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1.
Molecules ; 24(24)2019 Dec 07.
Artigo em Inglês | MEDLINE | ID: mdl-31817838

RESUMO

Phenothiazines are one of the more common dye scaffolds for dye-sensitized solar cells. However, these sensitizers are exclusively based on a 3,7-substitution pattern. Herein, we have synthesized and characterized novel 3,8-substituted phenothiazine dyes in order to evaluate the effect of auxiliary donor groups on the performance of this new dye class. The power conversion efficiency increased by 7%-10% upon insertion of an auxiliary donor in position 8 of the phenothiazine, but the structure of the auxiliary donor (phenyl, naphthyl, pyrene) had a low impact when electrodes were stained with chenodeoxycholic acid (CDCA) additive. In the absence of CDCA, the highest power conversion efficiency was seen for the phenyl-based sensitizer attributed to a higher quality dye-monolayer. By comparing the novel dyes to their previously reported 3,7- analogues, only subtle differences were seen in photophysical, electrochemical, and performance measurements. The most notable difference between the two geometries is a lowering of the oxidation potentials of the 3,8-dyes by 40-50 mV compared to the 3,7-analogues. The best auxiliary donor for the 3,8-phenothiazine dyes was found to be pyrenyl, with the best device delivering a power conversion efficiency of 6.23% (99 mW cm-2, 10 eq. CDCA, JSC = 10.20 mA cm-2, VOC = 791 mV, and FF = 0.765).


Assuntos
Ácido Quenodesoxicólico/química , Corantes/química , Fenotiazinas/química , Energia Solar , Ácido Quenodesoxicólico/síntese química , Corantes/síntese química , Fontes de Energia Elétrica , Eletroquímica , Oxirredução , Fenotiazinas/síntese química
2.
Analyst ; 144(23): 6962-6967, 2019 Nov 18.
Artigo em Inglês | MEDLINE | ID: mdl-31621707

RESUMO

The monitoring of heavy transition metals has increasingly attracted great attention because they pollute the environment and have unique physiological functions. Chemosensors are useful tools for monitoring heavy transition metals due to their simple visualization, excellent sensitivity and high selectivity. Herein, we have developed a novel chemosensor for the detection of water-soluble Cu2+ and Ni2+ species with different mechanisms, and low detection limits of 2.1 nM for Cu2+ and 1.2 nM for Ni2+ were obtained. The colorimetric probe CPH has been applied to qualitative and quantitative detection of Cu2+ and Ni2+ species in real samples.


Assuntos
Aminopiridinas/química , Cobre/sangue , Cumarínicos/química , Indicadores e Reagentes/química , Níquel/sangue , Poluentes Químicos da Água/análise , Aminopiridinas/síntese química , Colorimetria/métodos , Corantes/síntese química , Corantes/química , Cobre/química , Cumarínicos/síntese química , Água Potável/análise , Humanos , Indicadores e Reagentes/síntese química , Lagos/análise , Limite de Detecção , Níquel/química , Rios/química , Espectrofotometria/métodos , Poluentes Químicos da Água/química
3.
J Mater Sci Mater Med ; 30(9): 103, 2019 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-31493091

RESUMO

Metal-on-metal (MoM) hip arthroplasties produce abundant implant-derived wear debris composed mainly of cobalt (Co) and chromium (Cr). Cobalt-chromium (Co-Cr) wear particles are difficult to identify histologically and need to be distinguished from other wear particle types and endogenous components (e.g., haemosiderin, fibrin) which may be present in MoM periprosthetic tissues. In this study we sought to determine whether histological stains that have an affinity for metals are useful in identifying Co-Cr wear debris in MoM periprosthetic tissues. Histological sections of periprosthetic tissue from 30 failed MoM hip arthroplasties were stained with haematoxylin-eosin (HE), Solochrome Cyanine (SC), Solochrome Azurine (SA) and Perls' Prussian Blue (PB). Sections of periprosthetic tissue from 10 cases of non-MoM arthroplasties using other implant biomaterials, including titanium, ceramic, polymethylmethacrylate (PMMA) and ultra-high molecular weight polyethylene (UHMWP) were similarly analysed. Sections of 10 cases of haemosiderin-containing knee tenosynovial giant cell tumour (TSGCT) were also stained with HE, SC, SA and PB. In MoM periprosthetic tissues, SC stained metal debris in phagocytic macrophages and in the superficial necrotic zone which exhibited little or no trichrome staining for fibrin. In non-MoM periprosthetic tissues, UHMWP, PMMA, ceramic and titanium particles were not stained by SC. Prussian Blue, but not SC or SA, stained haemosiderin deposits in MoM periprosthetic tissues and TSGT. Our findings show that SC staining (most likely Cr-associated) is useful in distinguishing Co-Cr wear particles from other metal/non-metal wear particles types in histological preparations of periprosthetic tissue and that SC reliably distinguishes haemosiderin from Co-Cr wear debris.


