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U3633

Sigma-Aldrich

U 18666A

powder

Synonym(s):

(3β)-3-[2-(Diethylamino)ethoxy]androst-5-en-17-one hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C25H41NO2·HCl
CAS Number:
3039-71-2
Molecular Weight:
424.06
MDL number:
MFCD00210908
UNSPSC Code:
12352200
PubChem Substance ID:
24724638
NACRES:
NA.77

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

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

U18666A, a Niemann-Pick phenotype inducer, can inhibit the lysosomal cholesterol export and Ebola infection.
Inhibitor of cholesterol synthesis (inhibits desmosterol Δ24-reductase). Weak inhibitor of hedgehog (hh) signaling.

Preparation Note

U 18666A is soluble in water at 10 mg/ml.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Feiran Lu et al.
eLife, 4 (2015-12-10)
Niemann-Pick C1 (NPC1) is a lysosomal membrane protein that exports cholesterol derived from receptor-mediated uptake of LDL, and it also mediates cellular entry of Ebola virus. Cholesterol export is inhibited by nanomolar concentrations of U18666A, a cationic sterol. To identify
Haitang Wang et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 24(12), 2100-2108 (2016-11-02)
The therapeutic applications of lipid nanoparticle (LNP) formulations of small interfering RNA (siRNA), are hampered by inefficient delivery of encapsulated siRNA to the cytoplasm following endocytosis. Recent work has shown that up to 70% of endocytosed LNP-siRNA particles are recycled
Hanna Appelqvist et al.
The American journal of pathology, 178(2), 629-639 (2011-02-02)
In the past decade, lysosomal membrane permeabilization (LMP) has emerged as a significant component of cell death signaling. The mechanisms by which lysosomal stability is regulated are not yet fully understood, but changes in the lysosomal membrane lipid composition have
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