| Identification | Back Directory | [Name]
Dafadine-A | [CAS]
1065506-69-5 | [Synonyms]
CS-1223
Dafadine-A
Dafadine A >=98% (HPLC)
4-[1-({ 5-[(2,6-Dimethylphenoxy)methyl]-3-isoxazolyl}carbonyl)-4-piperidinyl]pyridine
Methanone, [5-[(2,6-dimethylphenoxy)methyl]-3-isoxazolyl][4-(4-pyridinyl)-1-piperidinyl]- | [Molecular Formula]
C23H25N3O3 | [MOL File]
1065506-69-5.mol | [Molecular Weight]
391.46 |
| Chemical Properties | Back Directory | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble15mg/mL, clear | [form ]
powder | [color ]
white to beige | [InChI]
1S/C23H25N3O3/c1-16-4-3-5-17(2)22(16)28-15-20-14-21(25-29-20)23(27)26-12-8-19(9-13-26)18-6-10-24-11-7-18/h3-7,10-11,14,19H,8-9,12-13,15H2,1-2H3 | [InChIKey]
WNSNPYIHDMIFOO-UHFFFAOYSA-N | [SMILES]
N3(CCC(CC3)c4ccncc4)C(=O)c1n[o]c(c1)COc2c(cccc2C)C |
| Hazard Information | Back Directory | [Uses]
Dafadine-A is a selective inhibitor of DAF-9 cytochrome P450 in the nematode Caenorhabditis elegans. Dafadine-A inhibits the mammalian ortholog of DAF-9 (CYP27A1). Dafadine-A does not inhibits DAF-12 and sterol- and oxysterol-metabolizing P450s[1]. | [Definition]
ChEBI: Dafadine A is an N-acylpiperidine obtained by formal condensation of the carboxy group of 5-[(2,6-dimethylphenoxy)methyl]-1,2-oxazole-3-carboxylic acid with the secondary amino group of 4-(pyridin-4-yl)piperidine. It has a role as a P450 inhibitor and a geroprotector. It is a member of pyridines, a N-acylpiperidine, a member of isoxazoles, an aromatic ether and an aromatic amide. | [Biological Activity]
Dafadine A is a selective inhibitor of C. elegans DAF-9 cytochrome P450a key regulator of dauer formationdevelopmental timing and longevity. C. elegans has four life stages. In harsh environmental conditionsnematodes can convert to the L3 stageknown as the ""non-aging"" dauer stagein which development ceases until improved conditions are sensed. Dafadine A can induce dauer formation and increased longevity in wild-type worms raised in nonstressful conditions. Dafadine A is the only inhibitor known to robustly inhibit DAF-9 in wild-type worms. It does not inhibit DAF-12 activity. Dafadine is active in mammalian systemsinhibiting CYP27A1the mammalian functional ortholog of DAF-9 th at oxidizes 4-cholesten-3-one to make 26-hydroxy-4-cholesten-3-one and Δ4-dafachronic acidwithout inhibiting other sterol- and oxysterol-metabolizing P450s such as CYP7A1 or CYP7B1. | [References]
[1] Luciani GM, et al. Dafadine inhibits DAF-9 to promote dauer formation and longevity of Caenorhabditis elegans. Nat Chem Biol. 2011 Nov 6;7(12):891-3. DOI:10.1038/nchembio.698
[2] Wang X, et al. Cholesterol neutralized vemurafenib treatment by promoting melanoma stem-like cells via its metabolite 27-hydroxycholesterol. Cell Mol Life Sci. 2024 May 22;81(1):226. DOI:10.1007/s00018-024-05267-3 |
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