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1.
Chem Commun (Camb) ; 56(9): 1349-1352, 2020 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-31904042

RESUMO

Herein, a novel two-photon ratiometric fluorescence assay was proposed for monitoring endogenous steroid sulfatase (STS) activity, which could be applied for the ratiometric imaging of STS activity in the endoplasmic reticulum of living cells and tissues and also could be used to distinguish estrogen-dependent tumor cells from other types of cells.


Assuntos
Corantes Fluorescentes/química , Naftalimidas/química , Esteril-Sulfatase/análise , Animais , Linhagem Celular Tumoral , Retículo Endoplasmático/metabolismo , Corantes Fluorescentes/metabolismo , Corantes Fluorescentes/toxicidade , Células HEK293 , Humanos , Limite de Detecção , Microscopia de Fluorescência/métodos , Simulação de Acoplamento Molecular , Naftalimidas/metabolismo , Naftalimidas/toxicidade , Fótons , Ligação Proteica , Esteril-Sulfatase/metabolismo
2.
Chemistry ; 26(2): 534-542, 2020 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-31638287

RESUMO

The interlocking of ring and axle molecular components in rotaxanes provides a way to combine chromophoric, electron-donor and electron-acceptor moieties in the same molecular entity, in order to reproduce the features of photosynthetic reaction centers. To this aim, the photoinduced electron transfer processes involving a 1,8-naphthalimide chromophore, embedded in several rotaxane-based dyads, were investigated by steady-state and time-resolved absorption and luminescence spectroscopic experiments in the 300 fs-10 ns time window. Different rotaxanes built around the dialkylammonium/ dibenzo[24]crown-8 ether supramolecular motif were designed and synthesized to decipher the relevance of key structural factors, such as the chemical deactivation of the ammonium-crown ether recognition, the presence of a secondary site for the ring along the axle, and the covalent functionalization of the macrocycle with a phenothiazine electron donor. Indeed, the conformational freedom of these compounds gives rise to a rich dynamic behavior induced by light and may provide opportunities for investigating and understanding phenomena that take place in complex (bio)molecular architectures.


Assuntos
Naftalimidas/química , Rotaxanos/química , Éteres de Coroa/química , Transporte de Elétrons , Luz , Fenotiazinas/química , Teoria Quântica , Rotaxanos/síntese química , Espectrometria de Fluorescência
3.
Chem Commun (Camb) ; 55(85): 12865-12868, 2019 Nov 04.
Artigo em Inglês | MEDLINE | ID: mdl-31599283

RESUMO

4-Oxime-1,8-naphthalimide was reported as a novel bioorthogonal turn-on probe based on 1,3-dipolar cycloaddition reactions between in situ generated nitrile oxide and alkenes/alkynes. The resulting isoxazole products displayed dramatically strong fluorescence enhancement upon photoirradiation through isoxazole-oxazole photoisomerization. This new methodology was successfully applied for in situ fluorogenic protein labeling.


Assuntos
Corantes Fluorescentes/química , Naftalimidas/química , Oximas/química , Proteínas/química , Reação de Cicloadição , Coloração e Rotulagem
4.
Inorg Chem ; 58(19): 13150-13160, 2019 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-31539237

RESUMO

Mitochondrial DNA (mtDNA) is an attractive cellular target for anticancer agents in addition to nuclear DNA (nDNA). The cationic platinum(II) complex cis-[Pt(NP)(NH3)2Cl]NO3 (PtNP, NP = N-(2-ethylpyridine)-1,8-naphthalimide) bearing the DNA-intercalating moiety NP was designed. The structure of PtNP was fully characterized by single-crystal X-ray crystallography, NMR, and HRMS. PtNP is superior to cisplatin in both in vitro and in vivo anticancer activities with low systemic toxicity. The interaction of PtNP with CT-DNA demonstrated that PtNP could effectively bind to DNA through both covalent and noncovalent double binding modes. In addition to causing significant damage to nDNA and remarkable inhibition to DNA damage repair, PtNP also distributed in mitochondria, inducing mtDNA damage and affecting the downstream transcriptional level of mitochondrion-encoded genes. In addition, PtNP disturbed the physiological processes of mitochondria by reducing the mitochondrial membrane potential and promoting the generation of reactive oxygen species. Mechanistic studies demonstrate that PtNP induced apoptosis via mitochondrial pathways by upregulating Bax and Puma and downregulating Bcl-2 proteins, leading to the release of cytochrome c and activation of caspase-3 and caspase-9. As a dual-DNA-damage agent, PtNP is able to improve the anticancer activity by damaging both nuclear and mitochondrial DNA, thus providing a new anticancer mechanism of action for the naphthalimide monofunctional platinum(II) complexes.


