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Multicharged Phthalocyanines as Selective Ligands for G-Quadruplex DNA Structures
摘要： The stabilization of G-Quadruplex DNA structures by ligands is a promising strategy for telomerase inhibition in cancer therapy since this enzyme is responsible for the unlimited proliferation of cancer cells. To assess the potential of a compound as a telomerase inhibitor, selectivity for quadruplex over duplex DNA is a fundamental attribute, as the drug must be able to recognize quadruplex DNA in the presence of a large amount of duplex DNA, in the cellular nucleus. By using different spectroscopic techniques, such as ultraviolet-visible, fluorescence and circular dichroism, this work evaluates the potential of a series of multicharged phthalocyanines, bearing four or eight positive charges, as G-Quadruplex stabilizing ligands. This work led us to conclude that the existence of a balance between the number and position of the positive charges in the phthalocyanine structure is a fundamental attribute for its selectivity for G-Quadruplex structures over duplex DNA structures. Two of the studied phthalocyanines, one with four peripheral positive charges (ZnPc1) and the other with less exposed eight positive charges (ZnPc4) showed high selectivity and affinity for G-Quadruplex over duplex DNA structures and were able to accumulate in the nucleus of UM-UC-3 bladder cancer cells.
关键词： telomerase inhibition,selectivity,salmon sperm DNA,UV-Vis,circular dichroism,hyperchromism,G-Quadruplexes,G4-FID,multicharged phthalocyanines
更新于2025-11-21 11:08:12
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Selective Detection of Trinitrophenol by Amphiphilic Dimethylaminopyridine-Appended Zn(II)phthalocyanines at the Near-Infrared Region
摘要： Novel amphiphilic Zn(II)phthalocyanines (ZnPcs) peripherally substituted with four and eight dimethylaminopyridinium units (ZnPc1 and ZnPc2) were synthesized by cyclotetramerization of the corresponding phthalonitriles. The effect of aggregation and photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties was investigated. The chemosensing ability of ZnPcs toward explosive nitroaromatic compounds was explored in aqueous medium. This study demonstrates that ZnPc1 and ZnPc2 show fluorescence quenching behavior upon interaction with different nitro analytes and show unprecedented selectivity toward 2,4,6-trinitrophenol with a limit of detection (LOD) of 0.7?1.1 ppm with a high quenching rate constant (Ksv) of 1.6?2.02 × 105. The near-infrared (NIR) fluorescence in thin films was quenched efficiently because of the photoinduced electron-transfer process through strong intermolecular π?π and electrostatic interactions. The sensing process is highly reversible and free from the interference of other commonly encountered nitro analytes. Further, experiments were performed to demonstrate the use of ZnPcs as efficient heterogeneous photocatalysts in the reduction of nitro explosives. The smart dual performance of multicharged ZnPcs in aqueous media quantifies them as attractive candidates in developing sensor materials at the NIR region and to possibly convert the toxic explosives into useful scaffolds. These results provide an interesting perspective toward elaboration of stable fluorescent systems for the selective sensing behavior of nitro explosives and their facile heterogeneous catalytic behavior in the reduction reactions.
关键词： trinitrophenol,photocatalysis,explosive detection,near-infrared,fluorescence quenching,dimethylaminopyridinium,Zn(II)phthalocyanines
更新于2025-11-21 11:08:12
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Synthesis and spectral luminescent properties of 4,4′,4′′,4′′′-tetra(tert-butyl)-5,5′,5′′,5′′′-tetrakis(phenylsulfanyl)phthalocyanines and their sulfo acids
摘要： Magnesium and zinc complexes of 4,4′,4′′,4′′′-tetra(tert-butyl)-5,5′,5′′,5′′′-tetrakis(phenylsulfanyl)phthalocyanine were synthesized. The corresponding sulfo acids were prepared by sulfochlorination and further hydrolysis. Spectral luminescent properties of the synthesized phthalocyanine derivatives were studied. Introduction of sulfo groups resulted in a bathochromic shift of Q-band in the spectra recorded in DMF and pyridine regardless of the metal nature as well as in a hypsochromic shift in sulfuric acid.
