Your browser doesn't support javascript.
loading
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 89
Filtrar
Mais filtros

Base de dados
Tipo de documento
Intervalo de ano de publicação
1.
Molecules ; 28(3)2023 Jan 29.
Artigo em Inglês | MEDLINE | ID: mdl-36770961

RESUMO

Hydrogen sulfide (H2S) is an essential signaling gas within the cell, and its endogenous levels are correlated with various health diseases such as Alzheimer's disease, diabetes, Down's syndrome, and cardiovascular disease. Because it plays such diverse biological functions, being able to detect H2S quickly and accurately in vivo is an area of heightened scientific interest. Using probes that fluoresce in the near-infrared (NIR) region is an effective and convenient method of detecting H2S. This approach allows for compounds of high sensitivity and selectivity to be developed while minimizing cytotoxicity. Herein, we report a review on the synthesis, mechanisms, optical properties, and selected biomedical applications of H2S sensors.


Assuntos
Corantes Fluorescentes , Sulfeto de Hidrogênio , Transdução de Sinais
2.
Molecules ; 27(9)2022 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-35566055

RESUMO

Viruses have been a long-term source of infectious diseases that can lead to large-scale infections and massive deaths. Especially with the recent highly contagious coronavirus (COVID-19), antiviral drugs were developed nonstop to deal with the emergence of new viruses and subject to drug resistance. Nitrogen-containing heterocycles have compatible structures and properties with exceptional biological activity for the drug design of antiviral agents. They provided a broad spectrum of interference against viral infection at various stages, from blocking early viral entry to disrupting the viral genome replication process by targeting different enzymes and proteins of viruses. This review focused on the synthesis and application of antiviral agents derived from various nitrogen-containing heterocycles, such as indole, pyrrole, pyrimidine, pyrazole, and quinoline, within the last ten years. The synthesized scaffolds target HIV, HCV/HBV, VZV/HSV, SARS-CoV, COVID-19, and influenza viruses.


Assuntos
Antivirais , Tratamento Farmacológico da COVID-19 , Antivirais/química , Humanos , Nitrogênio/farmacologia , SARS-CoV-2 , Replicação Viral
3.
Angew Chem Int Ed Engl ; 61(17): e202117330, 2022 04 19.
Artigo em Inglês | MEDLINE | ID: mdl-35150468

RESUMO

The residual tumor after surgery is the most significant prognostic factor of patients with epithelial ovarian cancer. Near-infrared (NIR) fluorescence-guided surgery is actively utilized for tumor localization and complete resection during surgery. However, currently available contrast-enhancing agents display low on-target binding, unfavorable pharmacokinetics, and toxicity, thus not ideal for clinical use. Here we report ultrabright and stable squaraine fluorophores with optimal pharmacokinetics by introducing an asymmetric molecular conformation and surface charges for rapid transporter-mediated cellular uptake. Among the tested, OCTL14 shows low serum binding and rapid distribution into cancer tissue via organic cation transporters (OCTs). Additionally, the charged squaraine fluorophores are retained in lysosomes, providing durable intraoperative imaging in a preclinical murine model of ovarian cancer up to 24 h post-injection. OCTL14 represents a significant departure from the current bioconjugation approach of using a non-targeted fluorophore and would provide surgeons with an indispensable tool to achieve optimal resection.


Assuntos
Ciclobutanos , Neoplasias Ovarianas , Animais , Carcinoma Epitelial do Ovário/diagnóstico por imagem , Meios de Contraste , Ciclobutanos/química , Corantes Fluorescentes/química , Humanos , Ionóforos , Camundongos , Imagem Óptica/métodos , Neoplasias Ovarianas/diagnóstico por imagem , Neoplasias Ovarianas/patologia , Neoplasias Ovarianas/cirurgia , Fenóis
4.
Chemistry ; 27(13): 4230-4248, 2021 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-33137212

RESUMO

Cyanine dyes carrying quinoline moieties are an important class of organic molecules that are of great interest for applications in many fields like medicine, pharmacology, and engineering. Despite their exceptional properties, such as stability, high molar extinction coefficients, and high pH-sensitivity, this class of dyes has been less analyzed and reviewed in the last few decades. Therefore, this review article focuses on discussing the history of quinoline compounds, various synthetic routes to prepare quinolinium salts and symmetrical and asymmetrical mono-, di-, tri-, penta- and heptamethine cyanine dyes, containing quinoline moieties, together with their optical properties and applications as photosensitizers in photodynamic therapy, probes in biomolecules for labeling of nucleic acids, as well as imaging agents.

