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1.
Molecules ; 25(19)2020 Sep 23.
Artigo em Inglês | MEDLINE | ID: mdl-32977525

RESUMO

The problem of treating viral infections is extremely relevant due to both the emergence of new viral diseases and to the low effectiveness of existing approaches to the treatment of known viral infections. This review focuses on the application of porphyrin, chlorin, and phthalocyanine series for combating viral infections by chemical and photochemical inactivation methods. The purpose of this review paper is to summarize the main approaches developed to date in the chemical and photodynamic inactivation of human and animal viruses using porphyrins and their analogues and to analyze and discuss the information on viral targets and antiviral activity of porphyrins, chlorins, of their conjugates with organic/inorganic compounds obtained in the last 10-15 years in order to identify the most promising areas.


Assuntos
Antivirais/farmacologia , Betacoronavirus/efeitos dos fármacos , Infecções por Coronavirus/tratamento farmacológico , Fotoquimioterapia/métodos , Pneumonia Viral/tratamento farmacológico , Porfirinas/farmacologia , Antivirais/química , Humanos , Indóis/química , Indóis/farmacologia , Pandemias , Processos Fotoquímicos , Fármacos Fotossensibilizantes/química , Fármacos Fotossensibilizantes/farmacologia , Porfirinas/química , Ligação Viral/efeitos dos fármacos
3.
Food Chem ; 327: 127075, 2020 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-32446026

RESUMO

The needing of rapid and sensitive detection method for pesticides is increasing, to facilitate its detection without complicated instruments. Herein, a novel paper-based senor was developed for the visual detection of three carbamate pesticides (metolcarb, carbofuran, and carbaryl) based on CdTe quantum dots (QDs) and nano zinc 5, 10, 15, 20-tetra(4-pyridyl)-21H-23H-porphine (nano ZnTPyP) with a "turn-off-on" mode. This fluorescence sensing model could be applied in the highly selective and sensitive detection of carbamate pesticides both by fluorescence spectrometry or paper-based sensors. Based on the extracted RGB color values of paper, the partial least squares regression (PLSR) was used to accurately quantify the concentrations of carbamate pesticides in different food matrices (apple, cabbage and tea water). This method featured in high speed, low price and high accuracy, and provided a new strategy for the detection of food safety.


Assuntos
Compostos de Cádmio/química , Carbamatos/análise , Análise de Alimentos , Resíduos de Praguicidas/análise , Porfirinas/química , Pontos Quânticos , Telúrio/química , Fluorescência , Alimentos , Limite de Detecção , Nanoestruturas , Espectrometria de Fluorescência
4.
SAR QSAR Environ Res ; 31(5): 347-371, 2020 May 03.
Artigo em Inglês | MEDLINE | ID: mdl-32460542

RESUMO

Two simple and reliable correlations are introduced for the prediction of emission and absorption of porphyrins and their derivatives, i.e. metalloporphyrins and ligand coordinated metalloporphyrins. They can be used to sense the extracted precious metals. The proposed models require only simple structural parameters such as the number of carbon, metal and metal-free molecular fragments of desirable porphyrins or their derivatives. Since the proposed models depend on molecular structures of the desired compounds, they can be easily applied for complex molecular structures. Experimental data of 272 porphyrin derivatives were used to derive and test the novel models for the assessment of their emission (Em.) and absorption (Abs.) values in three solvents namely dichloromethane, toluene and chloroform. The values of the coefficients of determination (r 2) for the training set (183 compounds) in dichloromethane and three different test sets, corresponding to the three mentioned solvents, for the emission and absorption correlations were greater than 0.70. The calculated values of the root-mean-square error (RMSE) for the training sets of Em. and Abs. correlations were equal to 7.56 and 4.86 nm, respectively. Further statistical parameters also confirm the high reliability of the new models.