关键词： metal complexes,phthalocyanines,sulfo acids,luminescence
更新于2025-11-14 15:32:45
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Photooxidase-mimicking nanovesicles with superior photocatalytic activity and stability based on amphiphilic amino acid and phthalocyanine co-assembly
摘要： Enzyme mimics have broad applications in catalysis and can assist elucidation of the catalytic mechanism of natural enzymes. However, challenges arise from the design of catalytic sites, the selection of host molecules and their integration into active three-dimensional structures. Herein, we develop a mimic photooxidase by synergetic molecular self-assembly. 9-Fluorenylmethyloxycarbonyl-L-histidine in combination with phthalocyanine shows efficient co-assembly into nanovesicles with flexibly tunable particle size and membrane thickness. The obtained nanovesicles are capable of reactive oxygen-mediated photosensitive oxidation with improved efficiency and stability. This work highlights the co-assembly of simple building blocks into a supramolecular photocatalyst, which might give insight into possible evolutionary paths of photocatalytic membraneous systems and will allow the facile transfer into photosensitive nanoreactors or artificial organelles.
关键词： self-assembly,photooxidase,amino acids,nanovesicles,phthalocyanines
更新于2025-09-23 15:23:52
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Photobiological properties of phthalocyanine photosensitizers Photosens, Holosens and Phthalosens: A comparative in vitro analysis
摘要： Photobiological properties of phthalocyanine photosensitizers, namely, clinically approved Photosens and new compounds Holosens and Phthalosens were analyzed on transitional cell carcinoma of the urinary bladder (T24) and human hepatic adenocarcinoma (SK-HEP-1). Photosens is a sulfated aluminum phthalocyanine with the number of sulfo groups 3.4, which is characterized by a high degree of hydrophilicity, slow cellular uptake, localization in lysosomes and the lowest photodynamic activity. Holosens is an octacholine zinc phthalocyanine, a cationic compound with significant charge. Holosens more efficiently enters the cells; it is localized in Golgi apparatus in addition to lysosomes and exhibits a significant inhibitory effect on cell viability upon irradiation. The highest photodynamic activity was demostrated by Phthalosens. Phthalosens is a metal-free analog of Photosens with a number of sulfo groups 2.5, which determines its amphiphilicity. Phthalosens is characterized by the highest rate of cellular uptake through the outer cell membrane, localization in cell membrane as well as in lysosomes and Golgi apparatus, and the highest activity upon irradiation among the photosensitizers studied. In general, changes in the physicochemical properties of Holosens and Phthalosens ensured an increase in their efficiency in vitro compared to Photosens. The features of accumulation, intracellular distribution and their interrelation with photodynamic activity, revealed in this work, indicate the prospects of Phthalosens and Holosens for clinical practice.
关键词： Photodynamic treatment,photodynamic activity,Holosens,dark toxicity,Phthalosens,Photosens,intracellular distribution,phthalocyanines
更新于2025-09-23 15:23:52
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High Photosensitized Singlet Oxygen Generating Zinc and Chloroindium Phthalocyanines Bearing (4-isopropylbenzyl)oxy Groups as Potential Agents for Photophysicochemical Applications
摘要： In this study, novel phthalonitrile derivatives (1 and 2) and their peripherally and non-peripherally tetra (4-isopropylbenzyl)oxy-substituted zinc and chloroindium phthalocyanine complexes (3-6) have been prepared for the first time. The synthesized phthalonitrile derivatives and phthalocyanine complexes were characterized spectroscopically. Not only the chloroindium phthalocyanines but also zinc phthalocyanines are essentially free from aggregation in THF at the studied micromolar concentration. The purpose is to compare the effects of two types of substitution on the phthalocyanines to be used as sensitizers in photodynamic therapy (PDT). Photophysical and photochemical properties of all phthalocyanines are investigated and the results showed that the peripheral phthalocyanines more effectively photooxidize DPBF through singlet oxygen. The photochemical results showed that both ZnPc (3 and 5) and InPc (4 and 6) can be used as sensitizers in PDT because of their very high singlet oxygen quantum yields (range from 0.80 to 0.97).
关键词： Singlet Oxygen,Photosensitizer,Phthalocyanines,Photodynamic Therapy
更新于2025-09-23 15:23:52
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Synthesis, characterization and DFT analysis of new phthalocyanine complexes containing sulfur rich substituents
摘要： Nine new tetrasubstituted metallophthalocyanines (MPc) bearing sulfur rich substituents on peripheral positions were synthesized and fully characterized. The new MPc compounds contain Co2+, Ni2+ and Cu2+. The photochemical and electrochemical properties of the new molecules were investigated. In addition to this investigation, a comparative study took place on the effect of the type of terminal ligand on properties of the MPc compound. Theoretical studies (DFT) were, also carried out in order to support the corresponding experimental results.
