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1.
Bioorg Chem ; 150: 107551, 2024 Jun 20.
Artigo em Inglês | MEDLINE | ID: mdl-38971094

RESUMO

Cancer is the most severe health problem facing most people today. Photodynamic therapy (PDT) for tumors has attracted attention because of its non-invasive nature, negligible adverse reactions, and high spatiotemporal selectivity. Developing biocompatible photosensitizers that can target, guide, and efficiently kill cancer cells is desirable in PDT. Here, two amphiphilic organic compounds, PS-I and PSS-II, were synthesized based on the D-π-A structure with a positive charge. The two AIEgens exhibited near-infrared emission, large Stokes shift, high 1O2 and O2-∙ generation efficiency, good biocompatibility, and photostability. They were co-incubated with cancer cells and eventually accumulated to lysosomes by cell imaging experiments. In vitro and in vivo experiments demonstrated that PS-I and PSS-II could effectively kill cancer cells and sufficiently inhibit tumor growth under light irradiation. PS-I had a higher fluorescence quantum yield in the aggregated state, which made it better for bio-imaging in imaging-guided photodynamic therapy. In contrast, PSS-II with a longer conjugated structure had more ROS generation to kill tumor cells under illumination, and the tumor growth inhibition of mice reached 71.95% during the treatment. No observable injury or undesirable outcomes were detected in the vital organs of the mice within the treatment group, suggesting that PSS-II/PS-I had a promising future in efficient imaging-guided PDT for cancer.

2.
Chem Asian J ; : e202400311, 2024 Jun 24.
Artigo em Inglês | MEDLINE | ID: mdl-38924357

RESUMO

Designing nanomedicines with low toxicity, high targeting, excellent therapeutic effects, and precise release is always the major challenges in clinical cancer treatment. Here, we report a light-enhanced tandem-responsive nano delivery platform COF-B@X-03 for amplified anti-tumor efficiency. Biotin-loaded COF-B@X-03 could precisely target tumor cells, and the azo and hydrazone bonds in it would be depolymerized by the overexpressed azoreductase and acidic microenvironment in hypoxic tumors. In vitro experimental results indicate mitochondrial and endoplasmic reticulum stress caused by COF-B@X-03 under light is the direct cause of tumor cell death. In vivo experimental data prove COF-B@X-03 achieves low oxygen dependent phototherapy, and the maintenance of intratumoral hypoxia provides the possibility for the continuous degradation of COF-B@X-03 to generate more reactive oxygen species for tumor photodynamic therapy by released X-03. In the end, COF-B@X-03 phototherapy group achieves higher tumor inhibition rate than X-03 phototherapy group, which is 81.37%. Meanwhile, COF-B@X-03 significantly eliminates the risk of tumor metastasis. In summary, the construction of this tandem-responsive nano delivery platform provides a new direction for achieving efficient removal of solid tumors in clinical practice.

3.
Chem Asian J ; 19(12): e202400305, 2024 Jun 17.
Artigo em Inglês | MEDLINE | ID: mdl-38651630

RESUMO

Designing and developing photosensitizers with cell membrane specificity is crucial for achieving effective multimodal therapy of tumors compared to other organelles. Here, we designed and screened a photosensitizer CM34 through donor/receptor regulation strategies, and it is able to achieve long-retention cell membrane targeting. It is not only an extremely excellent cell membrane targeted tumor theranostic agent, but also found to be a promising potential immune activator. Specifically, CM34 with a larger intramolecular twist angle is more likely to form larger aggregates in aqueous solutions, and the introduction of cyanide group also enhances its interaction with cell membranes, which were key factors hindering molecular penetration of the cell membrane and prolonging its residence time on the cell membrane, providing conditions for further membrane targeted photodynamic therapy. Furthermore, the efflux of contents caused by cell necrosis directly activates the immune response. In summary, this study realizes to clarify and refine all potential mechanisms of action through density functional theory calculations, photophysical property measurements, and cellular level mechanism exploration, providing a new direction for the clinical development of cell membrane targeted anti-tumor immune activators.