5.
Org Biomol Chem ; 19(8): 1835-1846, 2021 03 04.
Artigo em Inglês | MEDLINE | ID: mdl-33565564

RESUMO

Donor-π-acceptor (D-π-A) fluorophores consisting of a donor unit, a π linker, and an acceptor moiety have attracted attention in the last decade. In this study, we report the synthesis, characterization, optical properties, TD-DFT, and cytotoxicity studies of 17 near infrared (NIR) D-π-A analogs which have not been reported so far to the best of our knowledge. These fluorophores have chloroacrylic acid as the acceptor unit and various donor units such as indole, benzothiazole, benzo[e]indole, and quinoline. The fluorophores showed strong absorption in the NIR (700-970 nm) region due to their enhanced intramolecular charge transfer (ICT) between chloroacrylic acid and the donor moieties connected with the Vilsmeier-Haack linker. The emission wavelength maxima of the fluorophores were in between 798 and 870 nm. Compound 20 with a 4-quinoline donor moiety showed an emission wavelength above 1000 nm in the NIR II window. The synthesized fluorophores were characterized by 1H NMR and 13C NMR, and their optical properties were studied. Time dependent density functional theory (TD-DFT) calculations showed that the charge transfer occurs from the donor groups (indole, benzothiazole, benzo[e]indole, and quinoline) to the acceptor chloroacrylic acid moiety. Fluorophores with [HOMO] to [LUMO+1] transitions were shown to possess a charge separation character. The cytotoxicity of selected fluorophores, 4, 7, 10 and 12 was investigated against breast cancer cell lines and they showed better activity than the anti-cancer agent docetaxel.


Assuntos
Acrilatos/farmacologia , Antineoplásicos/farmacologia , Corantes Fluorescentes/farmacologia , Compostos Heterocíclicos com 2 Anéis/farmacologia , Acrilatos/síntese química , Acrilatos/efeitos da radiação , Antineoplásicos/síntese química , Antineoplásicos/efeitos da radiação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Teoria da Densidade Funcional , Ensaios de Seleção de Medicamentos Antitumorais , Estabilidade de Medicamentos , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/efeitos da radiação , Compostos Heterocíclicos com 2 Anéis/síntese química , Compostos Heterocíclicos com 2 Anéis/efeitos da radiação , Humanos , Luz , Modelos Químicos , Fenômenos Ópticos
6.
Bioorg Med Chem ; 39: 116140, 2021 06 01.
Artigo em Inglês | MEDLINE | ID: mdl-33905966

RESUMO

Carbonic anhydrases are ubiquitous, and their role in the hydration of carbon dioxide is essential for the survival of many tissues and organs. However, their association with many pathological diseases, especially in glaucoma, Alzheimer's, obesity, epilepsy, and tumorigenesis, has prompted the design and synthesis of novel carbonic anhydrase inhibitors (CAIs). Herein we describe (1) approaches used in the design of CAIs and (2) synthesis of small molecules as CAIs within the last five years. Despite the active research in this area, there are still more avenues to explore, especially selective inhibition of CA I, CA IX, and XII. These isoforms would continue to open up a diversity of carbonic anhydrase inhibitors containing 1,2,3-triazoles, imidazolone, pyrrolidone, thiadiazole, isatin, and glycoconjugates as part of their molecular frameworks.