关键词： Cobalt,Copper,Nickel,Microwave synthesis,Phthalocyanines,DFT calculations
更新于2025-09-23 15:23:52
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4-{(Z)-[4-(Diethylamino)phenyldiazenyl]}phthalonitirle and Phthalocyanines Thereof
摘要： 4{(Z)-[4-(Diethylamino)phenyldiazenyl]}phthalonitrile was synthesized by diazotization and azo coupling and used to prepare tetrakis-4-(4-{(Z)-[4-(diethylamino)phenyl]diazenyl})phthalocyanine and its cobalt, nickel, zinc and magnesium complexes by template synthesis. The spectral properties of the synthesized compounds were studied.
关键词： azo chromophore,4-aminophthalonitrile,electronic absorption spectra,metal phthalocyanines
更新于2025-09-23 15:21:21
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Nanostructures of functionalized zinc phthalocyanines prepared with colloidal lithography: Evaluation of surface orientation and dimensions using scanning probe microscopy
摘要： Patterned arrays of nanoholes and nanorings were prepared using colloidal lithography combined with steps of solution immersion and vapor deposition of organosilanes. Samples prepared with colloidal lithography exhibit millions of reproducible test structures with a periodic arrangement throughout areas of the surface according to the dimensions and spacing of the particle mask. Views of the size and morphology of nanopatterns obtained with atomic force microscopy (AFM) can provide information of progressive steps of chemical reactions as nanostructures are grown within spatially confined areas surrounded by a resist film. A surface mask of colloidal latex or silica spheres was used to protect discrete areas of a Si(111) substrate from the deposition of organosilanes. When the mask was removed, the uncovered areas of the surface revealed regularly-shaped, small sites of uncovered substrate available for further reaction steps to build hierarchical surface structures. Nanostructures of zinc phthalocyanines (ZnPcs) were constructed using amine-terminated nanopatterns as sites for binding. Spatial selectivity was achieved for directing the attachment of ZnPcs to the surface using resist films of 2-[methoxy(polyethyleneoxy)propyl]trichlorosilane (PEO-silane) and also with octadecyltrimethoxysilane (OTMS). The molecule chosen as a linker was (3-aminopropyl)triethoxysilane (APTES) which presents an amine group at the interface. In general, phthalocyanine molecules tend to bind in a coplanar orientation by physisorption to the surface and can stack together through pi-pi interactions between adjacent macrocycles. However, the nature of the substituents will also influence whether the molecules assemble on surfaces in a side-on orientation or with the macrocycle oriented in a coplanar arrangement. Hydroxyl and isothiocyanate pendant groups were attached to the macrocycles of ZnPcs chosen for this study, to investigate conformational differences when attached to APTES nanopatterns. The size and morphology of nanostructures was visualized and sensitively measured with tapping-mode AFM. The elastic response of samples patterned with ZnPc was mapped with force modulation AFM. Changes in the height of nanostructures indicate whether the macrocycles are oriented upright or parallel to the surface plane, or if multilayers were formed.
关键词： Atomic force microscopy,Colloidal lithography,Nanopatterning,Phthalocyanines
更新于2025-09-23 15:19:57
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Physicochemical and antimicrobial photodynamic chemotherapy (against E. Coli) by indium phthalocyanines in the presence of silver-iron bimetallic nanoparticles
摘要： In this work, Schiff base indium phthalocyanines: In-Cl tetra N,N-dimethyl-4-(methylimino) phthalocyanine (complex 1b) and In-Cl tetra-phenoxy N,N-dimethyl-4-(methylimino) phthalocyanine (complex 2b) substituted at the peripheral positions with 4-dimethyl benzaldehyde are synthesized from tetra amino and tetra phenoxy amino phthalocyanines, respectively. These complexes were further quartenised with 1,3-propanesultone to form zwitterionic complexes 1 and 2, respectively. Silver-iron dimers (Ag-Fe3O4) and silver-iron core shell (Ag@Fe3O4) nanoparticles (NPs) were linked to the synthesised complexes. The photophysical and photochemical behaviour of the complexes and their conjugates with NPs were investigated in dimethyl sulfoxide. Complexes 2 and 2b and their conjugates were then used for photodynamic antimicrobial chemotherapy on E. coli. The zwitter ionic photosensitiser 2 and its conjugates showed better efficiency for photodynamic antimicrobial chemotherapy compared to their neutral counterparts.
关键词： zwitterionic,Indium phthalocyanines,photodynamic antimicrobial chemotherapy,E-coli
更新于2025-09-19 17:15:36