorides Organonitrogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-phenylimidazole - 5-phenylimidazole - 4-phenylimidazole - Trifluoromethylbenzene - 1,2,4,5-tetrasubstituted imidazole - Benzamide - Benzoic acid or derivatives - Anisole - Phenoxy compound - Benzoyl - Phenol ether - Methoxybenzene - Alkyl aryl ether - Benzenoid - Monocyclic benzene moiety - N-substituted imidazole - Heteroaromatic compound - Primary carboxylic acid amide - Carboxamide group - Azacycle - Ether - Carboxylic acid derivative - Hydrocarbon derivative - Organohalogen compound - Alkyl fluoride - Organic oxygen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Alkyl halide - Organic oxide - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (50 mg/ml), and ethanol (5 mg/ml).
• Refractive Index: n20D~1.57 (Predicted)
• Melt Point(°C): 223-225° C
• Molecular Weight: 625.600 g/mol
• XLogP3: 7.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 625.18 Da
• Monoisotopic Mass: 625.18 Da
• Topological Polar Surface Area: 79.400 Ų
• Heavy Atom Count: 45
• Formal Charge: 0
• Complexity: 936.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wei Jiang, Zuoxiu Tie, Chi Yu, Yu Chen, Dan Liu, Bin Li.  (2023)  An engineered nanoplatform inhibiting energy metabolism and lysosomal activity of tumor cells to multiply cisplatin-based chemotherapy.  BIOMATERIALS,      [PMID:37879187] [10.1016/j.biomaterials.2023.122354]