Nat-20(S)-yne

Smoothened (SMO) is a GPCR-like receptor which, with Patched, mediates hedgehog signaling to regulate gene expression through the Gli transcription factors. 20(S)-hydroxy Cholesterol (20(S)-OHC) is an oxysterol which binds SMO and activates hedgehog signaling (EC50 = 3 µM), and this activation is selective for the nat-20(S)-OHC enantiomer. Nat-20(S)-OHC synergizes with the SMO agonist SAG, suggesting an allosteric effect. Nat-20(S)-yne is a form of nat-20(S)-OHC with a terminal alkyne group, which can be used in linking reactions known as click chemistry. Click chemistry involves highly dependable and specific azide-alkyne bioconjugation reactions and can be used to capture or immobilize bioactive molecules. Thus, nat-20(S)-yne has been conjugated with magnetic beads to demonstrate that nat-20(S)-OHC directly binds SMO.Formal Name: 26,27-dinorcholest-5-en-24-yne-3beta,20-diol. CAS Number: 1397692-46-4. Synonyms: Click Tag(TM) Nat-20(S)-yne. Molecular Formula: C25H38O2. Formula Weight: 370.6. Purity: >90%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 14 mg/ml, DMSO: 0.5 mg/ml, Ethanol: 10 mg/ml. SMILES: O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@](O)(C)CCC#C. InChi Code: InChI=1S/C25H38O2/c1-5-6-13-25(4,27)22-10-9-20-19-8-7-17-16-18(26)11-14-23(17,2)21(19)12-15-24(20,22)3/h1,7,18-22,26-27H,6,8-16H2,2-4H3/t18-,19-,20-,21-,22-,23-,24-,25-/m0/s1. InChi Key: SCMAJJQBADBBSM-PRQSBNOCSA-N.