Cyclopamine-KAAD

Cyclopamine-KAAD is a potent inhibitor of hedgehog signaling with an IC50 value of 20 nM in a Shh-LIGHT2 assay. It blocks binding of BODIPY-cyclopamine to cells expressing Smoothened (Smo) in a dose-dependent manner. Cyclopamine-KAAD is cell-permeable and binds to SmoA1 to promote its exit from the endoplasmic reticulum. It inhibits the invasion and migration (45.9 and 43.3% inhibition, respectively) of Bel-7402 hepatocarcinoma cells and decreases the expression of nuclear glioma-associated oncogene 1 (Gli1) and cytosolic MMP-9, pERK1, and pERK2 proteins in a dose-dependent manner. Cyclopamine-KAAD also increases TRAIL-mediated cell death in NCH82 and NCH89 human glioblastoma cultures and upregulates expression of the death receptors DR4 and DR5 in LN229 and U251 glioma cells.Formal Name: N-[6-[[2-[(3'R,3'aS,6'S,6aS,6bS,7'aR,2'R,11aS,11bR)-1,2,3,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-3-oxospiro[9H-benzo[a]fluorene-9,2'(4'H)-furo[3,2-b]pyridin]-4'-yl]ethyl]amino]-6-oxohexyl]-benzenepropanamide. CAS Number: 306387-90-6. Molecular Formula: C44H63N3O4. Formula Weight: 698.0. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Chloroform: Slightly soluble, Methanol: Slightly soluble. SMILES: CC1=C2[C@](CC[C@@]31O[C@@](C[C@H](C)CN4CCNC(CCCCCNC(CCC5=CC=CC=C5)=O)=O)([H])[C@]4([H])[C@H]3C)([H])[C@]6([H])CC=C7CC(CC[C@]7(C)[C@@]6([H])C2)=O. InChi Code: InChI=1S/C44H63N3O4/c1-29-25-39-42(47(28-29)24-23-46-40(49)13-9-6-10-22-45-41(50)17-14-32-11-7-5-8-12-32)31(3)44(51-39)21-19-35-36-16-15-33-26-34(48)18-20-43(33,4)38(36)27-37(35)30(44)2/h5,7-8,11-12,15,29,31,35-36,38-39,42H,6,9-10,13-14,16-28H2,1-4H3. InChi Key: WDHRPWOAMDJICD-FOAQWNCLSA-N.