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Biomimetic biosensor based on lipidic layers containing tyrosinase and lutetium bisphthalocyanine for the detection of antioxidants

APETREI, C.; ALESSIO, P.; CONSTANTINO, C. J. L.; SAJA, J. A. de; RODRIGUEZ-MENDEZ, M. L.; PAVINATTO, Felippe José; FERNANDES, E. Giuliani Ramos; ZUCOLOTTO, Valtencir; OLIVEIRA JUNIOR, Osvaldo Novais de
Fonte: ELSEVIER ADVANCED TECHNOLOGY Publicador: ELSEVIER ADVANCED TECHNOLOGY
Tipo: Artigo de Revista Científica
ENG
Relevância na Pesquisa
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This paper describes the preparation of a biomimetic Langmuir-Blodgett film of tyrosinase incorporated in a lipidic layer and the use of lutetium bisphthalocyanine as an electron mediator for the voltammetric detection of phenol derivatives, which include one monophenol (vanillic acid), two diphenols (catechol and caffeic acid) and two triphenols (gallic acid and pyrogallol). The first redox process of the voltammetric responses is associated with the reduction of the enzymatically formed o-quinone and is favoured by the lutetium bisphthalocyanine because significant signal amplification is observed, while the second is associated with the electrochemical oxidation of the antioxidant and occurs at lower potentials in the presence of an electron mediator. The biosensor shows low detection limit (1.98 x 10(-6)-27.49 x 10(-6) M), good reproducibility, and high affinity to antioxidants (Km in the range of 62.31-144.87 mu M). The excellent functionality of the enzyme obtained using a biomimetic immobilisation method, the selectivity afforded by enzyme catalysis, the signal enhancement caused by the lutetium bisphthalocyanine mediator and the increased selectivity of the curves due to the occurrence of two redox processes make these sensors exceptionally suitable for the detection of phenolic compounds. (C) 2010 Elsevier B.V. All rights reserved.; Spanish Ministry of Science[AGL2009-12660/ALI]; Spanish Ministry of Science; FAPESP; Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP); CNPq; Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq); CAPES (Brazil); Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Estudos eletroquímicos da reação de redução de oxigênio utilizando catalisadores a base de carbono contendo ftalocianinas metálicas; Electrochemical studies of oxygen reduction reaction using metallic phthalocianynes suportted in carbon

Reis, Rafael Machado
Fonte: Biblioteca Digitais de Teses e Dissertações da USP Publicador: Biblioteca Digitais de Teses e Dissertações da USP
Tipo: Tese de Doutorado Formato: application/pdf
Publicado em 13/03/2013 PT
Relevância na Pesquisa
398.9676%
Vários trabalhos na literatura reportam a utilização de catalisadores à base de compostos macrocíclicos metálicos no estudo da reação de redução do oxigênio (RRO). Esta reação possui mecanismos complexos que ainda não foram totalmente compreendidos, sendo que os principais produtos gerados são água e peróxido de hidrogênio. A maior parte dos artigos encontrados na literatura estudam estes catalisadores com intuito de se ter como produto único ou majoritário a água, principalmente para aplicações em células a combustível. Porém, este trabalho tem como objetivo principal identificar catalisadores a base de compostos macrocíclicos metálicos, mais em específico ftalocianinas metálicas, que promovam uma geração majoritária de peróxido de hidrogênio. Em trabalhos futuros, os melhores catalisadores encontrados servirão como modificadores em eletrodos de difusão gasosa (EDG) na aplicação em sistemas de degradação de compostos orgânicos através dos processos oxidativos avançados (POA).
Neste trabalho foram avaliados catalisadores contendo vários teores de ftalocianinas de manganês, ferro, cobre e cobalto incorporadas, separadamente, em uma matriz condutora de carbono Printex 6L. Para isto, foram realizadas medidas de fluorescência de raios X (XRF)...

