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1.
Chem Commun (Camb) ; 56(11): 1705-1708, 2020 Feb 06.
Artigo em Inglês | MEDLINE | ID: mdl-31942910

RESUMO

We report ultrathin organic photovoltaic elements optimized to run photofaradaic reactions in biological conditions. We demonstrate concurrent oxygen reduction to hydrogen peroxide and glucose oxidation. The devices are powered by deep-red irradiation in the tissue transparency window. We utilize bilayers of phthalocyanine, acting as the light absorber, and perylene diimide, functioning as both electron-acceptor and the hydrogen peroxide evolution electrocatalyst. These heterojunction bilayers are stable when irradiated in simulated physiological conditions, producing photovoltages sufficient to simultaneously drive cathodic oxygen reduction to H2O2 and anodic oxidation of glucose. We find that optimization of the anode metal is critical for sustained photofaradaic reactivity. Our results demonstrate a robust "wet" thin film photovoltaic with potential for physiological applications where localized electrochemical manipulation is desired, in particular the delivery of reactive oxygen species.


Assuntos
Técnicas Eletroquímicas/métodos , Peróxido de Hidrogênio/síntese química , Imidas/química , Indóis/química , Perileno/análogos & derivados , Técnicas Eletroquímicas/instrumentação , Desenho de Equipamento , Glucose/química , Ouro/química , Imidas/efeitos da radiação , Indóis/efeitos da radiação , Luz , Membranas Artificiais , Oxirredução , Oxigênio/química , Perileno/química , Perileno/efeitos da radiação , Fotoquímica/métodos
2.
Chem Biodivers ; 17(1): e1900596, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31782894

RESUMO

Within Sicilian flora, the genus Hypericum (Guttiferae) includes 10 native species, the most popular of which is H. perforatum. Hypericum's most investigated active compounds belong to naphtodianthrones (hypericin, pseudohypericin) and phloroglucinols (hyperforin, adhyperforin), and the commercial value of the drug is graded according to its total hypericin content. Ethnobotanical sources attribute the therapeutic properties recognized for H. perforatum, also to other Hypericum species. However, their smaller distribution inside the territory suggests that an industrial use of such species, when collected from the wild, would result in an unacceptable depletion of their natural stands. This study investigated about the potential pharmacological properties of 48 accessions from six native species of Hypericum, including H. perforatum and five 'minor' species, also comparing, when possible, wild and cultivated sources. The variability in the content of active metabolites was remarkably high, and the differences within the species were often comparable to the differences among species. No difference was enlightened between wild and cultivated plants. A carefully planned cultivation of Hypericum seems the best option to achieve high and steady biomass yields, but there is a need for phytochemical studies, aimed to identify for multiplication the genotypes with the highest content of the active metabolites.


Assuntos
Hypericum/química , Perileno/análogos & derivados , Floroglucinol/análogos & derivados , Terpenos/química , Hypericum/metabolismo , Perileno/química , Perileno/metabolismo , Floroglucinol/química , Floroglucinol/metabolismo , Sicília , Especificidade da Espécie , Terpenos/metabolismo
3.
Chemistry ; 26(12): 2741-2748, 2020 Feb 26.
Artigo em Inglês | MEDLINE | ID: mdl-31886910

RESUMO

To achieve a highly efficient, dual-state emission platform for picric acid (PA) detection and latent fingerprint (LFP) visualization, flexible alkyl chains have been facilely attached to the commercial organic dye 3,4,9,10-perylenetetracarboxylic dianhydride to provide the target perylenetetracarboxylate molecules PTCA-C4, PTCA-C6, and PTCA-C12. Interestingly, all these molecules exhibited impressive fluorescence characteristics with high photoluminescence quantum yields (PLQYs) of around 93.0 % in dilute solution. Also, emissive features were observed in the solid state because close molecular packing is prevented by the alkyl chains, especially for PTCA-C6, which has a high PLQY value of 49.0 %. Benefiting from its impressive fluorescence performance in both solution and as aggregates, PTCA-C6 was used as a dual-state emission platform for PA detection and also LFP visualization. For example, double-responsive fluorescence quenching in solution was observed in PA detection studies, resulting in high quenching constants (KSV ) and also low limit-of-detection values. Furthermore, the fingerprint powder based on PTCA-C6 also presented an impressive performance on various substrates in terms of fluorescence intensity and resolution, clearly providing the specific fine details of latent fingerprints. These results demonstrate that the facilely synthesized PTCA-C6 with efficient dual-state emission exhibits great potential in the real-world applications of PA detection and LFP visualization.