Assuntos
Antineoplásicos/farmacologia , Dano ao DNA/efeitos dos fármacos , Substâncias Intercalantes/farmacologia , Compostos Organoplatínicos/farmacologia , Animais , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Cristalografia por Raios X , Humanos , Substâncias Intercalantes/química , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos Endogâmicos ICR , Modelos Moleculares , Naftalimidas/química , Naftalimidas/farmacologia , Neoplasias/tratamento farmacológico , Neoplasias/genética , Compostos Organoplatínicos/química , Piridinas/química , Piridinas/farmacologia
6.
Eur J Med Chem ; 181: 111599, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31408807

RESUMO

In this work, five naphthalimide-modified half-sandwich iridium and ruthenium complexes ([(η5-Cpx)Ir(NˆN)Cl]PF6, [(η6-p-cym)Ru(NˆN)Cl]PF6) have been presented. The anticancer activities of the complexes against various cancer cell lines were investigated, among them, complexes 2 and 4 showed better anticancer activity than cisplatin, and their anticancer activity is better than complex 5 without fluorophore. In addition, a series of biological tests of complex 2 were performed using flow cytometry, the results indicated that the complex could induce cell death in a variety of ways. By changing of the ligands, the complexes exhibited different photophysical properties, and the mechanism of action of the complexes entering the cell and inducing apoptosis are different. Moreover, complex 2 successfully targeted mitochondria, while complex 4 targeted lysosomes, causing mitochondrial damage and lysosomal damage to induce apoptosis. Excitingly, complex 2 has good antimetastatic ability to cancer cells. Furthermore, complexes 2 and 4 did not have a significant effect on the NADH binding reaction, but they had a moderate binding ability to BSA.


Assuntos
Antineoplásicos/farmacologia , Complexos de Coordenação/farmacologia , Irídio/farmacologia , Naftalimidas/farmacologia , Rutênio/farmacologia , Antineoplásicos/química , Linhagem Celular Tumoral , Complexos de Coordenação/química , Ensaios de Seleção de Medicamentos Antitumorais , Corantes Fluorescentes/química , Corantes Fluorescentes/farmacologia , Humanos , Irídio/química , Lisossomos/efeitos dos fármacos , Lisossomos/patologia , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/patologia , Naftalimidas/química , Neoplasias/tratamento farmacológico , Neoplasias/patologia , Rutênio/química
7.
Anal Chim Acta ; 1080: 153-161, 2019 Nov 08.
Artigo em Inglês | MEDLINE | ID: mdl-31409465

RESUMO

A red-emitting and ratiometric fluorescence probe 1 for detecting H2O2, based on a styrylnaphthalimide-boronate ester was developed. Upon a H2O2-mediated hydrolysis of boronate ester, probe 1 was transformed to 2 with a ratiometric fluorescence change, decrease at 535 and increase at 640 nm. It was also found that the fluorescent reaction of 1 with H2O2 in solution could be completed within 10 min and the detection limit was estimated to be 0.30 µM. Moreover, this ratiometric change was highly selective for H2O2 over other redox species, metal ions, and anions. Also, this system was found to be capable of detecting H2O2 in the pH range of 6-9. Furthermore, probe 1 was preferentially accumulated into the endoplasmic reticulum (ER) in the live HeLa cells, and an increased H2O2 level in the presence of an ER stress inducer, thapsigargin was revealed.


