Phospholipidic Colchicinoids as Promising Prodrugs Incorporated into Enzyme-Responsive Liposomes: Chemical, Biophysical, and Enzymological Aspects

Shchegravina, Ekaterina S.; Tretiakova, Daria; Алексеева, А. С.; Galimzyanov, Timur R.; Utkin, Yuri N.; Ermakov, Yu. A.; Svirshchevskaya, E. V.; Negrebetsky, Vadim V.; Karpechenko, Natalia Y.; Chernikov, Valery P.; Onishchenko, Natalia; Водовозова, Е. Л.; Fedorov, Alexey Yu.; Болдырев, Иван

doi:10.1021/acs.bioconjchem.9b00051

Cited by 24 publications

(20 citation statements)

References 84 publications

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“…The over expression of proteases and phospholipases in tumor tissue, when compared to the normal tissue, has been explored to develop enzyme-triggered liposomes ( 125 , 126 ). Enzyme-responsive liposomes release their content in response to pathologically increased enzyme levels at the target site ( 127 ).…”

Section: Triggered Drug Release By Endogenous Stimulimentioning

confidence: 99%

“…Phospholipase A2 (PLA2) degrades phospholipids and is over expressed in a variety of cancer types, namely prostate, lung, breast and pancreatic ( 126 , 127 ). This catalytic activity is enhanced when phospholipids are organized, such as in liposomes, compared to lipid monomers; and is dependent on the lipid composition and membrane charge.…”

Section: Triggered Drug Release By Endogenous Stimulimentioning

confidence: 99%

“…PLA2 acts at the lipid−water interface. Initially, interacts with the membrane by its interfacial binding surface and later the lipid is hydrolyzed in the active site of the enzyme ( 127 ).…”

Section: Triggered Drug Release By Endogenous Stimulimentioning

confidence: 99%

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Triggered Drug Release From Liposomes: Exploiting the Outer and Inner Tumor Environment

et al. 2021

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Since more than 40 years liposomes have being extensively studied for their potential as carriers of anticancer drugs. The basic principle behind their use for cancer treatment consists on the idea that they can take advantage of the leaky vasculature and poor lymphatic drainage present at the tumor tissue, passively accumulating in this region. Aiming to further improve their efficacy, different strategies have been employed such as PEGlation, which enables longer circulation times, or the attachment of ligands to liposomal surface for active targeting of cancer cells. A great challenge for drug delivery to cancer treatment now, is the possibility to trigger release from nanosystems at the tumor site, providing efficacious levels of drug in the tumor. Different strategies have been proposed to exploit the outer and inner tumor environment for triggering drug release from liposomes and are the focus of this review.

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Section: Triggered Drug Release By Endogenous Stimulimentioning

confidence: 99%

Section: Triggered Drug Release By Endogenous Stimulimentioning

confidence: 99%

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Triggered Drug Release From Liposomes: Exploiting the Outer and Inner Tumor Environment

et al. 2021

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“…In 2019, prodrugs 7 and 8 ( Figure 2 ) encapsulated into phosphatidylcholine-based enzyme responsive liposomes were reported by Ivan A. Boldyrev et al. 25 . Being exposed to elevated levels of phospholipases A2, especially in the case of a sPLA2 analogue, the liposomes release colchicinoid-containing fatty acids.…”

Section: Introductionmentioning

confidence: 75%

Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents

Wang

Zhang

Wang

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Chemical drug design based on the biochemical characteristics of cancer cells has become an important strategy for discovering new anti-tumour drugs to improve tumour targeting effects and reduce off-target toxicities. Colchicine is one of the most prominent and historically microtubule-targeting drugs, but its clinical applications are hindered by notorious adverse effects. In this study, we presented a novel tumour-specific conjugate 9 that consists of deacetylcolchicine (Deac), biotin, and a cleavable disulphide linker. 9 was found to exhibit potent anti-tumour activity and exerted higher selectivity between tumour and nontarget cells than Deac. The targeting moiety biotin might enhance the transport capability and selectivity of 9 to tumour cells via biotin receptor-mediated endocytosis. The tubulin polymerisation activity of 9 (with DTT) was close to the parent drug Deac. These preliminary results suggested that 9 is a high potency and reduced toxicity antitumor agent and worthy of further investigation.

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“…At the same time, liposomes could release colchicine-containing fatty acids upon the action of high levels of phospholipase A2. The latter further hydrolyzed and released colchicine analogues by non-specific enzymes [ 91 ]. Besides, in a recent report, an enzyme reactive liposome containing 1,2-dipalmitoyl-sn-glycerin-3-phosphocholine (DPPC) and 1-o-stearyl-2-retinoic acid receptor (RAR)-C6-sn-glycerin-3-phosphoglycerol with c6-RAR as a prodrug was designed.…”

Section: Stimulus-responsive Systemsmentioning

confidence: 99%

Stimulus-Responsive Nanomedicines for Disease Diagnosis and Treatment

Liu

Lovell

Zhang

et al. 2020

IJMS

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Stimulus-responsive drug delivery systems generally aim to release the active pharmaceutical ingredient (API) in response to specific conditions and have recently been explored for disease treatments. These approaches can also be extended to molecular imaging to report on disease diagnosis and management. The stimuli used for activation are based on differences between the environment of the diseased or targeted sites, and normal tissues. Endogenous stimuli include pH, redox reactions, enzymatic activity, temperature and others. Exogenous site-specific stimuli include the use of magnetic fields, light, ultrasound and others. These endogenous or exogenous stimuli lead to structural changes or cleavage of the cargo carrier, leading to release of the API. A wide variety of stimulus-responsive systems have been developed—responsive to both a single stimulus or multiple stimuli—and represent a theranostic tool for disease treatment. In this review, stimuli commonly used in the development of theranostic nanoplatforms are enumerated. An emphasis on chemical structure and property relationships is provided, aiming to focus on insights for the design of stimulus-responsive delivery systems. Several examples of theranostic applications of these stimulus-responsive nanomedicines are discussed.

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Phospholipidic Colchicinoids as Promising Prodrugs Incorporated into Enzyme-Responsive Liposomes: Chemical, Biophysical, and Enzymological Aspects

Cited by 24 publications

References 84 publications

Triggered Drug Release From Liposomes: Exploiting the Outer and Inner Tumor Environment

Triggered Drug Release From Liposomes: Exploiting the Outer and Inner Tumor Environment

Design, synthesis, and biological evaluation of biotinylated colchicine derivatives as potential antitumor agents

Stimulus-Responsive Nanomedicines for Disease Diagnosis and Treatment

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