Assuntos
Anidridos/química , Dermatoglifia , Corantes Fluorescentes/síntese química , Perileno/análogos & derivados , Picratos/análise , Teoria da Densidade Funcional , Humanos , Limite de Detecção , Estrutura Molecular , Perileno/química , Espectrometria de Fluorescência
4.
Chem Commun (Camb) ; 55(96): 14446-14449, 2019 Nov 28.
Artigo em Inglês | MEDLINE | ID: mdl-31724658

RESUMO

A rational design of a benzoperylene probe BP-3 with positive charge allows for turn-on excimer emission, and wash-free cell membrane imaging. BP-3 possesses excellent chemical, thermal and photo stability. And the Stokes shift of the excimer emission is considerably large (90-100 nm), which very much avoids the background fluorescence interference.


Assuntos
Membrana Celular/química , Corantes Fluorescentes/química , Perileno/análogos & derivados , Humanos , Células MCF-7 , Microscopia Confocal , Perileno/química , Solventes , Espectrometria de Fluorescência
5.
J Biomed Nanotechnol ; 15(12): 2305-2320, 2019 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-31748013

RESUMO

Verteporfin photodynamic therapy (PDT) has been approved for the treatment of exudative age-related macular degeneration (AMD) for over a decade. However, its extensive application has been impeded by inevitably collateral tissue damage and immediate induction of angiogenesis, in addition to the need of multiple treatments. In order to develop prospective photosensitizers for clinical use, a triphenyl phosphonium-modified cationic liposomal hypocrellin B (TPP cationic LHB) for angiogenic targeting and endothelial internalization was constructed. With optimal PDT parameters, TPP cationic LHB can lead to death of choroid-retinal vascular endothelial cells while cause negligible damage to collateral retinal pigment epithelium cells. This is likely due to the mitochondria targeting and effective intracellular singlet oxygen generation of TPP cationic LHB in vascular endothelial cells. Additionally, in vivo chick chorioallantoic membrane assay indicated the elevated neovessel-targeting ability and photo-induced anti-angiogenic activity of TPP cationic LHB. Furthermore, TPP cationic LHB PDT is able to maintain neovessel occlusion for an extended period of time compared with verteporfin PDT, without inducing significant increased expression of some angiogenic factors, such as vascular endothelial growth factor and integrin αvß3. This study describes a facile strategy that may be useful for developing new-generation photosensitizers to circumvent the limitations of PDT treatment of exudative AMD.


Assuntos
Degeneração Macular , Perileno/análogos & derivados , Fotoquimioterapia , Quinonas/uso terapêutico , Animais , Neovascularização de Coroide , Células Endoteliais , Lipossomos , Degeneração Macular/tratamento farmacológico , Perileno/uso terapêutico , Fármacos Fotossensibilizantes , Estudos Prospectivos , Fator A de Crescimento do Endotélio Vascular
6.
Analyst ; 144(21): 6193-6196, 2019 Oct 22.
Artigo em Inglês | MEDLINE | ID: mdl-31577279

RESUMO

We here describe a photocurrent generation system exploiting gold nanoparticles (AuNPs) that cover perylenediimide-DNA complexes on electrode surfaces. Enhanced photocurrents were generated by the irradiation of the AuNPs, attributed to the efficient excitation of the perylenediimides by a local electric field on the surface of the AuNPs.