Assuntos
Membrana Celular , Fármacos Fotossensibilizantes , Humanos , Membrana Celular/química , Membrana Celular/metabolismo , Fármacos Fotossensibilizantes/química , Fármacos Fotossensibilizantes/farmacologia , Fármacos Fotossensibilizantes/síntese química , Fotoquimioterapia , Nanomedicina Teranóstica , Antineoplásicos/química , Antineoplásicos/farmacologia , Antineoplásicos/síntese química , Teoria da Densidade Funcional , Neoplasias/tratamento farmacológico , Neoplasias/patologia , Estrutura Molecular
4.
Bioorg Chem ; 143: 107020, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38176374

RESUMO

Abnormally high levels of copper in tumors stimulate malignant proliferation and migration of cancer cells, which proposes a formidable challenge for the thorough therapy of malignant tumors. In this work, we developed a reliable, mitochondria-targeted near-infrared aggregation-induced emission fluorescent probe, TTQ-Th, whose thiourea moiety specifically could recognize mitochondria even both upon loss of mitochondrial membrane potential or in fixated cells, and can capture copper overexpressed by tumor cells, leading to severe copper deficiency. In parallel, TTQ-Th can generate sufficient reactive oxygen species (ROS) upon photoexcitation, while copper deficiency inhibits expression of related copper-based enzymes, resulting in a decline in ATP production. Such energy deficiency, combined with reduced MMP and elevated oxidative stress can lead to critical cell oncosis. Both in vitro and intracellular experiments can illustrate that the elevated ROS has remarkable damage to tumor cells and contributes to the elimination of the primary tumor, while copper deficiency further hinder tumor cell migration and induces G0/G1 cell cycle arrest in a dose-dependent manner, which is an efficacious strategy for the treatment of malignant tumors.


Assuntos
Neoplasias , Fotoquimioterapia , Humanos , Fármacos Fotossensibilizantes/farmacologia , Fármacos Fotossensibilizantes/uso terapêutico , Cobre/farmacologia , Cobre/metabolismo , Fotoquimioterapia/métodos , Espécies Reativas de Oxigênio/metabolismo , Mitocôndrias/metabolismo , Neoplasias/tratamento farmacológico
5.
Talanta ; 270: 125568, 2024 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-38150966

RESUMO

In most biophysiological processes, sulfur dioxide (SO2) is an important intracellular signaling molecule that plays an important role. The change of SO2 in cells are closely related to various diseases such as neurological disorders and lung cancer, so it is necessary to develop fluorescent probes with the ability to accurately detect SO2 during physiological processes. In this work, we designed and synthesized a multifunctional fluorescent probe TIS. TIS has excellent properties such as near-infrared emission, large stokes shift, excellent SO2 detection capabilities, low detection limit, high specificity and visualization of color change before and after reaction. Simultaneously, TIS has low cytotoxicity, good biocompatibility, clear cell imaging capability and mitochondrial targeting ability. In addition, the ability of TIS to be applied to different material surfaces for latent fingerprint fluorescence imaging was also explored. TIS provides an excellent method for the accurate detection of SO2 derivatives and shows great potential applications in near-infrared cellular imaging and latent fingerprint fluorescence imaging.


Assuntos
Corantes Fluorescentes , Dióxido de Enxofre , Humanos , Corantes Fluorescentes/metabolismo , Dióxido de Enxofre/metabolismo , Células HeLa , Mitocôndrias/metabolismo , Imagem Óptica
6.
Small ; 19(50): e2305101, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37635105

RESUMO

Design of effective nanodrugs to modulate the immunosuppression of tumor microenvironment is a desirable approach to boost the clinical tumor-therapeutic effect. Supramolecular nanomicelles PolyMN-TO-8, which are constructed by self-assembling supramolecular host MTX-MPEG2000, guest NPX-2S, and TO-8 through hydrophobic forces, have excellent stability and responsiveness to carboxylesterase and glutathione in turn. In vivo studies validate that PolyMN-TO-8 enable to trigger pyroptosis-mediated immunogenic cell death under laser, avoiding the occurrence of immune dysregulation simultaneously. This therapeutic mode strengthens dendritic cells' maturation and accelerates the infiltration of CD8+ T cells into tumors through moderate activation of pro-inflammatory factors with elimination of immune-escape, ultimately making the tumor inhibition rate as high as 87.44% via synergistic functions of photodynamic therapy, photothermal therapy, chemotherapy, etc. The loss of immune-escape quickens the infiltration of CD8+ T cells into lungs, and further eschews the generation of tumor nodules in it. Chemotherapy, the release of interferon-γ, and immune memory effect also strengthen the defense against metastasis. The generation of O2 catalyzed by PolyMN-TO-8 under laser is indispensable for tumor metastasis inhibition undoubtedly.


