New porphyrazine macrocycles with high viscosity-sensitive fluorescence parameters

Лермонтова, С. А.; Grigoryev, Ilya S.; Shilyagina, Natalia Yu.; Peskova, Nina N.; Balalaeva, Irina V.; Shirmanova, Marina V.; Klapshina, Larisa G.

doi:10.1134/s1070363216060189

Cited by 28 publications

(21 citation statements)

References 14 publications

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“…To estimate the capacities of the new cyano-aryl porphyrazine pigment PzIV containing peripheral 9-phenanthrenyl substituents we have investigated the photophysical properties (Table 1) and quantified its dark and photoinduced cytotoxicity to compare them with the same characteristics for relate porphyrazines pzI-pzIII. [11,13] Absorption spectra of cyano-aryl porphyrazines pzI-pzIV are typical for non-associated porphyrazine macrocycles (Figure 2A). But the noticeable shift of Q-band to longer wavelengths due to aryl substituent aromatic system extension (particularly, for pzIV) had beеn observed.…”

Section: Resultsmentioning

confidence: 99%

“…Our recent papers [11,13,20] presented the photophysical proofs that the cyano-aryl porphyrazine tetrapyrrol dyes pzI, pzII and pzIII were in fact fluorescent molecular rotors that could be potentially utilized to determine the local intracellular viscosity even under conditions of its dynamic change, for example, under the conditions of photodynamic therapy. Similarly, we found the significant dependence of the fluorescence intensity of pzIV on the medium viscosity ( Figure 7A).…”

Section: Resultsmentioning

confidence: 99%

“…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%

“…Synthesis of pzI-pzIII was carried out by the method previously described. [11,14] PzIV was prepared according to Scheme 1.…”

Section: Synthesismentioning

confidence: 99%

“…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%

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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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 97%

“…Synthesis of pzI-pzIII was carried out by the method previously described. [11,14] PzIV was prepared according to Scheme 1.…”

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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Effective delivery of porphyrazine photosensitizers to cancer cells by polymer brush nanocontainers

Shilyagina

Peskova

Лермонтова

et al. 2016

Journal of Biophotonics

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Efficient drug delivery can be assigned to tasks that attract the most acute attention of researchers in the field of anticancer drug design. We have reported the first case of using amphiphilic polymer brushes as nanocontainers for photosensitizer delivery to cancer cells. Regular graft-copolymers of hydrophobic polyimides with hydrophilic polymethacrylic acid side chains were loaded with photosensitive dye tetra(4-fluorophenyl)tetracyanoporphyrazine (Pz) providing a sufficiently stable homogeneous fraction of fluorescent Pz-loaded nanoparticles with a size of 100-150 nm. Pz-loaded polymer brushes were substantially more efficient for Pz delivery into cells compared with other types of particles examined, Pz-polyethyleneglycol and Pz-methylcellulose. In vivo, an efficient Pz delivery to tumor can also be expected since the Pz-PB particle size is in the optimal range for passive targeting. Pz-PB showed pronounced photodynamic activity, while, that is important, in the absence of irradiation the PB carrier itself was significantly less toxic than the dye itself. Summing up, water-soluble polymer brushes with polyimide backbones and polymethacrylic acid side chains can be regarded as a novel type of nanocontainers providing efficient intracellular drug delivery for photodynamic therapy of cancers.

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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 porphyrazine macrocycles with high viscosity-sensitive fluorescence parameters

Cited by 28 publications

References 14 publications

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

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

Effective delivery of porphyrazine photosensitizers to cancer cells by polymer brush nanocontainers

Effect of novel porphyrazine photosensitizers on normal and tumor brain cells

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