Assuntos
Benzenossulfonatos , Corantes/farmacologia , Análise de Falha de Equipamento/métodos , Articulação do Quadril/patologia , Nanopartículas Metálicas/análise , Próteses Articulares Metal-Metal , Coloração e Rotulagem/métodos , Artroplastia de Quadril/efeitos adversos , Artroplastia de Quadril/instrumentação , Azurina/química , Azurina/farmacologia , Benzenossulfonatos/química , Benzenossulfonatos/farmacologia , Cromo/química , Corantes/síntese química , Corantes/química , Amarelo de Eosina-(YS)/química , Amarelo de Eosina-(YS)/farmacologia , Ferrocianetos/química , Ferrocianetos/farmacologia , Células Gigantes de Corpo Estranho/efeitos dos fármacos , Células Gigantes de Corpo Estranho/patologia , Hematoxilina/química , Hematoxilina/farmacologia , Articulação do Quadril/química , Articulação do Quadril/efeitos dos fármacos , Prótese de Quadril , Técnicas Histológicas/métodos , Humanos , Macrófagos/efeitos dos fármacos , Macrófagos/patologia , Próteses Articulares Metal-Metal/efeitos adversos , Polietilenos/análise , Polietilenos/química
4.
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
5.
Photochem Photobiol Sci ; 18(8): 2003-2011, 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31268087

RESUMO

Here we report the activatable photosensitizer BromoAcroB, a brominated BODIPY dye incorporating a reactive acrolein warhead. The acrolein moiety serves as an intramolecular switch, deactivating the BODIPY dye in its singlet and triplet excited states via internal conversion. Thiolate addition to this moiety disables the intramolecular quenching mechanism restoring the photosensitizing properties of the parent dye, characterized by a quantum yield of singlet oxygen photosensitization of 0.69 ± 0.02. In cell cultures, and upon thiol adduct formation, BromoAcroB induced light-dependent cell death in MRC-5 and HeLa cell lines. Using fluorescence microscopy and upon measuring the low yet non-negligible emission of the activated compound, we show that the phototoxicity of the dormant photosensitizer correlated with the quantity of BromoAcroB adducts generated. BromoAcroB thus serves as a dormant photosensitizer sensitive to intracellular electrophile response. Our results highlight the effective control of a triplet state process by modulation of an unsaturated moiety on the BODIPY scaffold and underscore the mechanistic opportunities arising for controlled singlet oxygen production in cells specifically sensitive to electrophile stress.


Assuntos
Acroleína/farmacologia , Compostos de Boro/farmacologia , Corantes/farmacologia , Cisteína/farmacologia , Fármacos Fotossensibilizantes/farmacologia , Oxigênio Singlete/farmacologia , Acroleína/química , Compostos de Boro/química , Morte Celular/efeitos dos fármacos , Corantes/síntese química , Corantes/química , Cisteína/química , Células HeLa , Humanos , Luz , Microscopia de Fluorescência , Estrutura Molecular , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/química , Teoria Quântica , Oxigênio Singlete/química
6.
Spectrochim Acta A Mol Biomol Spectrosc ; 222: 117226, 2019 Nov 05.
Artigo em Inglês | MEDLINE | ID: mdl-31181504

