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1.
J Phys Chem Lett ; 12(32): 7671-7687, 2021 Aug 19.
Artigo em Inglês | MEDLINE | ID: mdl-34351771

RESUMO

Carbon dots (CDs) have excellent luminescence characteristics, such as good light stability, high quantum yield (QY), long phosphorescence lifetime, and a wide emission wavelength range, resulting in CDs' great success in optical applications. Understanding the structure-property relationships in CDs is essential for their use in optoelectronic applications. However, because of the complex nature of CD structures and synthesis processes, understanding the luminescence mechanism and structure-property relationships of CDs is a big challenge. This Perspective reviews the theoretical efforts toward the understanding of structure-property relationships and discusses the challenges that need to be overcome in future development of CDs.


Assuntos
Corantes Fluorescentes/química , Pontos Quânticos/química , Carbono/química , Teoria da Densidade Funcional , Fluorescência , Corantes Fluorescentes/síntese química , Aprendizado de Máquina , Modelos Químicos , Relação Estrutura-Atividade
2.
Theranostics ; 11(16): 7767-7778, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34335963

RESUMO

Background: Lipid droplets (LDs) establish a considerable number of contact sites with mitochondria to enable energy transfer and communication. In this study, we developed a fluorescent biosensor to image LD-mitochondria interactions at the nanoscale and further explored the function of LD-mediated matrix transmission in processes involving multi-organelle interactions. Methods: A fluorescent probe called C-Py (C21H19N3O2, 7-(diethylamino) coumarin-3-vinyl-4-pyridine acetonitrile) was designed and synthesized. Colocalization of C-Py and the commercial LD stain Nile Red was analyzed in HeLa cells. The fluorescence stability and signal to background ratio of C-Py under structured illumination microscopy (SIM) were compared to those of the commercial probe BODIPY493/503. The cytotoxicity of C-Py was assessed using CCK-8 assays. The uptake pattern of C-Py in HeLa cells was then observed under various temperatures, metabolic levels, and endocytosis levels. Contact sites between LDs and various organelles, such as mitochondria, nuclei, and cell membrane, were imaged and quantitated using SIM. Physical changes to the contact sites between LDs and mitochondria were monitored after lipopolysaccharide induction. Results: A LD-targeted fluorescent biosensor, C-Py, with good specificity, low background signal, excellent photostability, low cytotoxicity, and high cellular permeability was developed for tracking LD contact sites with multiple organelles using SIM. Using C-Py, the subcellular distribution and dynamic processes of LDs in living cells were observed under SIM. The formation of contact sites between LDs and multiple organelles was visualized at a resolution below ~200 nm. The number of LD-mitochondria contact sites formed was decreased by lipopolysaccharide treatment inducing an inflammatory environment. Conclusions: C-Py provides strategies for the design of ultra-highly selective biosensors and a new tool for investigating the role and regulation of LDs in living cells at the nanoscale.


Assuntos
Gotículas Lipídicas/metabolismo , Mitocôndrias/metabolismo , Imagem Individual de Molécula/métodos , Técnicas Biossensoriais/métodos , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/metabolismo , Células HeLa , Humanos , Metabolismo dos Lipídeos/fisiologia
3.
Chem Pharm Bull (Tokyo) ; 69(6): 526-528, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34078798

RESUMO

The optical property of fluorescent unit-conjugated aliphatic oxaboroles has been investigated. The oxaboroles provide good fluorescence quantum yields and selective recognition toward D-ribose and D-ribose containing molecules. The molecular recognition induced significant fluorescence quenching. The property of the boroles showed the possibility of the boron-based nicotinamide adenine dinucleotide (NAD) sensor probe.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , NAD/química , Açúcares/análise , Compostos de Boro/síntese química , Corantes Fluorescentes/síntese química , Estrutura Molecular , Fenômenos Ópticos
4.
Methods Mol Biol ; 2275: 127-140, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34118035

RESUMO

Hydrogen peroxide (H2O2) produced from mitochondria is intimately involved in human health and disease, but is challenging to selectively monitor inside living systems. The fluorescent probe MitoPY1 provides a practical tool for imaging mitochondrial H2O2 and has been demonstrated to function in a variety of diverse cell types. In this chapter, we describe the synthetic preparation of the small molecule probe MitoPY1 , methods for validating this probe in vitro and in live cells, and an example procedure for measuring mitochondrial H2O2 in a cell culture model of Parkinson's disease.


