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1.
Photochem Photobiol ; 99(2): 732-741, 2023 03.
Artigo em Inglês | MEDLINE | ID: mdl-35944220

RESUMO

Hydroxypyranoflavylium (HPF) cations are synthetic analogs possessing the same basic chromophore as the pyranoanthocyanins that form during the maturation of red wine. HPF cations absorb strongly in the visible spectral region, and most are fluorescent, triplet-sensitize singlet oxygen formation in solution and are strong photooxidants, properties that are desirable in a sensitizer for photodynamic therapy (PDT). The results of this study demonstrate that several simple HPF dyes can indeed function as PDT sensitizers. Of the eight HPF cations investigated in this work, four were phototoxic to a human cervical adenocarcinoma cell line (HeLa) at the 1-10 µmol dm-3 level, while only one of the eight compounds showed noticeable cytotoxicity in the dark. Neither a Type I nor a Type II mechanism can adequately rationalize the differences in phototoxicity of the compounds. Colocalization experiments with the most phototoxic compound demonstrated the affinity of the dye for both the mitochondria and lysosomes of HeLa cells. The fact that relatively modest structural differences, e.g., the exchange of an electron-donating substituent for an electron-withdrawing substituent, can cause profound differences in the phototoxicity, together with the relatively facile synthesis of substituted HPF cations, makes them interesting candidates for further evaluation as PDT sensitizers.


Assuntos
Fotoquimioterapia , Fármacos Fotossensibilizantes , Humanos , Fármacos Fotossensibilizantes/química , Fotoquimioterapia/métodos , Células HeLa , Corantes/química , Oxigênio Singlete/metabolismo
2.
ACS Omega ; 5(41): 26592-26600, 2020 Oct 20.
Artigo em Inglês | MEDLINE | ID: mdl-33110987

RESUMO

Flavylium cations are synthetic analogues of anthocyanins, the natural plant pigments that are responsible for the majority of the red, blue, and purple colors of flowers, fruits, and leaves. Unlike anthocyanins, the properties and reactivity of flavylium cations can be manipulated by the nature and position of substituents on the flavylium cation chromophore. Currently, the most promising strategies for stabilizing the color of anthocyanins and flavylium cations appear to be to intercalate and/or adsorb them on solid surfaces and/or in confined spaces. We report here that hybrid pigments with improved thermal stability, fluorescence, and attractive colors are produced by the cation-exchange-mediated adsorption of flavylium cations (FL) on two synthetic clays, the mica-montmorillonite SYn-1, and the laponite SYnL-1. Compared to the FL/SYn-1 hybrid pigments, the FL/SYnL-1 pigments exhibited improved thermal stability as judged by color retention, better preferential adsorption of the cationic form of FL1 at neutral to mildly basic pH (pH 7-8), and lower susceptibility to color changes at pH 10. Although both clays adsorb the cationic form on their external surfaces, SYnL-1 gave more evidence of adsorption in the interlayer regions of the clay. This interlayer adsorption appears to be the contributing factor to the better properties of the FL/SYnL-1 hybrid pigments, pointing to this clay to be a promising inorganic matrix for the development of brightly colored, thermally more stable hybrid pigments based on cationic analogues of natural plant pigments.

