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New 20-hydroxycholesterol-like compounds with fluorescent NBD or alkyne labels: Synthesis, in silico interactions with proteins and uptake by yeast cellsстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 1 апреля 2020 г.
- Авторы: Faletrov Y.V., Efimova .V.S, Horetski .M.S, Tugaeva K V., Frolova N.S., Quingquing Lin, Isaeva L.V., Rubtsov M A., Sluchanko N.N., Novikova L A., Shkumatov V M.
- Журнал: Chemistry and Physics of Lipids
- Том: 227
- Год издания: 2020
- Издательство: Elsevier BV
- Местоположение издательства: Netherlands
- Номер статьи: 104850
- DOI: 10.1016/j.chemphyslip.2019.104850
- Аннотация: 20-hydroxycholesterol is a signaling oxysterol with immunomodulating functions and, thus, structural analogueswith reporter capabilities could be useful for studying and modulating the cellular processes concerned. We havesynthesized three new 20-hydroxycholesterol-like pregn-5-en-3β-ol derivatives with fluorescent 7-nitrobenzofurazan(NBD) or Raman-sensitive alkyne labels in their side-chains. In silico computations demonstrated the compoundspossess good membrane permeability and can bind within active sites of known 20-hydroxycholesteroltargets (e.g. Smoothened and yeast Osh4) and some other sterol-binding proteins (human LXRβ and STARD1;yeast START-kins Lam4S2 and Lam2S2). Having found good predicted membrane permeability and binding tosome yeast proteins, we tested the compounds on microorganisms. Fluorescent microscopy indicated the uptakeof the steroids by both Saccharomyces cerevisiae and Yarrowia lipolytica, whereas only S. cerevisiae demonstratedconversion of the compounds into 3-O-acetates, likely because 3-O-acetyltransferase Atf2p is present only in itsgenome. The new compounds provide new options to study the uptake, intracellular distribution and metabolismof sterols in yeast cells as well as might be used as ligands for sterol-binding proteins.
- Добавил в систему: Новикова Людмила Александровна