Assuntos
Corantes Fluorescentes/síntese química , Peróxido de Hidrogênio/análise , Mitocôndrias/metabolismo , Doença de Parkinson/metabolismo , Piperazinas/síntese química , Compostos de Espiro/síntese química , Técnicas de Cultura de Células , Corantes Fluorescentes/química , Células HEK293 , Células HeLa , Humanos , Microscopia de Fluorescência , Modelos Biológicos , Estrutura Molecular , Piperazinas/química , Compostos de Espiro/química
5.
ACS Appl Mater Interfaces ; 13(26): 30337-30349, 2021 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-34159778

RESUMO

The efficient, versatile, and straightforward synthesis of the first N-alkyl analogues of induline 3B (8a and 8b) is reported. Thanks to the introduction of lipophilic substituents and their attractive photophysical properties (far-red emission and production of singlet oxygen), phenazinium 8b can be used as a theranostic agent and shows, at very low concentrations (100 nM), a remarkable ability to (i) image cells and zebrafish embryos with high quality under both mono- (514 nm) and biphotonic (790 and 810 nm) excitations, (ii) efficiently and quickly penetrate cancer cells rather than healthy fibroblasts, and (iii) induce a total or almost total cancer cell death in vitro and in vivo after illumination (λexc = 540-560 nm). The molecular structure of 8b is based on a triamino-phenazinium core only, with no need for additional components, highlighting the emergence of a minimalistic and versatile class of fluorescent probes for targeted photodynamic cancer therapy.


Assuntos
Antineoplásicos/uso terapêutico , Corantes Fluorescentes/uso terapêutico , Fenazinas/uso terapêutico , Fármacos Fotossensibilizantes/uso terapêutico , Animais , Antineoplásicos/síntese química , Antineoplásicos/metabolismo , Antineoplásicos/efeitos da radiação , Linhagem Celular Tumoral , Fibroblastos/metabolismo , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/metabolismo , Corantes Fluorescentes/efeitos da radiação , Humanos , Luz , Neoplasias/diagnóstico por imagem , Neoplasias/tratamento farmacológico , Fenazinas/síntese química , Fenazinas/metabolismo , Fenazinas/efeitos da radiação , Fotoquimioterapia , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/metabolismo , Fármacos Fotossensibilizantes/efeitos da radiação , Medicina de Precisão/métodos , Oxigênio Singlete/metabolismo , Ensaios Antitumorais Modelo de Xenoenxerto , Peixe-Zebra
6.
ACS Appl Mater Interfaces ; 13(24): 27991-27998, 2021 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-34110123

RESUMO

Porphyria is a group of genetic photodermatoses that cause too much porphyrin to accumulate in the blood, skin, and liver, resulting in skin photosensitivity and damage, liver disease, or potential liver failure. Conventional detection methods include high-performance liquid chromatography and fluorescence spectrometry. However, these methods usually require complicated pretreatment and time-consuming processes. Therefore, efficient and fast detection of porphyria is urgently needed. Herein, we develop a molecular afterglow reporter-based sensing scheme for the detection of porphyrins in whole blood. The afterglow reporter can respond to the production of singlet oxygen (1O2) of porphyrins after light excitation, and the detection signals can be amplified through adjusting the amount of singlet oxygen and afterglow reporter molecules. Moreover, without the use of a real-time excitation source, afterglow signals can avoid the scattering and autofluorescence interference in biological samples, thereby reducing background noise. More importantly, we prove the applicability of the afterglow reporter in the quantitative detection of porphyrins in whole blood and demonstrate its great clinical potential.