Assuntos
Neoplasias Pulmonares , Fotoquimioterapia , Neoplasias de Mama Triplo Negativas , Humanos , Linfócitos T CD8-Positivos , Piroptose , Neoplasias Pulmonares/tratamento farmacológico , Microambiente Tumoral , Linhagem Celular Tumoral , Imunoterapia
7.
Spectrochim Acta A Mol Biomol Spectrosc ; 296: 122657, 2023 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-37003147

RESUMO

High-fidelity imaging and long-term visualization of lysosomes are pivotal factors in the functional assessment of lysosomes, which perform an instrumental role in the physiological activity of cells. However, commercial probes have great limitations in lysosome exploration resulting from the aggregation-caused quenching effect as well as photobleaching instability and small Stokes shift. Therefore, we constructed a novel probe named TTAM with triphenylamine as the matrix and morpholine ring as the targeting group. In contrast with commonly accessible Lyso-tracker Red, TTAM has the merits of aggregation-induced emission effect, extremely high quantum yields (51.57 % solid-state) as well as fluorescence intensity, significant photostability, and high resolution. These properties make it ideal for imaging and activity monitoring lysosomes, which provides a powerful condition for bio-imaging.


Assuntos
Corantes Fluorescentes , Lisossomos , Corantes Fluorescentes/farmacologia , Fluorescência , Diagnóstico por Imagem
8.
Bioorg Chem ; 136: 106558, 2023 07.
Artigo em Inglês | MEDLINE | ID: mdl-37105001

RESUMO

In this study, we identified HIF 1α as a potential target for reversing taxol resistance in lung cancer by combining bioinformatics analysis with pharmacological analysis. Furthermore, pomalidomide derivative LY103 was also be synthesized by introducing an isatin analogue into the amino terminal ofpomalidomide, and it has a broad antitumor spectrum and showed excellent activity against A549/Taxol cells (IC50 = 6.33 ± 0.51 µM). The results of molecular docking showed that not only LY103 was inclined to bind to HIF 1α stably, it could also form multiple hydrogen bonds with VAL376, ASP256, ILE454, and GLU455 of HIF 1α even was reduced to LY103-NH2 by nitroreductase, which was further stabilized the complex formed by them, thereby inhibiting the activity of HIF 1α. LY103 was able to significantly induce DNA damage and inhibit angiogenesis. Concurrently, LY103 activated the immune response, reduced the expression of cytokines TNF-α, IL-6, and IL-1ß, thus might be inhibit the proliferation and metastasis of tumor cells. Pharmacological analysis proved that LY103 led to cell apoptosis through the mitochondrial pathway, and its combination with taxol significantly promoted this process. In general, the consumption of glutathione, the crosstalk of energy metabolism, and the improvement of the tumor microenvironment caused by LY103 eventually led to the decrease of ABCC1 protein expression and the drug resistance was reversed. The rational design of LY103 provided a basis for the application of nitro compounds in the treatment of hypoxic tumors and the reversal of taxol resistance.


Assuntos
Carcinoma Pulmonar de Células não Pequenas , Neoplasias Pulmonares , Humanos , Carcinoma Pulmonar de Células não Pequenas/metabolismo , Linhagem Celular Tumoral , Metabolismo Energético , Neoplasias Pulmonares/patologia , Simulação de Acoplamento Molecular , Paclitaxel/farmacologia , Microambiente Tumoral
9.
Bioorg Chem ; 132: 106361, 2023 03.
Artigo em Inglês | MEDLINE | ID: mdl-36720178

RESUMO

Organelle-targeted photodynamic therapy has been increasingly investigated in recent decades, but little attention has been paid to the damage caused to other non-primary target organelles during the course of action, even though these non-primary target organelles may play a substantial role in inhibiting the growth of cancer cells. In this contribution, we report an AIE-type strong endoplasmic reticulum-targeted luminogen (MTOQS) with a distorted structure, which is efficient in producing ROS both in cellular and non-cellular environment, causing an effective reduction of high levels of GSH and MDA in cancer cells through the efficient accumulation of intracellular ROS, and the levels of ATP, l-lactic acid, anti-apoptotic factor Bcl-2 and apoptotic protein caspase-3 were determined. Through the identification of these markers, it was evidenced that MTOQS-induced dual organelle oxidative stress could diminish the degree of oxidative phosphorylation and glycolysis in cancer cells and trigger an alteration in the culture environment of cancer cells, while causing damage to the endoplasmic reticulum and mitochondria through multiorganelle oxidative stress, turning on the pathway of apoptosis and consequently driving cancer cells to apoptosis.


