Your browser doesn't support javascript.
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 795
Filtrar
Mais filtros










Base de dados
Intervalo de ano de publicação
1.
Chem Commun (Camb) ; 55(73): 10920-10923, 2019 Sep 10.
Artigo em Inglês | MEDLINE | ID: mdl-31441463

RESUMO

The development of new NIR-II fluorophores, particularly those with facile syntheses, high fluorescence quantum yields, and stable and tunable photophysical properties, is challenging. Herein, we report a new class of small molecular NIR-II fluorophores based on aza-dipyrromethene boron difluoride (aza-BODIPY) dyes. We demonstrate promising photophysical properties of these dyes, such as large Stokes shift, superior photostability, and good fluorescence brightness as nanoparticles in aqueous solution. Because of these properties and high resolution and deep penetration NIR-II imaging ability, the aza-BODIPY based dyes show great potential as NIR-II imaging agents.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Imagem Óptica/métodos , Pirróis/química , Animais , Compostos de Boro/síntese química , Compostos de Boro/efeitos da radiação , Compostos de Boro/toxicidade , Linhagem Celular Tumoral , Teoria da Densidade Funcional , Desenho de Drogas , Fluorescência , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/efeitos da radiação , Corantes Fluorescentes/toxicidade , Raios Infravermelhos , Camundongos , Modelos Químicos , Nanopartículas/química , Poloxâmero/química , Pirróis/síntese química , Pirróis/efeitos da radiação , Pirróis/toxicidade
2.
J Enzyme Inhib Med Chem ; 34(1): 1498-1505, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31423863

RESUMO

Recent studies identified the benzoxaborole moiety as a new zinc-binding group able to interact with carbonic anhydrase (CA) active site. Here, we report a structural analysis of benzoxaboroles containing urea/thiourea groups, showing that these molecules are very versatile since they can bind the enzyme assuming different binding conformations and coordination geometries of the catalytic zinc ion. In addition, theoretical calculations of binding free energy were performed highlighting the key role of specific residues for protein-inhibitor recognition. Overall, these data are very useful for the development of new inhibitors with higher selectivity and efficacy for various CAs.


Assuntos
Compostos de Boro/farmacologia , Inibidores da Anidrase Carbônica/farmacologia , Anidrases Carbônicas/metabolismo , Compostos de Boro/síntese química , Compostos de Boro/química , Inibidores da Anidrase Carbônica/síntese química , Inibidores da Anidrase Carbônica/química , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Humanos , Modelos Moleculares , Conformação Molecular , Relação Estrutura-Atividade
3.
Chem Commun (Camb) ; 55(59): 8564-8566, 2019 Jul 18.
Artigo em Inglês | MEDLINE | ID: mdl-31271158

RESUMO

Diphenylalanine (FF), as the smallest unit and core recognition motif of ß-amyloid (Aß), could self-assemble into nanofibers, which induces an early onset of Alzheimer's disease (AD). Green/near-infrared fluorescent BODIPY probes were designed and synthesized to detect FF-assembly, providing unique insights into the chemical and molecular mechanism of Aß aggregation and drug development for AD.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Fenilalanina/análogos & derivados , Técnicas Biossensoriais/métodos , Compostos de Boro/síntese química , Corantes Fluorescentes/síntese química , Nanofibras/química , Fenilalanina/análise , Fenilalanina/química , Multimerização Proteica
4.
Chem Commun (Camb) ; 55(58): 8494-8497, 2019 Jul 16.
Artigo em Inglês | MEDLINE | ID: mdl-31268095

RESUMO

A rational strategy was reported to construct boranil complexes (DPFB derivatives) with unique aggregation-induced emission effects by installing phenyl rings in the anil ligand as the intramolecular rotors. In view of the good biocompatibility and suitable lipophilicity, DPFB derivatives can serve as excellent fluorescent probes for specific imaging of lipid droplets in living cells and yolk lipids in zebrafish.