Assuntos
DNA/química , Técnicas Eletroquímicas/métodos , Nanopartículas Metálicas/química , Fotoquímica/métodos , Técnicas Eletroquímicas/instrumentação , Eletrodos , Ouro/química , Ouro/efeitos da radiação , Imidas/química , Imidas/efeitos da radiação , Luz , Nanopartículas Metálicas/efeitos da radiação , Perileno/análogos & derivados , Perileno/química , Perileno/efeitos da radiação
7.
Int J Mol Sci ; 20(19)2019 Sep 26.
Artigo em Inglês | MEDLINE | ID: mdl-31561450

RESUMO

Indisputably, cancer is a global crisis that requires immediate intervention. Despite the use of conventional treatments over the past decades, it is acceptable to admit that these are expensive, invasive, associated with many side effects and, therefore, a reduced quality of life. One of the most possible solutions to this could be the use of gold nanoparticle (AuNP) conjugated photodynamic therapy (PDT) in combination with cannabidiol (CBD), a Cannabis derivative from the Cannabis sativa. Since the use of Cannabis has always been associated with recreation and psychoactive qualities, the positive effects of Cannabis or its derivatives on cancer treatment have been misunderstood and hence misinterpreted. On the other hand, AuNP-PDT is the most favoured form of treatment for cancer, due to its augmented specificity and minimal risk of side effects compared to conventional treatments. However, its use requires the consideration of several physical, biologic, pharmacologic and immunological factors, which may hinder its effectiveness if not taken into consideration. In this review, the role of gold nanoparticle mediated PDT combined with CBD treatment on breast cancer cells will be deliberated.


Assuntos
Antineoplásicos Fitogênicos/administração & dosagem , Neoplasias da Mama/terapia , Canabidiol/administração & dosagem , Ouro , Nanopartículas Metálicas , Fotoquimioterapia , Animais , Antineoplásicos Fitogênicos/química , Canabidiol/química , Terapia Combinada , Feminino , Ouro/química , Humanos , Nanopartículas Metálicas/química , Perileno/administração & dosagem , Perileno/análogos & derivados , Fotoquimioterapia/métodos , Fármacos Fotossensibilizantes/administração & dosagem , Resultado do Tratamento
8.
Chemistry ; 25(66): 15062-15066, 2019 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-31553484

RESUMO

The aldol reaction is one of the most fundamental stereocontrolled carbon-carbon bond-forming reactions and is mainly catalyzed by aldolases in nature. Despite the fact that the aldol reaction has been widely proposed to be involved in fungal secondary metabolite biosynthesis, a dedicated aldolase that catalyzes stereoselective aldol reactions has only rarely been reported in fungi. Herein, we activated a cryptic polyketide biosynthetic gene cluster that was upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection; this resulted in the production of the phytotoxic stemphyloxin II (1). Through heterologous reconstruction of the biosynthetic pathway and in vitro assay by using cell-free lysate from Aspergillus nidulans, we demonstrated that a berberine bridge enzyme (BBE)-like protein SthB catalyzes an intramolecular aldol reaction to establish the bridged tricyclo[6.2.2.02,7 ]dodecane skeleton in the post-assembly tailoring step. The characterization of SthB as an aldolase enriches the catalytic toolbox of classic reactions and the functional diversities of the BBE superfamily of enzymes.


Assuntos
Alcanos/química , Berberina/química , Frutose-Bifosfato Aldolase/metabolismo , Perileno/metabolismo , Ascomicetos/genética , Ascomicetos/metabolismo , Aspergillus nidulans/metabolismo , Biocatálise , Frutose-Bifosfato Aldolase/química , Proteínas Fúngicas/genética , Proteínas Fúngicas/metabolismo , Conformação Molecular , Família Multigênica , Perileno/análogos & derivados , Perileno/química , Estereoisomerismo
9.
Mater Sci Eng C Mater Biol Appl ; 105: 110052, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31546360

RESUMO

Novel duck reovirus (NDRV) disease is a serious infectious disease for poultry, for which no effective therapy has been established. Therefore, development of novel antivirals against NDRV is urgently needed. In present study, we developed a complex wherein hypericin (HY), which shows broad-spectrum antiviral activity, was loaded onto graphene oxide (GO), which has a high drug-loading capacity and low cytotoxicity. The antiviral activity of the complex (GO/HY) was studied in DF-1 cells and in ducklings infected with the NDRV TH11 strain. GO/HY showed a dose-dependent inhibition of NDRV replication, which may be attributed to direct virus inactivation or inhibition of virus attachment. Western blotting and indirect immunofluorescence assay (IFA) showed markedly suppressed protein expression in GO/HY-treated NDRV-infected DF-1 cells. Moreover, GO/HY prolonged the survival time of the ducklings by reducing pathological lesions caused by the infection and inhibiting viral replication in the liver and lungs. These results suggest that GO/HY has antiviral activity against NDRV both in vitro and in vivo.