Assuntos
Estresse do Retículo Endoplasmático , Neoplasias , Espécies Reativas de Oxigênio/metabolismo , Estresse Oxidativo , Retículo Endoplasmático/metabolismo , Mitocôndrias , Apoptose , Neoplasias/metabolismo
10.
Spectrochim Acta A Mol Biomol Spectrosc ; 286: 122013, 2023 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-36274536

RESUMO

The complex environment of solid tumors and the migration of cancer cells are important obstacles to the cure of tumors through conventional therapy. Developing secure and efficient photosensitizers (PSs) is the crux to the application of photodynamic therapy (PDT) in the noninvasive clinical treatment of tumors. Herein, a series of PSs (DCTPys) with the same skeleton structure was designed and prepared. The unique molecular structure of DCTPys endows them with aggregation-induced emission (AIE) property and efficient reactive oxygen species (ROS) generation ability. Interestingly, due to their hydrophilic and lipophilic nature, DCTPys have fine staining and visual identification performance for the plasma membrane. In addition (e.g., MeDCTPy-OH), ROS is produced by MeDCTPy-OH under white light irradiation, which could destroy the completeness of cell membranes and cause cell necrosis. Importantly, morphology imaging of the cell membrane using MeDCTPy-OH enables real-time tracking of cancer cell ablation. This allowed cell necrosis and PDT effects to be observed under mild conditions. We conclude that DCTPys are potential cell membrane-selective PSs for PDT, and it is worth systematically exploring the phototherapeutic effect of these PSs on tumors in vivo.


Assuntos
Neoplasias , Fotoquimioterapia , Humanos , Fármacos Fotossensibilizantes/química , Espécies Reativas de Oxigênio/metabolismo , Medicina de Precisão , Fotoquimioterapia/métodos , Membrana Celular/metabolismo , Neoplasias/patologia , Necrose/tratamento farmacológico , Necrose/metabolismo
11.
J Mol Graph Model ; 116: 108277, 2022 11.
Artigo em Inglês | MEDLINE | ID: mdl-35930820

RESUMO

The multiple thermal decomposition mechanisms of 1,2-propylene glycol are studied through theoretical calculation and experiment, including carbon chain break, dehydrogenation and dehydration mechanism. The wavefunction is employed to analyze the decomposition process from a micro perspective. DLPNO-CCSD(T)/CBS method is engaged in establishing potential energy surface. The results reveal that the dehydration and carbon chain break mechanism are the primary pyrolysis paths, and the former is the dominant pyrolysis mechanism at low temperature, while the latter is applicable at the high temperature. The pyrolysis products are mainly acetaldehyde, propanal and acetone, which is consistent with experimental results. Besides, the comparison results of 1,2-propylene glycol and glycerol pyrolysis products indicate that the increment of hydroxyls are conducive to the generation of carbonyl compounds during the polyol thermal decomposition. This work is aimed to comprehensively investigate the pyrolysis mechanism of 1,2-propylene glycol and provide the valuable thermodynamics and kinetic data for developing efficient polyol pyrolysis technology. Furthermore, it provides a reference for choosing low-toxic tobacco humectant.


Assuntos
Desidratação , Pirólise , Carbono , Teoria da Densidade Funcional , Humanos , Propilenoglicóis
12.
Adv Mater ; 33(43): e2103268, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34545631

RESUMO

Quasi-2D perovskites have long been considered to have favorable "energy funnel/cascade" structures and excellent optical properties compared with their 3D counterparts. However, most quasi-2D perovskite light-emitting diodes (PeLEDs) exhibit high external quantum efficiency (EQE) but unsatisfactory operating stability due to Auger recombination induced by high current density. Herein, a synergetic dual-additive strategy is adopted to prepare perovskite films with low defect density and high environmental stability by using 18-crown-6 and poly(ethylene glycol) methyl ether acrylate (MPEG-MAA) as the additives. The dual additives containing COC bonds can not only effectively reduce the perovskite defects but also destroy the self-aggregation of organic ligands, inducing the formation of perovskite nanocrystals with quasi-core/shell structure. After thermal annealing, the MPEG-MAA with its CC bond can be polymerized to obtain a comb-like polymer, further protecting the passivated perovskite nanocrystals against water and oxygen. Finally, state-of-the-art green PeLEDs with a normal EQE of 25.2% and a maximum EQE of 28.1% are achieved, and the operating lifetime (T50 ) of the device in air environment is over ten times increased, providing a novel and effective strategy to make high efficiency and long operating lifetime PeLEDs.