Assuntos
Compostos de Anilina/química , Compostos de Boro/química , Complexos de Coordenação/química , Corantes Fluorescentes/química , Gotículas Lipídicas/metabolismo , Compostos de Anilina/síntese química , Animais , Compostos de Boro/síntese química , Complexos de Coordenação/síntese química , Fluorescência , Corantes Fluorescentes/síntese química , Células HeLa , Humanos , Ligantes , Microscopia Confocal/métodos , Estrutura Molecular , Peixe-Zebra
5.
Photochem Photobiol Sci ; 18(8): 2012-2022, 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31282525

RESUMO

Organic-metal complexes are promising molecules for use in photodynamic therapy (PDT). The aim of this study was to investigate in vitro effects of novel Ru(ii) and Ir(iii) BODIPY complexes for PDT. These hybrid organic-metal molecules (Ru-BD and Ir-BD) have been synthesized via reactions of a BODIPY precursor (BD) with a phenanthroline unit bearing Ru(ii) (3) and novel Ir(iii) (4) compounds. The crystal structures of the new distyryl BODIPY (BD) and Ru(ii) complex (3) are also reported. The photophysical and singlet oxygen generation properties of Ru-BD and Ir-BD were investigated in comparison with unsubstituted BODIPY (BD). Moreover, Ru-BD and Ir-BD have been biologically evaluated in vitro in chronic myeloid leukemia and cervical cancer cell lines in terms of photodynamic therapy efficacy in the presence of BD control. These complexes were not toxic in the dark but red light was needed to induce cell death. These data support the fact that Ru-BD could be accepted as a valuable photosensitizer-drug for further PDT treatment.


Assuntos
Antineoplásicos/farmacologia , Compostos de Boro/farmacologia , Corantes/farmacologia , Compostos Organometálicos/farmacologia , Fotoquimioterapia , Fármacos Fotossensibilizantes/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Compostos de Boro/síntese química , Compostos de Boro/química , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Corantes/síntese química , Corantes/química , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Irídio/química , Irídio/farmacologia , Modelos Moleculares , Estrutura Molecular , Compostos Organometálicos/síntese química , Compostos Organometálicos/química , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/química , Rutênio/química , Rutênio/farmacologia , Oxigênio Singlete/análise , Oxigênio Singlete/metabolismo , Células Tumorais Cultivadas
6.
Anal Chim Acta ; 1067: 88-97, 2019 Aug 27.
Artigo em Inglês | MEDLINE | ID: mdl-31047153

RESUMO

Nitric oxide (NO), a ubiquitous gasotransmitter which plays critical roles in cardiovascular, nervous, and immune systems related diseases, is closely related in the physiological and pathological processes of mitochondria and lysosomes. Thus, monitoring NO in mitochondria or lysosomes is very meaningful for NO related chemical biology. Herein, we rationally designed four NO probes, BDP-NO, Mito-NO-T, Mito-NO and Lyso-NO, based on BODIPY dye substituted at meso position with 5-amino-2-methoxy-phenyl scaffold. These four probes all showed fast fluorescence off-on response toward NO with excellent selectivity and high sensitivity with the detection limit of BDP-NO to reach 5.7 nM. We introduced triphenylphosphonium and morpholine moieties onto BODIPY scaffold respectively to enable organelle-targetability. MTT and flow cytometry assay demonstrated that the probes exhibited low cytotoxicity, which was beneficial to the biological application in living cells. Confocal fluorescence microscopy experiments confirmed excellent mitochondria targeting for Mito-NO and lysosome-targeting with Lyso-NO for the detection of NO in living cells.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Lisossomos/química , Mitocôndrias/química , Óxido Nítrico/análise , Apoptose/efeitos dos fármacos , Compostos de Boro/síntese química , Compostos de Boro/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/farmacologia , Células HeLa , Humanos , Lisossomos/metabolismo , Microscopia Confocal , Mitocôndrias/metabolismo , Estrutura Molecular , Óxido Nítrico/metabolismo , Imagem Óptica , Células Tumorais Cultivadas
7.
Inorg Chem ; 58(13): 8587-8595, 2019 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-31117633

RESUMO

A new N,O-based BODIPY ligand was synthesized and further utilized to develop highly fluorescent and photostable Ru(II), Rh(III), and Ir(III) metal complexes. The complexes were fully characterized by different analytical techniques including single-crystal XRD studies. The photostabilities and live cell imaging capabilities of the complexes were investigated via confocal microscopy. The complexes localized specifically in the mitochondria of live cells and showed negligible cytotoxicities at a concentration used for imaging purposes. They also exhibited high photostabilities, with fluorescence intensities remaining above 50% after 1800 scans.