Assuntos
Ácidos Borônicos/química , Corantes Fluorescentes/química , Peróxido de Hidrogênio/análise , Naftalimidas/química , Estirenos/química , Ácidos Borônicos/síntese química , Estresse do Retículo Endoplasmático/efeitos dos fármacos , Corantes Fluorescentes/síntese química , Células HeLa , Humanos , Limite de Detecção , Microscopia Confocal/métodos , Microscopia de Fluorescência/métodos , Naftalimidas/síntese química , Estirenos/síntese química , Tapsigargina/farmacologia
8.
Chem Commun (Camb) ; 55(74): 11063-11066, 2019 Sep 21.
Artigo em Inglês | MEDLINE | ID: mdl-31454009

RESUMO

Elucidating lysosome polarity effect in complicated biosystems was impeded with the deficiency of lacking multi-disease models for researching the relation between lysosomal polarity and diseases. So far, dissecting the abnormal lysosome polarity in the inflamed and obese living mice has not been realized. To overcome this challenge, a robust probe MND-Lys was proposed for monitoring lysosomal polarity with two-photon emission. Using the probe, monitoring the intrinsic polarity variance in embryos and adult zebrafish has been achieved for the first time. Moreover, besides obviously discriminating tumors from normal ones, the probe also enabled tracing polarity changes in inflammatory and obese mice for the first time. The unique tracking and distinguishing polarity in lysosome make the probe a promising agent for fluorescence visualization studies of LD-lysosome related bioprocess and metabolism diseases.


Assuntos
Corantes Fluorescentes/química , Lisossomos/fisiologia , Naftalimidas/química , Animais , Polaridade Celular , Embrião não Mamífero , Feminino , Fluorescência , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/efeitos da radiação , Corantes Fluorescentes/toxicidade , Células HeLa , Humanos , Inflamação/metabolismo , Camundongos Endogâmicos BALB C , Microscopia Confocal/métodos , Microscopia de Fluorescência/métodos , Naftalimidas/síntese química , Naftalimidas/efeitos da radiação , Naftalimidas/toxicidade , Neoplasias/diagnóstico por imagem , Obesidade/metabolismo , Imagem Óptica/métodos , Fótons , Peixe-Zebra
9.
Molecules ; 24(17)2019 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-31454968

RESUMO

In this work, a highly selective fluorescent chemosensor N-(2-(2-butyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)hydrazine-1-carbonothioyl)benzamide (L) was prepared and characterized. An assay to detect the presence of cobalt(II) ions was developed by utilizing turn-on fluorescence enhancement with visual colorimetric response. Upon treatment with Co2+, a remarkable fluorescence enhancement located at 450 nm was visible to naked eyes accompanied with a distinct color change (from pink to colorless) in a CH3CN/HEPES (4/1, v/v, pH = 7.4) solution due to the formation of a 1:1 complex at room temperature. In addition, the linear concentration range for Co2+ was 0-25 µM with the limit of detection down to 0.26 µM. Thus, a highly sensitive fluorescent method based on chelation-assisted fluorescence enhancement was developed for the trace-level detection of Co2+. The sensor was found to be highly selective toward Co2+ ions with a large number of coexisting ions. Furthermore, the L probe can serve as a fluorescent sensor for Co2+ detecting in biological environments, demonstrating its low toxic properties to organisms and good cell permeability in live cell imaging.


Assuntos
Benzamidas/síntese química , Cobalto/análise , Corantes Fluorescentes/síntese química , Naftalimidas/química , Animais , Benzamidas/química , Benzamidas/farmacologia , Colorimetria , Corantes Fluorescentes/química , Corantes Fluorescentes/farmacologia , Humanos , Limite de Detecção , Modelos Moleculares , Estrutura Molecular
10.
Spectrochim Acta A Mol Biomol Spectrosc ; 223: 117334, 2019 Dec 05.
Artigo em Inglês | MEDLINE | ID: mdl-31284239