3.
Photochem Photobiol Sci ; 18(7): 1750-1760, 2019 Jul 10.
Artigo em Inglês | MEDLINE | ID: mdl-31107486

RESUMO

Flavylium cations serve as models for the chemical and photochemical reactivity of anthocyanins, the natural plant pigment responsible for many of the red, blue and purple colors of fruits and flowers. Likewise, pyranoflavylium cations serve as models of the fundamental chromophoric moiety of pyranoanthocyanins, molecules that can form from reactions of grape anthocyanins in red wines during their maturation. In the present work, hybrid pigments are prepared by the adsorption of a series of five synthetic flavylium cations (FL) and five synthetic pyranoflavylium cations (PFL) on sepiolite clay (SEP). The FL are smaller in size than the PFL, but both can in principle fit into the tunnels and/or external grooves (with dimensions of 3.7 × 10.6 Å) of SEP. Measurements of the fluorescence quantum yields of the adsorbed dyes indicate that they are at least as fluorescent as in acidic acetonitrile solution, and in a few cases substantially more fluorescent. The observation of biexponential fluorescence decays is consistent with emission from dye molecules adsorbed at two distinct sites, presumably tunnels and grooves. These hybrid materials also have improved properties in terms of stability of the color in contact with pH 10 aqueous solution and resistance to thermal degradation of the dye. SEP thus appears to be a promising substrate for the development of highly fluorescent flavylium or pyranoflavylium cation-derived hybrid pigments with improved color and thermal stability.

4.
Molecules ; 21(3): 258, 2016 Feb 23.
Artigo em Inglês | MEDLINE | ID: mdl-26907246

RESUMO

Five monoterpenes naturally occurring in essential oils were tested for their insecticidal and repellent activities against the bruchid beetle Callosobruchus maculatus and the maize weevil Sitophilus zeamais. The monoterpenes were highly efficient as inducers of mortality or repellency against both insect species. They were more efficient in their fumigant activity against C. maculatus than against S. zeamais, while this profile of action was inverted when considering the repellent activities. Eugenol was one the most effective fumigants against both insects and one the most effective repellent against C. maculatus, while citronellal and geranial were one the most effective repellents against S. zeamais. Functional and positional isomerism of the monoterpenes pairs appears to exert little or no influence on theirs effects, especially in case of repellency. The validation of the insecticidal/repellent efficacy of isolated monoterpenes may permit a more advantageous, rapid, economic and optimized approach to the identification of promising oils for commercial formulations when combined with ethnobotanical strategies.


Assuntos
Repelentes de Insetos/farmacologia , Inseticidas/farmacologia , Monoterpenos/farmacologia , Monoterpenos Acíclicos , Aldeídos/farmacologia , Animais , Besouros , Grão Comestível/parasitologia , Eugenol/farmacologia , Fumigação , Controle de Insetos , Óleos Voláteis/farmacologia , Terpenos/farmacologia , Gorgulhos
5.
Braz. j. phys. ther. (Impr.) ; 16(6): 495-501, Nov.-Dec. 2012. graf, tab
Artigo em Inglês | LILACS | ID: lil-662694

RESUMO

BACKGROUND: The aging process and its associated morphophysiological changes trigger a reduction in the regenerative ability of the satellite cells, a reduction of vascular tissue and an increase in the production of fibroblasts, developing a cellular environment unfavorable for muscle regeneration. OBJECTIVE: The aim of this study was to evaluate the effect of low-level laser therapy on the muscle regeneration of old experimental rat models after contusion. METHOD: A total of 25 old rats,18 months old, were divided into three groups: control group (CT) without treatment; injury group (IN) with muscle contusion and without treatment and laser group (LA) with contusion and low-level laser therapy, 830 nm, 30 mW e 4 J/cm². The no invasive contusion was induced in the Tibialis Anterior muscle and the samples were collected after 7 and 21 treatment sessions. The muscle was evaluated by Light Microscopy and Immunoblotting. RESULTS: After 21 days of treatment there was a significant reduction in the areas of inflammation/regeneration of the LA 21 group compared to IN 21 group. The cross-sectional area of the fibers in regeneration was not statistically different between the groups. Molecular analysis showed that the content of MyoD was statistically reduced in the IN 21 group compared to the CT group. The Myogenin content was increased in the IN 21 group compared to the CT group. Ultimately, the content of TGF-β1 on the IN 21 group was higher when compared to the CT group. CONCLUSION: Considering the parameters used, the laser therapy demonstrated to be effective for muscle regeneration in old rats, however only through its anti-inflammatory effect.