Assuntos
Adamantano/análogos & derivados , Corantes Fluorescentes/química , Porfirias/diagnóstico , Protoporfirinas/análise , Quinolinas/química , Espectrometria de Fluorescência/métodos , Adamantano/síntese química , Corantes Fluorescentes/síntese química , Humanos , Limite de Detecção , Porfirias/sangue , Protoporfirinas/efeitos da radiação , Quinolinas/síntese química , Oxigênio Singlete/metabolismo
7.
ACS Appl Mater Interfaces ; 13(24): 28610-28626, 2021 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-34110776

RESUMO

The development of aggregation-induced emission enhancement (AIEE) active nanoprobes without any synthetic complication for solution-state and organic thin-film transistor (OTFT)-based sensory applications is still a challenging task. In this study, the novel pyrene-incorporated Schiff base (5-phenyl-4-((pyren-1-ylmethylene)amino)-4H-1,2,4-triazole-3-thiol; PT2) with an AIEE property was synthesized via a one-pot reaction and was reported for detecting Zn2+ and tyrosine in the solution state and OTFT. In the AIEE studies of PT2 (in CH3CN) at various water fractions (fw: 0-97.5%), the existence of J-aggregation, crystalline changes, and nanofibers formation was confirmed by ultraviolet absorption/photoluminescence (UV/PL) spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), and dynamic-light scattering (DLS) techniques. Similarly, PT2-based Zn2+ detection and sensory reversibility with tyrosine were demonstrated by UV/PL studies with evidence related to crystalline/nanolevel changes in PXRD, SEM, TEM, AFM, and DLS data. Distinct decay profiles associated with the AIEE and sensory responses of PT2 were observed in time-resolved photoluminescence spectra. From the standard deviation and linear fittings of PL titrations, detection limits (LODs) of the Zn2+ with PT2 and the tyrosine with PT2-Zn2+ were estimated as 0.79 and 45 nM, respectively. High-resolution mass and 1H NMR results confirmed 2:1 and 1:1 stoichiometry and binding sites of PT2-Zn2+-PT2* and tyrosine-Zn2+ complexes. Moreover, the values of association constants determined by linear fittings were 4.205 × 10-7 and 1.73 × 10-8 M-2, correspondingly. Optimization via the density functional theory disclosed the binding sites and suppression of twisted intramolecular charge transfer/photoinduced electron transfer (TICT/PET) as well as the involvement of restricted intramolecular rotation in the AIEE and PET "ON-OFF-ON" mechanisms in the Zn2+ and tyrosine sensors. Results from the B16-F10 cellular and zebrafish imaging of AIEE, Zn2+, and tyrosine sensors further attested the applicability of PT2 in biological samples. Finally, the PT2 and pentacene-incorporated OTFT devices were fabricated. The devices displayed more than 90% change in drain-source current when reacted with Zn2+ with an LOD of 5.46 µM but showed no response to tyrosine, thereby confirming the reversibility. Moreover, the OTFT devices also demonstrated Zn2+ ion detection in tap water and lake water samples.


Assuntos
Corantes Fluorescentes/química , Pirenos/química , Tirosina/análise , Zinco/análise , Animais , Teoria da Densidade Funcional , Água Potável/análise , Técnicas Eletroquímicas/métodos , Corantes Fluorescentes/síntese química , Lagos/análise , Limite de Detecção , Modelos Químicos , Pirenos/síntese química , Bases de Schiff/síntese química , Bases de Schiff/química , Transistores Eletrônicos , Peixe-Zebra
8.
J Med Chem ; 64(12): 8798-8805, 2021 06 24.
Artigo em Inglês | MEDLINE | ID: mdl-34081463

RESUMO

We have synthesized and characterized a library of near-infrared (NIR) heptamethine cyanine dyes for biomedical application as photoacoustic imaging and photothermal agents. These hydrophobic dyes were incorporated into a polymer-based nanoparticle system to provide aqueous solubility and protection of the photophysical properties of each dye scaffold. Among those heptamethine cyanine dyes analyzed, 13 compounds within the nontoxic polymeric nanoparticles have been selected to exemplify structural relationships in terms of photostability, photoacoustic imaging, and photothermal behavior within the NIR (∼650-850 nm) spectral region. The most contributing structural features observed in our dye design include hydrophobicity, rotatable bonds, heavy atom effects, and stability of the central cyclohexene ring within the dye core. The NIR agents developed within this project serve to elicit a structure-function relationship with emphasis on their photoacoustic and photothermal characteristics aiming at producing customizable NIR photoacoustic and photothermal tools for clinical use.