Assuntos
Quelantes/química , Porfirinas/química , Relação Quantitativa Estrutura-Atividade , Solventes/química , Clorofórmio/química , Hidroquinonas/química , Ligantes , Substâncias Macromoleculares/química , Metais Pesados/química , Cloreto de Metileno/química
5.
J Chromatogr A ; 1620: 461008, 2020 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-32252985

RESUMO

Table olives, a widely consumed delicacy, are often selected by consumers based on the shade of their green color. The appealing coloration of fresh olives fades to brown or pale yellow during the industrial processing necessary for commercialization and storage, as a result of the degradation of chlorophyll a and b to their corresponding pheophytins and other chlorophyll degradation products (CDP). The re-greening of table olives may be achieved by complexation of CDP with Cu2+, to form stable bright green copper CDP (Cu-CDP) complexes. To study this phenomenon, we developed a novel method to separately extract lipophilic and hydrophilic Cu-CDP and quantify Cu-CDP by UHPLC combined with inductively coupled plasma isotope dilution mass spectrometry (UHPLC-ICP-ID-MS) using post-column isotopic dilution with 65Cu. This technique does not require species-specific calibration standards and was applied to survey the Cu-CDP composition of the various types of table olives sold in the US market. The CDP and Cu-CDP extracted from table olives were identified by high resolution full-scan mass spectrometry. Total elemental Cu in table olives was measured by microwave digestion followed by ICP-MS detection and correlated with the content of Cu-CDP. Pale yellow olives contained <1 mg/kg lipophilic Cu-CDP and <3.5 mg/kg total elemental Cu. Bright green table olives contained 4-22 mg/kg lipophilic Cu-CDP and 14.4-161 mg/kg total elemental Cu in contrast to <6 mg/kg reported for natural abundance, indicating the formation of Cu-CDP was achieved by addition of copper salts. A dark green sample with 2.5 mg/kg of total copper and 0.267 mg/kg lipophilic Cu-CDP may have been processed by addition of sodium copper chlorophyllin (SCC); the higher content of Cu isochlorin e4 compared to Cu 152-Me-chlorin e6 supports this conclusion.


Assuntos
Clorofila/análise , Cromatografia Líquida de Alta Pressão/métodos , Cobre/análise , Espectrometria de Massas/métodos , Sulfato de Cobre/química , Interações Hidrofóbicas e Hidrofílicas , Técnicas de Diluição do Indicador , Isótopos , Olea/química , Porfirinas/química , Sódio/análise
6.
Nat Commun ; 11(1): 1724, 2020 04 07.
Artigo em Inglês | MEDLINE | ID: mdl-32265490

RESUMO

Vesicular photothermal therapy agents (PTAs) are highly desirable in photothermal therapy (PTT) for their excellent light-harvesting ability and versatile hollow compartments. However, up to now, the reported vesicular PTAs are generally self-assembled from small molecules like liposomes, and polymer vesicles have seldom been used as PTAs due to the unsatisfactory photothermal conversion efficiency resulting from the irregular packing of chromophores in the vesicle membranes. Here we report a nano-sized polymer vesicle from hyperbranched polyporphyrins with favorable photothermal stability and extraordinarily high photothermal efficiency (44.1%), showing great potential in imaging-guided PTT for tumors through in vitro and in vivo experiments. These excellent properties are attributed to the in situ supramolecular polymerization of porphyrin units inside the vesicle membrane into well-organized 1D monofilaments driven by π-π stacking. We believe the supramolecular polymerization-enhanced self-assembly process reported here will shed a new light on the design of supramolecular materials with new structures and functions.


Assuntos
Sobrevivência Celular/efeitos dos fármacos , Hipertermia Induzida/métodos , Nanopartículas/química , Fototerapia/métodos , Polímeros/química , Porfirinas/química , Animais , Dicroísmo Circular , Feminino , Humanos , Interações Hidrofóbicas e Hidrofílicas , Células MCF-7 , Membranas Artificiais , Camundongos , Camundongos Nus , Microscopia Eletrônica de Varredura , Simulação de Dinâmica Molecular , Células NIH 3T3 , Nanopartículas/uso terapêutico , Nanopartículas/ultraestrutura , Polimerização , Polímeros/síntese química , Polímeros/farmacocinética , Polímeros/uso terapêutico , Porfirinas/síntese química , Porfirinas/farmacocinética , Porfirinas/uso terapêutico , Ratos , Espectrometria de Fluorescência , Temperatura , Transplante Heterólogo
7.
Nanotechnology ; 31(25): 255101, 2020 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-32143196

