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1.
Article in English | MEDLINE | ID: mdl-26232579

ABSTRACT

Two Schiff-base fluorescent sensors have been synthesized, which both can act as fluorescent probes for Al(3+), upon addition of Al(3+), they exhibit a large fluorescence enhancement which might be attributed to the formation of 1:1 ligand-Al complexes which inhibit photoinduced electron transfer (PET) progress, and that the proposed binding modes of the sensors and Al(3+) are identified by theoretical calculations.


Subject(s)
Aluminum/analysis , Fluorescent Dyes/chemistry , Schiff Bases/chemistry , Cations/analysis , Electron Transport , Fluorescence , Ligands , Models, Molecular , Spectrometry, Fluorescence
2.
Article in English | MEDLINE | ID: mdl-24929313

ABSTRACT

A fluorescence probe, 8-formyl-7-hydroxyl-4-methyl coumarin - (2'-methylquinoline-4-formyl) hydrazone (L) has been synthesized. The chemosensor is found preferential binding to Al(3+) in presence of other competitive ions with associated changes in its optical and fluorescence spectra behavior. Upon addition of Al(3+) to a solution of L, it shows 200-fold enhancement of fluorescence intensity which might be attributed to form a 2:1 stoichiometry of the binding mode of LAl(III) and the chelation enhanced fluorescence (CHEF) process at 479nm in ethanol. The lowest detection limit for Al(3+) is determined as 8.2×10(-7)M.


Subject(s)
Aluminum/analysis , Cations/analysis , Coumarins/chemistry , Fluorescent Dyes/chemistry , Quinolines/chemistry , Coumarins/chemical synthesis , Fluorescent Dyes/chemical synthesis , Limit of Detection , Quinolines/chemical synthesis , Spectrometry, Fluorescence/methods
3.
Article in English | MEDLINE | ID: mdl-24463240

ABSTRACT

A new Schiff-base ligand (1) with good fluorescence response to Al(3+), derived from 2-oxo-quinoline-3-carbaldehyde and nicotinic hydrazide, had been synthesized and investigated in this paper. Spectroscopic investigation revealed that the compound 1 exhibited a high selectivity and sensitivity toward Al(III) ions over other commonly coexisting metal ions in ethanol, and the detection limit of Al(3+) ions is at the parts per billion level. The mass spectra and Job's plot confirmed the 1:1 stoichiometry between 1 and Al(3+). Potential utilization of 1 as intracellular sensors of Al(3+) ions in human cancer (HeLa) cells was also examined by confocal fluorescence microscopy.


Subject(s)
Aluminum/analysis , Hydrazones/chemistry , Quinolines/chemistry , Quinolones/chemistry , Schiff Bases/chemistry , Binding, Competitive , Cell Death , Cell Survival , Dimethyl Sulfoxide/chemistry , Ethanol/chemistry , HeLa Cells , Humans , Intracellular Space/metabolism , Proton Magnetic Resonance Spectroscopy , Solutions , Spectrometry, Fluorescence
4.
Dalton Trans ; 43(7): 2713-7, 2014 Feb 21.
Article in English | MEDLINE | ID: mdl-24352216

ABSTRACT

A new Zn(II) complex was synthesized based on a new Salen-type tetradentate N2O2 bisoxime chelate ligand (H2L) derived from 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) and 1,2-bis(aminooxy)ethane. Single-crystal X-ray diffraction analysis reveals that the structure of the Zn(II) complex features a three-dimensional (3D) cyclic supramolecular system via intermolecular hydrogen bonds. Moreover, the solid-state photoluminescent properties demonstrate that the Zn(II) complex exhibits unusual luminescence mechanochromism tuned by CH3OH.

5.
Article in English | MEDLINE | ID: mdl-24140792

ABSTRACT

A simple Schiff-base receptor 7-methoxychromone-3-carbaldehyde-(pyridylformyl) hydrazone (MCNH) was prepared. It exhibits an "off-on-type" mode with high sensitivity in the presence of Al(3+). This compound could be used as Al(3+) probe in ethanol and it features visible light excitation (433 nm) and emission (503 nm) profiles. Upon binding of Al(3+), a significant fluorescence enhancement with a turn-on ratio over 800-fold was triggered. However, other metal ions had no such significant effect on the fluorescence. MCNH can also be used as a colorimetric chemosensor for Al(3+), which is easily observed from colorless to yellow-green by the naked-eye. The detection limit of MCNH for Al(3+) was as low as 1.9×10(-7) M.