RESUMO

Six novel amino acid chromophores were synthesized and their spectroscopic, acid-base, and electrochemical properties are discussed in this work. In studied compounds, selected amino acid residues (l-Aspartic acid, l-Glutamic acid, l-Glutamine, l-Histidine, l-Lysine, l-Arginine) are attached to the 1-(piperazine) 9,10-anthraquinone skeleton via the amide bond between the carboxyl group of amino acid and nitrogen atom of the piperazine ring. All derivatives have been characterized using a variety of spectroscopic techniques (mass spectrometry, 1HNMR, UV-Vis, IR spectroscopy), acid-base (electrochemical and UV-Vis) titrations, and cyclic voltammetry methods. Basing on observed experimental effects, supported by quantum chemical simulations, the structure-properties links were established. They are indicative of the specific interactions within and/or in-between amino acid side groups, which are prone to form both, intra- and intermolecular hydrogen bonds as well as electrostatic interactions with the anthraquinone system.


Assuntos
Aminoácidos/química , Antraquinonas/química , Corantes/química , Aminoácidos/síntese química , Antraquinonas/síntese química , Corantes/síntese química , Técnicas Eletroquímicas , Ligação de Hidrogênio , Modelos Moleculares , Prótons , Espectrofotometria Ultravioleta
7.
Theranostics ; 9(2): 381-390, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30809281

RESUMO

Near infrared (NIR) dyes are useful for in vivo optical imaging. Liposomes have been used extensively for delivery of diverse cargos, including hydrophilic cargos which are passively loaded in the aqueous core. However, most currently available NIR dyes are only slightly soluble in water, making passive entrapment in liposomes challenging for achieving high optical contrast. Methods: We modified a commercially-available NIR dye (IR-820) via one-step Suzuki coupling with dicarboxyphenylboronic acid, generating a disulfonated heptamethine; dicarboxyphenyl cyanine (DCP-Cy). DCP-Cy was loaded in liposomes and used for optical imaging. Results: Owing to increased charge in mildly basic aqueous solution, DCP-Cy had substantially higher water solubility than indocyanine green (by an order of magnitude), resulting in higher NIR absorption. Unexpectedly, DCP-Cy tended to form J-aggregates with pronounced spectral red-shifting to 934 nm (from 789 nm in monomeric form). J-aggregate formation was dependent on salt and DCP-Cy concentration. Dissolved at 20 mg/mL, DCP-Cy J-aggregates could be entrapped in liposomes. Full width at half maximum absorption of the liposome-entrapped dye was just 25 nm. The entrapped DCP-Cy was readily detectable by fluorescence and photoacoustic NIR imaging. Upon intravenous administration to mice, liposomal DCP-Cy circulated substantially longer than the free dye. Accumulation was largely in the spleen, which was visualized with fluorescence and photoacoustic imaging. Conclusions: DCP-Cy is simple to synthesize and exhibits high aqueous solubility and red-shifted absorption from J-aggregate formation. Liposomal dye entrapment is possible, which facilitates in vivo photoacoustic and fluorescence imaging around 930 nm.


Assuntos
Corantes/administração & dosagem , Corantes Fluorescentes/administração & dosagem , Verde de Indocianina/administração & dosagem , Lipossomos/administração & dosagem , Imagem Óptica/métodos , Técnicas Fotoacústicas/métodos , Administração Intravenosa , Animais , Corantes/síntese química , Corantes/química , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Verde de Indocianina/síntese química , Verde de Indocianina/química , Camundongos , Solubilidade
8.
Eur J Mass Spectrom (Chichester) ; 25(5): 419-427, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-30764664

