SML1503

Apcin

≥98% (HPLC)

• Synonym(s): 2-(2-Methyl-5-nitroimidazol-1-yl)ethyl N-[2,2,2-trichloro-1-(pyrimidin-2-ylamino)ethyl]carbamate, 3-(2-Methyl-5-nitro-imidazol-1-yl)-N-(2,2,2-trichloro-1-phenylamino-ethyl)-propionamide
• Empirical Formula (Hill Notation): C₁₃H₁₄Cl₃N₇O₄
• CAS Number: 300815-04-7
• Molecular Weight: 438.65
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825924
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 25 mg/mL, clear
• storage temp.: room temp
• SMILES string: CC1=NC=C([N+]([O-])=O)N1CCOC(NC(C(Cl)(Cl)Cl)NC2=NC=CC=N2)=O
• InChI: 1S/C13H14Cl3N7O4/c1-8-19-7-9(23(25)26)22(8)5-6-27-12(24)21-10(13(14,15)16)20-11-17-3-2-4-18-11/h2-4,7,10H,5-6H2,1H3,(H,21,24)(H,17,18,20)
• InChI key: ZEXHXVOGJFGTRX-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Apcin is an inhibitor of the anaphase-promoting complex/cyclosome (APC/C), a large multimeric complex that functions as a ubiquitin ligase, initiating the metaphase–anaphase transition and regulating ordered transitions through the cell cycle by controlling the ubiquitin-mediated proteolysis of cell cycle proteins. Apcin prevents substrate recognition and inhibits APC/C-dependent ubiquitylation by binding to the D-box binding site of Cdc20, a coactivator required for full activation of APC/C and substrate recognition. The effectiveness of apcin in blocking mitotic exit was synergistically amplified by co-addition of TAME (tosyl-L-arginine methyl ester) or its cell permeable prodrug proTAME, which block Cdc20 binding to the APC/C at a different site than apcin.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3