Assuntos
Compostos de Boro/metabolismo , Complexos de Coordenação/metabolismo , Corantes Fluorescentes/metabolismo , Mitocôndrias/metabolismo , Transporte Biológico , Compostos de Boro/síntese química , Compostos de Boro/efeitos da radiação , Compostos de Boro/toxicidade , Complexos de Coordenação/síntese química , Complexos de Coordenação/efeitos da radiação , Complexos de Coordenação/toxicidade , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/efeitos da radiação , Corantes Fluorescentes/toxicidade , Células HeLa , Humanos , Irídio/química , Ligantes , Microscopia Confocal , Fotodegradação , Ródio/química , Rutênio/química
8.
Food Chem ; 294: 468-476, 2019 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-31126489

RESUMO

Detection of pathogenic bacteria by polymerase chain reaction (PCR) is progressively emerging, although it is still hindered by a complex matrix, long-term bacterial enrichment and low bacterial abundance. Here, we report a novel material based on boronate affinity for recognition and enrichment of bacteria using a pre-PCR method. After optimization, the material exhibited high boronate affinity toward bacteria, with adsorption capacities of S. aureus and Salmonella spp. incubated in 0.01 M PBS (pH 7.4) at 37 °C for 15 min calculated as (906.60 ±â€¯15.73) × 107 cfu/g and (582.59 ±â€¯13.19) × 107 cfu/g, respectively, without any bacterial death during the binding process. The material was then applied to enrich S. aureus and Salmonella spp. from the spiked water and 25% cow milk samples followed by mPCR, which resulted in high bacterial enrichment and demonstrated great potential for selective enrichment of bacteria in food samples.


Assuntos
Compostos de Boro/química , Microbiologia de Alimentos/métodos , Salmonella/isolamento & purificação , Staphylococcus aureus/isolamento & purificação , Adsorção , Animais , Compostos de Boro/síntese química , Bovinos , Água Potável/microbiologia , Doenças Transmitidas por Alimentos/microbiologia , Concentração de Íons de Hidrogênio , Leite/microbiologia , Polietilenoimina/química , Reação em Cadeia da Polimerase , Salmonella/genética , Sensibilidade e Especificidade , Sefarose/química , Staphylococcus aureus/genética
9.
Analyst ; 144(12): 3756-3764, 2019 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-31070195

RESUMO

Protein phosphorylation is a very important regulatory mechanism in a majority of biological processes, and the determination of protein kinase activity plays a key role in the pathological study and drug development of kinase-related diseases. However, it is very challenging to in situ study endogenous protein kinase activity in a single living cell due to the shortage of in vivo efficient methods. Here, we propose a new strategy for direct determination of protein kinase activity in a single living cell by combining single molecule fluorescence correlation spectroscopy (FCS) with activity-based probes (ABPs). Ribosomal S6 kinase-2 (RSK2) was used as a model, and the ABPs were synthesized on the basis of RSK2 inhibitor FMK to specially label active RSK2 in living cells. Conventional FCS and MEMFCS (maximum entropy method) single molecule techniques were used to in situ determine RSK2 activity in living cells based on the difference in molecular weight between free probes and probe-RSK2 complexes. Furthermore, wild-type and mutated RSK2 were fused with enhanced green fluorescent protein (EGFP) using lentivirus infection, and fluorescence cross-correlation spectroscopy (FCCS) was used to verify the selective binding of ABPs to RSK2-EGFP fusion protein in living cells. Finally, FCS with ABPs was applied for in situ monitoring of the activation of endogenous RSK2 in the stimulation of serum, epidermal growth factor, kinase inhibitors and ultraviolet irradiation; we observed that endogenous RSK2 showed different behaviors in the cytoplasm and the nucleus in some stimulation. Our results document that FCS with ABPs is a very promising method for studying endogenous protein kinases in living cells.


