| Identification | Back Directory | [Name]
(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol | [CAS]
1397692-46-4 | [Synonyms]
Nat-20(S)-yne
Nat20(S)yne,Nat 20(S) yne
Nat-20(S)-yne Exclusive
SCMAJJQBADBBSM-CMJRPVKTSA-N
(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol
26,27-Dinorcholest-5-en-24-yne-3,20-diol, (3β)- | [Molecular Formula]
C25H38O2 | [MOL File]
1397692-46-4.mol | [Molecular Weight]
370.57 |
| Chemical Properties | Back Directory | [Boiling point ]
510.0±25.0 °C(Predicted) | [density ]
1.08±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 14 mg/ml; DMSO: 0.5 mg/ml; Ethanol: 10 mg/ml | [form ]
A crystalline solid | [pka]
14.68±0.29(Predicted) |
| Hazard Information | Back Directory | [Description]
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. | [Uses]
(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol is a byproduct of cholesterol (C432501) oxidation and a potential agonists of the hedgehog signaling pathway. | [References]
[1] YOONJUNG KHO. A tagging-via-substrate technology for detection and proteomics of farnesylated proteins.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101 34: 12479-12484. DOI: 10.1073/pnas.0403413101
[2] JEAN-FRAN?OIS LUTZ Zoya Z. Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide–alkyne “click” chemistry[J]. Advanced drug delivery reviews, 2008, 60 9: Pages 958-970. DOI: 10.1016/j.addr.2008.02.004
[3] SIGRID NACHTERGAELE. Oxysterols are allosteric activators of the oncoprotein Smoothened[J]. Nature chemical biology, 2012, 8 2: 211-220. DOI: 10.1038/nchembio.765 |
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Energy Chemical
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http://www.energy-chemical.com |
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