Assuntos
Inibidores da Anidrase Carbônica/síntese química , Inibidores da Anidrase Carbônica/farmacologia , Desenvolvimento de Medicamentos , Isoenzimas/antagonistas & inibidores , Bibliotecas de Moléculas Pequenas/síntese química , Bibliotecas de Moléculas Pequenas/farmacologia , Inibidores da Anidrase Carbônica/química , Anidrases Carbônicas/metabolismo , Catálise , Humanos , Isoenzimas/metabolismo , Cinética , Bibliotecas de Moléculas Pequenas/química , Relação Estrutura-Atividade
7.
Molecules ; 26(4)2021 Feb 22.
Artigo em Inglês | MEDLINE | ID: mdl-33671600

RESUMO

The synthesis of fluorine-containing small molecules has had numerous benefits of improving the quality and efficiency of many applications of these compounds. For example, fluorine adds promising functionalities in various areas of imaging (MRI, PET, and NIR); gives cell-targeting properties; and has demonstrated improvements in cell permeability, solubility, and other pharmacologic properties. For these and other numerous reasons, fluorination of molecules has grown in popularity in various fields of chemistry. Many reports show the effects observed from increasing the number of fluorine atoms on a fluorophore scaffold. This report will cover the most significant applications and improvements that fluorine has contributed to in various dye scaffolds such as BODIPY, rhodamine, phthalocyanine, and cyanine in the recent decade.


Assuntos
Corantes Fluorescentes/síntese química , Flúor/química , Corantes Fluorescentes/química , Estrutura Molecular
8.
Bioconjug Chem ; 31(2): 194-213, 2020 02 19.
Artigo em Inglês | MEDLINE | ID: mdl-31365819

RESUMO

Squaraine dyes are a class of organic dyes with strong and narrow absorption bands in the near-infrared. Despite high molar absorptivities and fluorescence quantum yields, these dyes have been less explored than other dye scaffolds due to their susceptibility to nucleophilic attack. Recent strategies in probe design including encapsulation, conjugation to biomolecules, and new synthetic modifications have seen squaraine dyes emerging into the forefront of biomedical imaging and other applications. Herein, we provide a concise overview of (1) the synthesis of symmetrical and unsymmetrical squaraine dyes, (2) the relationship between structure and photophysical properties of squaraine dyes, and (3) current applications of squaraine dyes in the literature. Given the recent successes at overcoming the limitations of squaraine dyes, they show high potential in biological imaging, in photodynamic and photothermal therapies, and as molecular sensors.


Assuntos
Ciclobutanos/química , Corantes Fluorescentes/química , Fenóis/química , Animais , Técnicas de Química Sintética/métodos , Ciclobutanos/síntese química , Ciclobutanos/uso terapêutico , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/uso terapêutico , Humanos , Imagem Óptica/métodos , Fenóis/síntese química , Fenóis/uso terapêutico , Fotoquimioterapia/métodos , Terapia Fototérmica/métodos
9.
Molecules ; 25(12)2020 Jun 25.
Artigo em Inglês | MEDLINE | ID: mdl-32630496

RESUMO

Here, we report the syntheses of two pentamethine cyanine dyes containing quinolinium rings and substituted with either hydrogen (3) or bromine (4) at the meso carbon. The electron withdrawing bromine atom stabilizes dye 4 in aqueous buffer, allowing complex formation to occur between the dye and double-helical DNA. UV-visible, CD, and fluorescence spectra recorded at low DNA concentrations suggest that dye 4 initially binds to the DNA as a high-order aggregate. As the ratio of DNA to dye is increased, the aggregate is converted to monomeric and other low-order dye forms that interact with DNA in a non-intercalative fashion. The brominated dye 4 is relatively unreactive in the dark, but, under 707-759 nm illumination, generates hydroxyl radicals that cleave DNA in high yield (pH 7.0, 22 °C). Dye 4 is also taken up by ES2 ovarian carcinoma cells, where it is non-toxic under dark conditions. Upon irradiation of the ES2 cells at 694 nm, the brominated cyanine reduces cell viability from 100 ± 10% to 14 ± 1%. Our results suggest that 2-quinolinium-based carbocyanine dyes equipped with stabilizing electron withdrawing groups may have the potential to serve as sensitizing agents in long-wavelength phototherapeutic applications.