RESUMO

Drug delivery carriers hold tremendous promise for improving cancer treatment, and polyrotaxane (PR) has shown excellent drug-carrying properties. However, there have been some reports that, when used as a drug carrier, water-soluble PR is not easily labeled with organic fluorescent dyes. Herein, we synthesized a drug-loaded fluorescent porphyrin-terminated PR (PR-COOH) which can be used as a tracer material in drug and gene delivery. The structure, morphology and zeta potential of PR-COOH were characterized by nuclear magnetic resonance, high-resolution transmission electron microscopy and zeta potentiometry. In this research, cisplatin (CDDP) is used as a model drug. The zeta potential, drug encapsulation efficiency and drug release of CDDP-loaded PR (PR-COOH-Pt) were studied. Confocal laser scanning microscopy showed that PR-COOH could be internalized by HeLa and CT26 cells. The antitumor efficacy of PR-COOH-Pt was investigated in vitro by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and in vivo by a xenograft tumor model. The results showed that PR-COOH-Pt could significantly inhibit tumor growth; thus PR-COOH-Pt has a promising role in cancer therapy.


Assuntos
Antineoplásicos/administração & dosagem , Cisplatino/administração & dosagem , Ciclodextrinas/síntese química , Neoplasias Hepáticas/tratamento farmacológico , Poloxâmero/síntese química , Porfirinas/química , Rotaxanos/síntese química , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cisplatino/química , Cisplatino/farmacologia , Ciclodextrinas/química , Portadores de Fármacos/química , Liberação Controlada de Fármacos , Células HeLa , Humanos , Espectroscopia de Ressonância Magnética , Camundongos , Nanopartículas , Poloxâmero/química , Rotaxanos/química , Ensaios Antitumorais Modelo de Xenoenxerto
8.
Food Chem ; 319: 126584, 2020 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-32197216

RESUMO

Tea polyphenols content in green tea has an indirect relationship with the aroma quality of tea. This study innovatively proposed a method for quantitative determination of tea polyphenols in green tea based on the self-developed color sensitive sensor. Firstly, the color sensitive sensor was prepared to acquire the aroma information of green tea. Secondly, color components were extracted and then optimized using ant colony optimization (ACO) algorithm. Finally, extreme learning machine (ELM) model was built using the optimized color feature components for quantitative determination of tea polyphenols content in green tea. Results showed that the correlation coefficient (RP) of the best ELM model is 0.8035, and the root mean square error prediction (RMSEP) is 1.6003% in the validation set. The overall results sufficiently demonstrate that it is feasible to quantitative detect tea polyphenols content in green tea by the homemade color sensitive sensor combined with appropriate chemometrics methods.


Assuntos
Algoritmos , Análise de Alimentos/métodos , Polifenóis/análise , Chá/química , Cor , Análise de Alimentos/estatística & dados numéricos , Concentração de Íons de Hidrogênio , Aprendizado de Máquina , Análise Multivariada , Porfirinas/química , Compostos Orgânicos Voláteis/análise
9.
Chemistry ; 26(34): 7602-7608, 2020 Jun 18.
Artigo em Inglês | MEDLINE | ID: mdl-32068310

RESUMO

In this study a bispidine ligand has been applied to the complexation of gallium(III) and radiolabelled with gallium-68 for the first time. Despite its 5-coordinate nature, the resulting complex is stable in serum for over two hours, demonstrating a ligand system well matched to the imaging window of gallium-68 positron emission tomography (PET). To show the versatility of the bispidine ligand and its potential use in PET, the bifunctional chelator was conjugated to a porphyrin, producing a PET/PDT-theranostic, which showed the same level of stability to serum as the non-conjugated gallium-68 complex. The PET/PDT complex killed >90 % of HT-29 cells upon light irradiation at 50 µm. This study shows bispidines have the versatility to be used as a ligand system for gallium-68 in PET.