Electroactive layer-by-layer films of iron tetrasulfonated phthalocyanine

Zucolotto, V; Ferreira, M.; Cordeiro, M. R.; Constantino, CJL; Moreira, W. C.; Oliveira, O. N.
Fonte: Elsevier B.V. Publicador: Elsevier B.V.
Tipo: Artigo de Revista Científica Formato: 945-946
ENG
Relevância na Pesquisa
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Electroactive films of iron tetrasulfonated phthalocyanine (FeTsPc) were assembled via the electrostatic layer-by-layer technique (LBL), in which FeTsPc layers were alternated with the polycationic poly(allylamine hydrochloride) (PAN). The multilayer formation was monitored via UV-Vis spectroscopy by measuring the increase in the Q Band of FeTsPc at 676 nm. Film thickness was estimated by profilometry as ca. 10 Angstrom per bilayer. Fourier transform infrared and UV-Vis absorption spectroscopy suggested specific interactions between FeTsPc and PAR Cyclic voltammograms showed reproducible pairs of oxidation-reduction peaks at 0.92 mV and 0.70 mV, respectively, for a 50-bilayer PAH/FeTsPc film at 50 mV/s (vs Ag/AgNO3).

Determination of the phthalocyanine textile dye, reactive turquoise blue, by electrochemical techniques

Osugi, Marly E.; Carneiro, Patrícia A.; Zanoni, Maria Valnice Boldrin
Fonte: Universidade Estadual Paulista Publicador: Universidade Estadual Paulista
Tipo: Conferência ou Objeto de Conferência Formato: 660-665
ENG
Relevância na Pesquisa
680.531%
Turquoise blue 15 (AT15) is a reactive dye widely used in the textile industry to color natural fibers. The presence of these dyes in effluent and industrial wastewater is of considerable interest due ecotoxicological and environmental problems. The electrochemical reduction of this dye has been investigated in aqueous solution using cyclic voltammetry, controlled potential electrolysis and cathodic stripping voltammetry. Optimum conditions for dye discoloration by controlled potential electrolysis use an alkaline medium. Using cathodic stripping voltammetry a linear calibration graph was obtained from 5.00×10-8 mol L-1 to 1.00×10 -6 mol L-1 of AT15 at pH 4.0, using accumulation times of 180 and 240 s and an accumulation potential of 0.0 V. The proposed method was applied in direct determination of the dye in tap water and in textile industry effluent.

Synergistic electrocatalytic effect of nanostructured mixed films formed by functionalised gold nanoparticles and bisphthalocyanines

Medina-Plaza, C.; Furini, L. N.; Constantino, C. J. L.; Saja, J. A. de; Rodriguez-Mendez, M. L.
Fonte: Elsevier B.V. Publicador: Elsevier B.V.
Tipo: Artigo de Revista Científica Formato: 95-102
ENG
Relevância na Pesquisa
370.30566%
A synergistic electrocatalytic effect was observed in sensors where two electrocatalytic materials (functionalized gold nanoparticles and lutetium bisphthalocyanine) were co-deposited using the Langmuir-Blodgett technique. Films were prepared using a novel method where water soluble functionalised gold nanoparticles [(11-mercaptoundecyl)tetra(ethylene glycol)] (SAuNPs) were inserted in floating films of lutetium bisphthalocyanine (LuPc2) and dimethyldioctadecylammonium bromide (DODAB) as the amphiphilic matrix. The formation of stable and homogeneous mixed films was confirmed by pi-A isotherms, BAM, UV-vis and Raman spectroscopy, as well as by SEM and TEM microscopy. The synergistic effect towards hydroquinone of the electrodes modified with LuPc2:DODAB/SAuNP was characterised by an increase in the intensity of the redox peaks and a reduction of the overpotential. This synergistic electrocatalytic effect arose from the interaction between the SAuNPs and the phthalocyanines that occur in the Langmuir-Blodgett films and from the high surface area provided by the nanostructured films. The sensitivity increased with the amount of LuPc2 and SAuNPs inserted in the films and limits of detection in the range of 10(-7) mol L-1 were attained. (C) 2014 Elsevier B.V. All rights reserved.

