ABSTRACT
We synthesized novel boron chelate complexes by the reaction of pyrazoline derivatives and boron trifluoride diethyl etherate followed by a new rearrangement. The structures of the compounds were characterized by IR, NMR and HRMS, especially, a typical compound 3c was confirmed by X-ray single crystal analysis. We proposed a mechanism of the rearrangement. Moreover, the absorption and fluorescence spectroscopy of these compounds were measured.
Subject(s)
Boron/chemistry , Chelating Agents/chemistry , Coordination Complexes/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Methylene Chloride/chemistry , Models, Molecular , Molecular Conformation , Solvents/chemistry , Spectrometry, FluorescenceABSTRACT
A novel pyrazoline-based fluorescent probe, 2-[4-(3,5-diphenyl-4,5-dihydro-pyrazol-1-yl)-benzylidene]-malononitrile, with a simple structure and low detection limit (6.16×10(-6)M) for the detection of hydrazine is designed and synthesized. The probe responds selectively to hydrazine over other molecules with marked fluorescence enhancement. The probe can detect hydrazine effectively at pH 5.0-9.0 with a special emission wavelength at 520nm. Moreover, the probe can be used to detect hydrazine from variety of natural source water.
Subject(s)
Fluorescent Dyes/chemistry , Hydrazines/chemistry , Pyrazoles/chemistry , Water Pollutants, Chemical/analysis , Acetates/chemistry , Acetonitriles/chemistry , Hydrogen-Ion Concentration , Limit of Detection , Magnetic Resonance Spectroscopy , Molecular Structure , Solvents/chemistry , Spectrometry, Fluorescence , Water/chemistry , Water PurificationABSTRACT
A new compound, N-(4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-acrylamide (probe L), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting thiol from other amino acids. On being mixed with thiol in buffered DMSO:HEPES=1:1 solution at pH 7.4, the probe exhibited the blue emission at 474 nm. This probe is very sensitive and displayed a linear fluorescence off-on response to thiol. The fluorescence emission of the probe is pH independent in the physiological pH range. Living cell imaging of HeLa cells confirmed its cell permeability and its ability to selectively detect thiol in cells. The structure of the probe was characterized by IR, NMR and HRMS spectroscopy analysis.
Subject(s)
Fluorescent Dyes/chemistry , Molecular Biology/methods , Sulfhydryl Compounds/analysis , Acrylamides/chemistry , Aniline Compounds/chemistry , Buffers , Chemistry Techniques, Synthetic , Cysteine/chemistry , Dimethyl Sulfoxide/chemistry , Fluorescent Dyes/chemical synthesis , Fluorescent Dyes/toxicity , HEPES/chemistry , HeLa Cells/drug effects , Humans , Hydrogen-Ion Concentration , Magnetic Resonance Spectroscopy , Microscopy, Confocal , Molecular Structure , Permeability , Pyrazoles/chemistry , Sensitivity and Specificity , Spectrometry, Fluorescence , Spectrophotometry, Infrared , Sulfhydryl Compounds/chemistryABSTRACT
A series of 2'-hydroxychalcone derivatives was synthesized and the effects of all the compounds on growth of A549 lung cancer cell were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound possessed the highest growth inhibitory effect and induced autophagy of A549 lung cancer cells.
Subject(s)
Autophagy/drug effects , Chalcones/pharmacology , Drug Discovery , Lung Neoplasms/pathology , Apoptosis/drug effects , Blotting, Western , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Shape/drug effects , Chalcones/chemical synthesis , Chalcones/chemistry , Humans , Inhibitory Concentration 50 , L-Lactate Dehydrogenase/metabolism , Microtubule-Associated Proteins/metabolism , NecrosisABSTRACT
Acrylic acid 3-acetyl-2-oxo-2 H-chromen-7-yl ester (ACA) was rationally designed and synthesized as a simple and effective fluorescent probe for sensing cysteine with high selectivity and naked-eye detection. The probe can detect cysteine by fluorescence spectrometry with a detection limit of 0.657 µM and can be used with calf serum and in live cell imaging. The conjugate addition/cyclization sequence mechanism of the reaction between ACA and cysteine was conï¬rmed by ESI-MS and fluorescence spectra.
Subject(s)
Coumarins/chemistry , Cysteine/analysis , Cysteine/blood , Fluorescent Dyes/chemistry , Animals , Biosensing Techniques/methods , Cattle , Fluorescence , HeLa Cells , Humans , Limit of Detection , Optical Imaging/methods , Spectrometry, Fluorescence/methodsABSTRACT
A novel compound, 2-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl acrylate (probe L), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting glutathione among cysteine, homocysteine and other amino acids. The structures of related compounds were characterized using IR, NMR and HRMS spectroscopy analysis. The probe is a non-fluorescent compound. On being mixed with glutathione in buffered EtOH:PBS=3:7 solution at pH 7.4, the probe exhibited the blue emission of the pyrazoline at 474 nm and a 83-fold enhancement in fluorescence intensity. This probe is very sensitive and displayed a linear fluorescence off-on response to glutathione with fluorometric detection limit of 8.2 × 10(-8)M. The emission of the probe is pH independent in the physiological pH range. Live-cell imaging of HeLa cells confirmed the cell permeability of the probe and its ability to selectively discriminate GSH from Cys and Hcy in cells. The toxicity of the probe was low in cultured HeLa cells.