Assuntos
Compostos Bicíclicos Heterocíclicos com Pontes/química , Quelantes/química , Gálio/química , Porfirinas/química , Compostos Bicíclicos Heterocíclicos com Pontes/análise , Radioisótopos de Gálio , Humanos , Ligantes , Tomografia por Emissão de Pósitrons/métodos , Nanomedicina Teranóstica/métodos
10.
Nanoscale ; 12(9): 5587-5600, 2020 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-32100776

RESUMO

As one of the most promising noninvasive therapeutic modalities, sonodynamic therapy (SDT) can focus the ultrasound energy on tumor sites located in deep tissue and locally activate the preloaded sonosensitizer to kill tumor cells. However, exploring sonosensitizers with high SDT efficacy and desirable biosafety is still a significant challenge. Herein, we utilized the hydrophilic-hydrophobic self-assembly technology to assemble the hydrophobic organic dye Ce6 and broad spectral anti-cancer agent Paclitaxel with hydrophilic organic dye IR783 to generate a nanoscale sonosensitizer, Ce6-PTX@IR783, without the introduction of extra nanomaterials into the fabrication to guarantee high therapeutic biosafety and further potential clinical translation. The constructed nanodrug was endowed with an external ultrasound-activatable chemo-sonodynamic effect and photoacoustic imaging performance via integrating multiple moieties into one nanosystem. Ce6 could enhance the sonodynamic effect, while PTX exerted a chemotherapeutic effect, and IR783 was applied to increase tumor-specific accumulation and assist in fulfilling photoacoustic imaging. In particular, the small particle size (70 nm) of Ce6-PTX@IR783 contributed to the increased tumor accumulation via the enhanced permeability and retention effect. The high synergistically chemo-sonodynamic therapeutic efficacy has been successfully demonstrated in vitro and in vivo, in addition to the demonstrated high biodegradability, biocompatibility and biosafety. This facile self-assembly procedure provides an intriguing strategy for highly efficient utilization of hydrophobic drugs and is liable to realize large-scale production and further clinical translation.


Assuntos
Antineoplásicos Fitogênicos/química , Nanopartículas/química , Paclitaxel/química , Porfirinas/química , Radiossensibilizantes/química , Nanomedicina Teranóstica/métodos , Animais , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/uso terapêutico , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Portadores de Fármacos/química , Portadores de Fármacos/metabolismo , Endocitose , Feminino , Corantes Fluorescentes/química , Humanos , Camundongos , Camundongos Endogâmicos BALB C , Nanopartículas/metabolismo , Neoplasias/tratamento farmacológico , Neoplasias/patologia , Paclitaxel/farmacologia , Paclitaxel/uso terapêutico , Porfirinas/farmacologia , Porfirinas/uso terapêutico , Radiossensibilizantes/farmacologia , Radiossensibilizantes/uso terapêutico , Oxigênio Singlete/metabolismo , Distribuição Tecidual , Transplante Heterólogo
11.
J Fluoresc ; 30(2): 397-406, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32088851

RESUMO

New porphyrin analogues have been designed and synthesized using pyrrole, various aldehydes and propionic acid. The formation of desired compounds was analyzed by utilizing the spectral analysis such as IR, NMR and Mass spectroscopy. The studies on absorption and fluorescence emission of synthesized porphyrins were used to evaluate photophysical characteristics such as molar excitation coefficient and Stokes shift. The estimated values of fluorescence lifetime and fluorescence quantum yield of synthesized porphyrins were found to be variable due to the presence of change in the electron donating and withdrawing characters. The efficiency of generation of singlet oxygen by each synthesized porphyrin as photosensitizer was measured in terms of singlet oxygen quantum yield through photooxidation of 9,10-dimethylantharacene. The obtained singlet oxygen quantum yield values were found to be higher in case of porphyrins those have more electron withdrawing characters rather than donating characters as compared to reference 5,10,15,20-tetraphenylporphyrin (H2TPP). The singlet oxygen quantum yield values of synthesized porphyrins varied from 0.52 to 0.66. Pleasingly, some of synthesized porphyrins are found to be photostable and competent to discover as PDT agents as compared to reference H2TPP.


Assuntos
Desenho de Fármacos , Fotoquimioterapia , Fármacos Fotossensibilizantes/síntese química , Porfirinas/síntese química , Estrutura Molecular , Fármacos Fotossensibilizantes/química , Porfirinas/química , Espectrometria de Fluorescência
12.
Int J Nanomedicine ; 15: 347-361, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32021184