Assuntos
Corantes Fluorescentes/farmacologia , Indóis/farmacologia , Nanopartículas/química , Linhagem Celular Tumoral , Corantes Fluorescentes/síntese química , Humanos , Indóis/síntese química , Microscopia de Fluorescência , Técnicas Fotoacústicas/métodos , Terapia Fototérmica/métodos
9.
Chem Asian J ; 16(15): 2048-2054, 2021 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-34075705

RESUMO

Photopolymerization of diacetylenes usually requires stringent reaction conditions like high energy irradiation of 254-nm light or even γ-rays, which are generally harmful to the human body and thus mild conditions with lower energy irradiation are required. In this study, different diphenyldiacetylene (DPDA) derivatives were rationally designed followed by the investigation of their photopolymerization behavior. It was found that the para-substituted amino groups could render the absorption band of DPDA bathochromically shifted, ensuring a 365-nm light wavelength coverage. On this basis, an organogel system was constructed by chemically modifying cholesteryl and lipoic acid onto the DPDA moiety in aromatic solvents. Such uniform self-assemblies further facilitated to a rather high degree of polymerization by 365-nm irradiation. As a kind of fluorescent materials, the whole polymerization process of this system can be visualized by a photoluminescent signal.


Assuntos
Acetileno/síntese química , Corantes Fluorescentes/síntese química , Raios Ultravioleta , Acetileno/análogos & derivados , Acetileno/química , Corantes Fluorescentes/química , Teste de Materiais , Estrutura Molecular , Tamanho da Partícula , Polimerização
10.
Chem Commun (Camb) ; 57(58): 7083-7095, 2021 Jul 20.
Artigo em Inglês | MEDLINE | ID: mdl-34180471

RESUMO

Proteins provide an excellent means to monitor and regulate biological processes. Hence, a precise chemical toolbox for their modification becomes indispensable. In this perspective, this feature article outlines our efforts to establish the core principles of chemoselectivity, site-selectivity, site-specificity, site-modularity, residue-modularity, and protein-specificity. With the knowledge to systematically regulate these parameters, the field has access to technological platforms that can address multiple challenges at the interface of chemistry, biology, and medicine.


Assuntos
Proteínas/química , Animais , Técnicas de Química Sintética , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Humanos , Imunoconjugados/química , Modelos Moleculares , Proteínas/síntese química
11.
J Med Chem ; 64(13): 9567-9576, 2021 07 08.
Artigo em Inglês | MEDLINE | ID: mdl-34160227

RESUMO

For the early diagnosis of cancer, leading to a better chance of full recovery, marker genes whose expression is already altered in precancerous lesions are desirable, and the tumor-suppressor gene FHIT is one candidate. The gene product, FHIT protein, has a unique dinucleoside triphosphate hydrolase (AP3Aase) activity, and in this study, we designed and synthesized a series of FHIT fluorescent probes utilizing this activity. We optimized the probe structure for high and specific reactivity with FHIT and applied the optimized probe in a screening assay for FHIT inhibitors. Screening of a compound library with this assay identified several hits. Structural development of a hit compound afforded potent FHIT inhibitors. These inhibitors induce apoptosis in FHIT-expressing cancers via caspase activation. Our results support the idea that FHIT binders, no matter whether inhibitors or agonists of AP3Aase activity, might be promising anticancer agents.


Assuntos
Hidrolases Anidrido Ácido/antagonistas & inibidores , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Desenho de Fármacos , Inibidores Enzimáticos/farmacologia , Corantes Fluorescentes/farmacologia , Proteínas de Neoplasias/antagonistas & inibidores , Hidrolases Anidrido Ácido/genética , Hidrolases Anidrido Ácido/metabolismo , Antineoplásicos/síntese química , Antineoplásicos/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Humanos , Estrutura Molecular , Proteínas de Neoplasias/genética , Proteínas de Neoplasias/metabolismo , Relação Estrutura-Atividade
12.
Chem Asian J ; 16(15): 2087-2099, 2021 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-34107175

