Use Of Phthalocyanines Research Articles

The effect of silicon phthalocyanine on cell death and mitochondrial membrane potential in pancreatic cancer cells

Silicon (SiPcs) phthalocyanines are advantageous because they do not aggregate due to their special structural features. Therefore, they have been widely used in a range of areas in chemical and biological technology. One of the common applications is the use of phthalocyanines on cancer therapies. Pancreas cancer is one of the most common cancers with a high rate of mortality around the world. In this study we therefore aimed to investigate the potential of SiPcs molecules which we previously synthesized for the first time, on increased cell death and the effect on mitochondrial activity in pancreatic cancer cells. The results showed the significantly selective cytotoxic effect of SiPc on cancer cells compared to normal cells. Mitochondrial membrane potential was not different in cancer cells but in normal cells after SiPcs treatment. Pre-incubation time (24h) of SiPcs before light irradiation induced more significant cytotoxicity in pancreatic cancer cells but not in normal cells compared to prolonged pre-incubation (48). This study revisited the biological function of previously synthesized SiPcs, and the results conclude the cytotoxic activity of SiPcs on pancreas cancer. These preliminary findings can be extended for other cancer types and detailed with in vivo models in the future.

Zinc(II), Palladium(II), and Metal-Free Phthalocyanines Bearing Nipagin-Functionalized Substituents against Candida auris and Selected Multidrug-Resistant Microbes.

Due to the rapidly increasing problem of antibiotic resistance in recent years, the use of phthalocyanines as photosensitizers with their superior properties in photodynamic antimicrobial therapy (PACT) applications has become important. In this study, magnesium(II) 1,4,8,11,15,18,22,25-octakis(4-[4-butoxycarbonylphenoxy]butyloxy)phthalocyanine was used in the demetalation reaction in trifluoroacetic acid, and subsequently subjected to metalation reaction in dimethylformamide with zinc(II) acetate and bis(benzonitrile)palladium(II) chloride towards zinc(II) and palladium(II) derivatives. Three phthalocyanines, including a demetalated one as well as two metalated, in the core with zinc(II) and palladium(II) were characterized using 1D and 2D NMR spectroscopy and mass spectrometry. In addition, all macrocycles were subjected to absorption and emission studies as well as photostability tests. In a photochemical study, zinc(II) and palladium(II) phthalocyanine complexes appeared to be efficient singlet oxygen generators. There were noted quantum yields of singlet oxygen generation for zinc(II) phthalocyanine derivative in DMF and DMSO at 0.55 and 0.72, whereas for palladium(II) complex at 0.73 and 0.77, respectively. Liposomal formulations of phthalocyanine derivatives were prepared, and their activity was evaluated against a broad spectrum of antibiotic-resistant microorganisms, such as methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli (ESBL+), Candida albicans resistant to fluconazole, C. auris, and against dermatophytes. Phthalocyanine palladium(II) complex showed the highest bactericidal activity against all antibiotic-resistant microorganisms, including reducing C. auris growth at 3.54 log.

Ultrasound versus Light: Exploring Photophysicochemical and Sonochemical Properties of Phthalocyanine-Based Therapeutics, Theoretical Study, and In Vitro Evaluations.

Photodynamic therapy (PDT) applications carried out with the assistance of ultrasound have attracted significant attention in recent years. The use of phthalocyanines, which are an important component as photosensitizers in PDT, is becoming more important day by day. In therapeutic applications, phthalocyanines can promote the production of reactive oxygen species. Motivated by this fact, the syntheses of metal-free (2), gallium (3), and indium (4) phthalocyanines have been achieved by substituting 4-(cinnamyloxy)phthalonitrile for the first time to evaluate their therapeutic applications. Additionally, photophysicochemical, sonophotochemical, and in vitro evaluations of phthalocyanines have been reported. To the best of our knowledge, this is the first study of the use of phthalocyanines with different metal ions as potential photosensitizers for sonophotodynamic therapy (SPDT) applications in gastric cancer cell lines. The results show that the quantum yield of the generation of singlet oxygen increased in sonophotochemical studies (ΦΔ = 0.55 (2), 0.85 (3), 0.96 (4)), compared to photochemical studies (ΦΔ = 0.22 (2), 0.61 (3), 0.78 (4)). The density functional theory (DFT) results are in good agreement with the experimental results and suggest increased reactivity of phthalocyanines 3 and 4 in various redox processes, thus implying their applicability and usefulness as potential therapeutic agents. These phthalocyanines are effective sensitizers for PDT, sonodynamic therapy (SDT), and SPDT against MKN-28 gastric cancer cell line in vitro. All three treatments decreased cell viability and induced apoptosis in the gastric cancer cell line. However, indium phthalocyanine (4)-mediated SPDT was a more effective treatment modality compared to indium phthalocyanine (4)-mediated PDT and SDT. Also, indium phthalocyanine (4) was found to be a more effective sensitizer to activate apoptosis compared to the other phthalocyanines. To sum up, phthalocyanine-mediated SPDT enhances the cytotoxic effect on gastric cancer cells more than the effect of SDT or PDT alone.