Assuntos
Carbocianinas/química , Clivagem do DNA , DNA de Neoplasias/química , Corantes Fluorescentes/química , Neoplasias Ovarianas/metabolismo , Fotoquímica , Compostos de Quinolínio/química , Apoptose , Proliferação de Células , Feminino , Fluorescência , Humanos , Neoplasias Ovarianas/patologia , Espectroscopia de Luz Próxima ao Infravermelho , Células Tumorais Cultivadas
10.
Bioconjug Chem ; 30(10): 2647-2663, 2019 10 16.
Artigo em Inglês | MEDLINE | ID: mdl-31518105

RESUMO

G-Quadruplex DNA has been recognized as a highly appealing target for the development of new selective chemotherapeutics, which could result in markedly reduced toxicity toward normal cells. In particular, the cyanine dyes that bind selectively to G-quadruplex structures without targeting duplex DNA have attracted attention due to their high amenability to structural modifications that allows fine-tuning of their biomolecular interactions. We have previously reported pentamethine and symmetric trimethine cyanines designed to effectively bind G-quadruplexes through end stacking interactions. Herein, we are reporting a second generation of drug candidates, the asymmetric trimethine cyanines. These have been synthesized and evaluated for their quadruplex binding properties. Incorporating a benz[c,d]indolenine heterocyclic unit increased overall quadruplex binding, and elongating the alkyl length increases the quadruplex-to-duplex binding specificity.


Assuntos
Alcinos/química , Alcinos/farmacologia , Quadruplex G/efeitos dos fármacos , Sequência de Bases , DNA/química , DNA/genética , Desenho de Fármacos , Indóis/química , Modelos Moleculares
11.
Photochem Photobiol Sci ; 17(10): 1409-1416, 2018 Oct 10.
Artigo em Inglês | MEDLINE | ID: mdl-30234861

RESUMO

The unique optical properties of cyanine dyes have prompted their use in numerous applications. Heptamethine cyanines are commonly modified on the methine bridge after synthesis of a meso-chlorine containing cyanine. Herein, a series of heptamethine cyanines containing modified methine bridges were synthesized using substituted dianil linkers. Their optical properties including, molar absorptivity, fluorescence, and quantum yield were measured as well as their hydrophobic effects in polar buffer solution. It was shown that dyes containing cyclopentene in the methine bridge or a phenyl ring in the meso position display increased molar absorptivity while the increased flexibility of the dye containing a cycloheptene in the methine bridge prevented fluorescence.

12.
Bioorg Med Chem Lett ; 28(3): 509-514, 2018 02 01.
Artigo em Inglês | MEDLINE | ID: mdl-29249562

RESUMO

Eight near-infrared heptamethine cyanines have been successfully synthesized based on IR 786 with oxygen, sulfur and amine moieties at the central position. These dyes show diverse optical properties resulting from different substitutions. Particularly, the heptamethine dyes with amine moieties have larger Stokes shifts and higher quantum yields of fluorescence. We also investigated these dyes for tumor cell cytotoxicity using cell viability and in vitro proliferation assays. Two of the compounds showed high cytotoxicity against PC-3 cancer cells.


Assuntos
Antineoplásicos/farmacologia , Carbocianinas/química , Carbocianinas/farmacologia , Corantes Fluorescentes/farmacologia , Indóis/química , Indóis/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Carbocianinas/síntese química , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Fluorescência , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Humanos , Indóis/síntese química , Estrutura Molecular , Fenômenos Ópticos , Células PC-3 , Relação Estrutura-Atividade
13.
Molecules ; 23(2)2018 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-29364846

RESUMO

Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF) probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.


Assuntos
Carbocianinas/química , Corantes Fluorescentes/química , Carbocianinas/síntese química , Técnicas de Química Sintética , Corantes Fluorescentes/síntese química , Humanos , Estrutura Molecular , Ligação Proteica , Albumina Sérica Humana/química , Albumina Sérica Humana/metabolismo , Análise Espectral
14.
Molecules ; 23(11)2018 Oct 25.
Artigo em Inglês | MEDLINE | ID: mdl-30366395