RESUMO

Purpose: Chemotherapy in head and neck squamous cell carcinoma (HNSCC) has many systemic side effects, as well as hypoxia-induced chemoresistance. To reduce side effects and enhance chemosensitivity are urgently needed. Methods: We synthesized a drug delivery system (named CECMa NPs) based on cisplatin (CDDP) and metformin (chemotherapeutic sensitizer), of which chlorin e6 (Ce6) and polyethylene glycol diamine (PEG) were synthesized as the shell, an anti-LDLR antibody (which can target to hypoxic tumor cells) was modified on the surface to achieve tumor targeting. Results: The NPs possessed a great synergistic effect of chemotherapy and phototherapy. After laser stimulation, both CDDP and metformin can be released in situ to achieve anti-tumor effects. Meanwhile, PDT and PTT triggered by a laser have anticancer effects. Furthermore, compared with free cisplatin, CECMa exhibits less systemic toxicity with laser irradiation in the xenograft mouse tumor model. Conclusion: CECMa effectively destroyed the tumors via hypoxia targeting multimodal therapy both in vitro and in vivo, thereby providing a novel strategy for targeting head and neck squamous cell carcinoma.


Assuntos
Protocolos de Quimioterapia Combinada Antineoplásica/administração & dosagem , Neoplasias de Cabeça e Pescoço/terapia , Nanopartículas Multifuncionais/química , Carcinoma de Células Escamosas de Cabeça e Pescoço/terapia , Animais , Linhagem Celular Tumoral , Cisplatino/administração & dosagem , Cisplatino/farmacologia , Terapia Combinada , Sistemas de Liberação de Medicamentos , Neoplasias de Cabeça e Pescoço/patologia , Humanos , Masculino , Metformina/administração & dosagem , Metformina/farmacologia , Camundongos Endogâmicos BALB C , Nanopartículas Multifuncionais/administração & dosagem , Nanopartículas Multifuncionais/uso terapêutico , Fotoquimioterapia , Fototerapia/métodos , Polietilenoglicóis/química , Porfirinas/química , Carcinoma de Células Escamosas de Cabeça e Pescoço/patologia , Hipóxia Tumoral/efeitos dos fármacos , Ensaios Antitumorais Modelo de Xenoenxerto
13.
Nanoscale ; 12(3): 1707-1718, 2020 Jan 23.
Artigo em Inglês | MEDLINE | ID: mdl-31894823

RESUMO

Oxygen deficient TiO2-x nanoparticles (NPs) have been recognized as a category of new-fashioned photothermal agents to offer safer PTT. However, the surface of TiO2-x NPs is deficient in free active groups or radicals to conjugate functional therapeutic molecules, which seriously impedes their in-depth development for versatile medical applications. In this study, surface activation of TiO2-x NPs was realized by the facile conjugation of (3-aminopropyl)triethoxysilane (APTES) through the formation of a stable Si-O-Ti bond, and photosensitizer chlorin e6 (Ce6) was successfully modified onto the TiO2-x NP surface and with a considerably high loading content. The resultant TiO2-x@APTES/Ce6 (TAC) NPs displayed decent biosafety, rapid tumor enrichment and outstanding performance in photoacoustic (PA) imaging. Taking advantage of the intense photo-absorption in the near-infrared (NIR) region and high dose of conjugated Ce6, a powerful antitumor effect was realized based on the combination of hyperthermia-induced cell ablation and cytotoxic reactive oxygen species (ROS)-triggered apoptosis both in vitro and in vivo. Moreover, PA imaging guidance was exceptionally useful for locating the tumor position and optimizing the treatment regimens. Apart from Ce6, this elaborate modification strategy for TiO2-x is believed to be universal for steadily binding more versatile therapeutic agents, which would definitely favor the development of multifunctional TiO2-x-based nanocomplexes for enhanced tumor treatment.


Assuntos
Hipertermia Induzida , Nanopartículas , Neoplasias Experimentais , Técnicas Fotoacústicas , Fototerapia , Porfirinas , Titânio , Animais , Feminino , Células HeLa , Humanos , Camundongos , Camundongos Endogâmicos BALB C , Nanopartículas/química , Nanopartículas/uso terapêutico , Neoplasias Experimentais/diagnóstico por imagem , Neoplasias Experimentais/metabolismo , Neoplasias Experimentais/patologia , Neoplasias Experimentais/terapia , Porfirinas/química , Porfirinas/farmacologia , Titânio/química , Titânio/farmacologia , Ensaios Antitumorais Modelo de Xenoenxerto
14.
Molecules ; 25(2)2020 Jan 09.
Artigo em Inglês | MEDLINE | ID: mdl-31936458

