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1.
Bioorg Med Chem Lett ; 24(2): 535-8, 2014 Jan 15.
Artículo en Inglés | MEDLINE | ID: mdl-24368214

RESUMEN

A new rhodamine B-based pH fluorescent probe has been synthesized and characterized. The probe responds to acidic pH with short response time, high selectivity and sensitivity, and exhibits a more than 20-fold increase in fluorescence intensity within the pH range of 7.5-4.1 with the pKa value of 5.72, which is valuable to study acidic organelles in living cells. Also, it has been successfully applied to HeLa cells, for its low cytotoxicity, brilliant photostability, good membrane permeability and no 'alkalizing effect' on lysosomes. The results demonstrate that this probe is a lysosome-specific probe, which can selectively stain lysosomes and monitor lysosomal pH changes in living cells.


Asunto(s)
Colorantes Fluorescentes/química , Colorantes Fluorescentes/metabolismo , Lisosomas/metabolismo , Rodaminas/química , Rodaminas/metabolismo , Relación Dosis-Respuesta a Droga , Células HeLa , Humanos , Concentración de Iones de Hidrógeno , Lisosomas/química
2.
Bioorg Med Chem Lett ; 22(2): 844-9, 2012 Jan 15.
Artículo en Inglés | MEDLINE | ID: mdl-22209459

RESUMEN

A series of substituted 5-benzyl-2-phenylpyrazolo[1,5-a]pyrazin-4,6(5H,7H)-dione derivatives was synthesized by one-step reaction of ethyl 3-phenyl-1H-pyrazole-5-carboxylate derivatives and N-arylalkyl-2-chloroacetamide. Structures of the compounds were determined by IR, (1)H NMR and mass spectroscopy. In addition, a representative single-crystal structure was characterized by using X-ray diffraction analysis. The compound 5j could selectively inhibit the growth of H322 lung cancer cells which contain a mutated p53 gene in a dose-dependent manner through inducing apoptosis of cells.


Asunto(s)
Antineoplásicos/farmacología , Apoptosis/efectos de los fármacos , Descubrimiento de Drogas , Pirazinas/farmacología , Pirazoles/farmacología , Antineoplásicos/síntesis química , Antineoplásicos/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Cristalografía por Rayos X , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Modelos Moleculares , Estructura Molecular , Pirazinas/síntesis química , Pirazinas/química , Pirazoles/síntesis química , Pirazoles/química , Estereoisomerismo , Relación Estructura-Actividad
3.
Arch Pharm (Weinheim) ; 345(11): 870-7, 2012 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-22836682

RESUMEN

A series of novel N-aryl-3-aryl-1-arylmethyl-1H-pyrazole-5-carboxamide derivatives 4a-l was synthesized by the reaction of 3-aryl-1-arylmethyl-1H-pyrazole-5-carbonyl chloride with substituted aniline in good to excellent yields. Structures of the compounds were determined by IR, (1) H NMR, and HR-MS spectroscopy. The molecular structure was confirmed by the X-ray crystal analysis of one compound (4j) that was prone to crystallization. These compounds were used to induce mouse osteoblast precursors MC3T3-E1 into osteoblasts and the induction was assessed by alkaline phosphatase (ALP) activity and the gene expression of bone sialoprotein (BSP). The results showed that the compounds 4a-d, 4g, 4h, and 4k could increase the ALP activity in comparison with the negative control group and compound 4h was the most effective one which could induce osteogenesis. Furthermore, mRNA expression of BSP which is a marker of osteogenesis was up-regulated by the compound 4h.


Asunto(s)
Sialoproteína de Unión a Integrina/genética , Osteoblastos/efectos de los fármacos , Osteogénesis/efectos de los fármacos , Pirazoles/farmacología , Células 3T3 , Fosfatasa Alcalina/metabolismo , Animales , Línea Celular , Cristalización , Cristalografía por Rayos X , Espectroscopía de Resonancia Magnética/métodos , Ratones , Osteoblastos/metabolismo , Pirazoles/síntesis química , Pirazoles/química , ARN Mensajero/metabolismo , Espectrofotometría Infrarroja , Regulación hacia Arriba/efectos de los fármacos
4.
J Fluoresc ; 21(4): 1797-804, 2011 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-21380498

RESUMEN

Novel pyrazoly 1,3,4-oxadiazole derivatives were synthesized and characterized by (1)H NMR, IR, HRMS and X-ray diffraction analysis. UV-vis absorption and fluorescence properties of these compounds in different solutions showed that the maximum absorption wavelength was not significantly changed in different solvents; however, maximal emission wavelength was red-shifted with the increase of solvent polarity. Absorption λ(max) and emission λ(max) was less correlated with substituent groups on aryl rings.