Síntese de derivados oligoméricos de porfirinas e ftalocianinas

Pereira, Ana Mafalda Vaz Martins
Fonte: Universidade de Aveiro Publicador: Universidade de Aveiro
Tipo: Tese de Doutorado
POR
Relevância na Pesquisa
170.5462%
A presente dissertação contempla estudos de funcionalização de 5,10,15,20- tetrafenilporfirina via grupos nitro e amino e a preparação de sistemas porfirina-ftalocianina. Este trabalho encontra-se dividido em quatro partes. Na primeira parte descrevem-se as características gerais de porfirinas e ftalocianinas bem como algumas metodologias de síntese utilizadas na sua preparação e suas potenciais aplicações. Na segunda parte desta dissertação descreve-se a funcionalização de 5,10,15,20-tetrafenilporfirina com arilaminas recorrendo a duas rotas sintéticas diferentes. A reacção de 2-nitro-5,10,15,20-tetrafenilporfirina com anilina ou aminas aromáticas substituídas com grupos dadores de electrões permitiu, através do ataque do nucleófilo ao carbono beta-pirrólico onde está ligado o grupo nitro, ataque ipso, a obtenção de derivados do tipo 2-arilaminoporfirinas e derivados porfirínicos de anéis fundidos, sendo estes últimos resultantes da ciclização oxidativa de 2-arilaminoporfirinas. A reacção entre (2-amino- 5,10,15,20-tetrafenilporfirinato)níquel(II) e brometos de arilo na presença de paládio, reacção de aminação de Buchwald-Hartwig, permitiu, após descomplexação, a preparação de novos derivados do tipo 2- arilaminoporfirinas com grupos substituintes dadores e aceitadores de electrões. Um dos derivados porfirínicos de anéis fundidos foi submetido a reacção de complexação com diferentes iões metálicos e foram estudadas as respectivas propriedades fotoquímicas e electroquímicas. Esses estudos revelaram que estes compostos são bons geradores de oxigénio singuleto e que sofrem processos de oxidação-redução electroquimicamente reversíveis. Esta metodologia foi estendida ainda a brometos de hetarilo (derivados de piridina e tiofeno). Recorrendo ao acoplamento...

Synthesis and antibacterial activity of cationic phthalocyanines; Síntese e atividade antibacteriana de ftalocianinas catiónicas

Pereira, Joana Brás
Fonte: Universidade de Aveiro Publicador: Universidade de Aveiro
Tipo: Dissertação de Mestrado
ENG
Relevância na Pesquisa
310.66977%
Antimicrobial photodynamic therapy (aPDT) was described more than 100 years ago, but its potential as an alternative to combating microorganisms, was only recognized when antibiotic resistance became an important public health issue. aPDT refers to the action of 3 non-toxic elements: a photosensitizer, light and molecular oxygen that, when combined, results in the production of singlet oxygen (1O2) and/or free radicals which are cytotoxic to target cells. The aim of this work was to synthetize, evaluate and compare the photoinactivation efficiency of new cationic phthalocyanines (Pcs) derivatives. Three new derivatives, tetra and octa-thio-pyridinium Pcs, 17, 18 and 19, were tested against Gram-negative bacteria. A recombinant bioluminescent Escherichia coli strain was used to assess, in real time, the photoinactivation efficiency of these cationic Pcs, under white and red light. After a pre-incubation period with 20 μmol L-1 of PS in the dark, the pure bacterial suspensions were irradiated with white light (400-800 nm) or red light (620- 750 nm) at a fluence rate of 150 mW cm-2, for 30 minutes. Dark and light controls were performed in all experiments. The cellular localization, uptake, 1O2, photophysical and photochemical tests such as photostability...

Determination of the phthalocyanine textile dye, reactive turquoise blue, by electrochemical techniques

Osugi,Marly E.; Carneiro,Patrícia A.; Zanoni,Maria Valnice B.
Fonte: Sociedade Brasileira de Química Publicador: Sociedade Brasileira de Química
Tipo: Artigo de Revista Científica Formato: text/html
Publicado em 01/08/2003 EN
Relevância na Pesquisa
677.0161%
Turquoise blue 15 (AT15) is a reactive dye widely used in the textile industry to color natural fibers. The presence of these dyes in effluent and industrial wastewater is of considerable interest due ecotoxicological and environmental problems. The electrochemical reduction of this dye has been investigated in aqueous solution using cyclic voltammetry, controlled potential electrolysis and cathodic stripping voltammetry. Optimum conditions for dye discoloration by controlled potential electrolysis use an alkaline medium. Using cathodic stripping voltammetry a linear calibration graph was obtained from 5.00x10-8 mol L-1 to 1.00x10-6 mol L-1 of AT15 at pH 4.0, using accumulation times of 180 and 240 s and an accumulation potential of 0.0 V. The proposed method was applied in direct determination of the dye in tap water and in textile industry effluent.

Photocytotoxic efficacy of sulphonated species of aluminium phthalocyanine against cell monolayers, multicellular spheroids and in vivo tumours.

