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U3633

Sigma-Aldrich

U 18666A

powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C25H41NO2·HCl
Numéro CAS:
3039-71-2
Poids moléculaire :
424.06
Numéro MDL:
MFCD00210908
Code UNSPSC :
12352200
ID de substance PubChem :
24724638
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Pf

195-196.5 °C (lit.)

Solubilité

H2O: 10 mg/mL≥

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

GZFYZYBWLCYBMI-MYZJJQSMSA-N

Description générale

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

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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
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