Synthesis and biological evaluation of cationic TopFluor cholesterol analogues.
Cholesterol transport
Fluorescence imaging
Sterol
TopFluor cholesterol analogues
Trafficking disorders
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
12 2021
12 2021
Historique:
received:
21
10
2020
revised:
25
04
2021
accepted:
03
10
2021
pubmed:
27
10
2021
medline:
15
1
2022
entrez:
26
10
2021
Statut:
ppublish
Résumé
Cholesterol is not only a major component of the cell membrane, but also plays an important role in a wide range of biological processes and pathologies. It is therefore crucial to develop appropriate tools for visualizing intracellular cholesterol transport. Here, we describe new cationic analogues of BODIPY-Cholesterol (TopFluor-Cholesterol, TF-Chol), which combine a positive charge on the sterol side chain and a BODIPY group connected via a C-4 linker. In contrast to TF-Chol, the new analogues TF-1 and TF-3 possessing acetyl groups on the A ring (C-3 position on steroid) internalized much faster and displayed slightly different levels of intracellular localization. Their applicability for cholesterol monitoring was indicated by the fact that they strongly label compartments with accumulated cholesterol in cells carrying a mutation of the Niemann-Pick disease-associated cholesterol transporter, NPC1.
Identifiants
pubmed: 34700109
pii: S0045-2068(21)00787-2
doi: 10.1016/j.bioorg.2021.105410
pii:
doi:
Substances chimiques
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
0
Boron Compounds
0
Cholesterol
97C5T2UQ7J
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
105410Informations de copyright
Copyright © 2021 Elsevier Inc. All rights reserved.