10Z-Hymenialdisine | 2212

Isolated from sponge Axinella carteri. A potent inhibitor of mitogen-activated protein kinase kinase-1 (MEK-1) (IC₅₀ = 6nM). Blocks the in vivo phosphorylation of the microtubule-binding protein tau at sites that are hyperphosphorylated by glycogen synthase kinase-β (GSK-3β) and CDK5/p35 in Alzheimer’s disease. Inhibitor of DNA damage checkpoint at G2 phase (IC₅₀ = 6 µM), cyclin-dependent kinases CDK1/cyclin B (IC₅₀ = 22 nM), CDK2/cyclin A (IC₅₀= 70 nM), CDK2/cyclin E (IC₅₀= 40 nM), CDK4/cyclin D1 (IC₅₀ = 600 nM), CDK5/p25 (IC₅₀ = 28 nM), GSK-3β (IC₅₀ = 10 nM), and casein kinase 1 (CK1) (IC₅₀ = 35 nM).

10Z-Hymenialdisine is a potent inhibitor of mitogen-activated protein kinase kinase-1 (MEK-1) (IC₅₀ = 6nM). Blocks the in vivo phosphorylation of the microtubule-binding protein tau at sites that are hyperphosphorylated by glycogen synthase kinase-β (GSK-3β) and CDK5/p35 in Alzheimer’s disease. Inhibitor of DNA damage checkpoint at G2 phase (IC₅₀ = 6 µM), cyclin-dependent kinases CDK1/cyclin B (IC₅₀ = 22 nM), CDK2/cyclin A (IC₅₀= 70 nM), CDK2/cyclin E (IC₅₀= 40 nM), CDK4/cyclin D1 (IC₅₀ = 600 nM), CDK5/p25 (IC₅₀ = 28 nM), GSK-3β (IC₅₀ = 10 nM), and casein kinase 1 (CK1) (IC₅₀ = 35 nM).

2212 | 10Z-Hymenialdisine DataSheet

Alternate Name/Synonyms: 4-(2-Amino-4-oxo-2-imidazolidin-5-ylidene)-2-bromo-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one; Hymenialdisine

Appearance: Yellow oil

Formulation: N/A

CAS Number: 82005-12-7

Structure Available?: Yes

Peptide sequence: N/A

Salt Form: No

Molecular Formula: C₁₁H₁₀BrN₅O₂

Molecular Weight: 324.13

Cell-Permeable?: Yes

Purity: ≥97% by HPLC

Solubilities: DMSO (5 mg/ml)

Handling: Protect from air and light

Country of Origin: USA

Tag Line: A MEK-1 inhibitor

MDL Number: MFCD04037007

PubChem CID: 3036831

SMILES: C1CNC(=O)C2=C(C1=C3C(=O)N=C(N3)N)C=C(N2)Br

InChi: InChI=1S/C11H10BrN5O2/c12-6-3-5-4(7-10(19)17-11(13)16-7)1-2-14-9(18)8(5)15-6/h3,15H,1-2H2,(H,14,18)(H3,13,16,17,19)/b7-4+

InChi Key: ATBAETXFFCOZOY-QPJJXVBHSA-N