RESUMO

Hypochlorous acid (HClO) is an important reactive oxygen species (ROS) and plays a significant role in living organisms. Highly selective and lysosome-targetable probes for sensing hypochlorous acid are rare. In this article, we designed and prepared a new lysosome-targeting and ratiometric fluorescent probe for monitoring the levels of hypochlorous acid. 4-Aminonaphthalimide was chosen as the fluorescent group and (2-aminoethyl) thiourea group was used as a specific recognition group for HClO. A morpholine unit was employed as a lysosome-targeting group. In the absence of HClO the probe underwent intramolecular charge transfer (ICT) and showed a green emission. When excess HClO is present, the ICT process was interrupted which caused a 57 nm blue-shift of fluorescence emission from 533 nm to 476 nm. The ratiometric fluorescent probe showed outstanding selectivity toward HClO over other various bioactive species. Furthermore, the ratiometric fluorescent probe exhibited rapid response time and ability of working in a wide pH range. The linear response of I476nm/I533nm toward HClO was obtained in a concentration range of HClO from 1.0 × 10-6 to 1.0 × 10-4 mol·L-1. The detection limit was estimated to be 8.0 × 10-7 mol·L-1 for HClO. Moreover, the probe showed a perfect lysosome-targeting ability, and has been successfully used to the confocal imaging of HClO in lysosomes of HepG2 cells with little cell toxicity. All of such good properties illustrated that it could be applied to determine HClO at lysosomes in living cells.


Assuntos
Corantes Fluorescentes/química , Ácido Hipocloroso/análise , Lisossomos/metabolismo , Naftalimidas/química , Sobrevivência Celular , Corantes Fluorescentes/síntese química , Células Hep G2 , Humanos , Concentração de Íons de Hidrogênio , Espectrometria de Fluorescência , Fatores de Tempo
11.
Anal Chim Acta ; 1077: 273-280, 2019 Oct 24.
Artigo em Inglês | MEDLINE | ID: mdl-31307719

RESUMO

As a multifunctional signaling molecule, hydrogen sulfide (H2S) plays an essential role in diverse physiological and pathological processes. The two-photon fluorescence probes detecting H2S selectively in vivo could be useful tools to better study the mechanism of diseases. Then, an efficient two-photon lysosome-specific probe 1 has been developed to detect endogenous H2S in living cells and mice. Probe 1 displays excellent properties with 28-fold fluorescence enhancement, marked color changes in naked-eye and fluorescence, high selectivity and sensitivity, and low detection limit (0.22 µM) to H2S. These remarkable properties of probe 1 enable its practical applications in detecting H2S in environment (wastewater) and food (beer). Moreover, as a two-photon probe under near infrared excitation at 790 nm, probe 1 can monitor the level changes of endogenous H2S of lysosome and tumor in living system with good membrane permeability and high imaging resolution. Specially, the probe detecting H2S distribution in lysosome could provide more evidences to explain the association of target-organelle and H2S.


Assuntos
4-Cloro-7-nitrobenzofurazano/análogos & derivados , Neoplasias da Mama/metabolismo , Corantes Fluorescentes/química , Sulfeto de Hidrogênio/análise , Lisossomos/metabolismo , Naftalimidas/química , 4-Cloro-7-nitrobenzofurazano/síntese química , 4-Cloro-7-nitrobenzofurazano/toxicidade , Animais , Cerveja/análise , Linhagem Celular Tumoral , Colorimetria/métodos , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/toxicidade , Humanos , Limite de Detecção , Camundongos Nus , Microscopia Confocal/métodos , Microscopia de Fluorescência/métodos , Naftalimidas/síntese química , Naftalimidas/toxicidade , Fótons , Espectrometria de Fluorescência/métodos , Águas Residuárias/análise
12.
Talanta ; 204: 633-640, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31357346

RESUMO

Fluorogenic substrates are used to visualize the activity of cancer-associated enzymes and to interpret biological events. Certain types of glutathione S-transferase (GST), such as Pi class GST (referred to as GSTP1), are more highly expressed in a wide variety of human cancer tissues compared to their corresponding normal tissues. Pi class GST is thus a cancer cell molecular marker and potential target for overcoming resistance to chemotherapy. Here, we report that 4-bromo-1,8-naphthalimide (BrNaph) is a practical fluorogenic GST substrate. We have found that HE-BrNaph, an N-hydroxyethyl derivative, shows remarkable fluorescence enhancement upon GST-catalyzed SNAr replacement of the bromo group with a glutathionyl group. This substitution was highly selective and occurred only in the presence of GSH/GSTs; no non-enzymatic reaction was observed. We demonstrated that HE-BrNaph allows visualization of GST activity in living cells and enables to distinguish cancer cells from normal cells. Further, various N-substitutions in BrNaph retain susceptibility to enzymatic activity and isozyme selectivity, suggesting the applicability of BrNaph derivatives. Thus, BrNaph and its derivatives are GST substrates useful for fluorescence imaging and the intracellular detection of GSTP1 activity in living cells.