RESUMO

Taxol is one of the potential anticancer drugs; however, the yield of Taxol and its cytotoxicity are common challenges. Thus, manipulating the Taxol biosynthetic pathway from endophytic fungi, in addition to chemical modification with biocompatible polymers, is the challenge. Four fungal isolates, namely, Aspergillus flavipes, A. terreus, A. flavus, and A. parasiticus, were selected from our previous study as potential Taxol producers, and their potency for Taxol production was evaluated in response to fluconazole and silver nitrate. A higher Taxol yield was reported in the cultures of A. flavipes (185 µg/L) and A. terreus (66 µg/L). With addition of fluconazole, the yield of Taxol was increased 1.8 and 1.2-fold for A. flavipes and A. terreus, respectively, confirming the inhibition of sterol biosynthesis and redirecting the geranyl phosphate pool to terpenoids synthesis. A significant inhibition of ergosterol biosynthesis by A. flavipes with addition of fluconazole was observed, correlating with the increase on Taxol yield. To increase the Taxol solubility and to reduce its cytotoxicity, Taxol was modified via chemical conjugation with porphyrin, and the degree of conjugation was checked from the Thin layer chromatography and UV spectral analysis. The antiproliferative activity of native and modified Taxol conjugates was evaluated; upon porphyrin conjugation, the activity of Taxol towards HepG2 was increased 1.5-fold, while its cytotoxicity to VERO cells was reduced 3-fold.


Assuntos
Antineoplásicos/química , Proliferação de Células/efeitos dos fármacos , Paclitaxel/química , Porfirinas/química , Animais , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Aspergillus/química , Chlorocebus aethiops , Células Hep G2 , Humanos , Paclitaxel/síntese química , Paclitaxel/isolamento & purificação , Paclitaxel/farmacologia , Porfirinas/síntese química , Porfirinas/farmacologia , Células Vero
15.
Nanoscale ; 12(3): 1801-1810, 2020 Jan 23.
Artigo em Inglês | MEDLINE | ID: mdl-31898712

RESUMO

Black titanium dioxide (TiO2) nanoparticles have attracted great attention due to their application in photothermal therapy (PTT). However, single-mode phototherapy has the risk of recurrence, and the high-dose laser usually imposed to improve the PTT performance can bring a potential threat to security. Here, polydopamine (PDA)-coated black TiO2 (b-P25@PDA) nanoparticles with a core-shell structure were synthesized for enhanced PTT; then, synergistic phototherapy nanoprobes (b-P25@PDA-Ce6 (Mn)) were constructed by coupling chlorin e6 (Ce6) and chelating Mn2+ for simultaneous photodynamic therapy (PDT)/PTT and magnetic resonance (MR) imaging, in which a low-dose laser was used and imaging-guided phototherapy with high efficiency and high safety was achieved. The prepared nanoprobes showed high photothermal conversion efficiency (32.12%), high reactive oxygen generation and excellent MR imaging. In the 4T1 tumor-bearing nude mouse model, the tumors completely disappeared under the combination of PDT/PTT with a low-dose laser but were only partially inhibited by single PDT and single PTT. The current work developed a multifunctional black TiO2-based nanoprobe for enhanced synergistic PDT/PTT and MR imaging, which will be important for the safe and efficient visualized theranostics of cancers.


Assuntos
Meios de Contraste , Indóis , Imagem por Ressonância Magnética , Neoplasias Mamárias Animais , Manganês , Nanopartículas , Fototerapia , Polímeros , Porfirinas , Titânio , Animais , Linhagem Celular Tumoral , Meios de Contraste/química , Meios de Contraste/farmacologia , Feminino , Indóis/química , Indóis/farmacologia , Neoplasias Mamárias Animais/diagnóstico por imagem , Neoplasias Mamárias Animais/tratamento farmacológico , Manganês/química , Manganês/farmacologia , Camundongos , Nanopartículas/química , Nanopartículas/uso terapêutico , Polímeros/química , Polímeros/farmacologia , Porfirinas/química , Porfirinas/farmacologia , Titânio/química , Titânio/farmacologia
16.
Nanotechnology ; 31(19): 195103, 2020 May 08.
Artigo em Inglês | MEDLINE | ID: mdl-31978912

