Photobiological properties of phthalocyanine photosensitizers Photosens, Holosens and Phthalosens: A comparative in vitro analysis

Brilkina, Anna A.; Dubasova, Lubov V.; Сергеева, Е. А.; Pospelov, Anton D.; Shilyagina, Natalia Yu.; Shakhova, Natalia M.; Balalaeva, Irina V.

doi:10.1016/j.jphotobiol.2018.12.020

Cited by 55 publications

(36 citation statements)

References 31 publications

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“…First, we analyzed the absorption and fluorescence spectra of PD belonging to the chlorins derivatives. For PS, we observed the typical absorption and fluorescence spectra (Additional file 1: Figure S1A), which is in agreement with the previously published data [19]. On the other hand, for PD, absorption peaks were present in the short-wave (Soret band) and long-wave (Q-band) regions of the spectrum (Additional file 1: Figure S1B).…”

Section: Resultssupporting

confidence: 90%

“…This procedure is often associated with secondary effects such as damage to the microvasculature and induction of a local inflammatory reaction [16]. An ideal photosensitizer should accumulate selectively in tumors, have low dark toxicity and be easy to synthesize [17–19]. Importantly, it should also be able to induce ICD in cancer cells.…”

Section: Introductionmentioning

confidence: 99%

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Immunogenic cell death induced by a new photodynamic therapy based on photosens and photodithazine

Turubanova

Balalaeva

Mishchenko

et al. 2019

j. immunotherapy cancer

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BackgroundAnti-cancer therapy is more successful when it can also induce an immunogenic form of cancer cell death (ICD). Therefore, when developing new treatment strategies, it is extremely important to choose methods that induce ICD and thereby activate anti-tumor immune response leading to the most effective destruction of tumor cells. The aim of this work was to analyze whether the clinically widely used photosensitizers, photosens (PS) and photodithazine (PD), can induce ICD when used in photodynamic therapy (PDT).MethodsCell death in murine glioma GL261 or fibrosarcoma MCA205 cells was induced by PS- or PD-PDT and cell death was analyzed by MTT or flow cytometry. Intracellular distribution of PS and PD was studied by using the laser scanning microscope. Calreticulin exposure and HMGB1 and ATP release were detected by flow cytometry, ELISA and luminescence assay, respectively. Immunogenicity in vitro was analyzed by co-culturing of dying cancer cells with bone-marrow derived dendritic cells (BMDCs) and rate of phagocytosis and maturation (CD11c+CD86+, CD11c+CD40+) of BMDCs and production of IL-6 in the supernatant were measured. In vivo immunogenicity was analyzed in mouse tumor prophylactic vaccination model.ResultsWe determined the optimal concentrations of the photosensitizers and found that at a light dose of 20 J/cm2 (λex 615–635 nm) both PS and PD efficiently induced cell death in glioma GL261 and fibrosarcoma MCA205 cells. We demonstrate that PS localized predominantly in the lysosomes and that the cell death induced by PS-PDT was inhibited by zVAD-fmk (apoptosis inhibitor) and by ferrostatin-1 and DFO (ferroptosis inhibitors), but not by the necroptosis inhibitor necrostatin-1 s. By contrast, PD accumulated in the endoplasmic reticulum and Golgi apparatus, and the cell death induced by PD-PDT was inhibited only by z-VAD-fmk. Dying cancer cells induced by PS-PDT or PD-PDT emit calreticulin, HMGB1 and ATP and they were efficiently engulfed by BMDCs, which then matured, became activated and produced IL-6. Using dying cancer cells induced by PS-PDT or PD-PDT, we demonstrate the efficient vaccination potential of ICD in vivo.ConclusionsAltogether, these results identify PS and PD as novel ICD inducers that could be effectively combined with PDT in cancer therapy.

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Immunogenic cell death induced by a new photodynamic therapy based on photosens and photodithazine

Turubanova

Balalaeva

Mishchenko

et al. 2019

j. immunotherapy cancer

Self Cite

201

158

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“…Bovine serum albumin (BSA), Chloroauric acid (HAuCl4*3H2O), Sodium citrate monobasic (HOC(COONa)(CH2COOH)2), N-(3-Dimethylaminopropyl)-N -ethylcarbodiimide hydrochloride (EDC), N-Hydroxysuccinimide (NHS), Sodium chloride (NaCl), and agarose were all purchased from Sigma-Aldrich (Darmstadt, Germany). Holosens ® , octachloride octakis [N(2-hydroxyethyl)-N,N,-(dimethylammoniomethyl)] zinc (II) phthalocyanine (ZnPc) was chosen as a photodynamic dye [33,42] and purchased from the Organic Intermediates and Dyes Institute (Moscow, Russia). Indocyanine green was also used as a photodynamic dye because of its long-time clinical application and approval for use by the U.S. Food and Drug Administration [43] and was purchased from Dynamic Diagnostics (Plymouth, MI, USA).…”

