U3633
U 18666A
≥98% (HPLC), cholesterol synthesis inhibitor, powder
Sinónimos:
(3β)-3-[2-(Diethylamino)ethoxy]androst-5-en-17-one hydrochloride
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Fórmula empírica (notación de Hill):
C25H41NO2·HCl
Número CAS:
Peso molecular:
424.06
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Servicio técnico
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Permítanos ayudarleNombre del producto
U 18666A, powder
assay
≥98% (HPLC)
Quality Level
form
powder
color
white to off-white
mp
195-196.5 °C (lit.)
solubility
H2O: 10 mg/mL≥
storage temp.
2-8°C
SMILES string
Cl[H].[H][C@@]12CC=C3C[C@H](CC[C@]3(C)[C@@]1([H])CC[C@]4(C)C(=O)CC[C@@]24[H])OCCN(CC)CC
InChI
1S/C25H41NO2.ClH/c1-5-26(6-2)15-16-28-19-11-13-24(3)18(17-19)7-8-20-21-9-10-23(27)25(21,4)14-12-22(20)24;/h7,19-22H,5-6,8-17H2,1-4H3;1H/t19-,20-,21-,22-,24-,25-;/m0./s1
InChI key
GZFYZYBWLCYBMI-MYZJJQSMSA-N
General description
U18666A, a cationic amphiphile/sterol, has a diethylaminoethyl chain linked to the 3-hydroxyl. It is an androstenolone derivative.
Application
U 18666A has been used in fibroblast controls to study the mechanism of increase in autophagy in Niemann-Pick Disease Type C (NPC) cells.
U 18666A has been used:
- as a competitive inhibitor of the Niemann-Pick disease, type C (NPC2) binding partner Niemann-Pick C1 (NPC1) to treat symbiotic and aposymbiotic adult Aiptasia to study the effect of global sterol transport inhibition
- in treating seminiferous tubules to study its effects on the localization pattern of VPS35-positive vesicles
- to study the U18666A treatment effects on early endosomes and late endosomes/multivesicular bodies (MVBs)
- as an NPC1 inhibitor to test its in vivo efficacy and study its effects on filovirus entry and infection
Biochem/physiol Actions
Inhibitor of cholesterol synthesis (inhibits desmosterol Δ24-reductase). Weak inhibitor of hedgehog (hh) signaling.
U18666A, a Niemann-Pick phenotype inducer, can inhibit the lysosomal cholesterol export and Ebola infection.
Preparation Note
U 18666A is soluble in water at 10 mg/ml.
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Anton I Rosenbaum et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(12), 5477-5482 (2010-03-10)
Niemann-Pick type C disease (NPC) is a lysosomal storage disorder causing accumulation of unesterified cholesterol in lysosomal storage organelles. Recent studies have shown that hydroxypropyl-beta-cyclodextrin injections in npc1(-/-) mice are partially effective in treating this disease. Using cultured fibroblasts, we
Elena Piccoli et al.
Biochemical pharmacology, 82(9), 1234-1249 (2011-09-01)
Patients treated with amiodarone accumulate lysobisphosphatidic acid (LBPA), also known as bis(monoacylglycero)phosphate, in airway secretions and develop in different tissues vacuoles and inclusion bodies thought to originate from endosomes. To clarify the origin of these changes, we studied in vitro
Mee Kian Poh et al.
Antiviral research, 93(1), 191-198 (2011-12-08)
The level of cholesterol in host cells has been shown to affect viral infection. However, it is still not understood why this level of regulation is important for successful infection. We have shown in this study that dengue virus infection