Assuntos
Portadores de Fármacos , Patos , Grafite , Orthoreovirus Aviário/metabolismo , Perileno/análogos & derivados , Doenças das Aves Domésticas , Infecções por Reoviridae , Animais , Linhagem Celular , Portadores de Fármacos/química , Portadores de Fármacos/farmacologia , Patos/metabolismo , Patos/virologia , Grafite/química , Grafite/farmacologia , Perileno/química , Perileno/farmacologia , Doenças das Aves Domésticas/tratamento farmacológico , Doenças das Aves Domésticas/metabolismo , Doenças das Aves Domésticas/patologia , Doenças das Aves Domésticas/virologia , Infecções por Reoviridae/tratamento farmacológico , Infecções por Reoviridae/metabolismo , Infecções por Reoviridae/patologia , Infecções por Reoviridae/veterinária
10.
Int J Pharm ; 570: 118666, 2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31494239

RESUMO

The naturally occurring anthraquinone derivative hypericin is a highly potent photosensitiser. Several in vitro studies show high phototoxicity of the pigment towards gram-positive bacteria. Nevertheless, the highly lipophilic nature and poor bioavailability prevent its application in daily clinical practice thus leading to a limited therapeutic value of hypericin. Liposomal encapsulation could help overcome these limitations and would make hypericin available for daily clinical practice. The use of liposomes as carriers for hypericin in antimicrobial photodynamic therapy (aPDT) is quite new. The aim of this work was to improve the photodynamic efficiency of the previously mentioned carriers by entrapping hypericin in the aqueous compartment of the liposomes. Therefore, a water-soluble inclusion complex of hypericin and (2-hydroxypropyl)-beta-cyclodextrin (Hyp-HPßCD) was prepared. After encapsulation of the inclusion complex into DSPC and DSPC/DPPC/DSPE-PEG liposomes with the dehydration-rehydration vesicle (DRV) method, the formulations were physicochemical characterised. The photodynamic efficiency towards the gram-positive model strain Staphylococcus saprophyticus subsp. bovis. was tested on planktonic cells as well as on biofilms. DSPC liposomes achieved a 4.1log reduction and the DSPC/DPPC/DSPE-PEG liposomes a 2.6log reduction in growth of planktonic bacteria, while Hyp-HPßCD showed total eradication. Even bacterial cells growing in a biofilm could be treated effectively in vitro.


Assuntos
Antibacterianos/química , Lipossomos/química , Perileno/análogos & derivados , Antibacterianos/farmacologia , Biofilmes/efeitos dos fármacos , Composição de Medicamentos/métodos , Perileno/química , Fosfatidiletanolaminas/química , Fotoquimioterapia/métodos , Fármacos Fotossensibilizantes/química , Polietilenoglicóis/química , Staphylococcus saprophyticus/efeitos dos fármacos , beta-Ciclodextrinas/química
11.
Molecules ; 24(17)2019 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-31470637

RESUMO

Metastatic melanoma (MM) has a poor prognosis and is attributed to late diagnoses only when metastases has already occurred. Thus, early diagnosis is crucial to improve its overall treatment efficacy. The standard diagnostic tools for MM are incisional biopsies and/or fine needle aspiration biopsies, while standard treatments involve surgery, chemotherapy, or irradiation therapy. The combination of photodynamic diagnosis (PDD) and therapy (PDT) utilizes a photosensitizer (PS) that, when excited by light of a low wavelength, can be used for fluorescent non-destructive diagnosis. However, when the same PS is activated at a higher wavelength of light, it can be cytotoxic and induce tumor destruction. This paper focuses on PS drugs that have been used for PDD as well as PDT treatment of MM. Furthermore, it emphasizes the need for continued investigation into enhanced PS delivery via active biomarkers and passive nanoparticle systems. This should improve PS drug absorption in MM cells and increase effectiveness of combinative photodynamic methods for the enhanced diagnosis and treatment of MM can become a reality.


