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Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action

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dc.contributor.author Terekhova N.V.
dc.contributor.author Tatarinov D.A.
dc.contributor.author Shaihutdinova Z.M.
dc.contributor.author Pashirova T.N.
dc.contributor.author Lyubina A.P.
dc.contributor.author Voloshina A.D.
dc.contributor.author Sapunova A.S.
dc.contributor.author Zakharova L.Y.
dc.contributor.author Mironov V.F.
dc.date.accessioned 2021-02-25T20:35:54Z
dc.date.available 2021-02-25T20:35:54Z
dc.date.issued 2020
dc.identifier.issn 0960-894X
dc.identifier.uri https://dspace.kpfu.ru/xmlui/handle/net/161945
dc.description.abstract © 2020 Elsevier Ltd Here we report the synthesis and biological evaluation of a series of new 2-hydroxybenzylphosphonium salts (QPS) with antimicrobial and antitumor dual action. The most active compounds exhibit antimicrobial activity at a micromolar level against Gram-positive bacteria Sa (ATCC 209p and clinical isolates), Bc (1–2 μM) and fungi Tm and Ca, and induced no notable hemolysis at MIC. The change in nature of substituents of the same length led to a drastic change of biological activity. Self-assembly behavior of the octadecyl and oleyl derivatives was studied. QPS demonstrated self-assembly within the micromolar range with the formation of nanosized aggregates capable of the solubilizing hydrophobic probe. The synthesized phosphonium salts were tested for cytotoxicity. The most potent salt was active against on M−Hela cell line with IC50 on the level of doxorubicin and good selectivity. According to the cytofluorimetry analysis, the salts induced mitochondria-dependent apoptosis.
dc.relation.ispartofseries Bioorganic and Medicinal Chemistry Letters
dc.subject Antimicrobial activity
dc.subject BGMCQHOJBCLKIT-UHFFFAOYSA-N
dc.subject Critical micelle concentration
dc.subject Cyclization
dc.subject Cytofluorimetry
dc.subject Cytotoxicity
dc.subject GIKWOZJMLXCSOT-UHFFFAOYSA-N
dc.subject Grignard reagents
dc.subject JWPDILQILBQNLB-UHFFFAOYSA-N
dc.subject MMUTZBOOZAYZBN-UHFFFAOYSA-N
dc.subject NJWLFPGSOXIJQM-UHFFFAOYSA-N
dc.subject NQWHOPCJTGVYOX-UHFFFAOYSA-N
dc.subject Phosphine oxides
dc.subject Phosphonium salts
dc.subject PXDVKGAYQYIEIQ-UHFFFAOYSA-M
dc.subject QLAUKJDVVZODHE-UHFFFAOYSA-N
dc.subject UFFMKUDAZLHCFZ-UHFFFAOYSA-N
dc.subject VPSJJDVAWGOWKD-UHFFFAOYSA-N
dc.subject XBAAOMWVUJLTQH-UHFFFAOYSA-N
dc.subject YFJJZULFCDIQII-UHFFFAOYSA-N
dc.subject YODIJYRCKHUXQS-KVVVOXFISA-N
dc.subject ZTHITSXAOYPAIU-UHFFFAOYSA-N
dc.title Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action
dc.type Article
dc.relation.ispartofseries-issue 13
dc.relation.ispartofseries-volume 30
dc.collection Публикации сотрудников КФУ
dc.source.id SCOPUS0960894X-2020-30-13-SID85084634658


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  • Публикации сотрудников КФУ Scopus [22633]
    Коллекция содержит публикации сотрудников Казанского федерального (до 2010 года Казанского государственного) университета, проиндексированные в БД Scopus, начиная с 1970г.

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