SP-8356

SP-8356 is a derivative of (1S)-(-)-verbenone and an inhibitor of CD147, also known as extracellular matrix metalloproteinase (MMP) inducer (EMMPRIN) and previously known as tumor cell-derived collagenase stimulatory factor (TCSF). It inhibits the dimerization of CD147 and the protein-protein interaction between CD147 and its ligand cyclophilin A. SP-8356 (10 µM) decreases recombinant human CD147-induced migration of A-10 vascular smooth muscle cells (VSMCs) and reduces cyclophilin A-induced increases in MMP-9 activity in, and adhesion of, isolated rat monocyte-derived macrophages. It also prevents glucose-oxygen deprivation-induced increases in reactive oxygen species (ROS) and lactate dehydrogenase (LDH) release in primary rat cortical neurons in an in vitro model of ischemia when used at a concentration of 10 µM. SP-8356 (5 µM) inhibits the migration and invasion of MDA-MB-231 breast cancer cells. In vivo, SP-8356 (50 mg/kg in the drinking water) decreases plaque size in an ApoE-/- mouse model of atherosclerosis induced by partial carotid artery ligation and a high-fat diet.Formal Name: (1S,5R)-4-[(1E)-2-(3,4-dihydroxy-5-methoxyphenyl)ethenyl]-6,6-dimethyl-bicyclo[3.1.1]hept-3-en-2-one. CAS Number: 1454885-45-0. Molecular Formula: C18H20O4. Formula Weight: 300.4. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: 25 mg/ml, DMSO: 25 mg/ml, Ethanol: 10 mg/ml. lambdamax: 266, 381 nm. SMILES: O=C1C=C(/C=C/C2=CC(O)=C(O)C(OC)=C2)[C@@H]3C[C@H]1C(C)3C. InChi Code: InChI=1S/C18H20O4/c1-18(2)12-9-13(18)14(19)8-11(12)5-4-10-6-15(20)17(21)16(7-10)22-3/h4-8,12-13,20-21H,9H2,1-3H3/b5-4+/t12-,13+/m0/s1. InChi Key: ITCSXIQQWJYZHT-QITAHTHBSA-N.