Assuntos
Melanoma/diagnóstico por imagem , Melanoma/tratamento farmacológico , Fármacos Fotossensibilizantes/uso terapêutico , Neoplasias Cutâneas/diagnóstico por imagem , Neoplasias Cutâneas/tratamento farmacológico , Ácido Aminolevulínico/química , Ácido Aminolevulínico/farmacocinética , Ácido Aminolevulínico/uso terapêutico , Biópsia por Agulha Fina , Portadores de Fármacos/síntese química , Diagnóstico Precoce , Humanos , Indóis/química , Indóis/farmacocinética , Indóis/uso terapêutico , Luz , Metástase Linfática , Melanoma/patologia , Imagem Molecular/métodos , Nanopartículas/administração & dosagem , Nanopartículas/química , Perileno/análogos & derivados , Perileno/química , Perileno/farmacocinética , Perileno/uso terapêutico , Fotoquimioterapia/métodos , Fármacos Fotossensibilizantes/química , Fármacos Fotossensibilizantes/farmacocinética , Neoplasias Cutâneas/patologia
12.
Nat Commun ; 10(1): 3986, 2019 09 04.
Artigo em Inglês | MEDLINE | ID: mdl-31484929

RESUMO

We demonstrate excitation of photosensitisers (PSs) by accelerated protons to produce fluorescence and singlet oxygen. Their fluorescence follows a pattern similar to the proton energy loss in matter, while proton-derived fluorescence spectra match the photon-induced spectra. PSs excited in dry gelatin exhibit enhanced phosphorescence, suggesting an efficient PSs triplet state population. Singlet oxygen measurements, both optically at ~1270 nm and through the photoproduct of protoporphyrin IX (PpIX), demonstrate cytotoxic singlet oxygen generation by proton excitation. The singlet oxygen-specific scavenger 1,4-diazabicyclo[2.2.2]octane (DABCO) abrogates the photoproduct formation under proton excitation, but cannot countermand the overall loss of PpIX fluorescence. Furthermore, in two cell lines, M059K and T98G, we observe differential cell death upon the addition of the PS cercosporin, while in U87 cells we see no effect at any proton irradiation dose. Our results pave the way for a novel treatment combining proton therapy and "proton-dynamic therapy" for more efficient tumour eradication.


Assuntos
Fármacos Fotossensibilizantes/farmacologia , Terapia com Prótons/métodos , Prótons , Protoporfirinas/metabolismo , Oxigênio Singlete/metabolismo , Morte Celular/efeitos dos fármacos , Morte Celular/efeitos da radiação , Linhagem Celular Tumoral , Quimiorradioterapia , Fluorescência , Humanos , Neoplasias/tratamento farmacológico , Neoplasias/patologia , Neoplasias/radioterapia , Perileno/análogos & derivados , Perileno/farmacologia , Piperazinas/farmacologia , Protetores contra Radiação/farmacologia , Espectrometria de Fluorescência
13.
Anim Reprod Sci ; 208: 106116, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31405452

