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Study of the photoresponse of a titanium anode coated with solution-processed fullerene-containing metal porphyrin/phthalocyanine films
摘要： The present paper deals with the recent studies on the preparation of porphyrin-based donor-acceptor complexes capable of photoinduced electron transfer for solution-processed organic solar cells. Here the synthesis and chemical structure of (octakis(3,5-di-tert-butylphenoxy)phthalocyaninato) cobalt(II) (1) and (2,3,7,8,12,18-hexamethyl,13,17-diethyl,5-(2-pyridyl)porphinato) manganese(III) chloride (2) are performed and self-assembly in toluene solution of 1 and 1′-N-methyl-2′-(pyridin-4-yl)pyrrolidino[3′,4′:1,2][60]fullerene (PyC60) were discussed in more details. The structure of the obtained dyad 1-PyC60 is con?rmed by means of chemical thermodynamics/kinetics, UV–vis, IR, 1H NMR spectroscopy. Photoelectrochemical studies of the phthalocyanine-fullerene dyad and its precursors were carried out by voltammetry and amperometry methods. A comparative analysis of the photoelectrochemical characteristics obtained in this paper and these for recent described cobalt(II)/manganese(III) porphyrin/phthalocyanine-fullerene dyads are introduced from which ideas for the future design of high performance organic solar cells will be developed.
关键词： donor-acceptor complexes,organic solar cells,phthalocyanine,photoinduced electron transfer,fullerene,porphyrin
更新于2025-11-14 15:14:40
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Aminopyrazole-substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition properties
摘要： The synthesis, characterization, aggregation behavior, theoretical studies, and investigation of antimicrobial, antidiabetic, and anticholinergic properties of 4-(2-(5-amino-4-(4-bromophenyl)-3-methyl-1H-pyrazol-1-yl)ethoxy)phthalonitrile (2) and its soluble aminopyrazole-substituted peripheral metallo (Mn, Co, and Ni)-phthalocyanine complexes (3–5) are reported for the first time. The synthesized compounds and phthalocyanine complexes were characterized spectroscopically. The new phthalonitrile derivative (2) and its peripheral metallophthalocyanine complexes (3–5) were found to be effective inhibitors of α-glycosidase, acetylcholinesterase (AChE), human carbonic anhydrase I and II isoforms (hCA I and II), and butyrylcholinesterase (BChE) with Ki values in the range of 1.55 ± 0.47 to 10.85 ± 3.43 nM for α-glycosidase, 8.44 ± 0.32 to 21.31 ± 7.91 nM for hCA I, 11.73 ± 2.82 to 31.03 ± 4.81 nM for hCA II, 101.62 ± 26.58 to 326.54 ± 89.67 nM for AChE, and 68.68 ± 11.15 to 109.53 ± 19.55 nM for BChE. This is the first study of peripherally substituted phthalocyanines containing an aminopyrazole group as potential carbonic anhydrase enzyme inhibitor. Also, the antimicrobial activities of the synthesized compounds were evaluated against six microorganisms (four bacteria and two Candida species) using the broth microdilution method. The gram-positive bacteria were detected to be more sensitive than gram-negative bacteria and yeasts in the synthesized compounds.
关键词： acetylcholinesterase,antimicrobial,phthalocyanine,anticholinergic,antidiabetic,carbonic anhydrase,aminopyrazole
更新于2025-09-23 15:23:52
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Oxidative stress generated by irradiation of a zinc(II) phthalocyanine induces a dual apoptotic and necrotic response in melanoma cells
摘要： Melanoma is an aggressive form of skin carcinoma, highly resistant to traditional therapies. Photodynamic therapy (PDT) is a non-invasive therapeutic procedure that can exert a selective cytotoxic activity toward malignant cells. In this work we evaluated the effect of a cationic zinc(II) phthalocyanine (Pc13) as photosensitizer on a panel of melanoma cells. Incubation with Pc13 and irradiation induced a concentration and light dose-dependent phototoxicity. In order to study the mechanism underlying Pc13-related cell death and to compare the effect of different doses of PDT, the most sensitive melanoma B16F0 cells were employed. By confocal imaging we showed that Pc13 targeted lysosomes and mitochondria. After irradiation, a marked increase in intracellular reactive oxygen species was observed and a complete protection from Pc13 phototoxicity was reached in the presence of the antioxidant trolox. Acridine orange/ethidium bromide staining showed morphological changes indicative of both apoptosis and necrosis. Biochemical hallmarks of apoptosis, including a significant decrease in the expression levels of Bcl-2, Bcl-xL and Bid and mitochondrial membrane permeabilization, were observed at short times post irradiation. The consequent release of cytochrome c to cytosol and caspase-3 activation led to PARP-1 cleavage and DNA fragmentation. Simultaneously, a dose dependent increase of lactate dehydrogenase in the extracellular compartment of treated cells revealed plasma membrane damage characteristic of necrosis. Taken together, these results indicate that a dual apoptotic and necrotic response is triggered by Pc13 PDT-induced oxidative stress, suggesting that combined mechanisms of cell death could result in a potent alternative for melanoma treatment.