RESUMO

Almost every variety of medical imaging technique relies heavily on exogenous contrast agents to generate high-resolution images of biological structures. Organic small molecule contrast agents, in particular, are well suited for biomedical imaging applications due to their favorable biocompatibility and amenability to structural modification. PET/SPECT, MRI, and fluorescence imaging all have a large host of small molecule contrast agents developed for them, and there exists an academic understanding of how these compounds can be developed. Optoacoustic imaging is a relatively newer imaging technique and, as such, lacks well-established small molecule contrast agents; many of the contrast agents used are the same ones which have found use in fluorescence imaging applications. Many commonly-used fluorescent dyes have found successful application in optoacoustic imaging, but others generate no detectable signal. Moreover, the structural features that either enable a molecule to generate a detectable optoacoustic signal or prevent it from doing so are poorly understood, so design of new contrast agents lacks direction. This review aims to compile the small molecule optoacoustic contrast agents that have been successfully employed in the literature to bridge the information gap between molecular design and optoacoustic signal generation. The information contained within will help to provide direction for the future synthesis of optoacoustic contrast agents.


Assuntos
Meios de Contraste/química , Fluorescência , Imageamento por Ressonância Magnética , Tomografia por Emissão de Pósitrons combinada à Tomografia Computadorizada , Espectroscopia de Luz Próxima ao Infravermelho
15.
Acc Chem Res ; 49(9): 1731-40, 2016 09 20.
Artigo em Inglês | MEDLINE | ID: mdl-27564418

RESUMO

Near-infrared (NIR) fluorescence light has been widely utilized in clinical imaging by providing surgeons highly specific images of target tissue. The "NIR window" from 650 to 900 nm is especially useful due to several special features such as minimal autofluorescence and absorption of biomolecules in tissue, as well as low light scattering. Compared with visible wavelengths, NIR fluorescence light is invisible, thus allowing highly sensitivity real-time image guidance in human surgery without changing the surgical field. The benefit of using NIR fluorescence light as a clinical imaging technology can be attributed to its molecular fluorescence as an exogenous contrast agent. Indeed, whole body preoperative imaging of single-photon emission computed tomography (SPECT) and positron emission tomography (PET) remains important in diagnostic utility, but they lack the efficacy of innocuous and targeted NIR fluorophores to simultaneously facilitate the real-time delineation of diseased tissue while preserving vital tissues. Admittedly, NIR imaging technology has been slow to enter clinical use mostly due to the late-coming development of truly breakthrough contrast agents for use with current imaging systems. Therefore, clearly defining the physical margins of tumorous tissue remains of paramount importance in bioimaging and targeted therapy. An equally noteworthy yet less researched goal is the ability to outline healthy vital tissues that should be carefully navigated without transection during the intraoperative surgery. Both of these paths require optimizing a gauntlet of design considerations to obtain not only an effective imaging agent in the NIR window but also high molecular brightness, water solubility, biocompatibility, and tissue-specific targetability. The imaging community recognizes three strategic approaches which include (1) passive targeting via the EPR effect, (2) active targeting using the innate overall biodistribution of known molecules, and (3) activatable targeting through an internal stimulus, which turns on fluorescence from an off state. Recent advances in nanomedicine and bioimaging offer much needed promise toward fulfilling these stringent requirements as we develop a successful catalog of targeted contrast agents for illuminating both tumors and vital tissues in the same surgical space by employing spectrally distinct fluorophores in real time. These tissue-specific contrast agents can be versatile arsenals to physicians for real-time intraoperative navigation as well as image-guided targeted therapy. There is a versatile library of tissue-specific fluorophores available in the literature, with many discussed herein, which offers clinicians an array of possibilities that will undoubtedly improve intraoperative success and long-term postoperation prognosis.


Assuntos
Meios de Contraste/farmacologia , Corantes Fluorescentes/farmacologia , Neoplasias/diagnóstico por imagem , Meios de Contraste/efeitos da radiação , Fluorescência , Corantes Fluorescentes/efeitos da radiação , Humanos , Raios Infravermelhos , Nanoconjugados/efeitos da radiação , Neoplasias/metabolismo , Distribuição Tecidual
17.
Chemistry ; 22(39): 13764-13782, 2016 Sep 19.
Artigo em Inglês | MEDLINE | ID: mdl-27406265

RESUMO

Nile red and Nile blue are highly fluorescent and photostable organic dyes from the benzo[a]phenoxazine family. They have been used as histological stains for imaging lysosomes and lipids in vitro. The dyes' high quantum yields and solvent-dependent optical properties make them ideal scaffolds for the development of pH probes and local polarity indicators. Reviews of the literature in this area are scarce with only one review ever published in 2006. It has been 10 years since and the field has evolved. This review aims to expand upon topics covered by the previous reviewers and to report on recent advances in the literature. As authors, we hope to convey a sense of scope and to spark renewed interest in this useful niche of dye chemistry.