Assuntos
Ensaios Enzimáticos/métodos , Proteínas Quinases S6 Ribossômicas 90-kDa/análise , Análise de Célula Única/métodos , Espectrometria de Fluorescência/métodos , Compostos de Boro/síntese química , Compostos de Boro/química , Carbocianinas/síntese química , Carbocianinas/química , Linhagem Celular Tumoral , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Proteínas de Fluorescência Verde/genética , Proteínas de Fluorescência Verde/metabolismo , Humanos , Mutação , Proteínas Recombinantes de Fusão/genética , Proteínas Recombinantes de Fusão/metabolismo , Proteínas Quinases S6 Ribossômicas 90-kDa/genética , Proteínas Quinases S6 Ribossômicas 90-kDa/metabolismo , Imagem Individual de Molécula/métodos
10.
Org Lett ; 21(10): 3760-3763, 2019 05 17.
Artigo em Inglês | MEDLINE | ID: mdl-31066564

RESUMO

Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.


Assuntos
Compostos de Boro/síntese química , Ácidos Borônicos/síntese química , Compostos de Boro/química , Ácidos Borônicos/química , Estrutura Molecular , Oxirredução
11.
Anal Bioanal Chem ; 411(15): 3229-3240, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31025181

RESUMO

Copper is one of the most important transition metals in many organisms where it catalyzes a manifold of different processes. As a result of copper's redox activity, organisms have to avoid unbound ions, and a dysfunctional copper homeostasis may lead to multifarious pathological processes in cells with very severe ramifications for the affected organisms. In many neurodegenerative diseases, however, the exact role of copper ions is still not completely clarified. In this work, a high-affinity and highly selective copper probe molecule, based on the naturally occurring tetrapeptide DAHK is synthesized. The sensor (log KD = - 12.8 ± 0.1) is tagged with a fluorescent BODIPY dye whose fluorescence lifetime distinctly decreases from 5.8 ns ± 0.2 ns to 0.4 ns ± 0.1 ns on binding to copper(II) cations. It is shown by using fluorescence lifetime correlation spectroscopy that the concentration of both probe and probe-copper complex can be simultaneously measured even at nanomolar concentration levels. This work presents a possible starting point for a new type of probe and method for future in vivo studies to further reveal the exact role of copper ions in organisms. Graphical abstract.


Assuntos
Compostos de Boro/química , Cobre/análise , Corantes Fluorescentes/química , Oligopeptídeos/química , Espectrometria de Fluorescência/métodos , Compostos de Boro/síntese química , Cátions Bivalentes/análise , Fluorescência , Corantes Fluorescentes/síntese química , Humanos , Oligopeptídeos/síntese química
12.
Chem Commun (Camb) ; 55(32): 4691-4694, 2019 Apr 16.
Artigo em Inglês | MEDLINE | ID: mdl-30938736

RESUMO

An efficient Cu(ii)-catalyzed, C-H alkylation of BODIPY with a variety of alkyl diacyl peroxides has been developed for the first time, providing a late-stage and straightforward method for controllable synthesis of monoalkylated and dialkylated BODIPYs via a radical process that otherwise is difficult to obtain by literature methods. This chemo- and site-selective transformation will allow for the introduction of a variety of functionalities on the BODIPY core for highly versatile tethering to receptors and to other molecules of interest.


Assuntos
Compostos de Boro/química , Cobre/química , Corantes Fluorescentes/química , Peróxidos/química , Alquilação , Compostos de Boro/síntese química , Catálise , Corantes Fluorescentes/síntese química , Estrutura Molecular
13.
Molecules ; 24(7)2019 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-30979032

RESUMO

Boryl ligands play a very important role in catalysis because of their very high electron-donating property. In this paper, NNB-type boryl anions were designed as tridentate ligands to promote aryl C-H borylation. In combination with [IrCl(COD)]2, they generate a highly active catalyst for a broad range of (hetero)arene substrates, including highly electron-rich and/or sterically hindered ones. This work provides a new NNB-type tridentate boryl ligand to support homogeneous organometallic catalysis.


