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1.
Int J Mol Sci ; 24(4)2023 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-36835310

RESUMO

Photodynamic therapy (PDT) can eradicate not only cancer cells but also stimulate an antitumor immune response. Herein, we describe two efficient synthetic methodologies for the preparation of Chlorin e6 (Ce6) from Spirulina platensis and address the phototoxic effect of Ce6 in vitro along with antitumor activity in vivo. Melanoma B16F10 cells were seeded and phototoxicity was monitored by the MTT assay. The C57BL/6 mice were subcutaneously inoculated on the left and right flank with B16F10 cells. The mice were intravenously injected with Ce6 of 2.5 mg/kg and then exposed to red light (660 nm) on the left flank tumors 3 h after the injection. The immune response was studied by analyzing Interferon-gamma (IFN-γ), tumor necrosis factor-alpha (TNF-α), and Interleukin-2 (IL-2) of the right flank tumors through qPCR. Our results revealed that the tumor was suppressed not only in the left flank but also in the right flank, where no PDT was given. The upregulated gene and protein expression of IFN-γ, TNF-α, and IL-2 revealed antitumor immunity due to Ce6-PDT. The findings of this study suggest an efficient methodology of Ce6 preparation and the efficacy of Ce6-PDT as a promising antitumor immune response.


Assuntos
Clorofilídeos , Melanoma Experimental , Fotoquimioterapia , Fármacos Fotossensibilizantes , Animais , Camundongos , Linhagem Celular Tumoral , Clorofilídeos/síntese química , Clorofilídeos/uso terapêutico , Imunoterapia/métodos , Interleucina-2 , Camundongos Endogâmicos C57BL , Fotoquimioterapia/métodos , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/uso terapêutico , Fator de Necrose Tumoral alfa , Melanoma Experimental/tratamento farmacológico
2.
J Mater Chem B ; 9(47): 9700-9710, 2021 12 08.
Artigo em Inglês | MEDLINE | ID: mdl-34779468

RESUMO

Gold nanoparticles (AuNPs) were surface-engineered with a cationic corona to enhance the incorporation of photosensitizers for photodynamic therapy (PDT). The cationic corona composed of poly(2-(dimethylamino)ethyl methacrylate) was atom transfer radical-polymerized on the surface of the AuNPs. The cationic corona of the engineered surface was characterized by dynamic light scattering, electron microscopy, Raman spectroscopy, and mass spectroscopy. Chlorin-e6 (Ce6) incorporated onto the surface-engineered AuNPs exhibited higher cell incorporation efficiency than bare AuNPs. Ce6-incorporated AuNPs were confirmed to release singlet oxygen upon NIR irradiation. Compared to Ce6, Ce6-incorporated AuNPs exhibited higher cellular uptake and cytotoxicity against cancer cells in an irradiation time-dependent manner. Near-infrared-irradiated animals administered Ce6-incorporated AuNPs exhibited higher levels of tumor suppression without noticeable body weight loss. This result was attributed to the higher localization of Ce6 at the tumor sites to induce cancer cell apoptosis. Thus, we envision that engineered AuNPs with cationic corona can be tailored to effectively deliver photosensitizers to tumor sites for photodynamic therapy.


Assuntos
Antineoplásicos/uso terapêutico , Nanopartículas Metálicas/uso terapêutico , Neoplasias/tratamento farmacológico , Fármacos Fotossensibilizantes/uso terapêutico , Animais , Antineoplásicos/síntese química , Antineoplásicos/efeitos da radiação , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Clorofilídeos/síntese química , Clorofilídeos/efeitos da radiação , Clorofilídeos/uso terapêutico , Feminino , Ouro/química , Ouro/efeitos da radiação , Humanos , Raios Infravermelhos , Nanopartículas Metálicas/química , Nanopartículas Metálicas/efeitos da radiação , Metacrilatos/síntese química , Metacrilatos/química , Metacrilatos/efeitos da radiação , Camundongos Endogâmicos BALB C , Camundongos Nus , Nylons/síntese química , Nylons/química , Nylons/efeitos da radiação , Fotoquimioterapia , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/efeitos da radiação , Polimerização , Oxigênio Singlete/metabolismo , Ensaios Antitumorais Modelo de Xenoenxerto
3.
Biomolecules ; 11(8)2021 07 28.
Artigo em Inglês | MEDLINE | ID: mdl-34439782