RESUMO

In this work, a method combining ultra-high performance liquid chromatography and hybrid quadrupole-Orbitrap high-resolution mass spectrometry (HR-MS) was developed and validated for use in the simultaneous screening, identification, and quantification of 21 synthetic dyes in herbal medicines. To optimize the chromatographic conditions, we used a combined Full mass scan and data-dependent MS/MS (Full MS/dd-MS2) approach in positive and negative ion mode. Under this mode, selected ions with given fragmentation energy were subjected to a dd-MS2 scan following a Full MS scan. The selectivity of this method was effectively improved using 70,000 full width at half maximum mass resolution and narrow mass window (typically 5 ppm), and a single injection was sufficient for simultaneous identification and quantification of 21 synthetic dyes within 10 min. The combined method was fully validated and complies with all criteria for selectivity, sensitivity, calibration curve linearity, accuracy, precision, recovery, matrix effect, and stability. All analytes showed excellent linear relationships as all the coefficients of determination (r2) are greater than 0.9978 over wide ranges of concentrations (e.g. 1.0-500 ng/mL for sunset yellow). The validated method was employed to detect synthetic dyes in herbal medicines and was demonstrated to provide a reliable technical basis for drug regulation and public health protection.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Corantes/análise , Preparações de Plantas/análise , Espectrometria de Massas em Tandem/métodos , Corantes/síntese química , Contaminação de Medicamentos/estatística & dados numéricos , Medicina Herbária , Limite de Detecção
9.
Talanta ; 194: 469-474, 2019 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-30609560

RESUMO

The severity and cost of wound infections strongly demands for simple and fast methods for wound infection determination. Point-of-care testing devices play a crucial role in order to achieve a fast diagnosis and early treatment. Myeloperoxidase (MPO) enzyme, detected in fluids of infected wounds has been postulated as a suitable biomarker for wound diagnostics. Here we present a new system for MPO detection, based on enzyme-catalysed oxidative synthesis of a dye that can be incorporated into paper-based point of care devices. Visual MPO detection has been achieved through the use of phenylenediamine, a common colourless hair dye precursor. MPO oxidation of these compounds yielded bright coloured products distinguishable from the colour of the wound environment. Immobilisation of the MPO substrates on paper strips was achieved through in situ interaction of the oxidised coloured product with branched polyethyleneimine. The colour reaction of the immobilized substrates, detectable by naked eye, responds to the MPO levels present in infected wound fluids revealing an easy system for incorporation of MPO detection in paper based diagnostic devices.


Assuntos
Biocatálise , Corantes/química , Corantes/síntese química , Ensaios Enzimáticos/métodos , Papel , Peroxidase/metabolismo , Testes Imediatos , Animais , Benzotiazóis/química , Cor , Humanos , Oxirredução , Fenilenodiaminas/química , Ácidos Sulfônicos/química
10.
Colloids Surf B Biointerfaces ; 175: 314-323, 2019 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-30554009

RESUMO

Blending of xanthan and acacia gives a unique hybrid that was used for the synthesis of semi-interpenetrating network (semi-IPN) in which poly(acrylamide) chains were grafted onto hybrid of xanthan-acacia followed by their cross-linking (Xan-Aca-cl-poly(AAm)). Optimization was carried out under response surface methodology-central composite design (RSM-CCD). Maximum percentage swelling of semi-IPN obtained was 496.57%. The concentrations of acrylamide, citric acid and ammonium persulphate used as monomer, cross-linker and initiator, respectively were found to be significant parameters. The blend was highly effective in removal of both cationic (crystal violet) and anionic dyes (eosin yellow) showing maximum dye removal capacity of 97.58% and 95.42%, respectively under optimized parameters - 0.4 g semi-IPN dose in 15 ml dye solution of 10 mg L-1 concentration within 16 h. Adsorption mechanism of both the dyes followed three steps in accordance with intraparticle diffusion model along with mono layer langmuir adsorption criteria. Second order kinetics was followed in case of both dyes. Thermodynamic studies gave idea about the exothermic nature of adsorption. Semi-IPN could be recycled up to eight consecutive cycles and hence, can be utilized for industrial purpose for removal of dyes.


Assuntos
Amarelo de Eosina-(YS)/química , Violeta Genciana/química , Goma Arábica/química , Polissacarídeos Bacterianos/química , Resinas Acrílicas/química , Adsorção , Algoritmos , Corantes/síntese química , Corantes/química , Cinética , Microscopia Eletrônica de Varredura , Espectroscopia de Infravermelho com Transformada de Fourier , Termodinâmica
11.
Appl Microbiol Biotechnol ; 102(24): 10327-10343, 2018 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-30406827

