Triphenylphosphonium-conjugated glycol chitosan microspheres for mitochondria-targeted drug delivery

Lee, Young Hwa; Park, Hae In; Chang, Woo-Suk; Choi, Ji Soo

doi:10.1016/j.ijbiomac.2020.11.129

Cited by 27 publications

(15 citation statements)

References 27 publications

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“…[36]. Similar actions were obtained with QPS-modified glycol-chitosan polymer microspheres [37] and QPS-functionalized epigallocatechin gallate capped gold nanoparticles [38].…”

Section: Introductionsupporting

confidence: 66%

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

et al. 2021

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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.

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“…[36]. Similar actions were obtained with QPS-modified glycol-chitosan polymer microspheres [37] and QPS-functionalized epigallocatechin gallate capped gold nanoparticles [38].…”

Section: Introductionsupporting

confidence: 66%

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

et al. 2021

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“…Lee et al prepared the triphenylphosphonium-glycol chitosan derivative (GME-TPP) with 36% substitution by Michael addition. GME-TPP microspheres successfully targeted DOX delivery to mitochondria in cells, which indicated the microsphere possess great potential as effective drug delivery carrier [ 103 ]. Babii et al synthesized mannosyl chitosan with a degree of substitution of 15%.…”

Section: Polymersmentioning

confidence: 99%

Application of Non-Viral Vectors in Drug Delivery and Gene Therapy

Ren

Wang

et al. 2021

Polymers

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Vectors and carriers play an indispensable role in gene therapy and drug delivery. Non-viral vectors are widely developed and applied in clinical practice due to their low immunogenicity, good biocompatibility, easy synthesis and modification, and low cost of production. This review summarized a variety of non-viral vectors and carriers including polymers, liposomes, gold nanoparticles, mesoporous silica nanoparticles and carbon nanotubes from the aspects of physicochemical characteristics, synthesis methods, functional modifications, and research applications. Notably, non-viral vectors can enhance the absorption of cargos, prolong the circulation time, improve therapeutic effects, and provide targeted delivery. Additional studies focused on recent innovation of novel synthesis techniques for vector materials. We also elaborated on the problems and future research directions in the development of non-viral vectors, which provided a theoretical basis for their broad applications.

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“…Triphenylphosphine (TPP), with its high lipophilicity and delocalized positive charge, thus possessing both mitochondrial targeting and mitochondrial damaging functions, is the first small molecule applied to mitochondrial targeting. Till now, TPP has been extensively used to design various mitochondria-targeting nanosystems ( Wang R. et al, 2020 ; Lee et al, 2021 ; Sun et al, 2021 ). On the other hand, all-trans retinoic acid (RA), a metabolite of vitamin A, can bind to cellular retinoic acid-binding protein II (CRABP-II) very easily, and this tight-binder exhibits super affinity to the nuclear RA receptor, which allows for the precise nuclear targeting ( Majumdar et al, 2011 ; Zhou, et al, 2017 ; Ghyselinck and Duester., 2019 ).…”

Section: Mitochondria Targeting With the Aid Of Multifunctional Nanosystemsmentioning

confidence: 99%

Multifunctional Mitochondria-Targeting Nanosystems for Enhanced Anticancer Efficacy

Zhou

Shen

et al. 2021

Front. Bioeng. Biotechnol.

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Mitochondria, a kind of subcellular organelle, play crucial roles in cancer cells as an energy source and as a generator of reactive substrates, which concern the generation, proliferation, drug resistance, and other functions of cancer. Therefore, precise delivery of anticancer agents to mitochondria can be a novel strategy for enhanced cancer treatment. Mitochondria have a four-layer structure with a high negative potential, which thereby prevents many molecules from reaching the mitochondria. Luckily, the advances in nanosystems have provided enormous hope to overcome this challenge. These nanosystems include liposomes, nanoparticles, and nanomicelles. Here, we summarize the very latest developments in mitochondria-targeting nanomedicines in cancer treatment as well as focus on designing multifunctional mitochondria-targeting nanosystems based on the latest nanotechnology.

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Triphenylphosphonium-conjugated glycol chitosan microspheres for mitochondria-targeted drug delivery

Cited by 27 publications

References 27 publications

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

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

Application of Non-Viral Vectors in Drug Delivery and Gene Therapy

Multifunctional Mitochondria-Targeting Nanosystems for Enhanced Anticancer Efficacy

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