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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About This Item
Fórmula empírica (notación de Hill):
C25H41NO2·HCl
Número CAS:
Peso molecular:
424.06
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Nombre del producto
U 18666A, powder
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 key
GZFYZYBWLCYBMI-MYZJJQSMSA-N
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
assay
≥98% (HPLC)
form
powder
color
white to off-white
mp
195-196.5 °C (lit.)
solubility
H2O: 10 mg/mL≥
storage temp.
2-8°C
Quality Level
Categorías relacionadas
General description
U18666A, a cationic amphiphile/sterol, has a diethylaminoethyl chain linked to the 3-hydroxyl. It is an androstenolone derivative.
Preparation Note
U 18666A is soluble in water at 10 mg/ml.
Application
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
U 18666A has been used in fibroblast controls to study the mechanism of increase in autophagy in Niemann-Pick Disease Type C (NPC) cells.
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.
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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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
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
Jing Xu et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(10), 4764-4769 (2010-02-24)
Mammalian target of rapamycin (mTOR) constitutes a nodal point of a signaling network that regulates cell growth and proliferation in response to various environmental cues ranging from growth factor stimulation to nutrients to stress. Whether mTOR is also affected by
Marie-Claude Battista et al.
The Prostate, 70(9), 921-933 (2010-02-19)
Seladin-1 belongs to a subgroup of androgen-dependent genes associated with anti-proliferative, pro-differentiation, and pro-apoptotic functions and plays a protective role against oncogenic stress. The present study aims to investigate the localization and expression of Seladin-1 protein in normal and tumoral
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
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