RESUMO

Cryptorchidism, the failure of one or both testes to descend to an extra-abdominal location during mammalian development, is a common reproductive malady that often requires surgical intervention to remedy. Leydig cells are responsible for producing insulin-like peptide 3 (INSL3), a peptide hormone that is essential for normal testicular descent. The insl3 promoter in Leydig cells can be activated by cAMP through the transcription factor Nur77, which also regulates the promoters of the steroidogenic enzymes, cyp17 and 3ß-hsd. While the mechanism of LH action on testosterone production is well characterized, the effect of LH on insl3 abundance has not been described. The MA-10 Leydig cell line was used to test the hypothesis that abundance of insl3 mRNA is increased by LH/CG via the cAMP pathway. Cells treated with hCG had a transient robust increase in abundance of nur77 mRNA, while insl3 mRNA abundance remained unchanged. Further, while cAMP addition increased nur77 mRNA abundance, it failed to affect insl3 mRNA. Inhibition of LH-receptor-linked signal transduction pathways in the presence of hCG implicated multiple signaling networks in the regulation of both the insl3 and nur77 genes. Treatment with hCG and cAMP also increased abundance of cyp17 mRNA but not 3ß-hsd. Abundance of insl3 mRNA was not affected by hCG, testosterone or the combination of hCG and testosterone. Collectively, these results provide support for the constitutive regulation of insl3 mRNA abundance in the MA-10 Leydig cell line rather than acute regulation by LH/CG and cAMP.


Assuntos
Regulação da Expressão Gênica/efeitos dos fármacos , Insulina/metabolismo , Células Intersticiais do Testículo/fisiologia , Proteínas/metabolismo , Animais , Linhagem Celular , Gonadotropina Coriônica/farmacologia , Flavonoides/farmacologia , Regulação da Expressão Gênica/fisiologia , Insulina/genética , Isoquinolinas/farmacologia , Masculino , Camundongos , Membro 1 do Grupo A da Subfamília 4 de Receptores Nucleares/genética , Membro 1 do Grupo A da Subfamília 4 de Receptores Nucleares/metabolismo , Perileno/análogos & derivados , Perileno/farmacologia , Proteínas/genética , Transdução de Sinais/efeitos dos fármacos , Transdução de Sinais/fisiologia , Sulfonamidas/farmacologia , Testosterona/farmacologia , Wortmanina/farmacologia
14.
Chemistry ; 25(62): 14214-14222, 2019 Nov 07.
Artigo em Inglês | MEDLINE | ID: mdl-31452291

RESUMO

A series of new ruthenium(II) vinyl complexes has been prepared incorporating perylenemonoimide (PMI) units. This fluorogenic moiety was functionalised with terminal alkyne or pyridyl groups, allowing attachment to the metal either as a vinyl ligand or through the pyridyl nitrogen. The inherent low solubility of the perylene compounds was improved through the design of poly-PEGylated (PEG=polyethylene glycol) units bearing a terminal alkyne or a pyridyl group. By absorbing the compounds on silica, vapours and gases could be detected in the solid state. The reaction of the complexes [Ru(CH=CH-PerIm )Cl(CO)(py-3PEG)(PPh3 )2 ] and [Ru(CH=CH-3PEG)Cl(CO)(py-PerIm )(PPh3 )2 ] with carbon monoxide, isonitrile or cyanide was found to result in modulation of the fluorescence behaviour. The complexes were observed to display solvatochromic effects and the interaction of the complexes with a wide range of other species was also studied. The study suggests that such complexes have potential for the detection of gases or vapours that are toxic to humans.


Assuntos
Monóxido de Carbono/análise , Cianetos/análise , Corantes Fluorescentes/química , Imidas/química , Nitrilos/análise , Perileno/análogos & derivados , Rutênio/química , Alquinos/química , Monóxido de Carbono/toxicidade , Complexos de Coordenação/química , Cianetos/toxicidade , Nitrilos/toxicidade , Perileno/química , Piridinas/química
15.
ACS Appl Mater Interfaces ; 11(37): 33676-33683, 2019 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-31433148

RESUMO

In the field of clinical diagnosis, it is important to construct a potential-resolved multiplex electrochemiluminescence (ECL) biosensor for decreasing the false-positive rate and improving the diagnostic accuracy. However, the shortage of low-potential cathodic luminophores between -1 and 0 V (vs Ag/AgCl) severely limited the development of the biosensor. Herein, we synthesized a novel luminophore N,N-bis-(3-dimethyl aminopropyl)-3,4,9,10-perylene tetracarboxylic acid diimide (PDI), which gave dual emissions at -0.25/-0.26 V with K2S2O8 as a co-reactant in aqueous solution. The ECL was assigned to excited J-type PDI dimers. Then, PDI and luminol were used as luminophores to respectively combine with graphite oxide and gold nanoparticles and form potential-resolved ECL nanoprobes. Also, this potential-resolved ECL nanoprobes were respectively functionalized by secondary antibodies (Ab2) to construct a low-potential sandwiched ECL immunosensor for tumor markers carcinoembryonic antigen (CEA) and α-fetoprotein (AFP) simultaneous determination during linear scanning potential range from -0.6 to 0.6 V. The prepared multiplex immunosensor exhibited sensitive ECL response for CEA at -0.6 V due to PDI and that for AFP at 0.6 V due to luminol, and both linear semilogarithmical ranges were from 0.1 pg to 1 ng mL-1. In addition, PDI with dual ECL peaks showed enticing prospect of built-in self-calibration for a precise quantitative and bioimaging analysis.


