Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates <b>3</b> substituted in the 3-position with an alkoxy, alkylca...

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Autores principales:	Vladimir F. Mironov, Andrey V. Nemtarev, Olga V. Tsepaeva, Mudaris N. Dimukhametov, Igor A. Litvinov, Alexandra D. Voloshina, Tatiana N. Pashirova, Eugenii A. Titov, Anna P. Lyubina, Syumbelya K. Amerhanova, Aidar T. Gubaidullin, Daut R. Islamov
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	phosphonium salt P–C bond formation oxirane glycidyl ether triphenylphosphine addition reaction Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/1662b04eefc84a19928de2f673979a4f
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spelling	oai:doaj.org-article:1662b04eefc84a19928de2f673979a4f2021-11-11T18:22:54ZRational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties10.3390/molecules262163501420-3049https://doaj.org/article/1662b04eefc84a19928de2f673979a4f2021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6350https://doaj.org/toc/1420-3049It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates <b>3</b> substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride etherate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides <b>4</b> were also obtained. The molecular and supramolecular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt <b>3</b> and <i>L</i>-α-phosphatidylcholine (PC) was employed for improving the bioavailability and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts <b>3</b> and <b>4</b> has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.Vladimir F. MironovAndrey V. NemtarevOlga V. TsepaevaMudaris N. DimukhametovIgor A. LitvinovAlexandra D. VoloshinaTatiana N. PashirovaEugenii A. TitovAnna P. LyubinaSyumbelya K. AmerhanovaAidar T. GubaidullinDaut R. IslamovMDPI AGarticlephosphonium saltP–C bond formationoxiraneglycidyl ethertriphenylphosphineaddition reactionOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6350, p 6350 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	phosphonium salt P–C bond formation oxirane glycidyl ether triphenylphosphine addition reaction Organic chemistry QD241-441
spellingShingle	phosphonium salt P–C bond formation oxirane glycidyl ether triphenylphosphine addition reaction Organic chemistry QD241-441 Vladimir F. Mironov Andrey V. Nemtarev Olga V. Tsepaeva Mudaris N. Dimukhametov Igor A. Litvinov Alexandra D. Voloshina Tatiana N. Pashirova Eugenii A. Titov Anna P. Lyubina Syumbelya K. Amerhanova Aidar T. Gubaidullin Daut R. Islamov Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
description	It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates <b>3</b> substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride etherate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides <b>4</b> were also obtained. The molecular and supramolecular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt <b>3</b> and <i>L</i>-α-phosphatidylcholine (PC) was employed for improving the bioavailability and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts <b>3</b> and <b>4</b> has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.
format	article
author	Vladimir F. Mironov Andrey V. Nemtarev Olga V. Tsepaeva Mudaris N. Dimukhametov Igor A. Litvinov Alexandra D. Voloshina Tatiana N. Pashirova Eugenii A. Titov Anna P. Lyubina Syumbelya K. Amerhanova Aidar T. Gubaidullin Daut R. Islamov
author_facet	Vladimir F. Mironov Andrey V. Nemtarev Olga V. Tsepaeva Mudaris N. Dimukhametov Igor A. Litvinov Alexandra D. Voloshina Tatiana N. Pashirova Eugenii A. Titov Anna P. Lyubina Syumbelya K. Amerhanova Aidar T. Gubaidullin Daut R. Islamov
author_sort	Vladimir F. Mironov
title	Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
title_short	Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
title_full	Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
title_fullStr	Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
title_full_unstemmed	Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
title_sort	rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: synthesis, structure, and biological properties
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/1662b04eefc84a19928de2f673979a4f
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Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

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