Subject(s)
Fluorescent Dyes/chemical synthesis , Glutathione/metabolism , Molecular Probe Techniques , Pyrazoles/chemical synthesis , Spectrometry, Fluorescence/methods , Subcellular Fractions/metabolism , Cell Survival/drug effects , Fluorescent Dyes/analysis , Fluorescent Dyes/toxicity , HeLa Cells , Humans , Pyrazoles/toxicity , Subcellular Fractions/drug effectsABSTRACT
This paper presents the preparation of a pyrazoline compound and the properties of its UV-Vis absorption and fluorescence emission. Moreover, this compound can be used to determine Hg(2+) ion with selectivity and sensitivity in the EtOH:H2O =9:1 (v/v) solution. This sensor forms a 1:1 complex with Hg(2+) and shows a fluorescent enhancement with good tolerance of other metal ions. This sensor is very sensitive with fluorometric detection limit of 3.85 × 10(-10) M. In addition, the fluorescent probe has practical application in cells imaging.
Subject(s)
Biosensing Techniques , Fluorescent Dyes/chemistry , Mercury/analysis , Pyrazoles/chemistry , Molecular Structure , Spectrometry, FluorescenceABSTRACT
A new fluorescent probe, N-(4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-2,4-dinitrobenzenesulfonamide (probe 3), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting glutathione among biological thiols in aqueous media. Probe 3 is a nonfluorescent compound. On being mixed with biothiols under neutral aqueous conditions, the 2,4-dinitrobenzenesulfoyl moiety can be cleaved off by glutathione, and the blue emission of the pyrazoline at 464 nm is switched on, with a fluorescence enhancement of 488-fold for glutathione. Furthermore, probe 3 was highly selective for glutathione without interference from some biologically relevant analytes. The detection limit of glutathione was 4.11 × 10(-7) M. The emission of the probe is pH independent in the physiological pH range. Moreover, the probe can be used for fluorescent imaging of cellular glutathione and can be used for detecting glutathione in calf serum.
Subject(s)
Fluorescent Dyes/chemistry , Glutathione/analysis , Pyrazoles/chemistry , Hydrogen-Ion Concentration , Kinetics , Limit of Detection , Microscopy, FluorescenceABSTRACT
A series of novel 1,3,5-triarylpyrazoline derivatives was synthesized by the reaction of chalcone and 5-aryl-2-hydrazinyl-1,3,4-thiadiazole in 43.3-84.7% yields. The structures of compounds were characterized using IR, (1)H NMR and HRMS spectroscopy and X-ray diffraction analysis. The absorption and fluorescence characteristics of the compounds were investigated in dichloromethane, toluene, acetonitrile, N,N-dimethylformamide and tetrahydrofuran. The results showed that the absorption maxima of the compounds vary from 366 to 370nm depending on the group bound to benzene rings. The maximum emission spectra of the compounds in dichloromethane were dependent on nature of groups in benzene ring. Furthermore, the compound 3b can be used to determine Cu(2+) ion with high selectivity and a low detection limit in the DMF:H2O=1:1 (v/v) solution.
Subject(s)
Copper/analysis , Fluorescent Dyes/chemistry , Pyrazoles/chemistry , Cations, Divalent/analysis , Crystallography, X-Ray , Fluorescent Dyes/chemical synthesis , Limit of Detection , Models, Molecular , Pyrazoles/chemical synthesis , Spectrometry, Fluorescence , Spectrophotometry, UltravioletABSTRACT
We develop a pyrazoline-based fluorescent sensor for biological Zn(2+) detection. The sensor shows good binding selectivity for Zn(2+) over competing metal with 40-fold fluorescence enhancement in response to Zn(2+). The new probe is cell-permeable and can be used to detect intracellular zinc ions in living neuron cells.
Subject(s)
Fluorescent Dyes/chemistry , Neurons/chemistry , Pyrazoles/chemistry , Zinc/analysis , Animals , Fluorescent Dyes/chemical synthesis , Molecular Structure , Neurons/cytology , PC12 Cells , Pyrazoles/chemical synthesis , RatsABSTRACT
OBJECTIVE: In order to get the method for improving the salt resistance of Hedysarum polybotrys seeds and seedlings under different salt-alkaline stress, the seed germination and physiological characteristics of H. polybotrys seedlings were studied. METHOD: Several physiological indexes of H. polybotrys seeds under different salt-alkaline stress, such as the germination vigor, germination rate, relative germination rate, relative salt damage rate were measured. And others indexes of the seedlings like chlorophyll contents, soluble protein contents, the permeability of plasmalemma, the activities of POD and SOD were also measured. RESULT: Different salt-alkaline stress decreased the germination rate, vigor of germinate, germination index, while relative salt damage rate increased. With the increased salt-alkaline concentration, the adverse effects became more obvious. The strength of the salts: Na2CO3 > Na2SO4 > NaCl. With the increase of the salt-alkaline concentration, the chlorophyll contents and the soluble protein contents decreased, but the permeability of plasmalemma increased. The change trend of SOD and POD activity was similar, it is increased firstly, and then decreased as the stress intensity extended, the most significant increase of Na2SO4 and Na2CO3 in the concentration of salt-alkaline was 25 mmol x L(-1), but NaCl was 50 mmol x L(-1). CONCLUSION: The seeds and seedlings inhibition of the salts was Na2CO3 > Na2SO4 > NaCl.