Assuntos
Compostos de Boro/química , Irídio/química , Compostos de Boro/síntese química , Catálise , Ligantes , Estrutura Molecular
14.
Eur J Med Chem ; 171: 11-24, 2019 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-30904754

RESUMO

A series of 22 benzosiloxaboroles, silicon analogues of strong antimicrobial agents - benzoxaboroles, have been synthesized and tested against ß-lactamases KPC- and pAmpC-producing strains of Gram-negative rods. Comprehensive structural-property relationship studies supported by molecular modelling as well as biological studies reveal that 6-B(OH)2-substituted derivative 27 strongly inhibits the activity of cephalosporinases (chromosomally encoded AmpC and plasmid encoded CMY-2) and KPC carbapenemases. It also shows strong ability to inhibit growth of the strains producing KPC-3 when combined with meropenem. In addition, halogen-substituted (mono-, di- or tetra-) benzosiloxaboroles demonstrate high antifungal activity (MIC 1.56-6.25 mg/L) against C. tropicalis, C. guilliermondii and S. cerevisiae. The highest activity against pathogenic yeasts (C. albicans, C. krusei and C. parapsilosis - MICs 12.5 mg/L) and against Gram-positive cocci (S. aureus and E. faecalis - 6.25 mg/L and 25 mg/L respectively) was displayed by 6,7-dichloro-substituted benzosiloxaborole. The studied systems exhibit low cytotoxity toward human lung fibroblasts.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Bactérias/efeitos dos fármacos , Compostos de Boro/farmacologia , Fungos/efeitos dos fármacos , Inibidores de beta-Lactamases/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/síntese química , Antifúngicos/química , Compostos de Boro/síntese química , Compostos de Boro/química , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Testes de Sensibilidade Microbiana , Modelos Moleculares , Estrutura Molecular , Relação Estrutura-Atividade , Inibidores de beta-Lactamases/síntese química , Inibidores de beta-Lactamases/química , beta-Lactamases/metabolismo
15.
Chem Asian J ; 14(7): 1059-1065, 2019 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-30776197

RESUMO

By using a copper-promoted alkyne-azide cycloaddition reaction, two boron dipyrromethene (BODIPY) derivatives bearing a bis(1,2,3-triazole)amino receptor at the meso position were prepared and characterized. For the analogue with two terminal triethylene glycol chains, the fluorescence emission at 509 nm responded selectively toward Hg2+ ions, which greatly increased the fluorescence quantum yield from 0.003 to 0.25 as a result of inhibition of the photoinduced electron transfer (PET) process. By introducing two additional rhodamine moieties at the termini, the resulting conjugate could also detect Hg2+ ions in a highly selective manner. Upon excitation at the BODIPY core, the fluorescence emission of rhodamine at 580 nm was observed and the intensity increased substantially upon addition of Hg2+ ions due to inhibition of the PET process followed by highly efficient fluorescence resonance energy transfer (FRET) from the BODIPY core to the rhodamine moieties. The Hg2+ -responsive fluorescence change of these two probes could be easily seen with the naked eye. The binding stoichiometry between the probes and Hg2+ ions in CH3 CN was determined to be 1:2 by Job's plot analysis and 1 H NMR titration, and the binding constants were found to be (1.2±0.1)×1011 m-2 and (1.3±0.3)×1010 m-2 , respectively. The overall results suggest that these two BODIPY derivatives can serve as highly selective fluorescent probes for Hg2+ ions. The rhodamine derivative makes use of a combined PET-FRET sensing mechanism which can greatly increase the sensitivity of detection.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Mercúrio/análise , Pirróis/química , Triazóis/química , Compostos de Boro/síntese química , Fluorescência , Transferência Ressonante de Energia de Fluorescência , Corantes Fluorescentes/síntese química , Limite de Detecção , Pirróis/síntese química , Rodaminas/síntese química , Rodaminas/química , Espectrometria de Fluorescência/métodos , Triazóis/síntese química
16.
Anal Chim Acta ; 1049: 219-225, 2019 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-30612654