Assuntos
Corantes Fluorescentes/química , Glutationa S-Transferase pi/análise , Naftalimidas/química , Linhagem Celular Tumoral , Ensaios Enzimáticos/métodos , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/toxicidade , Glutationa S-Transferase pi/química , Humanos , Cinética , Microscopia Confocal/métodos , Microscopia de Fluorescência/métodos , Naftalimidas/síntese química , Naftalimidas/toxicidade , Neoplasias/diagnóstico
13.
Analyst ; 144(17): 5075-5080, 2019 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-31305811

RESUMO

Herein, we report the design of a novel fluorescent probe consisting of a naphthalimide fluorophore and a silicone small molecule for the reversible detection of hypochlorous acid and biothiol amino acids. The response mechanism of BSi-1 is based on the concept of the S-based oxidation/reduction. The probe was found to be suitable for imaging HOCl in HeLa, RAW 264.7 cells and zebrafish, demonstrating its utility in biological applications.


Assuntos
Cisteína/análise , Corantes Fluorescentes/química , Glutationa/análise , Homocisteína/análise , Ácido Hipocloroso/análise , Naftalimidas/química , Animais , Cisteína/química , Glutationa/química , Células HeLa , Homocisteína/química , Humanos , Limite de Detecção , Camundongos , Microscopia Confocal/métodos , Microscopia de Fluorescência/métodos , Estrutura Molecular , Oxirredução , Células RAW 264.7 , Peixe-Zebra
14.
Spectrochim Acta A Mol Biomol Spectrosc ; 222: 117242, 2019 Nov 05.
Artigo em Inglês | MEDLINE | ID: mdl-31207489

RESUMO

An effective morpholine-type naphthalimide chemsensor, N-p-chlorophenyl-4-(2-aminoethyl)morpholine-1,8-naphthalimide (CMN) has been developed as a lysosome-targeted fluorometric sensor for trivalent metal ions (Fe3+, Al3+ and Cr3+). Upon the addition of Fe3+, Al3+ or Cr3+ ions, the probe CMN showed an evident naked-eye color changes which pale yellow solution of CMN turned deepened and it displayed turn-on fluorescence response in methanol. CMN showed a significant selective and sensitive toward Fe3+, Al3+ or Cr3+ ions, while there was no obvious behavior to other monovalent or divalent metal ions from the UV-vis and fluorescence spectrum. Based on the Job's plot analyses the 1:1 coordination mode of CMN with Fe3+, Al3+ or Cr3+ was proposed. The limit of detection (LOD) observed were 0.65, 0.69 and 0.68 µM for Fe3+, Al3+ and Cr3+ ions, respectively. The N-atom of morpholine directly involved in complex formation, CMN emitted fluorescence through inhibition of photoinduced electron transfer (PET). This probe exhibited excellent imaging ability for Fe3+, Al3+and Cr3+ ions in living cells with low cytotoxicity. Significantly, the cellular confocal microscopic research indicated that the lysosome-targeted group of morpholine moiety was introduced which realized the capability of imaging lysosomal trivalent metal ions in living cells for the first time.


Assuntos
Alumínio/análise , Cromo/análise , Corantes Fluorescentes/química , Ferro/análise , Lisossomos/química , Animais , Cátions/análise , Linhagem Celular , Humanos , Camundongos , Naftalimidas/química , Imagem Óptica/métodos , Espectrometria de Fluorescência/métodos
15.
Eur J Med Chem ; 177: 401-413, 2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31158753