RESUMO

Laccases are multicopper enzymes present in plants, fungi, bacteria, and insects, which catalyze oxidation reactions together with four electron reduction of oxygen to water. Plant, bacterial, and insect laccases have a polymerizing role in nature, implicated in biosynthesis of lignin, melanin formation, and cuticle hardening, respectively. On the other hand, fungal laccases carry out both polymerizing (melanin synthesis and fruit body formation) as well as depolymerizing roles (lignin degradation). This bifunctionality of fungal laccases can be attributed to the presence of multiple isoforms within the same as well as different genus and species. Interestingly, by manipulating culture conditions, these isoforms with their different induction patterns and unique biochemical characteristics can be expressed or over-expressed for a targeted biotechnological application. Consequently, laccases can be considered as one of the most important biocatalyst which can be exploited for divergent industrial applications viz. paper pulp bleaching, fiber modification, dye decolorization, bioremediation as well as organic synthesis. The present review spotlights the role of fungal laccases in various antagonistic applications, i.e., polymerizing and depolymerizing, and co-relating this dual role with potential industrial significance.


Assuntos
Biodegradação Ambiental , Biotecnologia/métodos , Lacase/metabolismo , Corantes/síntese química , Indústria Farmacêutica/métodos , Proteínas Fúngicas/metabolismo , Indústrias , Lacase/química , Papel , Polimerização
12.
Bioorg Med Chem Lett ; 28(18): 3099-3104, 2018 10 01.
Artigo em Inglês | MEDLINE | ID: mdl-30055886

RESUMO

Dithienopyrrole-based organic dyes that combine an electron-donating moiety (D), a π-conjugated bridge moiety (π), and an electron-accepting moiety (A) were designed and synthesized in short steps by previously developed one-pot Suzuki-Miyaura coupling approach. Absorption wavelengths of the dyes were readily tuned by altering the D and A moieties. The use of a strongly electron-withdrawing cyanopyridone acceptor enabled NIR absorption. A synthesized sensitizer, 2j, exerted potent phototoxicity mainly via a Type I mechanism in cells. A nitrogen atom in the dithienopyrrole ring serves as a connecting point for the introduction of functional building blocks that can improve the properties of sensitizers, which makes this D-π-A sensitizer a valuable template for the further development of sensitizers.


Assuntos
Antineoplásicos/farmacologia , Corantes/farmacologia , Desenho de Fármacos , Fotoquimioterapia , Fármacos Fotossensibilizantes/farmacologia , Pirróis/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Corantes/síntese química , Corantes/química , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Estrutura Molecular , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/química , Pirróis/química , Relação Estrutura-Atividade
13.
Colloids Surf B Biointerfaces ; 169: 486-493, 2018 09 01.
Artigo em Inglês | MEDLINE | ID: mdl-29860013

RESUMO

We study how cell motility affects the stains left by the evaporation of droplets of a biofluid suspension containing mouse spermatozoa. The suspension, which contains also a high concentration of salts usually needed by motile cells, forms, upon drying, a crystallized pattern. We examine the structural characteristics of such patterns by optical microscopy. The analysis reveals that cell motility affects the formation of elongated crystals with lateral tips, as well as the creation of interlocked aggregates. We prove that a lacunarity algorithm based on polar symmetry, distinguishes among deposits generated by motile and non-motile cells with an accuracy greater than 95%.


Assuntos
Corantes/química , Espermatozoides/citologia , Algoritmos , Animais , Corantes/síntese química , Epididimo/citologia , Masculino , Camundongos , Tamanho da Partícula , Propriedades de Superfície
14.
Macromol Rapid Commun ; 39(17): e1700860, 2018 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-29504172

RESUMO

A light-triggered shape change of supramolecular nanostructures is achieved through electrostatically self-assembly of linear polyelectrolytes and oppositely charged dyes in aqueous solution: Upon UV-irradiation, 1-µm-long, flexible cylinders with a cross-section of 10 nm convert into ellipsoids of 400 nm × 40 nm. The nano-object shape is encoded in the molecular dye structure.