RESUMO

The integration of chemotherapy drugs and photosensitizers to form versatile nanoplatforms for achieving chemo-photodynamic synergetic therapy has shown great superiority in tumor theranostic applications. We constructed pH-responsive nanoparticles (DOX/PB NPs) encapsulating the chemotherapeutic drug doxorubicin (DOX) into the cores of PLGA NPs coated with bovine serum albumin (BSA) via a water-in-oil (W/O/W) emulsion method. A simple and efficient chemo-photodynamic synergetic nanoplatform (DOX/PB@Ce6 NPs) was obtained by the adsorption of photosensitizer chlorin e6 (Ce6) onto the surface of the DOX/PB NPs. With optimal size, pH-responsive drug release behavior and excellent singlet oxygen production, the DOX/PB@Ce6 NPs have the potential to enhance anti-tumor efficiency. The cellular uptake, cytotoxicity, chemo-photodynamic synergetic effect and biocompatibility of the NPs were evaluated based on HeLa cells via in vitro experiments. The in vitro chemo-photodynamic synergetic experiments indicated that the DOX/PB@Ce6 NPs had remarkable cancer cell killing efficiency under laser irradiation. Notably, by hemolysis assay, all the NPs displayed excellent blood compatibility and were expected to be applicable for intravenous injection. In summary, the designed DOX/PB@Ce6 NPs multifunctional theranostic nanoplatform had excellent reactive oxygen species generation and would be a potential therapeutic platform for chemo-photodynamic synergetic therapy.


Assuntos
Antibióticos Antineoplásicos/farmacologia , Doxorrubicina/farmacologia , Porfirinas/farmacologia , Radiossensibilizantes/farmacologia , Antibióticos Antineoplásicos/química , Cápsulas , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Doxorrubicina/química , Sinergismo Farmacológico , Células HeLa , Humanos , Concentração de Íons de Hidrogênio , Nanopartículas , Tamanho da Partícula , Fotoquimioterapia , Fármacos Fotossensibilizantes , Porfirinas/química , Radiossensibilizantes/química , Espécies Reativas de Oxigênio/metabolismo
17.
Biomater Sci ; 8(4): 1106-1116, 2020 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-31994549

RESUMO

In this study, we sought to design a bionanomaterial that could exert anticancer effects against primary tumors and protect against rechallenged tumors via photodynamic immunotherapy. As a biomaterial, we used an amphiphilic phenylalanine derivative of poly-gamma glutamic acid, which forms nanoparticles by self-assembly. For anticancer effects, we co-entrapped hydrophobic chlorin e6 and monophosphoryl lipid A in the core of the plain amphiphilic phenylalanine nanoparticles (AN), to generate M/C/AN. For comparison, we used plain AN and chlorin e6-loaded AN (C/AN). In vitro studies showed that B16F10 cancer cells treated with C/AN or M/C/AN generated reactive oxygen species and exhibited an enhanced surface display of calreticulin upon exposure to 660 nm light irradiation. C/AN and M/C/AN exerted similar photodynamic anticancer effects; however, M/C/AN, but not C/AN, induced in vitro dendritic cell maturation. Our biodistribution study revealed that C/AN and M/C/AN showed higher accumulation at the tumor tissues compared to that seen in the free chlorin e6-treated group. In B16F10 tumor-bearing mice, the intravenous injection of C/AN or M/C/AN showed similar photodynamic anticancer effects against primary tumors. However, the growth of rechallenged tumors was more significantly inhibited in the M/C/AN group compared to the C/AN group. At day 40 after inoculation of the primary tumor, M/C/AN-treated mice showed 100% survival, whereas the other groups showed 0% survival. In the tumor microenvironment, higher infiltration of CD8+ T cells was observed in the M/C/AN group compared to the other groups. Our results suggest that AN co-loaded with a photosensitizer and an immune stimulant may hold great potential for use in photodynamic immunotherapy to inhibit both primary and metastatic tumors.