Assuntos
Técnicas de Química Sintética/métodos , Corantes Fluorescentes/química , Oxazinas/química , Animais , Técnicas Biossensoriais/métodos , Corantes Fluorescentes/síntese química , Humanos , Modelos Moleculares , Imagem Óptica/métodos , Oxazinas/síntese química , Espectrometria de Fluorescência/métodos , Coloração e Rotulagem/métodos
18.
Molecules ; 21(1): E23, 2015 Dec 24.
Artigo em Inglês | MEDLINE | ID: mdl-26712725

RESUMO

Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.


Assuntos
Carbocianinas/síntese química , Corantes Fluorescentes/síntese química , Ácidos Nucleicos/química , Carbocianinas/química , Biologia Computacional/métodos , Corantes Fluorescentes/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fenômenos Ópticos
19.
Angew Chem Int Ed Engl ; 54(30): 8648-52, 2015 Jul 20.
Artigo em Inglês | MEDLINE | ID: mdl-26095685

RESUMO

A novel class of near-infrared fluorescent contrast agents was developed. These agents target cartilage with high specificity and this property is inherent to the chemical structure of the fluorophore. After a single low-dose intravenous injection and a clearance time of approximately 4 h, these agents bind to all three major types of cartilage (hyaline, elastic, and fibrocartilage) and perform equally well across species. Analysis of the chemical structure similarities revealed a potential pharmacophore for cartilage targeting. Our results lay the foundation for future improvements in tissue engineering, joint surgery, and cartilage-specific drug development.


Assuntos
Cartilagem/metabolismo , Meios de Contraste/química , Meios de Contraste/farmacocinética , Corantes Fluorescentes/química , Corantes Fluorescentes/farmacocinética , Imagem Óptica , Administração Intravenosa , Animais , Meios de Contraste/administração & dosagem , Corantes Fluorescentes/administração & dosagem , Masculino , Camundongos , Imagem Óptica/métodos , Espectroscopia de Luz Próxima ao Infravermelho
20.
Analyst ; 139(19): 4862-73, 2014 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-25105177

RESUMO

In this study, a series of new, highly sensitive BF2-chelated tetraarylazadipyrromethane dyes are synthesized and analyzed to be suitable as on/off photo-induced electron transfer modulated fluorescent sensors for determination of intracellular pH. The ethanolic solutions of the new indicators feature absorption maxima in the range of 696-700 nm and a fluorescence emission maximum at 720 nm. Molar absorptivity and fluorescence quantum yield data were determined for the studied set of aza-BODIPY indicators. These indicators have high molar absorption coefficients of ∼80,000 M(-1) cm(-1) and quantum yields (up to 18%). Corresponding pKa values of indicators are determined from absorbance and fluorescence measurements and range from 9.1 to 10.8, depending on the selective positioning of electron-donating functionalities. The excellent photostability of the aza-BODIPY indicators makes them particularly suitable for long duration measurements. The in vitro cellular staining of living tissues in PC3 cells based on the isosbestic point at pH 7.8 and pH 9.3 has been employed which shows an increase in fluorescence intensity at 800 nm with increase in pH for certain compounds and fluorescence intensity decreases at 700 nm. Therefore, the new indicators are suitable for exploitation and adaptation in a diverse range of analytical applications.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Espectrometria de Fluorescência , Animais , Compostos de Boro/síntese química , Compostos de Boro/metabolismo , Linhagem Celular Tumoral , Transporte de Elétrons , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/metabolismo , Humanos , Concentração de Íons de Hidrogênio , Hidroxilação , Raios Infravermelhos , Camundongos , Microscopia de Fluorescência , Distribuição Tecidual
SELEÇÃO DE REFERÊNCIAS
DETALHE DA PESQUISA