Interactions of Co, Cu, and non-metal phthalocyanines with external structures of SARS-CoV-2 using docking and molecular dynamics

The new coronavirus, SARS-CoV-2, caused the COVID-19 pandemic, characterized by its high rate of contamination, propagation capacity, and lethality rate. In this work, we approach the use of phthalocyanines as an inhibitor of SARS-CoV-2, as they present several interactive properties of the phthalocyanines (Pc) of Cobalt (CoPc), Copper (CuPc) and without a metal group (NoPc) can interact with SARS-CoV-2, showing potential be used as filtering by adsorption on paints on walls, masks, clothes, and air conditioning filters. Molecular modeling techniques through Molecular Docking and Molecular Dynamics were used, where the target was the external structures of the virus, but specifically the envelope protein, main protease, and Spike glycoprotein proteases. Using the g_MM-GBSA module and with it, the molecular docking studies show that the ligands have interaction characteristics capable of adsorbing the structures. Molecular dynamics provided information on the root-mean-square deviation of the atomic positions provided values between 1 and 2.5. The generalized Born implicit solvation model, Gibbs free energy, and solvent accessible surface area approach were used. Among the results obtained through molecular dynamics, it was noticed that interactions occur since Pc could bind to residues of the active site of macromolecules, demonstrating good interactions; in particular with CoPc. Molecular couplings and free energy showed that S-gly active site residues interacted strongly with phthalocyanines with values ​​of − 182.443 kJ/mol (CoPc), 158.954 kJ/mol (CuPc), and − 129.963 kJ/mol (NoPc). The interactions of Pc's with SARS-CoV-2 may predict some promising candidates for antagonists to the virus, which if confirmed through experimental approaches, may contribute to resolving the global crisis of the COVID-19 pandemic.

Design, synthesis and use of phthalocyanines as a new class of visible-light photoinitiators for free-radical and cationic polymerizations

Phthalocyanines present excellent photochemical properties for use as photoinitiators under visible or IR light exposure.

A career in photophysicochemical and electrochemical properties of phthalocyanine — a Linstead Career Award paper

This manuscript highlights the author’s contributions to phthalocyanine chemistry, especially the applications based on their electrochemistry and photophysicochemistry. In particular, the use of phthalocyanines as electrocatalysts and photocatalysts is presented. For photocatalysis, photodynamic antimicrobial chemotherapy and pollution control using green technologies are highlighted. For electrocatalysis the phthalocyanines are employed for the detection of pollutants and environmentally important molecules. Phthalocyanines are combined with nanomaterials for improved photocatalysis and electrocatalysis.

NIR photocleavage of the Si-C bond in axial Si-phthalocyanines.

The use of light-triggered photolysis provides a powerful tool for unique syntheses and for applications that require remote operation such as drug delivery or molecular switches. Here, we describe the photochemistry of a recently developed alkylsilicon phthalocyanine Pc 227, which undergoes an exchange of the alkyl ligand for a ligand derived from the solvent when the axial Si-C bond is photolyzed in a solvent with low-energy visible light. In this work with methanol as the solvent, we investigate the formation of the methoxy analogue of the therapeutic drug Pc 4, (termed Pc 233) upon irradiation. Using steady-state spectroscopy and characterization of the photoproducts, the competing pathways between direct ligand exchange on the central silicon atom and delocalization of the radical produced by homolysis on the phthalocyanine ring is observed. The delocalized radical intermediate is quite long-lived. At long times this intermediate decomposes without significant formation of Pc 233. The results of this investigation provide insights into recent work utilizing Pc 227 for drug delivery applications and for future work on the use of phthalocyanines as long-wavelength phototriggers.

ChemInform Abstract: Phthalocyanine Conjugates with Carbohydrates: Synthesis and Aggregation in Aqueous Solutions

AbstractReview: [50 refs.

ChemInform Abstract: Recent Advances in Phthalocyanine‐Based Sensitizers for Dye‐Sensitized Solar Cells.

AbstractReview: 104 refs.

Recent Advances in Phthalocyanine‐Based Sensitizers for Dye‐Sensitized Solar Cells

AbstractDye‐sensitized solar cells (DSSCs) based on nanocrystalline semiconductors have attracted significant attention as lower‐cost alternatives to conventional silicon‐based solar cells. The photosensitizers are vital components for the development of photovoltaic devices of this kind. Over the years, the most successful sensitizers have been RuII polypyridyl complexes, achieving power conversion efficiencies up to 11.5 %. However, due to their limited light‐harvesting capacity and the high cost of Ru‐dyes, efforts have also been directed towards the use of organic dyes. Among the wide range of sensitizers of this kind, phthalocyanines (Pcs) are very attractive because of their light‐harvesting properties in the red and near‐IR spectral region, as well as their thermal and chemical stability. The performance of Pc‐based devices has improved over the years, reaching 5.9 %, thanks to rational design of the phthalocyanine structure. In this microreview we review recent advances in the use of phthalocyanines as photosensitizers for DSSC applications.