CONTEXTUALIZAÇÃO: O processo de envelhecimento e suas consequentes alterações morfofisiológicas desencadeiam redução da habilidade regenerativa das células satélites, redução da vascularização tecidual e aumento da produção de fibroblastos, desenvolvendo-se um ambiente celular desfavorável para a regeneração muscular. OBJETIVO: Avaliar o efeito do tratamento com laser de baixa intensidade sobre a regeneração muscular de modelos experimentais idosos após contusão. MÉTODO: Foram utilizados 25 ratos machos, com 18 meses de idade, divididos em três grupos: grupo controle (CT), sem intervenção; grupo lesão (LE), com contusão muscular e sem tratamento e grupo laser (LA), com contusão muscular e tratado com laser de baixa intensidade, 830 nm, 30 mW e 4 J/cm². A contusão foi realizada no músculo tibial anterior, e as amostras coletadas após sete e 21 sessões de tratamento. O músculo foi designado às técnicas de Microscopia de Luz e Immunoblotting. RESULTADOS: Após 21 dias de tratamento, houve redução significativa na área de inflamação/regeneração no grupo LA 21 comparado ao grupo LE 21. Na área de secção transversal das fibras em processo de regeneração, não houve diferença estatística entre os grupos LA e LE. A análise molecular evidenciou que o conteúdo de MyoD apresentou redução significativa no grupo LE 21 em relação ao CT. O conteúdo de Miogenina exibiu aumento no LE 21 comparado ao CT e, por fim, o conteúdo de TGF-β1 do grupo LE 21 aumentou em relação ao grupo CT. CONCLUSÃO: Para os parâmetros utilizados, o laser demonstrou eficácia na regeneração muscular em animais idosos somente por meio do seu efeito anti-inflamatório.


Assuntos
Animais , Masculino , Ratos , Terapia com Luz de Baixa Intensidade , Músculo Esquelético/fisiologia , Regeneração , Assistência ao Convalescente , Fatores Etários , Contusões , Ratos Wistar
6.
Rev Bras Fisioter ; 16(6): 495-501, 2012.
Artigo em Inglês, Português | MEDLINE | ID: mdl-23060238

RESUMO

BACKGROUND: The aging process and its associated morphophysiological changes trigger a reduction in the regenerative ability of the satellite cells, a reduction of vascular tissue and an increase in the production of fibroblasts, developing a cellular environment unfavorable for muscle regeneration. OBJECTIVE: The aim of this study was to evaluate the effect of low-level laser therapy on the muscle regeneration of old experimental rat models after contusion. METHOD: A total of 25 old rats,18 months old, were divided into three groups: control group (CT) without treatment; injury group (IN) with muscle contusion and without treatment and laser group (LA) with contusion and low-level laser therapy, 830 nm, 30 mW e 4 J/cm². The no invasive contusion was induced in the Tibialis Anterior muscle and the samples were collected after 7 and 21 treatment sessions. The muscle was evaluated by Light Microscopy and Immunoblotting. RESULTS: After 21 days of treatment there was a significant reduction in the areas of inflammation/regeneration of the LA 21 group compared to IN 21 group. The cross-sectional area of the fibers in regeneration was not statistically different between the groups. Molecular analysis showed that the content of MyoD was statistically reduced in the IN 21 group compared to the CT group. The Myogenin content was increased in the IN 21 group compared to the CT group. Ultimately, the content of TGF-ß1 on the IN 21 group was higher when compared to the CT group. CONCLUSION: Considering the parameters used, the laser therapy demonstrated to be effective for muscle regeneration in old rats, however only through its anti-inflammatory effect.


Assuntos
Terapia com Luz de Baixa Intensidade , Músculo Esquelético/fisiologia , Regeneração , Assistência ao Convalescente , Fatores Etários , Animais , Contusões , Masculino , Ratos , Ratos Wistar
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