关键词： Necrosis,Mitochondrial membrane permeabilization,Apoptosis,Reactive oxygen species,Photodynamic therapy,Cationic phthalocyanine
更新于2025-09-23 15:23:52
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Bioinspired Color Changing Molecular Sensor toward Early Fire Detection Based on Transformation of Phthalonitrile to Phthalocyanine
摘要： The fire detection plays a critical role in the maintenance of public security. Previous approaches of early fire warning, based on smoke or temperature response must be set in the proximity of a fire. They cannot provide the additional information of fire location or size and are susceptible to complicated situations. It is still a big challenge to make rapid and accurate early fire warning in precombustion because of the lack of reliable alarm signals. Herein, a precursor molecular sensor (PMS) is designed and synthesized that can present the chemical structure transformation to form phthalocyanines (Pcs) and release a color change signal at about 180 °C, learning from the plant chlorophyll metabolism. Further, the PMS is assembled to an early fire warning component (EWC) and an intelligent image recognition algorithm is introduced for unburned fire detection. The EWC generates a colorful alarm within 20 s at 275 °C. Therefore, the facile PMS provides a reliable real-time monitoring strategy to the early fire warning detection in precombustion.
关键词： color change,molecular sensor,image recognition algorithm,phthalocyanine,early fire detection
更新于2025-09-23 15:23:52
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Blue Copper Peroksidase and Phthalocyanine Conjugate: Synthesis, Characterization and Applications
摘要： Trametes versicolor can degrade barks as a source for carbon necessity. Therefore it secretes lignin peroxidase, mangan peroxidase and laccase. The laccase enzyme was produced high yield at pH and glucose concentration 5 and 10 gL-1, respectively. In optimized medium, the enzyme activity was between 200-250 UL-1 when inducer was absent. It was seen that the activity reached 400 UL-1 when phenol used as an inducer. The molecular weight of purified laccase was found 80 kDa with SDS-PAGE and kinetic constant Km and Vmax values for ABTS were determined 3.66x10-4 μM and 1652 UL-1, respectively. Hence, due to these properties, these enzymes are widely used in industrial areas free or immolized. Laccase enzyme decolorization of 6 different dyes was carried out. A decolorization capacity of 50-99% was achieved by cultivation in 20 days using a beginning dye concentration of 20 ppm. The removal of color with active enzyme is obtained around 90%. Also laccase enzyme was conjugated amine functionalized low symmetrically phthalocyanine. This conjugate was examined both photodynamic therapy and chemosensor application. This conjugate fluorescence had a quantum yield of 0.32 (lifetime 3.59 ns) and generates efficiently singlet oxygen (quantum yield 0.4). The conjugate was successfully photodamage displayed in HeLa and HuH-7 cells in photodynamic therapy application. These results indicate that conjugate represent interesting agent with potential applications in photodynamic therapy. In addition that the chemosensor behavior of this compound to different metal ions has been studied and this conjugate display as fluorescence chemosensor for determination of Fe3+ions.
关键词： Conjugate,Zinc phthalocyanine,Metal Sensor,Laccase,Photodynamic Therapy
更新于2025-09-23 15:23:52
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A Lesson from Nature: Biomimetic Self-assembling Phthalocyanines for High-efficient Photothermal Therapy within the Biological Transparent Window
摘要： Development of facile but high-efficient small organic molecule based photothermal therapy (PTT) in the in vivo transparent window (800-900 nm) has been regarded as a minimally invasive and most promising strategy for potential clinical cancer treatment. Phthalocyanine (Pc) molecules with remarkable photophysical and photochemical properties as well as high extinction coefficients in the near-infrared region are highly desirable for PTT, but as far satisfying single-component Pc-based PTT within the in vivo transparent window (800-900 nm) has very rarely been reported. Herein, inspired by the self-assembly algorithm of natural bacteriochlorophylls (BChl's) c, d, and e, biomimetic self-assembling tetrahexanoyl Pc Bio-ZnPc with outstanding light-harvesting capacity was demonstrated to exhibit excellent PTT efficacy evidenced by both in vitro and in vivo results, within the biological transparent window.
关键词： photothermal therapy,phthalocyanine,biological transparent window,self-assembly,biomimetics
更新于2025-09-23 15:23:52
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Synthesis of N-CuMe2Pc nanorods/graphene oxide nanocomposite for symmetric supercapacitor electrode with excellent cyclic stability
摘要： Recent progress in the construction of non-peripheral octamethyl-substituted copper(II) phthalocyanine (N-CuMe2Pc) has opened up new strategies for energy storage applications. Since metal phthalocyanines can deliver excellent redox activities, we have prepared composite based on different ratios of N-CuMe2Pc and graphene oxide (GO) through a simple ultrasound process and evaluated their electrochemical performance for supercapacitor applications. As-prepared composites exhibit superior electrochemical activities as the results of the synergistic effect. A maximum specific capacitance of 291.6 F g?1 is achieved for the G10P2 electrode (Graphene oxide 10 mg and N-CuMe2Pc 2 mg) at 0.5 A g?1 which two times higher than their individual components. Further, the fabricated symmetric device shows that the excellent cyclic stability of about 100.1% over 5000 cycles. The experimental findings ensure the potential application of copper-phthalocyanine/GO composite as an electrode material for the next-generation supercapacitor applications.