RESUMO

Chlorophyllides can be found in photosynthetic organisms. Generally, chlorophyllides have a-, b-, c-, d-, and f-type derivatives, and all chlorophyllides have a tetrapyrrole structure with a Mg ion at the center and a fifth isocyclic pentanone. Chlorophyllide a can be synthesized from protochlorophyllide a, divinyl chlorophyllide a, or chlorophyll. In addition, chlorophyllide a can be transformed into chlorophyllide b, chlorophyllide d, or chlorophyllide f. Chlorophyllide c can be synthesized from protochlorophyllide a or divinyl protochlorophyllide a. Chlorophyllides have been extensively used in food, medicine, and pharmaceutical applications. Furthermore, chlorophyllides exhibit many biological activities, such as anti-growth, antimicrobial, antiviral, antipathogenic, and antiproliferative activity. The photosensitivity of chlorophyllides that is applied in mercury electrodes and sensors were discussed. This article is the first detailed review dedicated specifically to chlorophyllides. Thus, this review aims to describe the definition of chlorophyllides, biosynthetic routes of chlorophyllides, purification of chlorophyllides, and applications of chlorophyllides.


Assuntos
Técnicas Biossensoriais/métodos , Química Farmacêutica/métodos , Clorofila/análogos & derivados , Clorofilídeos/síntese química , Aditivos Alimentares/química , Protoclorifilida/metabolismo , Anti-Infecciosos/síntese química , Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/biossíntese , Antineoplásicos Fitogênicos/síntese química , Antineoplásicos Fitogênicos/farmacologia , Antivirais/síntese química , Antivirais/farmacologia , Técnicas Biossensoriais/instrumentação , Clorofila/biossíntese , Clorofila/farmacologia , Clorofilídeos/biossíntese , Clorofilídeos/farmacologia , Técnicas Eletroquímicas , Aditivos Alimentares/metabolismo , Humanos , Luz , Estrutura Molecular , Fotossíntese/fisiologia , Plantas/química , Plantas/metabolismo
4.
Nat Prod Res ; 33(21): 3120-3126, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30449159

RESUMO

The complex formation between metals (Ni, Co, Zn, Fe, Pb, Sn and Ag) and natural chlorophyll extracted from green leaves was monitored in the present study. The respective metallochlorophyllin was prepared by the reaction of metal chloride or nitrate (1M) to chlorophyll extracted from Ficus leaves extract. All synthesized metallochlorophyllins were stable and Na-Cu-chlorohyllin (E141) which is permitted to add in food and are listed in European Directive 94/36/EC on food colouring materials, was identified in commercially available food commodities (candies). In this study different synthesized metallochlorophyllins were characterised by using UV-Vis, FT-IR, HPLC, AAS and HR-MS techniques. Many food commodities (i.e. candy, chips, drink, and cream biscuits) were monitored for metallochlorophyllins and Na-Cu-Chlorophyllin was detected only in real candy samples.


Assuntos
Clorofilídeos/análise , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia de Fase Reversa/métodos , Análise de Alimentos/métodos , Metais/química , Doces/análise , Clorofila/química , Clorofilídeos/síntese química , Clorofilídeos/química , Corantes de Alimentos/análise , Corantes de Alimentos/síntese química , Corantes de Alimentos/química , Espectrometria de Massas/métodos , Espectrofotometria Ultravioleta , Espectroscopia de Infravermelho com Transformada de Fourier
5.
Anal Biochem ; 419(2): 271-6, 2011 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-21925479

RESUMO

Chlorophyllide a is a metabolite late in the biosynthesis of chlorophylls and bacteriochlorophylls. Isolation procedures for chlorophyllide a from Rhodobacter capsulatus CB1200 and barley (Hordeum vulgare L.) are described and compared. R. capsulatus CB1200 is a double mutant in the bacteriochlorophyllide a biosynthetic pathway, and chlorophyllide a is excreted by the cells when grown in Tween 80-containing liquid medium. It was purified by liquid or solid phase extraction, yielding 7 mg of chlorophyllide a from 1 L of culture. In a second approach, intrinsic chlorophyllase activity was used to dephytylate chlorophyll in an acetonic preparation of leaves of wild-type or chlorophyll b-deficient barley. Purification was achieved by liquid phase extraction, yielding 14 µg of chlorophyllide a per gram of barley leaves. Chlorophyllide a was identified by thin layer chromatography, absorption spectroscopy, and mass spectrometry.