RESUMO

2-N-aminoquinazolines were prepared by consecutive SN Ar functionalization. X-ray structures display the nitrogen lone pair of the 2-N-morpholino group in conjugation with the electron deficient quinazoline core and thus representing electronic push-pull systems. 2-N-aminoquinazolines show a positive solvatochromism and are fluorescent in solution and in solid state with quantum yields up to 0.73. Increase in electron donor strength of the 2-amino substituent causes a red-shift of the intramolecular charge transfer (ICT) band (300-400 nm); whereas the photoluminescence emission maxima (350-450 nm) is also red-shifted significantly along with an enhancement in photoluminescence efficiency. HOMO-LUMO energies were estimated by a combination of electrochemical and photophysical methods and correlate well to those obtained by computational methods. ICT properties are theoretically attributed to an excitation to Rydberg-MO in SAC-CI method, which can be interpreted as n-π* excitation. 7-Amino-2-N-morpholino-4-methoxyquinazoline responds to acidic conditions with significant increases in photoluminescence intensity revealing a new turn-on/off fluorescence probe.


Assuntos
Corantes Fluorescentes/química , Quinazolinas/química , Bibliotecas de Moléculas Pequenas/química , Teoria da Densidade Funcional , Corantes Fluorescentes/síntese química , Estrutura Molecular , Processos Fotoquímicos , Quinazolinas/síntese química , Bibliotecas de Moléculas Pequenas/síntese química , Soluções
13.
Chem Asian J ; 16(15): 2014-2017, 2021 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-34128347

RESUMO

A dilactosyl-dicyanovinyl-functionalized tetraphenylethene (TPELC) was designed, synthesized and used for ratiometric sensing of cyanide. TPELC was comprised of three moieties (tetraphenylethylene, dicyanovinyl group and lactose unit) in one molecule, making TPELC water-soluble and aggregation-induced emission (AIE)-active and selectively reactive to cyanide. Compared with other reported fluorescent probes containing dicyanovinyl group, TPELC is the first AIE luminogen to be assembled as fluorescent organic nanoparticles (FONs) for sensing of cyanide in water without the use of surfactant or the help of organic solvents based on the nucleophilic addition reaction. The detection mechanism was verified by liquid chromatograph mass spectrometry experiments and by protonation of cyanide to reduce the nucleophilicity of cyanide. In addition, TPELC was used for detection of the cyanide content of food samples and test strips were developed to simplify the detection procedure.


Assuntos
Cianetos/análise , Corantes Fluorescentes/química , Contaminação de Alimentos/análise , Nanopartículas/química , Estilbenos/química , Poluentes Químicos da Água/análise , Corantes Fluorescentes/síntese química , Estrutura Molecular , Solubilidade , Espectrometria de Fluorescência , Estilbenos/síntese química , Água/química
14.
Nat Commun ; 12(1): 3389, 2021 06 07.
Artigo em Inglês | MEDLINE | ID: mdl-34099672

RESUMO

Bioorthogonal late-stage diversification of amino acids and peptides bears enormous potential for drug discovery and molecular imaging. Despite major accomplishments, these strategies largely rely on traditional, lengthy prefunctionalization methods, heavily involving precious transition-metal catalysis. Herein, we report on a resource-economical manganese(I)-catalyzed C-H fluorescent labeling of structurally complex peptides ensured by direct alkynylation and alkenylation manifolds. This modular strategy sets the stage for unraveling structure-activity relationships between structurally discrete fluorophores towards the rational design of BODIPY fluorogenic probes for real-time analysis of immune cell function.


Assuntos
Técnicas de Química Sintética/métodos , Corantes Fluorescentes/síntese química , Manganês/química , Peptídeos/síntese química , Compostos de Boro/química , Linfócitos T CD8-Positivos/citologia , Linfócitos T CD8-Positivos/metabolismo , Carbono/química , Catálise , Membrana Celular/metabolismo , Humanos , Hidrogênio/química , Células Jurkat , Microscopia Confocal , Microscopia de Fluorescência , Imagem Molecular/métodos
15.
Molecules ; 26(10)2021 May 17.
Artigo em Inglês | MEDLINE | ID: mdl-34067859