13.
Phys Chem Chem Phys ; 23(36): 20466-20477, 2021 Sep 22.
Artigo em Inglês | MEDLINE | ID: mdl-34498629

RESUMO

The multiple thermal decomposition channels of glycerol are calculated at the M06-2X-D3/6-311+G(d,p) level. In addition, the CAM-B3LYP and ωB97X-D functionals are used to show the functional influence on the free energy barrier. For the highly competitive primary channels, the DLPNO-CCSD(T)/CBS method is applied for the energy calculations. The results show that the dominant paths are: (1) breakage of the C-C, C-O, and O-H bonds of glycerol successively to form carbonyl and alkene, and then generation of water, formaldehyde, and acetaldehyde; (2) glycerol undergoing an intramolecular dehydration reaction and producing 3-hydroxypropionaldehyde; it has two subsequent reactions: ① C-C bond fracture occurring to form formaldehyde, acetaldehyde, and water; and ② intramolecular dehydration forming acrolein and water. The ΔG1 is 65.6 kcal mol-1 while the ΔG2 is 65.5 kcal mol-1 at 101 kPa and 298 K, and fitted rate equations are 1.09 × 1013 exp[65.6 × 103/RT] s-1 and 8.07 × 1012 exp[65.4 × 103/RT] s-1, respectively. Besides, UPLC and TG-GC/MS are applied complementarily to investigate the anaerobic pyrolysis products of glycerol at different temperatures. The experimental results are consistent with theoretical calculations.

14.
Anal Chim Acta ; 1107: 172-182, 2020 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-32200892

RESUMO

Hydrogen sulfide and cysteine are momentous endogenous regulators of many physiological processes and maintain a dynamic balance of redox in living organisms. To investigate the inter-relationship of them in vivo, there is a pressing need to develop analytical molecular tools to identify related biomolecules. We construct a mitochondria-targeted single fluorescence probe (Mit-CM) for separately and continuously visualizing H2S, Cys and H2S/Cys with multi-response fluorescence signals. Mit-CM has the following advantages: (Ⅰ) colorimetric and ratiometric: two well-separated emission bands can ensure accurate detection of the analyte and significant color changes contribute to rapid identification of the analyte by the naked eye; (Ⅱ) mitochondrial localization: study the physiological functions of H2S and Cys in mitochondria; (Ⅲ) separate and continuous detection of H2S and Cys: reveal the inter-relationship and interconversion of them in biological system. Moreover, the desirable attributes of low cytotoxicity, better biocompatibility and excellent mitochondria enrichment ability indicate that Mit-CM can be employed to achieve detection and observe distribution of H2S, Cys and H2S/Cys in living organism.


Assuntos
Cisteína/análise , Corantes Fluorescentes/química , Sulfeto de Hidrogênio/análise , Mitocôndrias/metabolismo , Animais , Colorimetria , Cumarínicos/síntese química , Cumarínicos/química , Cisteína/química , Corantes Fluorescentes/síntese química , Células Hep G2 , Humanos , Sulfeto de Hidrogênio/química , Indóis/síntese química , Indóis/química , Limite de Detecção , Microscopia Confocal , Microscopia de Fluorescência , Peixe-Zebra
15.
Spectrochim Acta A Mol Biomol Spectrosc ; 225: 117490, 2020 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-31505388

RESUMO

Cysteine (Cys), an important organic small molecule containing sulfhydryl groups, plays paramount functions in human pathologies and physiologies. The detection of Cys in living vivo is essential for studying its roles. Here, we designed and synthesized a novel red-emission fluorescent probe AXPI-Cys with highly sensitivity (LOD = 48.9 ±â€¯0.23 nM), rapidly response (<7 min) and colorimetric for detection cysteine. More importantly, the AXPI-Cys was determined Cys in real cystinuria urine samples for the first time with the satisfactory results (92%-99.96%) and employed for specifically location of endogenous/exogenous Cys in living cancer/normal cells and almost non-toxic, that is very valuable for diagnosis of cystinuria and observation of the distribution of Cys in normal cells. Notably, the AXPI-Cys was applied to imaging Cys in BALB/c nude mice with good biocompatibility and desirable tissue-penetration depth. Owing to the superior capability of AXPI-Cys, it provided a desired method to detect Cys in urine samples and cells, and exhibited munificent potential usage in biosystems and imaging studies in vivo.


