Liposomal Form of Tetra(Aryl)Tetracyanoporphyrazine: Physical Properties and Photodynamic Activity In Vitro

Yudintsev, Andrey; Shilyagina, Natalia Yu.; Dyakova, Darya V.; Лермонтова, С. А.; Klapshina, Larisa G.; Guryev, Evgenii L.; Balalaeva, Irina V.; Vodeneev, Vladimir

doi:10.1007/s10895-018-2212-9

Cited by 11 publications

(8 citation statements)

References 29 publications

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“…Notably, in the dark, no toxicity of this compound was observed ( Figure 1 , black curve ). Earlier [ 27 ], it was shown that for A-431 human epidermoid carcinoma cells, the IC 50 value of porphyrazine under similar irradiation conditions was significantly lower: 0.68 μM. The difference may be due to a relatively high resistance of SKOV-3 cells to this photosensitizer.…”

Section: Resultsmentioning

confidence: 90%

“…One of the proposed approaches to solving the problem is to use vehicles capable to increase the tissue penetration of photodynamic agents. Liposomes, organic and hybrid nanoparticles, membrane-based vesicles have been tried for this role [ 27 , 32 , 35 , 37 ]. The advantages of such carriers are expected to increase the efficacy of photodynamic therapy.…”

Section: Resultsmentioning

confidence: 99%

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Model of Ovarian Adenocarcinoma Spheroids for Assessing Photodynamic Cytotoxicity

et al. 2020

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The aim of the study was to compare the relevance of ovarian adenocarcinoma spheroids with that of a monolayer culture for assessing photodynamic effect of the tetrakis(4-benzyloxyphenyl)tetracyanoporphyrazine photosensitizer. Materials and Methods. The work was performed on SKOV-3 human ovary adenocarcinoma cells grown in vitro in a monolayer culture and in the form of tumor spheroids obtained using culture plates with ultra-low attachment. We determined the photoinduced toxicity of porphyrazine on a monolayer culture using the MTT assay; the effect on the spheroids was tested by assessing the dynamics of their growth. Cellular uptake of porphyrazine was analyzed by confocal microscopy. Results. Porphyrazine has a pronounced photodynamic effect on SKOV-3 cells. When exposed to light at a dose of 20 J/cm 2 , the IC 50 value 24 h after exposure was 2.3 μM for SKOV-3 monolayer culture. For the spheroids, the effect manifested after a latency period: significant growth retardation of the treated spheroids appeared no sooner than 5 and 9 days after exposure. Notably, no decrease in the initial size of the treated spheroids was observed under any of the photodynamic regimes. The penetration depth of porphyrazine into spheroids was 50-100 μm during 24 h incubation. Conclusion. The limited penetration of the photosensitizer into the body of spheroids and its predominant accumulation in the surface layers can be one of the key factors behind the significant differences in the photodynamic response between the surface and deep layers of a spheroid. For cells located close to the spheroid surface, the photodynamic effect is comparable to that for a monolayer culture, while in deeper layers, the cells remain viable and support/maintain the growth of the spheroid even under intense photo-exposure. The fact that the in vitro distribution is similar to the inhomogeneous accumulation of photosensitizers in tumors in vivo allows us to consider spheroids more relevant than a monolayer culture for studying photodynamic anti-tumor effects.

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Model of Ovarian Adenocarcinoma Spheroids for Assessing Photodynamic Cytotoxicity

et al. 2020

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“…A comprehensive review on liposomal antitumor formulations is provided elsewhere [55,56]. The further directions in antitumor liposomal formulations progress are the development and improvement of stimuli-sensitive smart liposomes (thermo-, redox-, ultrasound-, enzyme-sensitive), magnetic liposomes, and liposomes for photodynamic therapy [57,58,59,60,61,62,63].…”

Section: Passive Targetingmentioning

confidence: 99%

Targeted Delivery to Tumors: Multidirectional Strategies to Improve Treatment Efficiency

Kutova

Guryev

Соколова

et al. 2019

Cancers

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Malignant tumors are characterized by structural and molecular peculiarities providing a possibility to directionally deliver antitumor drugs with minimal impact on healthy tissues and reduced side effects. Newly formed blood vessels in malignant lesions exhibit chaotic growth, disordered structure, irregular shape and diameter, protrusions, and blind ends, resulting in immature vasculature; the newly formed lymphatic vessels also have aberrant structure. Structural features of the tumor vasculature determine relatively easy penetration of large molecules as well as nanometer-sized particles through a blood–tissue barrier and their accumulation in a tumor tissue. Also, malignant cells have altered molecular profile due to significant changes in tumor cell metabolism at every level from the genome to metabolome. Recently, the tumor interaction with cells of immune system becomes the focus of particular attention, that among others findings resulted in extensive study of cells with preferential tropism to tumor. In this review we summarize the information on the diversity of currently existing approaches to targeted drug delivery to tumor, including (i) passive targeting based on the specific features of tumor vasculature, (ii) active targeting which implies a specific binding of the antitumor agent with its molecular target, and (iii) cell-mediated tumor targeting.

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“…Notably, the developed nanocarriers had less dark toxicity than the photosensitizer itself. Another example is the loading of tetracyanotetra(aryl)porphyrazines into liposomes [ 42 ]. Thus, in addition to their low toxicity, pz II and pz IV can be encapsulated in a nano-sized vehicle for improvement of the targeted delivery to the tumor tissue via an enhanced permeability and retention effect.…”

Section: Discussionmentioning

confidence: 99%

Cyanoarylporphyrazines with High Viscosity Sensitivity: A Step towards Dosimetry-Assisted Photodynamic Cancer Treatment

et al. 2021

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Despite the significant relevance of photodynamic therapy (PDT) as an efficient strategy for primary and adjuvant anticancer treatment, several challenges compromise its efficiency. In order to develop an “ideal photosensitizer” and the requirements applied to photosensitizers for PDT, there is still a need for new photodynamic agents with improved photophysical and photobiological properties. In this study, we performed a detailed characterization of two tetracyanotetra(aryl)porphyrazine dyes with 4-biphenyl (pz II) and 4-diethylaminophenyl (pz IV) groups in the periphery of the porphyrazine macrocycle. Photophysical properties, namely, fluorescence quantum yield and lifetime of both photosensitizers, demonstrate extremely high dependence on the viscosity of the environment, which enables them to be used as viscosity sensors. PzII and pz IV easily enter cancer cells and efficiently induce cell death under light irradiation. Using fluorescence lifetime imaging microscopy, we demonstrated the possibility of assessing local intracellular viscosity and visualizing viscosity changes driven by PDT treatment with the compounds. Thus, pz II and pz IV combine the features of potent photodynamic agents and viscosity sensors. These data suggest that the unique properties of the compounds provide a tool for PDT dosimetry and tailoring the PDT treatment regimen to the individual characteristics of each patient.

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Liposomal Form of Tetra(Aryl)Tetracyanoporphyrazine: Physical Properties and Photodynamic Activity In Vitro

Cited by 11 publications

References 29 publications

Model of Ovarian Adenocarcinoma Spheroids for Assessing Photodynamic Cytotoxicity

Model of Ovarian Adenocarcinoma Spheroids for Assessing Photodynamic Cytotoxicity

Targeted Delivery to Tumors: Multidirectional Strategies to Improve Treatment Efficiency

Cyanoarylporphyrazines with High Viscosity Sensitivity: A Step towards Dosimetry-Assisted Photodynamic Cancer Treatment

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