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Article

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

by
Vladimir F. Mironov
1,*,
Andrey V. Nemtarev
1,
Olga V. Tsepaeva
1,
Mudaris N. Dimukhametov
1,
Igor A. Litvinov
1,
Alexandra D. Voloshina
1,
Tatiana N. Pashirova
1,
Eugenii A. Titov
2,
Anna P. Lyubina
1,
Syumbelya K. Amerhanova
1,
Aidar T. Gubaidullin
1 and
Daut R. Islamov
1
1
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov St., 420088 Kazan, Russia
2
Alexander Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, 18 Kremlevskaya St., 420008 Kazan, Russia
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(21), 6350; https://doi.org/10.3390/molecules26216350
Submission received: 25 September 2021 / Revised: 9 October 2021 / Accepted: 11 October 2021 / Published: 20 October 2021
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Abstract

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 3 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 4 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 3 and L-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 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.
Keywords: phosphonium salt; P–C bond formation; oxirane; glycidyl ether; triphenylphosphine; addition reaction; nucleophilic substitution phosphonium salt; P–C bond formation; oxirane; glycidyl ether; triphenylphosphine; addition reaction; nucleophilic substitution

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MDPI and ACS Style

Mironov, V.F.; Nemtarev, A.V.; Tsepaeva, O.V.; Dimukhametov, M.N.; Litvinov, I.A.; Voloshina, A.D.; Pashirova, T.N.; Titov, E.A.; Lyubina, A.P.; Amerhanova, S.K.; et al. Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties. Molecules 2021, 26, 6350. https://doi.org/10.3390/molecules26216350

AMA Style

Mironov VF, Nemtarev AV, Tsepaeva OV, Dimukhametov MN, Litvinov IA, Voloshina AD, Pashirova TN, Titov EA, Lyubina AP, Amerhanova SK, et al. Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties. Molecules. 2021; 26(21):6350. https://doi.org/10.3390/molecules26216350

Chicago/Turabian Style

Mironov, Vladimir F., 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, and et al. 2021. "Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties" Molecules 26, no. 21: 6350. https://doi.org/10.3390/molecules26216350

APA Style

Mironov, V. F., Nemtarev, A. V., Tsepaeva, O. V., Dimukhametov, M. N., Litvinov, I. A., Voloshina, A. D., Pashirova, T. N., Titov, E. A., Lyubina, A. P., Amerhanova, S. K., Gubaidullin, A. T., & Islamov, D. R. (2021). Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties. Molecules, 26(21), 6350. https://doi.org/10.3390/molecules26216350

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