Assuntos
Corantes/síntese química , Nanoestruturas/química , Polímeros/síntese química , Raios Ultravioleta , Corantes/química , Eletrólitos/química , Substâncias Macromoleculares/síntese química , Substâncias Macromoleculares/química , Estrutura Molecular , Tamanho da Partícula , Polímeros/química , Eletricidade Estática
15.
Biotech Histochem ; 93(3): 211-219, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29415574

RESUMO

The long history of eosin Y, eosin B and the methyl and ethyl eosins is recounted as well as their synthesis, the variety of their molecular species and some of the myriad applications of these dyes. Chromatographic techniques are described that reveal the purity or lack of it in commercial samples. Toxicological studies are discussed that suggest that the eosins are virtually non toxic, but efforts to remove them from the environment imply that there may be some risk.


Assuntos
Corantes/química , Amarelo de Eosina-(YS)/análogos & derivados , Amarelo de Eosina-(YS)/química , Corantes/síntese química , Estrutura Molecular , Terminologia como Assunto
16.
Artigo em Inglês | MEDLINE | ID: mdl-29336720

RESUMO

The objective of this study was to develop a ratiometric and colorimetric organic sensor for Pb2+ detection in environmental samples. A new probe 4-phenyl amino thiourea (PAT) was designed and synthesized using hydrazine hydrate and phenyl isothiocyanate as raw materials. After its structure was characterized and confirmed, its UV-vis spectral property was investigated in detail. PAT possesses a specifically real-time, ratiometric and colorimetric response to Pb2+ in dimethyl formamide (DMF)/H2O (v/v = 9:1, pH = 7.0) within 18.0 s. There was little interference in the presence of some other common metal ions, such as Fe3+, Cd2+, Zn2+, Mg2+, Cr3+, Ca2+, Ba2+, Sn2+, Na+, Mn2+, Hg2+, and Pb2+. Under the optimized conditions (DMF/H2O with v/v of 9:1, cPAT = 1.0 × 10-3 mol·L-1, pH = 7.0), the present sensor PAT was successfully applied for Pb2+ determination in environmental water samples with satisfied recoveries (83.0%-106.0%) and analytical precision (≤7.2%). The recognition mechanism was confirmed to form a stable 1:1 six-member ring complex between the target dye and Pb2+ with a coordination constant of 4.96 × 104.


Assuntos
Corantes/síntese química , Corantes/farmacologia , Chumbo/análise , Tioureia/análogos & derivados , Poluentes Químicos da Água/análise , Técnicas Biossensoriais/métodos , Colorimetria/métodos , Íons/análise , Íons/toxicidade , Chumbo/toxicidade , Metais/análise , Metais/toxicidade , Tioureia/síntese química , Poluentes Químicos da Água/toxicidade , Poluição Química da Água/análise
17.
Molecules ; 23(1)2018 Jan 09.
Artigo em Inglês | MEDLINE | ID: mdl-29315241

RESUMO

Novel red and purple reactive disperse silicon-containing dyes were designed and synthesized using p-nitroaniline and 6-bromo-2,4-dinitro-aniline as diazonium components, the first condensation product of cyanuric chloride and 3-(N,N-diethyl)amino-aniline as coupling component, and 3-aminopropylmethoxydimethylsilane, 3-aminopropylmethyldimethoxysilane, and 3-aminopropyltrimethoxysilane as silicone reactive agents. These dyes were characterized by UV-Vis, ¹H-NMR, FT-IR, and MS. The obtained reactive disperse silicon-containing dyes were used to color silicone rubbers and the color fastness of the dyes were evaluated. The dry/wet rubbing and washing fastnesses of these dyes all reached 4-5 grade and the sublimation fastness was also above 4 grade, indicating outstanding performance in terms of color fastness. Such colored silicone rubbers showed bright and rich colors without affecting its static mechanical properties.