Assuntos
Antígeno Carcinoembrionário/análise , Técnicas Eletroquímicas , Ouro/química , Imidas/química , Medições Luminescentes , Luminol/química , Nanopartículas Metálicas/química , Perileno/análogos & derivados , alfa-Fetoproteínas/análise , Humanos , Imunoensaio , Limite de Detecção , Perileno/química
16.
Chemistry ; 25(52): 12137-12144, 2019 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-31276238

RESUMO

Isomerism heavily influences the optoelectronic properties and self-assembly behavior of compounds and subsequently affects their device performance. Herein, two pairs of isomeric perylene diimide (PDI) dimers, PDI and PDI2, were designed and synthesized. The electron-deficient 9,10-anthraquinone group was employed as the bridge, and thus, the resultant dimers exhibited an acceptor-acceptor-acceptor (A-A-A) structure. To determine the isomeric effects on the optoelectronic properties and photovoltaic performance of these dimers, their absorptivity, luminescence, and redox behavior were studied. Bulk heterojunction organic solar cells based on these four dimers were fabricated and measured. The two PDI dimers exhibited clear differences in photovoltaic performance, whereas the two PDI2 analogues showed similar power conversion efficiencies (PCEs). The PCEs of the two PDI2 dimers are much higher than those of the PDI dimers. These results illustrate that the isomeric effect of PDI dimers is much larger than that of PDI2 dimers on the device performance, and proper expansion of conjugation could improve the device performance.


Assuntos
Antraquinonas/química , Imidas/química , Perileno/análogos & derivados , Dimerização , Eletrônica , Isomerismo , Oxirredução , Perileno/química , Energia Solar
17.
Microb Cell Fact ; 18(1): 121, 2019 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-31277643

RESUMO

BACKGROUND: Fungal perylenequinonoid (PQ) pigments from Shiraia fruiting body have been well known as excellent photosensitizers for medical and agricultural uses. The fruiting bodies are colonized by a diverse bacterial community of unknown function. We screened the companion bacteria from the fruiting body of Shiraia sp. S9 and explored the bacterial elicitation on fungal PQ production. RESULTS: A bacterium Pseudomonas fulva SB1 isolated from the fruiting body was found to stimulate the production of fungal PQs including hypocrellins A, C (HA and HC), and elsinochromes A-C (EA, EB and EC). After 2 days of co-cultures, Shiraia mycelium cultures presented the highest production of HA (325.87 mg/L), about 3.20-fold of that in axenic culture. The co-culture resulted in the induction of fungal conidiation and the formation of more compact fungal pellets. Furthermore, the bacterial treatment up-regulated the expression of polyketide synthase gene (PKS), and activated transporter genes of ATP-binding cassette (ABC) and major facilitator superfamily transporter (MFS) for PQ exudation. CONCLUSIONS: We have established a bacterial co-culture with a host Shiraia fungus to induce PQ biosynthesis. Our results provide a basis for understanding bacterial-fungal interaction in fruiting bodies and a practical co-culture process to enhance PQ production for photodynamic therapy medicine.