Section: Methodsmentioning

confidence: 99%

“…Photodynamic therapy is now well established for the treatment of cancer, and multiple autoimmune and infectious diseases [31,32]. Chemical compounds that are used as photosensitizers can be divided into several groups, including non-porphyrin compounds, the most developed drugs based on cyanines (for example, indocyanine green (ICG)), as well as phthalocyanines, which are aromatic heterocycles consisting of four isoindole rings connected by nitrogen atoms and capable of coordinating metal in the center of the molecule (Photosens, Holosens) [33,34]. The main advantages of these compounds are chemical homogeneity, absorption of light in the long-wavelength range of the spectrum (675-700 nm), high extinction coefficient, and high quantum yield of singlet oxygen.…”

Section: Introductionmentioning

confidence: 99%

Air-Filled Bubbles Stabilized by Gold Nanoparticle/Photodynamic Dye Hybrid Structures for Theranostics

et al. 2021

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Microbubbles have already reached clinical practice as ultrasound contrast agents for angiography. However, modification of the bubbles’ shell is needed to produce probes for ultrasound and multimodal (fluorescence/photoacoustic) imaging methods in combination with theranostics (diagnostics and therapeutics). In the present work, hybrid structures based on microbubbles with an air core and a shell composed of bovine serum albumin, albumin-coated gold nanoparticles, and clinically available photodynamic dyes (zinc phthalocyanine, indocyanine green) were shown to achieve multimodal imaging for potential applications in photodynamic therapy. Microbubbles with an average size of 1.5 ± 0.3 μm and concentration up to 1.2 × 109 microbubbles/mL were obtained and characterized. The introduction of the dye into the system reduced the solution’s surface tension, leading to an increase in the concentration and stability of bubbles. The combination of gold nanoparticles and photodynamic dyes’ influence on the fluorescent signal and probes’ stability is described. The potential use of the obtained probes in biomedical applications was evaluated using fluorescence tomography, raster-scanning optoacoustic microscopy and ultrasound response measurements using a medical ultrasound device at the frequency of 33 MHz. The results demonstrate the impact of microbubbles’ stabilization using gold nanoparticle/photodynamic dye hybrid structures to achieve probe applications in theranostics.

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“…Light irradiation at this wavelength causes the generation of singlet oxygen from Cholosens molecule with a high quantum yield of 100 J/cm 2 [54]. A recent study revealed the photobiological properties of non-encapsulated phthalocyanine photosensitizers, including Cholosens [55]. The current work aims to determine the efficacy of dextran sulfate (DS) and poly-l-arginine (PArg) PMC ([DS/PAgr] 4 ) capsules loaded with Cholosens for the PDT treatment on eukaryotic cells and bacteria studied in vitro.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Bioeffects of Polyelectrolyte Multilayer Microcapsules Post-Loaded with Water-Soluble Cationic Photosensitizer

et al. 2020

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Microencapsulation and targeted delivery of cytotoxic and antibacterial agents of photodynamic therapy (PDT) improve the treatment outcomes for infectious diseases and cancer. In many cases, the loss of activity, poor encapsulation efficiency, and inadequate drug dosing hamper the success of this strategy. Therefore, the development of novel and reliable microencapsulated drug formulations granting high efficacy is of paramount importance. Here we report the in vitro delivery of a water-soluble cationic PDT drug, zinc phthalocyanine choline derivative (Cholosens), by biodegradable microcapsules assembled from dextran sulfate (DS) and poly-l-arginine (PArg). A photosensitizer was loaded in pre-formed [DS/PArg]4 hollow microcapsules with or without exposure to heat. Loading efficacy and drug release were quantitatively studied depending on the capsule concentration to emphasize the interactions between the DS/PArg multilayer network and Cholosens. The loading data were used to determine the dosage for heated and intact capsules to measure their PDT activity in vitro. The capsules were tested using human cervical adenocarcinoma (HeLa) and normal human dermal fibroblast (NHDF) cell lines, and two bacterial strains, Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli. Our results provide compelling evidence that encapsulated forms of Cholosens are efficient as PDT drugs for both eukaryotic cells and bacteria at specified capsule-to-cell ratios.

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Photobiological properties of phthalocyanine photosensitizers Photosens, Holosens and Phthalosens: A comparative in vitro analysis

Cited by 55 publications

References 31 publications

Immunogenic cell death induced by a new photodynamic therapy based on photosens and photodithazine

Immunogenic cell death induced by a new photodynamic therapy based on photosens and photodithazine

Air-Filled Bubbles Stabilized by Gold Nanoparticle/Photodynamic Dye Hybrid Structures for Theranostics

In Vitro Bioeffects of Polyelectrolyte Multilayer Microcapsules Post-Loaded with Water-Soluble Cationic Photosensitizer

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