Assuntos
Biomimética/métodos , Lipídeo A/análogos & derivados , Melanoma Experimental/tratamento farmacológico , Porfirinas/administração & dosagem , Administração Intravenosa , Animais , Cápsulas , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Imunoterapia , Lipídeo A/administração & dosagem , Lipídeo A/química , Lipídeo A/farmacocinética , Lipídeo A/farmacologia , Melanoma Experimental/imunologia , Camundongos , Nanopartículas , Fotoquimioterapia , Ácido Poliglutâmico/análogos & derivados , Ácido Poliglutâmico/química , Polímeros/química , Porfirinas/química , Porfirinas/farmacocinética , Porfirinas/farmacologia , Distribuição Tecidual , Microambiente Tumoral/efeitos dos fármacos
18.
Int J Mol Sci ; 21(1)2020 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-31948078

RESUMO

In this work, we studied the anthracene oxidation by hydroxyl radicals. Hydroxyl radical was generated by reaction of 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin Fe (III) (TPPFe) with hydrogen peroxide under visible radiation at a nitrogen atmosphere. The TPPFe was synthesized by Adler Method followed by metal complexation with Fe (III) chloride hexahydrate. Hydroxyl radical was detected by fluorescence emission spectroscopy and we studied kinetic of anthracene selective oxidation by hydroxyl radicals through the differential method. The TPPFe was characterized by UV-Vis spectrophotometry, Dynamic Light Scattering (DLS) and Scanning Electron Microscopy (SEM) measurements. The results indicated that TPPFE was compound by micro-particles with a size distribution of around 2500 nm. Kinetic results showed that the apparent rate constant for the oxidation of anthracene increased exponentially on as temperature increases, furthermore, the activation energy for the Anthracene oxidation by hydroxyl radicals under visible irradiation was 51.3 kJ/mol. Finally, anthraquinone was the main byproduct generated after oxidation of anthracene by TPP-Fe under visible irradiation.


Assuntos
Antracenos/química , Radical Hidroxila/química , Antracenos/efeitos da radiação , Difusão Dinâmica da Luz , Compostos Férricos/síntese química , Compostos Férricos/química , Peróxido de Hidrogênio/química , Cinética , Luz , Microscopia Eletrônica de Varredura , Nitrogênio , Oxirredução , Porfirinas/síntese química , Porfirinas/química , Porfirinas/efeitos da radiação , Espectrometria de Fluorescência
19.
Chem Soc Rev ; 49(3): 865-907, 2020 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-31957756

RESUMO

Supramolecular chemistry is a central topic in modern chemistry. It touches on many traditional disciplines, such as organic chemistry, inorganic chemistry, physical chemistry, materials chemistry, environmental chemistry, and biological chemistry. Supramolecular hosts, inter alia macrocyclic hosts, play critical roles in supramolecular chemistry. Calix[4]pyrroles, non-aromatic tetrapyrrolic macrocycles defined by sp3 hybridized meso bridges, have proved to be versatile receptors for neutral species, anions, and cations, as well as ion pairs. Compared to the parent system, octamethylcalix[4]pyrrole and its derivatives bearing simple appended functionalities, strapped calix[4]pyrroles typically display enhanced binding affinities and selectivities. In this review, we summarize advances in the design and synthesis of strapped calix[4]pyrroles, as well as their broad utility in molecular recognition, supramolecular extraction, separation technology, ion transport, and as agents capable of inhibiting cancer cell proliferation. Future challenges within this sub-field are also discussed.


Assuntos
Calixarenos/química , Calixarenos/metabolismo , Porfirinas/química , Porfirinas/metabolismo , Ânions/química , Apoptose , Cátions/química , Permeabilidade da Membrana Celular , Cristalização , Modelos Moleculares , Estrutura Molecular , Compostos Orgânicos/química , Relação Estrutura-Atividade , Termodinâmica
20.
Chemistry ; 26(37): 8262-8266, 2020 Jul 02.
Artigo em Inglês | MEDLINE | ID: mdl-31968144

RESUMO

Free base, zinc and palladium π-extended porphyrins containing fused naphthalenediamide units were employed as photosensitizers in antimicrobial photodynamic therapy (aPDT). Their efficacy, assessed by photophysical and in vitro photobiological studies on Gram-positive bacteria, was found to depend on metal coordination, showing a dramatic enhancement of photosensitizing activity for the palladium complex.


Assuntos
Antibacterianos/farmacologia , Bactérias Gram-Positivas/química , Metaloporfirinas/química , Porfirinas/química , Zinco/química , Antibacterianos/química , Humanos , Metaloporfirinas/farmacologia , Fotoquimioterapia , Fármacos Fotossensibilizantes , Porfirinas/farmacologia
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