RESUMO

Small molecules able to bind non-canonical G-quadruplex DNA structures (G4) have been recently tested as novel potential agents for the treatment of prostate cancer thanks to their repression of aberrant androgen receptor gene. However, metastatic castration-resistant prostate cancer (mCRPC), a letal form of prostate cancer, is still incurable. Here we tested two naphthalenediimide derivatives, previously reported as multitarget agents, on a couple of relevant mCRPC cell models (DU145 and PC-3). We showed that these compounds interfere with the RAS/MEK/ERK and PI3K/AKT pathways. Interestingly, both these two biological processes depend upon Epidermal Growth Factor Receptor (EGFR) activation. By means of biological and analytical tools we showed that our compounds are efficient inducers of the structural transition of the EGFR promoter towards a G-quadruplex conformation, ultimately leading to a reduction of the receptor production. The overall result is an interesting cytotoxic profile for these two derivatives. Thanks to their activity at different steps, these compounds can open the way to novel therapeutic approaches for mCRPC that could contribute to escape resistance to selective treatments.


Assuntos
DNA/metabolismo , Quadruplex G/efeitos dos fármacos , Naftalimidas/farmacologia , Linhagem Celular Tumoral , DNA/genética , Ensaios de Seleção de Medicamentos Antitumorais , Receptores ErbB/genética , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Humanos , Ligantes , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Masculino , Naftalimidas/química , Naftalimidas/metabolismo , Neoplasias de Próstata Resistentes à Castração/tratamento farmacológico
16.
Anal Bioanal Chem ; 411(17): 3929-3939, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31119347

RESUMO

The morpholine (ML) group can be used as a targeting unit for lysosomes. Here, a novel turn-off fluorescence probe for the highly selective imaging of peroxynitrite (ONOO-) produced by the endogenous stimulation of lysosomes in living cells is presented. The probe, denoted ML-NAP-DPPEA, comprises ML and 2-(diphenylphosphino)ethylamine (DPPE) groups attached to the fluorophore naphthalimide (NAP). ML-NAP-DPPEA shows excellent properties, including high selectivity for ONOO-, low cytotoxicity, and no interference, leading to low detection limits (17.6 nM). In the presence of ONOO-, the secondary amine group (NH) is oxidized to an electron-withdrawing group (HN → O), which quenches the fluorescence of ML-NAP-DPPEA. This intracellular lysosomal imaging technique was tested, and the results pointed to its potential use as a probe for studying the biological function and pathological effects of ONOO- in subcellular structure. Graphical abstract.


Assuntos
Corantes Fluorescentes/química , Lisossomos/metabolismo , Naftalimidas/química , Ácido Peroxinitroso/metabolismo , Células HeLa , Humanos , Limite de Detecção , Análise Espectral/métodos
17.
Talanta ; 200: 494-502, 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31036214

RESUMO

An effective dithiourea-appended 1,8-naphthalimide fluorescent probe was designed and synthesized. This probe could recognize Hg2+ and Ag+ sensitively and selectively in neutral and alkaline conditions. Moreover, the probe detected Hg2+ alone at pH between 2 and 6. The sensing ability of the probe was explored by UV-vis, fluorescence, FTIR and 1H NMR spectroscopy. The probe was quenched by Hg2+ and Ag+ with 1:1 binding ratios in MeCN/H2O (4/1, v/v) mixed solution with binding constants of 3.76 × 104 L mol-1 and 2.47 × 104 L mol-1, respectively. The linear concentration ranges for Hg2+ and Ag+ were 0-17 µmol L-1 and 0-24 µmol L-1 with detection limits of 0.83 µmol L-1 and 1.20 µmol L-1, respectively, which allowed for the quantitative determination of Hg2+ and Ag+. The new probe, 3a, was successfully applied to the fluorescence imaging of Hg2+ and Ag+ in HepG2 cells, demonstrating its potential application in biological science. Moreover, 3a was used to measure Hg2+ and Ag+ in tap water, drinking water and ultrapure water samples. The recoveries of Hg2+ and Ag+ in water samples were 96-99% and 98-103%, respectively. Therefore, the proposed method showed promising perspectives for its application, aimed at detecting Hg2+ and Ag+ in fluorescence imaging and real water samples.