Assuntos
Ascomicetos/metabolismo , Carpóforos/metabolismo , Perileno/análogos & derivados , Pseudomonas/fisiologia , Quinonas/metabolismo , Ascomicetos/genética , Técnicas de Cocultura , Proteínas Fúngicas/genética , Interações Microbianas , Perileno/metabolismo , Policetídeo Sintases/genética , Pseudomonas/isolamento & purificação , Esporos Fúngicos
18.
Photodiagnosis Photodyn Ther ; 27: 419-427, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31325521

RESUMO

BACKGROUND AND AIM: The extensive use of antifungal drugs has led to resistance from Candida albicans. The search for alternative treatment against drug-resistant C. albicans is highly desirable. Antimicrobial photodynamic therapy (aPDT) is an emerging and promising approach for treating localized and superficial C. albicans infections. The aim of this study was to investigate the photodynamic inactivation (PDI) effects of hypocrellin B (HB) on azole-sensitive and resistant C. albicans in vitro. METHODS: The PDI efficacies of HB on standard C. albicans strain (ATCC 10231), azole-sensitive clinical isolate of C. albicans, and azole-resistant clinical isolate of C. albicans were assessed. The uptake of HB in C. albicans cells was investigated by confocal laser scanning microscopy (CLSM). The PDI effects on cellular structure and surface characteristics were investigated by transmission electron microscopy (TEM) and scanning electron microscopy (SEM). RESULTS: HB exhibited no significant dark toxicity, but inactivated the azole-sensitive and resistant C. albicans in a light-dose and PS concentration-dependent manner. CLSM images indicated that PDI treated C. albicans cells showed stronger fluorescence compared to untreated cells. TEM images suggested that significant damage to the cell wall, membrane, and cytoplasm were induced by HB-mediated PDI. SEM analysis revealed that the surface of C. albicans cells became twisted and ruptured after PDI treatment. CONCLUSIONS: Azole-sensitive and resistant C. albicans could be effectively inactivated by HB in the presence of light, and HB-mediated aPDT shows promise as an antifungal treatment for C. albicans.


Assuntos
Candida albicans/efeitos dos fármacos , Perileno/análogos & derivados , Fotoquimioterapia/métodos , Quinonas/farmacologia , Farmacorresistência Fúngica , Humanos , Microscopia Eletrônica de Varredura , Microscopia Eletrônica de Transmissão , Perileno/farmacologia
19.
Anal Chim Acta ; 1077: 281-287, 2019 Oct 24.
Artigo em Inglês | MEDLINE | ID: mdl-31307720

RESUMO

Herein, a novel signal-off photoelectrochemical (PEC) aptasensor was proposed for sensitive detection of thrombin on the basis of C60@C3N4 nanocomposites as quencher and Au nanoparticles (depAu) decorated perylene tetracarboxylic acid (PTCA) as sensing platform. Owing to the excellent membrane-forming of PTCA and superior conductivity of depAu, the PTCA between two depAu layers can simply and effectively produce an extremely high initial photocurrent to afford a precondition for sensitive biodetection. Thereafter, the assembly of C60@C3N4 nanocomposites on electrode via typical sandwich reaction enabled the generation of a significantly decreased photocurrent. Here, the C3N4 with high surface area not only provided massive binding sites for C60 immobilization, but also partly competed with PTCA in light absorption for producing a significantly smaller photocurrent in the presence of electron donor ascorbic acid (AA). Additionally, both the C3N4 and C60 have the poor conductivity, which could inhibit the electron transfer to achieve a further decreased photocurrent, effectively improving the sensitivity of proposed biosensor. As a result, the PEC biosensor in a "signal-off" mode showed an extremely low detection limit down to 1.5 fM, providing a sensitive and universal strategy for protein detection.


Assuntos
Fulerenos/química , Grafite/química , Nanopartículas Metálicas/química , Nanocompostos/química , Compostos de Nitrogênio/química , Perileno/análogos & derivados , Trombina/análise , Aptâmeros de Nucleotídeos/química , Técnicas Biossensoriais/métodos , Técnicas Eletroquímicas/métodos , Fulerenos/efeitos da radiação , Ouro/química , Grafite/efeitos da radiação , Limite de Detecção , Nanocompostos/efeitos da radiação , Compostos de Nitrogênio/efeitos da radiação , Perileno/química , Reprodutibilidade dos Testes , Raios Ultravioleta
20.
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