New promising porphyrazine-based agents for optical theranostics of cancer

Лермонтова, С. А.; Grigor’ev, I. S.; Peskova, Nina N.; Ladilina, E. Yu.; Balalaeva, Irina V.; Klapshina, Larisa G.; Boyarskii, V. P.

doi:10.1134/s1070363217030173

Cited by 13 publications

(5 citation statements)

References 11 publications

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“…Porphyrazine photodynamic effect on human ovarian adenocarcinoma cells. The porphyrazine compound studied in this work is a photosensitizer with a wide absorption band in the red spectral region and fluorescence with the emission maximum at 670 nm [ 24 ]. The high lipophilicity of this compound ensures its entry and distribution in the plasma membrane and intracellular membranes.…”

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: 99%

“…We used a novel photoactive compound of the family of porphyrazines — tetrakis(4-benzyloxyphenyl)tetracyanoporphyrazine (hereinafter, porphyrazine), synthesized at the G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences (Nizhny Novgorod) [ 24 ].…”

Section: Methodsmentioning

confidence: 99%

Model of Ovarian Adenocarcinoma Spheroids for Assessing Photodynamic Cytotoxicity

et al. 2020

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“…It was found that potential therapeutic index (IC 50 (dark)/IC 50 (light)) of pzIV is much greater than that for another described cyano-aryl porphyrazines. [11][12][13]22] Additionally, this tetrapyrrol macrocycle as the most of cyano-aryl porphyrazines demonstrates photophysical behaviour of the fluorescent molecular rotor, i.e., high sensitivity of the fluorescence parameters to local viscosity. We believe that the combination of properties of highly efficient photosensitizer in PDT and the sensitive intracellular viscosity sensor enable significant enhancement of the pzIV functionality as a potential agent of optical theranostics.…”

Section: Discussionmentioning

confidence: 97%

“…We have found that the structure of peripheral aryl groups coupled with macrocycle core significantly affects photophysical and cytotoxic properties of porphyrazines. [11][12][13] So, the porphyrazine peripheral framing variation can be used as an effective tool for a therapeutic potential fine tuning.…”

Section: Introductionmentioning

confidence: 99%

Cyano-Aryl Porphyrazine Pigments with Polycyclic Substituents as the Promising Agents for Photodynamic Therapy and Potential Sensors of Local Viscosity

Лермонтова¹,

Grigoryev²,

Peskova³

et al. 2019

MHC

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The unique cyanoporphyrazine pigment with four bulky phenanthrenyl peripheral substituents has been prepared. It demonstrates the noticeable shift of Q-band to longer wavelengths due to phenanthryl aromatic system extension. The compound showed very strong predominance of photoinduced cytotoxicity over cytotoxicity in the dark. The presented results indicate the enhancement of photodynamic properties of porphyrazine containing polycyclic aryl substituents in peripheral framing. It is confirmed that the chemical design of the peripheral aryl groups is an efficient toolkit for a fine tuning of photodynamic properties. Furthermore, we have shown that in spite of the presence of bulky substituents new cyano-aryl porphyrazine demonstrates the properties of fluorescent molecular rotors, i.e. the segmental intramolecular mobility in environment of low viscosity. Previously on the example of related cyano-aryl porphyrazines combining the properties of fluorescent molecular rotors and photosensitizers we have demonstrated high potential of these compounds as the sensors of local viscosity and rigidity of biological submicrometer environment within a living cell. So, in respect to PDT it can be a significant expansion of photosensitizer functionality as a potential agent of optical theranostics.

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“…It has been shown that pz with para‐ fluorophenyl groups possess properties that enable their dual use as sensitizers as well as viscosity markers in PDT, thus providing a new type of diagnostic and dosimetry tool in PDT treatment . Moreover, the photodynamic properties of pz can be significantly improved by chemical design of the peripheral aryl groups . In his study, we analyzed four cyanoarylporphyrazines ( pz I‐IV ; Figure A) that are highly potent in PDT.…”

Section: Introductionmentioning

confidence: 99%

Effect of novel porphyrazine photosensitizers on normal and tumor brain cells

Mishchenko

Turubanova

Митрошина

et al. 2019

Journal of Biophotonics

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Photodynamic therapy (PDT) is a clinically approved procedure for targeting tumor cells. Though several different photosensitizers have been developed, there is still much demand for novel photosensitizers with improved properties. In this study we aim to characterize the accumulation, localization and dark cytotoxicity of the novel photosensitizers developed in‐house derivatives of porphyrazines (pz I‐IV) in primary murine neuronal cells, as well as to identify the concentrations at which pz still effectively induces death in glioma cells yet is nontoxic to nontransformed cells. The study shows that incubation of primary neuronal and glioma cells with pz I‐IV leads to their accumulation in both types of cells, but their rates of internalization, subcellular localization and dark toxicity differ significantly. Pz II was the most promising photosensitizer. It efficiently killed glioma cells while remaining nontoxic to primary neuronal cells. This opens up the possibility of evaluating pz II for experimental PDT for glioma.

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New promising porphyrazine-based agents for optical theranostics of cancer

Cited by 13 publications

References 11 publications

Model of Ovarian Adenocarcinoma Spheroids for Assessing Photodynamic Cytotoxicity

Model of Ovarian Adenocarcinoma Spheroids for Assessing Photodynamic Cytotoxicity

Cyano-Aryl Porphyrazine Pigments with Polycyclic Substituents as the Promising Agents for Photodynamic Therapy and Potential Sensors of Local Viscosity

Effect of novel porphyrazine photosensitizers on normal and tumor brain cells

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