Assuntos
Cisteína/análise , Cisteína/urina , Corantes Fluorescentes/química , Animais , Linhagem Celular , Colorimetria , Cistinúria/diagnóstico , Cistinúria/urina , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/toxicidade , Células Hep G2 , Hepatócitos/química , Humanos , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Nus , Estrutura Molecular , Espectrometria de Fluorescência , Espectrofotometria , Espectrofotometria Ultravioleta
16.
ACS Appl Mater Interfaces ; 12(1): 1179-1189, 2020 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-31826613

RESUMO

Purely organic luminescent materials concurrently exhibiting thermally activated delayed fluorescence (TADF) and aggregation-induced emission (AIE) features are in great demand due to their high efficiency in aggregation-state toward efficient nondoped OLEDs. Herein, a class of TADF emitters adopting phenyl(pyridyl)methanone as electron-accepting segments and di(tert-butyl)carbazole and 9,9-dimethyl-9,10-dihydroacridine (or phenoxazine) as electron-donating groups are designed and synthesized. The existence of intramolecular hydrogen bonding is conducive to minish the energy difference between a singlet and a triplet (ΔEst), suppress nonradiative decay, and increase the luminescence efficiency. By using 3CPyM-DMAC as the emitter, the nondoped device via a solution process realize a high current efficiency (CE) and external quantum efficiency (EQE) of 35.4 cd A-1 and 11.4%, respectively, which is superior to that of CBM-DMAC with a CE and EQE of 14.3 cd A-1 and 6.7%. This work demonstrates a promising tactic to the establishment of TADF emitters with AIE features via introducing intramolecular hydrogen bonding.

17.
ACS Sens ; 5(1): 225-233, 2020 01 24.
Artigo em Inglês | MEDLINE | ID: mdl-31854187

RESUMO

Design and synthesis of water-soluble near-infrared (NIR) emissive fluorescent molecules with aggregation-induced emission (AIE) characteristics, perfect signal-to-noise ratio for imaging of organelle, and photodynamic therapy (PDT) functions has received enormous attention. However, the dual-functional NIR AIEgens of high-fidelity tracking lysosome and ablation cancer cells was rarely reported. Herein, a series of AIE luminogens (AIEgens) with a typical AIE effect, good biocompatibility, superior photostability, high brightness, and excellent reactive oxygen species (ROS) generation ability were developed, which had different electronic push-pull strength and conjugate system size in the molecular structure. These AIEgens could specifically "light up" and dynamically long-term track the lysosomes in living cells and zebrafish with ultrahigh colocalization imaging Pearson's correlation coefficients (Rr: 0.9687) and overlap coefficient (R: 0.9967). Additionally, the MPAT of NIR luminescence as a photosensitizer was used for photodynamic ablation of cancer cells, owing to prompt generation of the ROS under green light irradiation (495-530 nm, 10 mW cm-2). Hence, this research not only expands the application range of NIR AIEgens but also provides useful insights into design of split-new method for the treatment of cancer.


Assuntos
Lisossomos/química , Imagem Óptica/métodos , Fotoquimioterapia/métodos , Animais , Humanos , Peixe-Zebra
18.
Analyst ; 144(24): 7390-7397, 2019 Dec 02.
Artigo em Inglês | MEDLINE | ID: mdl-31670325