Assuntos
Bioquímica/métodos , Vias Biossintéticas , Clorofilídeos/síntese química , Absorção , Clorofilídeos/química , Clorofilídeos/isolamento & purificação , Cromatografia em Camada Fina , Meios de Cultura/química , Hordeum/metabolismo , Magnésio/metabolismo , Polissorbatos , Rhodobacter capsulatus/metabolismo , Análise Espectral
6.
Eur J Biochem ; 219(1-2): 267-75, 1994 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-8306994

RESUMO

Chlorophyll synthetase catalyzes the last step of chlorophyll biosynthesis, namely prenylation (esterification) of chlorophyllide with phytyl diphosphate or geranylgeranyl diphosphate. During investigation of various chlorophyllide derivatives as potential substrates we observed lower esterification with increasing percentages of chlorophyllide a' in epimeric mixtures of chlorophyllides a and a'. To avoid epimerization during esterification, we studied the reaction in detail with model compounds [zinc-13(2)(R)-methoxy-pheophorbide a and zinc-13(2)(S)-methoxy-pheophorbide a, zinc-13(2)(R)-methoxy-pyropheophorbide a and zinc-chlorine6-13(1), 15(2)-dimethylester]. We conclude that compounds which have the 13(2)-carbomethoxy group at the same side of the macrocycle as the propionic side chain of ring D are neither substrates nor competitive inhibitors. Only compounds having the 13(2)-carbomethoxy group at the opposite site are substrates for the enzyme. Naturally occurring chlorophyll a' must be formed by epimerization after esterification.


Assuntos
Carbono-Oxigênio Ligases , Clorofila/análogos & derivados , Clorofilídeos/metabolismo , Grão Comestível/enzimologia , Ligases/metabolismo , Plantas/metabolismo , Membrana Celular/enzimologia , Clorofila/análise , Clorofila/biossíntese , Clorofila/metabolismo , Clorofilídeos/síntese química , Cromatografia Líquida de Alta Pressão , Difosfatos , Indicadores e Reagentes , Ligases/isolamento & purificação , Estrutura Molecular , Estereoisomerismo , Especificidade por Substrato , Zinco/metabolismo
7.
Hua Xi Yi Ke Da Xue Xue Bao ; 21(3): 341-3, 1990 Sep.
Artigo em Chinês | MEDLINE | ID: mdl-2093078

RESUMO

A method for synthesis of zinc chlorophyllin a (I), a promising drug for clinical application, is presented. Taking silkworm faeces as a raw material. Chlorophyll was extracted with ethyl alcohol. After concentration the solid formed was dissolved in petroleum ether and the solution was subjected to column chromatography to separate pheophytin a and chlorophyll a. The products were dissolved in ethyl ether and the Mg in the products was stripped off with concentrated hydrochloric acid. The excess hydrochloric acid in the solution was neutralized with ammonia solution and the mixture was hydrolyzed with diluted hydrochloric acid to obtain pheophorbide a, then (I) was synthesized with pheophorbide a and zinc salt. The characteristics of (I) and pheophorbide a were checked by IR, UV and elemental analyses. All results of pheophorbide a coincided with those values reported in literature. The acute toxicity of (I) was tested in mice and the LD50 of (I) was 324 +/- 40 mg/kg. (I) has been applied in several hospitals for several months. It has been found that (I) has outstanding effects on burns and oral sepsis and that it increases the growth of granulation tissue and epithelium remarkably.


Assuntos
Anti-Infecciosos Locais/síntese química , Clorofilídeos/síntese química , Animais , Anti-Infecciosos Locais/uso terapêutico , Queimaduras/tratamento farmacológico , Clorofilídeos/uso terapêutico , Humanos , Camundongos , Estomatite Aftosa/tratamento farmacológico , Infecção dos Ferimentos/tratamento farmacológico
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