Asunto(s)
Oxadiazoles/química , Pirazoles/química , Cristalografía por Rayos X , Fluorescencia , Modelos Moleculares , Estructura Molecular , Fenómenos Ópticos , Oxadiazoles/síntesis química , Espectrometría de Fluorescencia , Espectrofotometría Ultravioleta , Estereoisomerismo
5.
J Fluoresc ; 21(1): 355-64, 2011 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-20890645

RESUMEN

A series of novel 5-aryl-3-ferrocenyl-1-pyridazinyl pyrazoline derivatives was synthesized by the reaction of ferrocenyl chalcone and 3-chloro-6-hydrazinylpyridazine in 10-65% yields. The compounds were characterized using IR, (1)H NMR, HRMS spectroscopic techniques and representative compounds 3c and 4c were assigned based on the X-ray crystallographic structure. The absorption and fluorescence characteristics of the compounds were investigated in chloroform, tetrahydrofuran and acetonitrile, respectively. The results showed that the absorption maxima of the compounds varied from 323 to 327 nm depending on the groups bonded to benzene and pyridazine ring. The maximum emission spectra of compounds in CHCl(3) were dependent on groups in pyridazine ring in which a strong donating-electron group such as propoxyl group on pyridazine ring in N-1 position of pyrazoline made the emission wavelength of 4a-4e small red shifte than that of compounds 3a-3e with chlorine group. The intensity of absorption and fluorescence was also correlated with substituent on aryl ring in C-5 position of pyrazoline. In addition, the absorption spectra of these compounds changed very little, but the fluorescence spectra had much change with increasing solvent polarity.

6.
Bioorg Med Chem Lett ; 20(16): 4766-70, 2010 Aug 15.
Artículo en Inglés | MEDLINE | ID: mdl-20637610

RESUMEN

A series of novel oxime-containing pyrazole derivatives were synthesized by the reaction of ethyl 3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-bromo-1-phenylethanone followed by the reaction with hydroxylamine hydrochloride. The structures were determined by IR, (1)H NMR, HRMS, and X-ray analysis. A dose- and time-dependent inhibition of proliferation was observed in A549 lung cancer cell after compound treatment. Inhibition of growth was mainly attributed to the autophagy induction.


Asunto(s)
Antineoplásicos/síntesis química , Apoptosis/efectos de los fármacos , Autofagia/efectos de los fármacos , Neoplasias Pulmonares/tratamiento farmacológico , Oximas/química , Pirazoles/química , Antineoplásicos/química , Antineoplásicos/uso terapéutico , Línea Celular Tumoral , Cristalografía por Rayos X , Evaluación Preclínica de Medicamentos , Humanos , Neoplasias Pulmonares/patología , Conformación Molecular , Pirazoles/síntesis química , Pirazoles/uso terapéutico , Relación Estructura-Actividad
7.
Bioorg Med Chem Lett ; 19(18): 5325-8, 2009 Sep 15.
Artículo en Inglés | MEDLINE | ID: mdl-19683442

RESUMEN

A series of novel 3-aryl-1-arylmethyl-1H-pyrazole-5-carboxamide derivatives 3a-l, were synthesized by the reaction of 3-aryl-1-arylmethyl-1H-pyrazole-5-carbonyl chloride with substituted amine in excellent yields. The compounds 3e-h could suppress A549 lung cancer cell growth. More interestingly, compounds 3e and 3f might inhibit the A549 cell growth by inducing apoptosis; whereas compounds 3g and 3h with fluorine group might inhibit the A549 cell growth by inducing autophagy.


Asunto(s)
Antineoplásicos/química , Antineoplásicos/farmacología , Apoptosis/efectos de los fármacos , Autofagia/efectos de los fármacos , Carcinoma/tratamiento farmacológico , Neoplasias Pulmonares/tratamiento farmacológico , Pirazoles/química , Pirazoles/farmacología , Antineoplásicos/síntesis química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Humanos , Pirazoles/síntesis química , Relación Estructura-Actividad
8.
Anal Chim Acta ; 788: 177-82, 2013 Jul 25.
Artículo en Inglés | MEDLINE | ID: mdl-23845498

RESUMEN

We designed and synthesized a new pH fluorescent probe, RCE, based on structural changes of rhodamine dye at different pH values. The probe exhibits high selectivity, high sensitivity and quick response to acidic pH, as well as low cytotoxicity, excellent photostability, reversibility and cell membrane permeability. Fluorescence intensity at 584 nm was increased more than 150-fold within pH range 7.51-3.53. This probe has pKa value 4.71, which is valuable for studying acidic organelles. Because of its long absorption and emission wavelengths, RCE can avoid associated cell damage. The probe can selectively stain lysosomes and monitor lysosomal pH changes in living cells.