关键词： Nanocomposite,Specific capacitance,Cyclic stability,Graphene oxide,Phthalocyanine
更新于2025-09-23 15:23:52
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Synthesis and characterization of novel imine substituted phthalocyanine for sensing of l-cysteine
摘要： New mono-nuclear cobalt (II) tetra[4-(2-{(E)-[(4-bromophenyl)imino]methyl}phenoxy)] phthalocyanine (CoTBrImPc) complex has been synthesized for the first time in pure state. The synthesized dark blue coloured complex was characterized by elemental analysis, IR, UV-Vis, NMR, Mass, powder X-ray diffraction and thermogravimetric analysis (TGA) to understand the structural integrity, purity and crystalline property of the complex. The synthesized phthalocyanine complex was found to be electrochemically active and it was immobilized on the glassy carbon electrode by drop-casting method and used for the detection of L-cysteine. The CoTBrImPc modified electrode was found to be a good electrocatalyst for the catalytic oxidation of L-cysteine with shift in the overpotential towards less positive potential and an increase in the catalytic current compared to bare glassy carbon electrode (GCE). The linear response was observed for the voltametric detection of L-cysteine in the concentration range 10-100 nM with coefficient of regression R2= 0.9993 and LOD of 3 nM and sensitivity of 2.99 μA nM-1 cm-2. The amperometric sensor was also developed for the detection of L-cysteine which showed linear response in the concentration range same as that of cyclic voltammertry technique with a linear equation y = 0.7582x+16.9535 and correlation coefficient of R2= 0.9961. The LOD and LOQ values for amperometric detection were 4 nM and 12 nM, respectively with the sensitivity value of 10.81 μA nM cm-2.
关键词： TGA,L-cysteine,XRD,Amperometry.,Phthalocyanine,cyclic voltammetry
更新于2025-09-23 15:23:52
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Determination of prostate cancer biomarker acid phosphatase at a copper phthalocyanine-modified screen printed gold transducer
摘要： In this work, a novel sensor based on immobilized copper phthalocyanine, 2,9,16,23-tetracarboxylic acid-polyacrylamide (Cu(II)TC Pc-PAA) was developed for determination of acid phosphatase (ACP) levels in nanomolar quantities. Detection was based on the measurement of enzymatically generated phosphate, with initial studies focused on phosphate detection at a Cu(II)TC Pc-PAA modified screen-printed gold transducer. The sensor was characterised in relation to operational performance (pH, response time, stability, linearity, and sensitivity) and common anionic interferents (nitrate, sulphate, chloride, and perchlorate). The functionalised surface also facilitated rapid detection of the enzyme bi-product 2-naphthol over the range 5-3000 μM. Quantitation of ACP was demonstrated, realising a linear response range of 0.5-20 nM and LOD of 0.5 nM, which is within the clinical range for this prostate cancer biomarker.
关键词： phosphate,Copper phthalocyanine,acid phosphatase,naphthol,gold screen-printed electrode.
更新于2025-09-23 15:23:52
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Intratumorally Injected Photothermal Agent-Loaded Photodynamic Nanocarriers for Ablation of Orthotopic Melanoma and Breast Cancer
摘要： Traditional chemotherapy of cancers may lead to serious adverse reactions due to little drug distribution in tumors. Here, a combination of photothermal therapy (PTT) and photodynamic therapy (PDT) was used for local treatment of orthotopic melanoma and breast cancer via intratumoral (i.t.) injection of photothermal agent-loaded photodynamic nanocarriers. A hydrophobic derivative of indocyanine green, DCC, was synthesized and entrapped into a pH-sensitive photosensitizer-core copolymer, PDCZP, to form DCC@PDCZP. The nanocarriers showed remarkable fluorescence, high singlet oxygen quantum yields, and strong photothermal effect. Flow cytometry suggested that the nanocarriers were efficiently internalized by cancer cells. Near infrared thermal imaging and fluorescence self-imaging showed that the i.t. injected DCC@PDCZP mainly remained in the tumors but the intravenous (i.v.) nanocarriers were distributed a little. One i.t. injection of DCC@PDCZP was enough to ablate the orthotopic B16-F10 and 4T1 mouse tumors under 830 nm and 660 nm irradiation at 4 hours post-injection. More importantly, no local recurrences were found though scabs were formed at 9 days post-treatment. The major anticancer mechanisms included improvement of cancer cell necrosis due to hyperthermia, inhibition of neovascularization, and enhancement of cell apoptosis. The i.t. injection of PTT/PDT nanoformulations is thus a promising local treatment of superficial tumors.
关键词： zinc phthalocyanine,intratumoral injection,melanoma,indocyanine green,breast cancer,photodynamic therapy,photothermal therapy
更新于2025-09-23 15:23:52