RESUMO

A chalcone series (3a-f) with electron push-pull effect was synthesized via a one-pot Claisen-Schmidt reaction with a simple purification step. The compounds exhibited strong emission, peaking around 512-567 nm with mega-stokes shift (∆λ = 93-139 nm) in polar solvents (DMSO, MeOH, and PBS) and showed good photo-stability. Therefore, 3a-f were applied in cellular imaging. After 3 h of incubation, green fluorescence was clearly brighter in cancer cells (HepG2) compared to normal cells (HEK-293), suggesting preferential accumulation in cancer cells. Moreover, all compounds exhibited higher cytotoxicity within 24 h toward cancer cells (IC50 values ranging from 45 to 100 µM) than normal cells (IC50 value >100 µM). Furthermore, the antimicrobial properties of chalcones 3a-f were investigated. Interestingly, 3a-f exhibited antibacterial activities against Escherichia coli and Staphylococcus aureus, with minimum bactericidal concentrations (MBC) of 0.10-0.60 mg/mL (375-1000 µM), suggesting their potential antibacterial activity against both Gram-negative and Gram-positive bacteria. Thus, this series of chalcone-derived fluorescent dyes with facile synthesis shows great potential for the development of antibiotics and cancer cell staining agents.


Assuntos
Chalcona/química , Chalcona/síntese química , Corantes Fluorescentes/síntese química , Antibacterianos/farmacologia , Chalcona/isolamento & purificação , Chalconas/química , Chalconas/isolamento & purificação , Chalconas/farmacologia , Escherichia coli/efeitos dos fármacos , Fluorescência , Corantes Fluorescentes/química , Corantes Fluorescentes/uso terapêutico , Bactérias Gram-Positivas/efeitos dos fármacos , Células HEK293 , Células Hep G2 , Humanos , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-Atividade
16.
Int J Mol Sci ; 22(11)2021 May 25.
Artigo em Inglês | MEDLINE | ID: mdl-34070488

RESUMO

The electronic nature of 4-hydroxy-1H-pyrrolo[3,4-c]pyridine-1,3,6(2H,5H)-trione (HPPT) was comprehensively investigated in liquid media at room temperature using steady-state and time-resolved femtosecond transient absorption spectroscopic techniques. The analysis of the linear photophysical and photochemical parameters of HPPT, including steady-state absorption, fluorescence and excitation anisotropy spectra, along with the lifetimes of fluorescence emission and photodecomposition quantum yields, revealed the nature of its large Stokes shift, specific changes in the permanent dipole moments under electronic excitation, weak dipole transitions with partially anisotropic character, and high photostability. Transient absorption spectra of HPPT were obtained with femtosecond resolution and no characteristic solvate relaxation processes in protic (methanol) solvent were revealed. Efficient light amplification (gain) was observed in the fluorescence spectral range of HPPT, but no super-luminescence and lasing phenomena were detected. The electronic structure of HPPT was also analyzed with quantum-chemical calculations using a DFT/B3LYP method and good agreement with experimental data was shown. The development and investigation of new pyrrolo[3,4-c]pyridine derivatives are important due to their promising fluorescent properties and potential for use in physiological applications.


Assuntos
Elétrons , Corantes Fluorescentes/química , Piridinas/química , Pirróis/química , Análise Espectral , Química Computacional , Fluorescência , Corantes Fluorescentes/síntese química , Estrutura Molecular , Teoria Quântica , Solventes/química
18.
Nanotheranostics ; 5(4): 448-460, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34055574

RESUMO

Increasing numbers of lung tumors are identified at early disease stages by diagnostic imaging in screening programs, but difficulties in locating these during surgical intervention has prevented an improved treatment outcome. Surgical biomarkers that are visible on diagnostic images, and that provide the surgeon with real-time image guidance during the intervention are thus highly warranted to bridge diagnostic precision into enhanced therapeutic outcome. In this paper, a liquid soft tissue marker for near infrared fluorescence and radio-guidance is presented. The biocompatible marker is based on the carbohydrate ester, sucrose acetate isobutyrate, ethanol, and a multifunctional naphthalocyanine dye, which enable near infrared fluorescence image-guided resection at short, medium and long tissue depths. Naphthalocyanine dyes have high quantum yields and may further act as chelators of radionuclides. Upon injection of the liquid marker, a gel-like depot is formed in situ at the site of injection, wherein the fluorescent dye and radionuclide is retained. The radiolabeled markers were optimized for minimal fluorescence quenching and high retention of the positron emission tomography radionuclide 64Cu. The performance of the radiolabeled marker was tested in vivo in mice, where it displayed high photostability over a period of 4 weeks, and high retention of 64Cu for 48 hours. The retention and biodistribution of 64Cu was quantified via PET/CT, and the fluorescence emission by an in vivo imaging system. The presented data demonstrate proof-of-concept for naphthalocyanine markers as multimodal imaging agents that can bridge the precision of diagnostic imaging into surgical interventions.


