Debromohymenialdisine

Damaged DNA in humans is detected by sensor proteins that transmit a signal through checkpoint kinases (Chks) Chk1 and Chk2. Debromohymenialdisine (DBH) is a marine sponge alkaloid that inhibits Chk1 and Chk2 (IC50 = 3 and 3.5 µM, respectively), blocking G2 arrest. Because it does not significantly affect the activity of ataxia-telangiectasia mutated (ATM) or ATM-Tad2-related protein, DBH is a useful tool for studying the roles of Chk1 and Chk2 in DNA repair and cell cycle regulation. DBH also inhibits MAP kinase kinase 1 (IC50 = 881 nM), glycogen synthase kinase 3beta (IC50 = 1.39 µM), cyclin-dependent kinase 5/p25 (IC50 = 9.12 µM), protein tyrosine kinase 6 (IC50 = 0.6 µM), and other kinases largely unrelated to DNA damage/repair and cell cycling.Formal Name: (4Z)-4-(2-amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one. CAS Number: 75593-17-8. Synonyms: DBH, SKF 108753. Molecular Formula: C11H11N5O2. Formula Weight: 245.2. Purity: >90%. Formulation: (Request formulation change), A yellow solid. Solubility: DMSO: soluble, Ethanol: soluble, Methanol: soluble. SMILES: O=C1/C(NC(N)=N1)=C2C(C=CN3)=C3C(NCC/2)=O. InChi Code: InChI=1S/C11H11N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/b8-6-. InChi Key: JYRJOQGKGMHTOO-VURMDHGXSA-N. Origin: Sponge/Axinella carteri.