RESUMO

In this work, taking full advantage of the intramolecular charge transfer (ICT) mechanism, a hydroxynaphthalimide-based ratiometric two-photon fluorescent probe RTP-PN was synthesized to detect ONOO-. Probe RTP-PN could accurately detect ONOO- in the range of 1.4 nM-1.4 µM with the detection limit of 1.4 nM by a ratiometric fluorescence spectroscopy method. Additionally, probe RTP-PN exhibited an ultrafast response for ONOO- than other various species including H2O2 and ClO-. Finally, probe RTP-PN was successfully adopted to detect intracellular ONOO- by the two-photon excitation microscopy.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Naftalimidas/química , Ácido Peroxinitroso/análise , Animais , Compostos de Boro/síntese química , Compostos de Boro/efeitos da radiação , Compostos de Boro/toxicidade , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/efeitos da radiação , Corantes Fluorescentes/toxicidade , Raios Infravermelhos , Limite de Detecção , Camundongos , Microscopia de Fluorescência/métodos , Naftalimidas/síntese química , Naftalimidas/efeitos da radiação , Naftalimidas/toxicidade , Células RAW 264.7
17.
Artigo em Inglês | MEDLINE | ID: mdl-30684882

RESUMO

The synthesized and sensing capability of two novel azaindole substituted mono and distyryl BODIPY dyes against bisulfate anion were reported. Structural characterizations of the targeted compounds were conducted by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, 1H and 13C NMR spectroscopies. Photophysical properties of the azaindole substituted BODIPY compounds were investigated employing absorption and fluorescence spectroscopies in acetonitrile solution. It was found that the final compounds 3 and 4 exhibited exclusively selective and sensitive turn-off sensor behavior on HSO4- anion. Additionally, the stoichiometry ratio of the targeted compounds to bisulfate anion was measured 0.5 by Job's method. Also, density function theory was performed to the optical response of the sensor for targeted compounds. Furthermore, the cytotoxicity of Azaindole-BODIPYs was examined against living human leukemia K562 cell lines.


Assuntos
Ânions/análise , Compostos de Boro/síntese química , Indóis/síntese química , Ácidos Sulfúricos/análise , Compostos de Boro/química , Calibragem , Sobrevivência Celular , Humanos , Indóis/química , Concentração Inibidora 50 , Células K562 , Conformação Molecular , Espectrometria de Fluorescência , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz , Eletricidade Estática
18.
Anal Chim Acta ; 1048: 194-203, 2019 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-30598150

RESUMO

BODIPY-based probes have excellent fluorescence properties. However, small Stokes shifts approximately 5-15 nm greatly affect their detection sensitivity. In this study, we compared the Stokes shifts of reported BODIPY-based probes with various of substituents, and found that the phenyl groups on the specific position of BODIPY core could expand the Stokes shift of BODIPY-based probes, and methoxy groups on these phenyl substituents could enhance such effects. Then, by quantum chemical calculations, we found that the number of methoxy groups might also have obvious effect on the Stokes shift of BODIPY. Taking nitric oxide (NO) as analyte, 4,4-difluoro-8-(3,4-diaminophenyl)-3,5-bis(2,4-dimethoxyphenyl)-4-bora-3a,4a-diaza-s-indancene (DMOPB) with diaminophenyl substituents has been designed and synthesized. Compared with monomethoxy-phenyl substituted BODIPY-based probes (MOPBs) in our previous work, Stokes shift of DMOPB was expanded by 10 nm when using dimethoxyphenyl instead of monomethoxyphenyl, which is basically consistent with the quantum chemistry calculation of 11 nm. DMOPB can react with NO in only 2 min to form the triazole DMOPB-T with a fluorescence quantum yield of 0.32. An excellent linear relationship was observed in the range of NO concentration from 0.5 µM to 4 µM and the detection limit was 1 nM. The experimental results indicate that DMOPB with high sensitivity, excellent selectivity, low toxicity and dark background can be a great candidate for imaging NO in cells and tissues. Considering the lack of practical way to increase Stokes shift of small-molecule fluorescent probes based on specific fluorophore, the proposed strategy has great potential for the designing of probes with large Stokes shift.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Óxido Nítrico/metabolismo , Animais , Compostos de Boro/síntese química , Compostos de Boro/toxicidade , Fluorescência , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/toxicidade , Células Endoteliais da Veia Umbilical Humana , Humanos , Concentração de Íons de Hidrogênio , Fígado/metabolismo , Camundongos , Microscopia Confocal , Microscopia de Fluorescência , Cebolas/metabolismo , Células RAW 264.7 , Triazóis/síntese química , Triazóis/química
19.
J Colloid Interface Sci ; 536: 208-214, 2019 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-30368092