Assuntos
Radioisótopos de Cobre , Corantes Fluorescentes , Neoplasias Pulmonares , Imagem Óptica , Tomografia por Emissão de Pósitrons combinada à Tomografia Computadorizada , Compostos Radiofarmacêuticos , Animais , Carboidratos/química , Carboidratos/farmacocinética , Carboidratos/farmacologia , Radioisótopos de Cobre/química , Radioisótopos de Cobre/farmacocinética , Radioisótopos de Cobre/farmacologia , Feminino , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Corantes Fluorescentes/farmacocinética , Corantes Fluorescentes/farmacologia , Neoplasias Pulmonares/diagnóstico por imagem , Neoplasias Pulmonares/cirurgia , Camundongos , Compostos Radiofarmacêuticos/síntese química , Compostos Radiofarmacêuticos/química , Compostos Radiofarmacêuticos/farmacocinética , Compostos Radiofarmacêuticos/farmacologia
19.
Chem Commun (Camb) ; 57(39): 4807-4810, 2021 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-33982709

RESUMO

Probing receptors at the cell surface to monitor their expression level can be performed with fluorogenic dyes. Biotin receptors (BRs) are particularly interesting as they are overexpressed in cancer cells. Herein, to image BRs, we adapted and systematically compared two fluorogenic systems based on BODIPYs: a molecular rotor and a self-quenched dimer that light up in response to high viscosity and low polarity of the membrane, respectively. The fluorogenic dimer proved to be more efficient than the rotor and allowed BRs to be imaged in cancer cells, which can effectively be discriminated from non-cancer cells.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Neoplasias/diagnóstico por imagem , Receptores de Fatores de Crescimento/análise , Animais , Compostos de Boro/síntese química , Linhagem Celular , Corantes Fluorescentes/síntese química , Humanos , Camundongos , Estrutura Molecular , Neoplasias/química
20.
Chem Commun (Camb) ; 57(51): 6229-6232, 2021 Jun 24.
Artigo em Inglês | MEDLINE | ID: mdl-34048518

RESUMO

Tracking the viral progression of SARS-CoV-2 in COVID-19 infected body tissues is an emerging need of the current pandemic. Imaging at near infrared second biological window (NIR-II) offers striking benefits over the other technologies to explore deep-tissue information. Here we design, synthesise and characterise a molecular probe that selectively targets the N-gene of SARS-CoV-2. Highly specific antisense oligonucleotides (ASOs) were conjugated to lead sulfide quantum dots using a UV-triggered thiol-ene click chemistry for the recognition of viral RNA. Our ex vivo imaging studies demonstrated that the probe exhibits aggregation induced NIR-II emission only in presence of SARS-CoV-2 RNA which can be attributed to the efficient hybridisation of the ASOs with their target RNA strands.


Assuntos
COVID-19/diagnóstico , COVID-19/virologia , Corantes Fluorescentes/química , Oligonucleotídeos Antissenso/química , Pontos Quânticos/química , SARS-CoV-2/isolamento & purificação , Espectroscopia de Luz Próxima ao Infravermelho/métodos , Animais , COVID-19/diagnóstico por imagem , COVID-19/metabolismo , Química Click/métodos , Corantes Fluorescentes/síntese química , Humanos , Pulmão/diagnóstico por imagem , Pulmão/metabolismo , Pulmão/virologia , Nanopartículas Metálicas/química , Camundongos , Camundongos Endogâmicos BALB C , Modelos Animais , SARS-CoV-2/genética , SARS-CoV-2/metabolismo
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