Chan, W. S.; West, C. M.; Moore, J. V.; Hart, I. R.
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em /11/1991 EN
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The problem of relying solely on in vitro data to predict photosensitiser efficacy was demonstrated by examining the uptake and the ability to mediate photocytotoxicity of mono-, di-, tri- and tetra-sulphonated species of chloroaluminium phthalocyanine (AlS1-4Pc) in monolayer cultures of murine Colo 26 cells and in both monolayer and spheroid cultures of human WiDr cells. Cells treated in vitro, whether in monolayer or as spheroids, with the less sulphonated derivatives, AlS1Pc and AlS2Pc, were more susceptible to photocytotoxicity than those treated with AlS3Pc, cells treated with AlS4Pc were even less susceptibile to the cytotoxic effects of light irradiation. Generally these results mirrored the cellular uptake in vitro. When WiDr spheroids were increased in size from 250 microns to 500 microns there was a reduction in uptake of AlS1Pc and AlS2Pc which was reflected by the decreased sensitivity of the larger spheroids to the effects of light irradiation. AlS1Pc had no effect against Colo 26 cells growing as s.c. tumours in syngeneic BALB/c mice; whereas AlS3Pc, AlS2Pc and AlS4Pc produced significant reductions in tumour weights 5 days post laser light irradiation. Of these, AlS2Pc had the most dramatic effect on the colony forming efficiency of tumour cells recovered 24 h after PDT. While...

Biological activities of phthalocyanines. XIV. Effect of hydrophobic phthalimidomethyl groups on the in vivo phototoxicity and mechanism of photodynamic action of sulphonated aluminium phthalocyanines.

Boyle, R. W.; Paquette, B.; van Lier, J. E.
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em /06/1992 EN
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Aluminium phthalocyanines substituted to different degrees with hydrophilic sulphonic acid and hydrophobic phthalimidomethyl groups were investigated in vivo as new agents for the photodynamic therapy of malignant tumours. Parameters studied included the photodynamic action on EMT-6 mammary tumours in BALB/c mice, the therapeutic window and the potential for direct cell killing, assayed via an in vivo/in vitro test. Although the efficiency of photoinactivation of the EMT-6 tumour increases by a factor of ten with reduction of the number of sulphonic acid groups from four to two, no further effect was seen with the addition of the hydrophobic phthalimidomethyl groups. Addition of the latter groups however increased the potential for direct cell killing by a factor of two and expanded the therapeutic window by a factor of four, thus improving the usefulness of the dye as a photosensitiser for the photodynamic therapy of cancer.

31P magnetic resonance spectroscopy as a predictor of efficacy in photodynamic therapy using differently charged zinc phthalocyanines

Bremner, J C M; Wood, S R; Bradley, J K; Griffiths, J; Adams, G E; Brown, S B
Fonte: Nature Publishing Group Publicador: Nature Publishing Group
Tipo: Artigo de Revista Científica
Publicado em /10/1999 EN
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Photodynamic therapy (PDT) is a developing approach to the treatment of solid tumours which requires the combined action of light and a photosensitizing drug in the presence of adequate levels of molecular oxygen. We have developed a novel series of photosensitizers based on zinc phthalocyanine which are water-soluble and contain neutral (TDEPC), positive (PPC) and negative (TCPC) side-chains. The PDT effects of these sensitizers have been studied in a mouse model bearing the RIF-1 murine fibrosarcoma line studying tumour regrowth delay, phosphate metabolism by magnetic resonance spectroscopy (MRS) and blood flow, using D2O uptake and MRS. The two main aims of the study were to determine if MRS measurements made at the time of PDT treatment could potentially be predictive of ultimate PDT efficacy and to assess the effects of sensitizer charge on PDT in this model. It was clearly demonstrated that there is a relationship between MRS measurements during and immediately following PDT and the ultimate effect on the tumour. For all three drugs, tumour regrowth delay was greater with a 1-h time interval between drug and light administration than with a 24-h interval. In both cases, the order of tumour regrowth delay was PPC > TDEPC = TCPC (though the data at 24 h were not statistically significant). Correspondingly...