RESUMO

Theranostics, integrating tumor treatment and diagnosis concurrently, has become an emerging and meaningful strategy in cancer therapy. In this work, an amphiphilic redox-sensitive near-infrared (NIR) BODIPY dye, which could be formed into nanoparticles (PEG-SS-BDP NPs) by self-assembly, was synthesized and possessed good capability of photothermal therapy (PTT), near-infrared fluorescence (NIRF) imaging, photoacoustic (PA) imaging and drug loading. The stable nanoparticles could be dissociated to turn on NIRF due to the rift of embedded disulfide bonds by glutathione (GSH). The enhanced fluorescence in vitro could be observed via confocal laser scanning microscopy (CLSM) after adding GSH, confirming the redox-sensitivity of disulfide bonds. NIRF and PA imaging demonstrated active accumulation in tumor and good imaging effect. At last, PEG-SS-BDP NPs could significantly suppress tumor growth in vivo upon irradiation. The amphiphilic redox-sensitive BODIPY nanoparticles provide a promising design strategy to formulate multifunctional stimuli-responsive theranostic nanoplatforms.


Assuntos
Antineoplásicos/farmacologia , Compostos de Boro/farmacologia , Corantes Fluorescentes/farmacologia , Imagem Óptica , Tensoativos/farmacologia , Neoplasias do Colo do Útero/diagnóstico por imagem , Neoplasias do Colo do Útero/tratamento farmacológico , Animais , Antineoplásicos/síntese química , Antineoplásicos/química , Compostos de Boro/síntese química , Compostos de Boro/química , Feminino , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Células HeLa , Humanos , Camundongos , Camundongos Endogâmicos , Camundongos Nus , Nanopartículas/química , Neoplasias Experimentais/diagnóstico por imagem , Neoplasias Experimentais/tratamento farmacológico , Oxirredução , Tamanho da Partícula , Fototerapia , Polietilenoglicóis/química , Polietilenoglicóis/farmacologia , Propriedades de Superfície , Tensoativos/síntese química , Tensoativos/química
20.
Inorg Chem ; 57(16): 10137-10145, 2018 Aug 20.
Artigo em Inglês | MEDLINE | ID: mdl-30074794

RESUMO

We report herein a new ZIF-90-based PDT agent which was synthesized by in situ assembly of imidazole-2-carboxaldehyde (IcaH), Zn(NO3)2, and heavy atom iodine-attached Bodipy. The obtained 2I-BodipyPhNO2@ZIF-90 (1) host-guest photosensitive system featured low cytotoxicity, good biocompatibility, pH-driven selective cancer cell uptake and release, mitochondria targeting, and highly efficient pH-triggered 1O2 generation. Therefore, it can be used as a high-performing PDT agent to selectively kill tumor cells. In comparison to free 2I-BodipyPhNO2, 1 exhibits a much higher antitumor efficacy and selectivity, which was confirmed by in vitro cell experiments.


Assuntos
Antineoplásicos/farmacologia , Compostos de Boro/farmacologia , Estruturas Metalorgânicas/farmacologia , Nanopartículas/química , Fármacos Fotossensibilizantes/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/efeitos da radiação , Antineoplásicos/toxicidade , Apoptose/efeitos dos fármacos , Compostos de Boro/síntese química , Compostos de Boro/efeitos da radiação , Compostos de Boro/toxicidade , Linhagem Celular Tumoral , Estabilidade de Medicamentos , Humanos , Concentração de Íons de Hidrogênio , Estruturas Metalorgânicas/síntese química , Estruturas Metalorgânicas/efeitos da radiação , Estruturas Metalorgânicas/toxicidade , Mitocôndrias/metabolismo , Nanopartículas/efeitos da radiação , Nanopartículas/toxicidade , Fotoquimioterapia/métodos , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/efeitos da radiação , Fármacos Fotossensibilizantes/toxicidade , Oxigênio Singlete/metabolismo
SELEÇÃO DE REFERÊNCIAS
DETALHE DA PESQUISA