Apcin
- Product Name
- Apcin
- CAS No.
- 300815-04-7
- Chemical Name
- Apcin
- Synonyms
- Apcin;Apcin >=98% (HPLC);Apcin, 10 mM in DMSO;3-(2-Methyl-5-nitroimidazol-1-yl)-N-(2,2,2-trichloro-1-phenylaminoethyl)propionamide;2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2,2,2-trichloro-1-(pyrimidin-2-ylamino)ethylcarbamate;2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl N-{2,2,2-trichloro-1-[(pyrimidin-2-yl)amino]ethyl}carbamate;Carbamic acid, N-[2,2,2-trichloro-1-(2-pyrimidinylamino)ethyl]-, 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester;Carbamic acid, [2,2,2-trichloro-1-(2-pyrimidinylamino)ethyl]-, 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester (9CI);ligase,pocket,anaphase-promoting,Apcin,recognition,complex,Inhibitor,Cdc20,Anaphase promoting complex,cyclosome,ubiquitylation,inhibit,mitosis,WD40-domain,APC/C,APC
- CBNumber
- CB03067532
- Molecular Formula
- C13H14Cl3N7O4
- Formula Weight
- 438.65
- MOL File
- 300815-04-7.mol
Apcin Property
- Density
- 1.68±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- DMF: 25 mg/ml; DMSO: 25 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
- form
- powder
- pka
- 9.67±0.46(Predicted)
- color
- white to beige
- 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)
- InChIKey
- ZEXHXVOGJFGTRX-UHFFFAOYSA-N
- SMILES
- CC1=NC=C([N+]([O-])=O)N1CCOC(NC(C(Cl)(Cl)Cl)NC2=NC=CC=N2)=O
Safety
- WGK Germany
- WGK 3
- Storage Class
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML1503
- Product name
- Apcin
- Purity
- ≥98% (HPLC)
- Packaging
- 5MG
- Price
- $154
- Updated
- 2025/07/31
- Product number
- SML1503
- Product name
- Apcin
- Purity
- ≥98% (HPLC)
- Packaging
- 25MG
- Price
- $308
- Updated
- 2025/07/31
- Product number
- 17080
- Product name
- Apcin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $37
- Updated
- 2024/03/01
- Product number
- 17080
- Product name
- Apcin
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $127
- Updated
- 2024/03/01
- Product number
- 17080
- Product name
- Apcin
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $178
- Updated
- 2024/03/01
Apcin Chemical Properties,Usage,Production
Uses
Apcin is a novel inhibitor of the anaphase-promoting complex/cyclosome (APC/C), blocking mitotic exit and being synergistically amplified by co-addition of Ts-Arg-OMe.
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.
Enzyme inhibitor
This Cdc20 inhibitor (FW = 438.65 g/mol; CAS 300815-04-7; Solubility: 100 mM in DMSO), also named 3-(2-methyl-5-nitroimidazol-1-yl)-N- (2,2,2-trichloro-1-phenylaminoethyl)propionamide, targets substrate interaction of Cell division control protein 20, blocking substrate-mediated Cdc20 loading onto the Anaphase-Promoting Complex. APC is a 13- subunit ubiquitin ligase that initiates the metaphase-anaphase transition and mitotic exit by targeting proteins such as securin and cyclin B1 for ubiquitin-dependent destruction by the proteasome. APC regulates cell cycle progression by forming APC·Cdc20 and APC·Cdh1, two closely related, but functionally distinct, E3 ubiquitin ligase sub-complexes. Cdh1 and Cdc20 have opposing functions in tumorigenesis, with the former largely functioning as a tumor suppressor, and the latter exhibiting an oncogenic function. Because blocking mitotic exit is an effective approach for inducing tumour cell death, the APC/C represents a potential novel target for cancer therapy. APC/C activation during mitosis requires Cdc20binding, forming a co-receptor with the APC/C to recognize substrates containing a destruction box (D-box). APC/C-dependent proteolysis and mitotic exit can be synergistically inhibited by simultaneously disrupting two protein-protein interactions within the APC/C-Cdc20-substrate ternary complex. APC inhibitor, or Apcin, binds to Cdc20, competitively inhibiting ubiquitylation of D-box-containing substrates. Analysis of the crystal structure of the apcin-Cdc20 complex suggests that apcin occupies the D-box-binding pocket on the side face of the WD40-domain. The ability of Apcin to block mitotic exit is enhanced by co-addition of tosyl-l-arginine methyl ester (See TAME), a small molecule that blocks the APC/C-Cdc20 interaction. Apcin also inhibits APC-dependent ubiquitylation and prolongs mitotic duration in RPE1 cells, when administered in combination with proTAME, a prodrug of TAME in vitro (See pro-TAME).
storage
Store at -20°C
Apcin Preparation Products And Raw materials
Raw materials
Preparation Products
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