Asunto(s)
Colorantes Fluorescentes/química , Concentración de Iones de Hidrógeno , Lisosomas/fisiología , Rodaminas/química , Permeabilidad de la Membrana Celular , Supervivencia Celular/efectos de los fármacos , Colorantes Fluorescentes/síntesis química , Colorantes Fluorescentes/farmacología , Células HeLa/efectos de los fármacos , Humanos , Lisosomas/efectos de los fármacos , Macrólidos/farmacología , Espectrometría de Fluorescencia/métodos
9.
Artículo en Inglés | MEDLINE | ID: mdl-22074885

RESUMEN

A series of novel 5-(3-aryl-1H-pyrazol-5-yl)-2-(6-methoxy-3-methylbenzofuran-2-yl)-1,3,4-oxadiazole derivatives has been synthesized from 6-methoxy-3-methylbenzofuran-2-carboxylic acid and ethyl 3-aryl-1H-pyrazole-5-carboxylate. The structures of compounds obtained were determined by IR, (1)H NMR and HRMS spectra. Typically, the spatial structure of compound 7e was determined by using X-ray diffraction analysis. UV-vis absorption and fluorescence spectral characteristics of the compounds in dichloromethane and acetonitrile were investigated. The results showed that the absorption maxima of the compounds vary from 321 to 339 nm depending on the substituents in N-1 position of pyrazole moiety and para position of benzene moiety. The maximum emission spectra of compounds in two different solvents were mainly dependent on groups in N-1 position of pyrazole moiety. The intensity of absorption and fluorescence was also correlated with substituents on the aryl ring bonded to pyrazole moiety. In addition, the absorption and emission spectra of these compounds change with increasing solvent polarity.


Asunto(s)
Benzofuranos/química , Benzofuranos/síntesis química , Fenómenos Ópticos , Oxadiazoles/química , Oxadiazoles/síntesis química , Absorción , Cristalografía por Rayos X , Enlace de Hidrógeno , Conformación Molecular , Espectrometría de Fluorescencia , Espectrofotometría Ultravioleta
10.
Artículo en Inglés | MEDLINE | ID: mdl-22579327

RESUMEN

We describe the development of a rhodamine chromene-based turn-on fluorescence probe to monitor the intracellular Cu(2+) level in living cells. The new fluorescent probe with a chlorine group in chromene moiety exhibits good membrane-permeable property than previous reported because the predicted lipophilicity of present probe 4 is stronger than that of methoxyl substituted probe in our previous work (CLogP of 4: 8.313, CLogP of methoxyl substituted probe: 7.706), and a fluorescence response toward Cu(2+) under physiological conditions with high sensitivity and selectivity, and facilitates naked-eye detection of Cu(2+). The fluorescence intensity was remarkably increased upon the addition of Cu(2+) within 1 or 2 min, while the other sixteen metal ions caused no significant effect.


Asunto(s)
Benzopiranos/química , Calcio/metabolismo , Colorantes Fluorescentes/química , Imagen Molecular/métodos , Rodaminas/química , Absorción , Benzopiranos/síntesis química , Supervivencia Celular , Espacio Extracelular/metabolismo , Células HeLa , Humanos , Concentración de Iones de Hidrógeno , Iones , Cinética , Microscopía Fluorescente , Conformación Molecular , Rodaminas/síntesis química , Espectrometría de Fluorescencia
11.
Spectrochim Acta A Mol Biomol Spectrosc ; 76(5): 531-6, 2010 Sep 01.
Artículo en Inglés | MEDLINE | ID: mdl-20452271

RESUMEN

A series of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives was synthesized by the reaction of 3-substituted-1H-1,2,4-triazole-5-thiol and chloroacetyl ferrocene in the presence of sodium hydride and potassium iodide at reflux. The structures of the new compounds were determined by IR and (1)H NMR spectroscopy and HRMS. The structure of compound 5c was established by X-ray crystallography. UV-vis absorption and fluorescence spectra were recorded in ethanol and dichloromethane. The results showed that compounds 5a-g display similar absorptions ranging from 300 to 500nm and maximal emission bands are about 566nm. The intensity of fluorescence and maximal emission bands are dependent on the groups bonded to triazole rings.


Asunto(s)
Compuestos Ferrosos/química , Triazoles/química , Triazoles/síntesis química , Cristalografía por Rayos X , Metalocenos , Modelos Moleculares , Estructura Molecular , Análisis Espectral/métodos
12.
Eur J Med Chem ; 45(1): 210-8, 2010 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-19879668

RESUMEN

A series of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives was synthesized and characterized by 1H NMR, 13C NMR, IR, HRMS and X-ray diffraction analysis. Preliminary evaluation of biological applications showed that the compounds 6c and 6f inhibit the growth of A549 cells in dosage-dependent manners through cell cycle arrest.


Asunto(s)
Antineoplásicos/síntesis química , Antineoplásicos/farmacología , Pirazinas/síntesis química , Pirazinas/farmacología , Antineoplásicos/química , Ciclo Celular/efectos de los fármacos , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Cristalografía por Rayos X , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Modelos Moleculares , Conformación Molecular , Pirazinas/química
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