Cationic porphycenes as potential photosensitizers for antimicrobial photodynamic therapy

Ragàs, Xavier; Sánchez-García, David; Ruiz-González, Rubén; Dai, Tianhong; Agut, Montserrat; Hamblin, Michael R.; Nonell, Santi
Fonte: PubMed Publicador: PubMed
Tipo: Artigo de Revista Científica
Publicado em 11/11/2010 EN
Relevância na Pesquisa
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Structures of typical photosensitizers used in antimicrobial photodynamic therapy are based on porphyrins, phthalocyanines and phenothiazinium salts, with cationic charges at physiological pH values. However derivatives of the porphycene macrocycle (a structural isomer of porphyrin) have barely been investigated as antimicrobial agents. Therefore, we report the synthesis of the first tricationic water-soluble porphycene and its basic photochemical properties. We successfully tested it for in vitro photoinactivation of different Gram-positive and Gram-negative bacteria, as well as a fungal species (Candida) in a drug-dose and light-dose dependent manner. We also used the cationic porphycene in vivo to treat an infection model comprising mouse 3rd degree burns infected with a bioluminescent methicillin-resistant Staphylococcus aureus strain. There was a 2.6-log10 reduction (p < 0.001) of the bacterial bioluminescence for the PDT-treated group after irradiation with 180 J·cm-2 of red light.

Calix[4]pirróis: síntese e aplicação como sensores de aniões

Farinha, Andreia Sofia Filipe
Fonte: Universidade de Aveiro Publicador: Universidade de Aveiro
Tipo: Tese de Doutorado
POR
Relevância na Pesquisa
270.58303%
A presente dissertação descreve, essencialmente, o desenvolvimento de novos métodos de funcionalização de calix[4]pirróis. O uso desses calix[4]pirróis, bem como o de porfirinas e ftalocianinas, como sensores de aniões, incluindo a determinação das suas constantes de afinidade é igualmente discutido. Esta dissertação encontra-se dividida em três partes distintas. Na primeira é feita uma revisão bibliográfica acerca das metodologias de síntese dos calix[4]pirróis, bem como das suas características e aplicações. A segunda parte encontra-se subdividida em diversos pontos de acordo com o tipo de funcionalização realizada nos calix[4]pirróis. No primeiro ponto desta parte encontram-se discutidos a síntese e a caracterização do mesooctametilcalix[ 4]pirrol-2-carbaldeído e do 3-(meso-octametilcalix[4]pirrol-2- il)propenal bem como os resultados obtidos da funcionalização destes aldeídos por reacções de cicloadição 1,3-dipolar. Esses aldeídos foram usados para gerar iletos de azometino, os quais foram “apanhados” com diversos dipolarófilos, tais como o fumaronitrilo, o fumarato de dimetilo, a N-(4- metoxifenil)maleimida, a 1,4-benzoquinona e a 1,4-naftoquinona. Ambos os calixpirróis com grupo formilo deram origem a aductos de cicloadição 1...

Electronic structure of metal phthalocyanines on Ag (100)

Krull, Cornelius
Fonte: [Barcelona] : Universitat Autònoma de Barcelona, Publicador: [Barcelona] : Universitat Autònoma de Barcelona,
Tipo: Tesis i dissertacions electròniques; info:eu-repo/semantics/doctoralThesis; info:eu-repo/semantics/publishedVersion Formato: application/pdf; application/pdf; application/pdf; application/pdf; application/pdf
Publicado em //2015 ENG
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El uso de moléculas orgánicas en dispositivos tecnológicos ofrece una serie de ventajas: su tamaño (~nm), su capacidad de auto ensamblan dando lugar a la formación de estructuras funcionales, y la posibilidad de adaptar sus propiedades electrónicas y magnéticas a través de los métodos de síntesis molecular. Sin embargo, la implementación de dispositivos orgánicos depende fundamentalmente de la comprensión entre la interacción de las moléculas y los electrodos de metal, así como las interacciones molécula-molécula. Esta tesis estudia las propiedades estructurales, electrónicas y magnéticas de las metal-ftalocianinas (MePc) adsorbidas sobre un sustrato metálico. MePcs son complejos metal-orgánicos con una química versátil y una estructura simple y robusta Mediante el uso de microscopía de efecto túnel (STM) y espectroscopia de efecto túnel de escaneo (STS) se ha estudiado la interacción molécula-sustrato y molécula-molécula de cuatro MePc (Me = Fe, Co, Ni y Cu) empezando desde moléculas individuales hasta multicapas de MePc en superficies de Ag (100). Se ha observado que la adsorción molecular de las MePc es paralela al plano del sustrato y es impulsada por la optimización del enlace entre el ligando con el sustrato de Ag...