Assuntos
Corantes Fluorescentes/química , Mercúrio/análise , Naftalimidas/química , Imagem Óptica , Prata/análise , Tioureia/química , Corantes Fluorescentes/síntese química , Células Hep G2 , Humanos , Imagem Molecular , Estrutura Molecular , Células Tumorais Cultivadas
18.
Chem Commun (Camb) ; 55(49): 7053-7056, 2019 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-31143885

RESUMO

A naphthalimide-aminal-based fluorescent donor (NAP-FAD-1) is a pH-sensitive smart donor, which features accelerated FA release at pH 5.0 compared to that at pH 7.4 and fluorescence turn-on readout for facile tracking and quantification of FA release. Confocal imaging studies of HeLa cells co-incubated with Lyso-Tracker Red suggested that its FA release is lysosome-targeted.


Assuntos
Fluorescência , Corantes Fluorescentes/química , Formaldeído/metabolismo , Lisossomos/metabolismo , Naftalimidas/química , Imagem Óptica , Formaldeído/química , Células HeLa , Humanos , Concentração de Íons de Hidrogênio , Lisossomos/química , Estrutura Molecular
19.
Org Biomol Chem ; 17(21): 5349-5366, 2019 05 29.
Artigo em Inglês | MEDLINE | ID: mdl-31099353

RESUMO

A series of novel naphthalimide-benzimidazoles was designed and synthesized for the first time and studied for their effect on antiproliferative activity. Some of these compounds possessed good antitumor activity towards the tested cancer cell lines. Noticeably, (diethylamino)ethyl 15 and (dimethylamino)ethyl 23 derivatives displayed superior antiproliferative activity towards human cancer cell lines with MG_MID GI50 values of 1.43 and 1.83 µM, respectively. Preliminary investigation revealed that compounds 15 and 23 might bind with ct-DNA through the intercalation mode which is responsible for potent bioactivity. Moreover, transportation behaviour indicated that these molecules could efficiently bind to and be carried by bovine albumin, and the hydrogen bonding and hydrophobic interactions played important roles in interaction with serum albumin.


Assuntos
Antineoplásicos/farmacologia , Benzimidazóis/farmacologia , Naftalimidas/farmacologia , Animais , Antineoplásicos/síntese química , Antineoplásicos/química , Benzimidazóis/química , Bovinos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , DNA/química , DNA/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Ligações de Hidrogênio , Interações Hidrofóbicas e Hidrofílicas , Estrutura Molecular , Naftalimidas/química , Albumina Sérica/química , Albumina Sérica/efeitos dos fármacos , Relação Estrutura-Atividade
20.
J Agric Food Chem ; 67(22): 6387-6396, 2019 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-31090403

RESUMO

Insect chitinolytic ß- N-acetylhexosaminidase OfHex1, from the agricultural pest Ostrinia furnacalis (Guenée), is considered as a potential target for green pesticide design. In this study, rational molecular design and optimization led to the synthesis of compounds 15r ( Ki = 5.3 µM) and 15y ( Ki = 2.7 µM) that had superior activity against OfHex1 than previously reported lead compounds. Both compounds 15r and 15y had high selectivity toward OfHex1 over human ß- N-acetylhexosaminidase B (HsHexB) and human O-GlcNAcase (hOGA). In addition, to investigate the basis for the potency of glycosylated naphthalimides against OfHex1, molecular docking and molecular dynamics simulations were performed to study possible binding modes. Furthermore, the in vivo biological activity of target compounds with efficient OfHex1 inhibitory potency was assayed against Myzus persicae, Plutella xylostella, and O. furnacalis. This present work indicates that glycosylated naphthalimides can be further developed as potential pest control and management agents targeting OfHex1.


Assuntos
Inibidores Enzimáticos/síntese química , Proteínas de Insetos/antagonistas & inibidores , Inseticidas/síntese química , Mariposas/enzimologia , Naftalimidas/síntese química , beta-N-Acetil-Hexosaminidases/antagonistas & inibidores , Animais , Avaliação de Medicamentos , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Glicosilação , Humanos , Proteínas de Insetos/química , Inseticidas/química , Inseticidas/farmacologia , Cinética , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Mariposas/efeitos dos fármacos , Naftalimidas/química , Naftalimidas/farmacologia , beta-N-Acetil-Hexosaminidases/química
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