RESUMO

Real-time monitoring of the cytochrome P450 1A1 (CYP1A1) activity in complex biological systems via a practical tool is highly sought after because of its significant role in the metabolism and bioactivation of various xenobiotics. Herein, according to slight differences in the 3D structure and substrate preference between CYP1A1 and its homologous CYP1A2, a series of novel ratiometric fluorescent probes were designed and synthesized using 1,8-naphthalimide because of its trait of naked-eye visualization and ratiometric fluorescence to achieve the detection of CYP1A1 in biological samples. Among these probes, NEiPN showed good water solubility, highly isoform selectivity and great sensitivity (LOD = 0.04874 nM) for CYP1A1 under simulated physiological conditions, which makes it favorable for monitoring CYP1A1 in vivo. Remarkably, NEiPN exhibited excellent reproducibility when it was used to detect the CYP1A1 content in human liver microsomes, which indicated that it has a great potential for quantifying the CYP1A1 content in real biological samples. Furthermore, NEiPN showed relatively low cytotoxicity and has been successfully applied in biological imaging in living cells and zebrafish. These findings indicate that NEiPN is capable of real-time monitoring of the activity of endogenous CYP1A1, which could provide support for CYP1A1-associated pathological processes.


Assuntos
Citocromo P-450 CYP1A1/análise , Corantes Fluorescentes/química , Naftalimidas/química , Proteínas de Peixe-Zebra/análise , Animais , Linhagem Celular Tumoral , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/toxicidade , Humanos , Limite de Detecção , Microscopia Confocal/métodos , Microscopia de Fluorescência/métodos , Microssomos Hepáticos/metabolismo , Naftalimidas/síntese química , Naftalimidas/toxicidade , Isoformas de Proteínas/análise , Reprodutibilidade dos Testes , Solubilidade , Água/química , Peixe-Zebra
19.
Spectrochim Acta A Mol Biomol Spectrosc ; 216: 365-374, 2019 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-30921659

RESUMO

Cysteine(Cys) is tightly related to physiological and pathological of human, and the imbalance of concentration of cysteine in the intracellular are associated with many diseases. Here, a novel NIR fluorescent probe TCF-Cys was designed and synthesized, and both the optimal excitation and emission wavelength of them were between 650 and 900 nm, that within the "optical window" of biological tissues. In aqueous solution, TCF-Cys, which with an acrylate extremity as a recognizing unit, exhibited excellent "turn-on" fluorescence response for Cys superior to other amino acids and thiols with a limit of detection of 0.1323 µM. Moreover, as an excellent naked-eye colorimetric indicator, TCF-Cys could effectively distinguishing the Cys, Hcy and GSH in aqueous solution through color change. Then, the response mechanism of TCF-Cys for Cys was revealed by TLC, 1H NMR, HPLC, HRMS and DFT calculation. Finally, TCF-Cys was successfully employed to fluorescence specifically map of exogenous and endogenous Cys in living cells and zebrafish with low toxicity.


Assuntos
Cisteína/análise , Corantes Fluorescentes/química , Nitrilas/química , Imagem Óptica/métodos , Animais , Colorimetria/métodos , Cisteína/análogos & derivados , Fluorescência , Células HeLa , Humanos , Limite de Detecção , Modelos Moleculares , Espectrometria de Fluorescência/métodos , Água/análise , Peixe-Zebra
20.
Spectrochim Acta A Mol Biomol Spectrosc ; 210: 281-288, 2019 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-30466034

RESUMO

Fast, highly selective and sensitive thiophenol probes are highly desirable in the field of bioimaging and environmental monitoring. For that, based on the mechanism that thiophenol can effectively cleave the sulfonamide bond selectively, we herein report a dicyanoisophorone-based Red-emitting/NIR probe for thiophenol detection. This probe had some desirable properties such as rapid response, high selectivity and sensitivity, remarkable large Stokes shift (181 nm), Red-emitting/NIR fluorescence region and low LOD value (80 nM, according to 3σ/s). Moreover, this novel Red-emitting/NIR probe can potentially be applied to the detection of thiophenols in real water samples quantitatively and fluorescent imaging in living cells and zebrafishes.


Assuntos
Cicloexanonas/química , Corantes Fluorescentes/química , Nitrilas/química , Fenóis/análise , Espectroscopia de Luz Próxima ao Infravermelho/métodos , Compostos de Sulfidrila/análise , Células A549 , Animais , China , Corantes Fluorescentes/toxicidade , Humanos , Concentração de Íons de Hidrogênio , Lagos/análise , Espectroscopia de Ressonância Magnética , Imagem Molecular/métodos , Sensibilidade e Especificidade , Testes de Toxicidade , Poluentes Químicos da Água/análise , Peixe-Zebra
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