Assuntos
Compostos de Anilina/química , Corantes/síntese química , Propilaminas/química , Silanos/química , Elastômeros de Silicone/química , Cor , Estrutura Molecular , Espectroscopia de Prótons por Ressonância Magnética/métodos , Espectrofotometria/métodos , Espectroscopia de Infravermelho com Transformada de Fourier/métodos , Relação Estrutura-Atividade
18.
J Biomol Struct Dyn ; 36(14): 3773-3790, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29092676

RESUMO

The interaction between a synthesized dye with proteins, bovine, and human serum albumin (BSA, HSA, respectively) under physiological conditions has been characterized in detail, by means of steady-state and time-resolved fluorescence, UV-vis absorption, and circular dichroism (CD) techniques. An extensive time-resolved fluorescence spectroscopic characterization of the quenching process has been undertaken in conjugation with temperature-dependent fluorescence quenching studies to divulge the actual quenching mechanism. From the thermodynamic observations, it is clear that the binding process is a spontaneous molecular interaction, in which van der Waals and hydrogen bonding interactions play the major roles. The UV-vis absorption and CD results confirm that the dye can induce conformational and micro-environmental changes of both the proteins. In addition, the dye binding provokes the functionality of the native proteins in terms of esterase-like activity. The average binding distance (r) between proteins and dye has been calculated using FRET. Cytotoxicity and antiviral effects of the dye have been found using Vero cell and HSV-1F virus by performing MTT assay. The AutoDock-based docking simulation reveals the probable binding location of dye within the sub-domain IIA of HSA and IB of BSA.


Assuntos
Antivirais/química , Corantes/química , Simulação de Acoplamento Molecular , Domínios e Motivos de Interação entre Proteínas , Albumina Sérica Humana/química , Análise Espectral , Animais , Antivirais/síntese química , Antivirais/farmacologia , Compostos Azo/síntese química , Compostos Azo/química , Compostos Azo/farmacologia , Sítios de Ligação , Linhagem Celular , Sobrevivência Celular , Corantes/síntese química , Corantes/farmacologia , Humanos , Simulação de Dinâmica Molecular , Ligação Proteica , Soroalbumina Bovina/química , Termodinâmica
19.
J Chromatogr A ; 1510: 40-50, 2017 Aug 11.
Artigo em Inglês | MEDLINE | ID: mdl-28648259

RESUMO

Condensation of anthocyanins and their aglycons with small organic molecules yields more stable natural dyes, e.g. pyranoanthocyanins arising spontaneously in various food products. Reaction of pelargonidin with acetone produces two isomeric anthocyanidin dyes - 5-methylpyranopelargonidin and 4-methylfuropelargonidin. A robust semipreparative liquid chromatographic method was developed to isolate both derivatives from a simple aged solution of pelargonidin in methanol: acetone: 37% aqueous hydrochloric acid (1:1:0.008, v/v/v). Detailed interpretation of mass and nuclear magnetic resonance spectra allowed to assign structures of both dyes in isolated fractions. A fast UHPLC-MS method was optimized for the control of their production in the reaction mixture. Use of reversed stationary phase and acidic mobile phases in gradient mode allowed separation of both isomers in less than one minute. Fragmentation of both dyes after collision activated dissociation in collision cell was studied comprehensively and the observed processes were compared with data from quantum calculations (computational chemistry utilizing DFT methods). When comparing both isomers, retro-Diels-Alder fragmentation appears preferred in furo-derivative, while small losses (i.e. methane and water molecules) were more pronounced in pyrano-derivative. Both studied isomeric dyes were found in laboratory prepared strawberry fruit wine and their content was compared with major present anthocyanins and their derivatives.


Assuntos
Antocianinas/análise , Antocianinas/isolamento & purificação , Técnicas de Química Analítica/métodos , Fragaria , Vinho/análise , Antocianinas/síntese química , Cromatografia Líquida de Alta Pressão , Corantes/análise , Corantes/síntese química , Corantes/isolamento & purificação , Fragaria/química , Frutas/química
20.
Chem Commun (Camb) ; 53(39): 5433-5436, 2017 May 11.
Artigo em Inglês | MEDLINE | ID: mdl-28462980

RESUMO

Novel glycoconjugated squaraine dyes were synthesized, which exhibited excellent internalization in tumor cells and are potent fluorogenic imaging probes for tumor selective optical imaging.


Assuntos
Corantes/síntese química , Ciclobutanos/química , Neoplasias/diagnóstico por imagem , Imagem Óptica/métodos , Fenóis/química , Linhagem Celular , Corantes/química , Humanos , Estrutura Molecular , Análise Espectral , Coloração e Rotulagem
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