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SML1503

Sigma-Aldrich

Apcin

≥98% (HPLC)

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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

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

Related Categories

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Certificates of Analysis (COA)

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Nadia Hégarat et al.
The EMBO journal, 39(11), e104419-e104419 (2020-05-01)
Two mitotic cyclin types, cyclin A and B, exist in higher eukaryotes, but their specialised functions in mitosis are incompletely understood. Using degron tags for rapid inducible protein removal, we analyse how acute depletion of these proteins affects mitosis. Loss
Filip Vujovic et al.
Nucleic acids research, 49(18), 10419-10430 (2021-09-15)
A core imprint of metazoan life is that perturbations of cell cycle are offset by compensatory changes in successive cellular generations. This trait enhances robustness of multicellular growth and requires transmission of signaling cues within a cell lineage. Notably, the

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