Phthalocyanine conjugates with carbohydrates: synthesis and aggregation in aqueous solutions

The review is focused on the current state of the synthesis of glycosylated phthalocyanines and their precursors, mono-, di-, and tetraglycosyl phthalonitriles. Features of the synthesis of phthalogen conjugates with carbohydrates and the formation of related metal phthalocyanine complexes are discussed. The formation of aggregates of phthalocyanines in various media exerts a significant effect on the physicochemical and photochemical properties of phthalocyanine macrocycles, which is especially important in the practical use of phthalocyanines as photosensitizes. An aggregation of phthalocyanine conjugates in aqueous solutions strongly decreases the quantum yield of singlet oxygen, thus diminishing the biological activity of these compounds. Specific features of phthalocyanine conjugate aggregation with carbohydrates in aqueous solutions, organic solvents, and some their mixtures are analyzed.

On the possibilities of the use of phthalocyanines in photovoltaic conversion

The electrical properties of semiconductor and semimetal composites (containing CuPc and different carbon blacks) were described. Their properties may be varied in a wide range, dependently on carbon black type and preparation conditions. We expect that the photovoltaic properties of the materials can be applied for photovoltaic conversion and we discuss possibility of their practical utilisation.

Applications of phthalocyanines in organic light emitting devices

Numerous experimental set-ups for organic light emitting devices including novel elaborate materials have been proposed during the last years. It is remarkable that in a large part of devices, phthalocyanines that are known for several decades are employed successfully in different functions. For this reason, a survey on the use of phthalocyanines in organic light emitting devices is provided. Owing to the great variety of device set-ups the findings of different working groups are not directly comparable in some cases. Nevertheless, it is shown that as a result of their advantageous physical properties phthalocyanines are a favourable choice for the increase in stability of such devices.

Inactivation by phthalocyanine photosensitization of multiple forms of human immunodeficiency virus in red cell concentrates.

The use of phthalocyanines in conjunction with red light has been shown to inactivate model lipid-enveloped viruses in red cell concentrates. The ability of this treatment to inactivate multiple forms of human immunodeficiency virus (HIV) was evaluated in this study. The phthalocyanines used were aluminum phthalocyanine tetrasulfonate (AIPcS4) and the silicon phthalocyanines HOSiPcOSi(CH3)2(CH2)3 N(CH3)2 (Pc 4), and HOSiPcOSi(CH3)2 (CH2)3N+(CH3)3I-(Pc 5). HIV was studied in a cell-free form, in an actively replicating form, in latently infected cells, and in blood from HIV-positive patients. All three phthalocyanines inactivate > or = 10(5) infectious doses of cell-free HIV. However, only Pc 4 effectively inactivated actively replicating HIV and latently infected cells. The latter was about four times as sensitive to inactivation as was actively replicating HIV. Increasing the hematocrit of red cells during treatment decreased the rate of inactivation, especially at lower light doses. Under treatment conditions that completely inactivated the laboratory isolates of HIV, cell-associated HIV in blood from HIV-positive patients was also completely inactivated. The polymerase chain reaction signal from the gag gene of HIV was not affected on treatment of cell-free virus, but it was reduced after treatment of cell-associated HIV, particularly in some latently infected cell lines. Pc 4 and red light are effective in eliminating the infectivity of HIV in red cell concentrates. The usefulness of this approach for blood banking depends on future demonstration of the preservation of red cell circulatory survival and function in vivo.

Gas adsorption on phthalocyanines and its effects on electrical properties

This review considers the factors which influence the adsorption of gases onto single crystals and films of phthalocyanines, and the consequent changes in their electrical properties, which form the basis for the use of phthalocyanines as semiconducting gas sensors. Experimental results on the structure, morphology and surface chemical composition of phthalocyanine films as a function of preparation conditions and subsequent treatment are first considered. The implications of these results and of the molecular and electronic structure of the phthalocyanine molecule for the interactions between gases and phthalocyanine surfaces are then discussed followed by a review of experimental methods for characterising adsorbed species, including infra red-, thermal desorption-, x-ray photoelectron- and Auger spectroscopies, and the study of heats of adsorption and of surface photovoltages. The effects of adsorbed gases on electrical properties of phthalocyanine single crystals and films are reviewed in detail in the light of the above information, with particular reference to the chemical and physical factors which control the magnitude, rate and reversibility of the observed changes in semiconductivity and photoconductivity. Finally, the implications of this extensive knowledge for the design and optimisation of improved chemical sensors are discussed.

Organic Dyes as Spectroscopic Tools: Effects of Solution Equilibria for Phthalocyanines and Carbocyanines

The use of phthalocyanines and carbocyanines in laser applications is reviewed from the perspective of the known solution chemistry of these two families of dyes. The optical behavior of such dyes is found to show certain effects which correlate with the chemistry of the dye family concerned. These chemical effects are identified for phthalocyanines and carbocyanines in their principal laser usages, so as to reduce their being confused with purely physical phenomena.