Subject(s)
Aluminum/analysis , Fluorescent Dyes/chemistry , Hydrazones/chemistry , Schiff Bases/chemistry , Cations/analysis , Colorimetry/methods , Limit of Detection , Spectrometry, Fluorescence/methods
6.
J Fluoresc ; 23(6): 1239-45, 2013 Nov.
Article in English | MEDLINE | ID: mdl-23828513

ABSTRACT

In the paper, a novel rhodamine6G based fluorescent chemosensor bearing 3-carbaldehyde chromone was designed and synthesized. According to the fluorescence behavior toward several metal ions, it showed highly selectivity and sensitivity to Zn(II) over other commonly coexistent metal ions (Cu(II), Cd(II), Hg(II), Mg(II), K(I), Pb(II), Fe(III) and Cr(III)) in aqueous environment (pH = 7.4). Meanwhile the binding constant between Zn(II) and chemosensor achieved 6.21 × 10(11) M(-1) in aqueous media. Moreover, according to the Job plot, 1:1 stoichiometry between Zn(II) and sensor was deduced in aqueous media (pH = 7.4). The good selectivity and sensitivity in aqueous media effectively enhanced the application value of the fluorescent chemosensor for Zn(II).


Subject(s)
Fluorescent Dyes/chemistry , Rhodamines/chemistry , Zinc/analysis , Fluorescent Dyes/chemical synthesis , Ions/analysis , Models, Molecular , Molecular Structure , Rhodamines/chemical synthesis , Spectrometry, Fluorescence , Water/chemistry
7.
Dalton Trans ; 40(37): 9370-3, 2011 Oct 07.
Article in English | MEDLINE | ID: mdl-21847485

ABSTRACT

In the article, a novel fluorescent probe for the copper cation based on fluorescence quenching mechanism was designed. It exhibited high selectivity for Cu(II) over other common metal ions in aqueous media. Furthermore the coordination between Cu(II) and the organic molecule sensor fabricated an interesting 1D chain coordination polymer framework.

8.
J Fluoresc ; 21(3): 1091-102, 2011 May.
Article in English | MEDLINE | ID: mdl-21161345

ABSTRACT

A novel Schiff base ligand, chromone-3-carbaldehyde-aminophenazone (L) and its Ln(III) (Ln = La, Yb) complexes were synthesized and characterized by physicochemical methods. The interaction between the ligand, Ln(III) complexes and calf thymus DNA in physiological buffer (pH=7.10) was investigated by using UV-vis spectroscopy, fluorescence spectra, ethidium bromide experiments and viscosity measurements, indicating that the studied compounds can all bind to DNA via an intercalation binding mode and the complexes have stronger binding affinity than the free ligand alone. Furthermore, antioxidant activity of the ligand and its complexes was determined by superoxide and hydroxyl radical scavenging methods in vitro, suggesting that Ln(III) complexes inhibit stronger antioxidant activity than the ligand alone and some standard antioxidants, such as mannitol and vitamin C.


Subject(s)
Antioxidants/chemistry , DNA/chemistry , Lanthanoid Series Elements/chemistry , Schiff Bases/chemistry , Aminopyrine , Chromones/chemistry , DNA/metabolism , Ligands
9.
Eur J Med Chem ; 45(11): 5353-61, 2010 Nov.
Article in English | MEDLINE | ID: mdl-20833453

ABSTRACT

Three novel 2-oxo-quinoline-3-carbaldehyde Schiff-bases and their Cu(II) complexes were synthesized. The molecular structures of Cu(II) complexes were determined by X-ray crystal diffraction. The DNA-binding modes of the complexes were also investigated by UV-vis absorption spectrum, fluorescence spectrum, viscosity measurement and EB-DNA displacement experiment. The experimental evidences indicated that the ligands and Cu(II) complexes could interact with CT-DNA (calf-thymus DNA) through intercalation, respectively. Comparative cytotoxic activities of ligands and Cu(II) complexes were also determined by MTT [3-(4,5-dimethyl-2-thiazoyl)-2,5-diphenyl-2H-tetrazolium bromide] and SRB (sulforhodamine B) methods. The results showed that the three Cu(II) complexes exhibited more effective cytotoxic activity against HL60 cells and HeLa cells than corresponding ligands. Also, CuL(3) showed higher cytotoxic activity than CuL(1) and CuL(2).


Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Copper/chemistry , DNA/chemistry , Quinolines/chemistry , Quinolines/pharmacology , Schiff Bases/chemistry , Cell Line, Tumor , Crystallography, X-Ray , Humans , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Structure , Spectrometry, Fluorescence , Viscosity
10.
Eur J Med Chem ; 44(11): 4477-84, 2009 Nov.
Article in English | MEDLINE | ID: mdl-19577824

ABSTRACT

Two novel 2-oxo-quinoline-3-carbaldehyde (4'-hydroxybenzoyl) hydrazone, thiosemicarbazone ligands and its corresponding Cu(2+) complexes were synthesized, and the two complexes' structures were determined by X-ray single crystal diffraction. The interaction of the two Cu(2+) complexes with calf thymus DNA (CT-DNA) was investigated by electronic absorption spectroscopy, fluorescence spectroscopy and viscosity measurement. The experimental evidences indicated that the two water-soluble Cu(2+) complexes could strongly bind to CT-DNA via an intercalation mechanism. The intrinsic binding constants of complexes 1 and 2 with CT-DNA were 7.31 x 10(6) and 2.33 x 10(6)M(-1), respectively. Furthermore, the antioxidant activities (hydroxyl radical and superoxide) of the two water-soluble metal complexes were determined by hydroxyl radical and superoxide scavenging method in vitro.


Subject(s)
Antioxidants/chemistry , Antioxidants/pharmacology , Copper/chemistry , DNA/metabolism , Quinolones/chemistry , Quinolones/pharmacology , Animals , Cattle , Copper/pharmacology , Crystallography, X-Ray , Fluorescence , Models, Molecular , Molecular Structure , Schiff Bases/chemistry , Schiff Bases/pharmacology , Viscosity
11.
Chem Pharm Bull (Tokyo) ; 56(11): 1528-34, 2008 Nov.
Article in English | MEDLINE | ID: mdl-18981601

ABSTRACT

A novel naringenin Schiff base ligand (1,2-di(4'-iminonaringenin)ethane, H6L) and its three transition metal complexes [Cu(II) complex (1), Zn(II) complex (2), and Ni(II) complex (3)] have been prepared and characterized on the basis of elemental analysis, molar conductivity, 1H-NMR, mass spectra, UV-vis spectra, and IR spectra. The DNA-binding properties of the ligand and its complexes have been investigated by absorption spectroscopy, fluorescence spectroscopy, ethidium bromide (EB) displacement experiments, and viscosity measurement. The results indicated that the ligand and its complexes can bind to DNA. The binding affinity of the Cu(II) complex (1) is higher than that of the ligand and the other two complexes. The intrinsic binding constant (Kb) of the complex (1) is 3.3x10(6). In addition, the suppression ratio for O2-. and HO. was determined. The 50% inhibition obtained for the ligand and its three complexes demonstrates that, compared to the ligand, the complexes exhibit higher antioxidative activity in the suppression of O2-. and HO..


Subject(s)
Antioxidants/chemical synthesis , Antioxidants/pharmacology , DNA/metabolism , Flavanones/chemistry , Flavanones/chemical synthesis , Flavanones/pharmacology , Organometallic Compounds/chemical synthesis , Organometallic Compounds/pharmacology , Antioxidants/metabolism , Copper/chemistry , Ethidium/chemistry , Flavanones/metabolism , Fluorescent Dyes , Hydroxyl Radical/chemistry , Ligands , Nickel/chemistry , Organometallic Compounds/metabolism , Spectrometry, Fluorescence , Spectrophotometry, Atomic , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform Infrared , Viscosity , Zinc Compounds/chemical synthesis
12.
Chem Pharm Bull (Tokyo) ; 56(4): 452-6, 2008 Apr.
Article in English | MEDLINE | ID: mdl-18379089

ABSTRACT

A new coumarin derivative (8-methylcoumaro-4a,10a-pyrone-3-carbaldehyde benzoyl hydrazone) ligand and its novel Cu(II) complex have been synthesized and characterized on the basis of elemental analyses, molar conductivities, (1)H-NMR, IR spectra, UV-visible spectroscopy and thermal analyses. In addition, the interactions of the Cu(II) complex and the ligand with calf-thymus DNA were investigated by spectrometric titrations, ethidium bromide displacement experiments and viscosity measurements. It was found that both the two compounds, specially the Cu(II) complex, strongly bind with calf-thymus DNA, presumably via an intercalation mechanism.


Subject(s)
Copper/chemistry , Coumarins/chemistry , DNA/chemistry , Intercalating Agents/chemical synthesis , Intercalating Agents/pharmacology , Animals , Cattle , Chemical Phenomena , Chemistry, Physical , Coumarins/chemical synthesis , Coumarins/pharmacology , Ethidium/chemistry , Ligands , Magnetic Resonance Spectroscopy , Models, Molecular , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform Infrared , Viscosity
13.
Eur J Med Chem ; 43(8): 1688-95, 2008 Aug.
Article in English | MEDLINE | ID: mdl-18037194

ABSTRACT

Two novel rare earth complexes, Y(III) complex (1) and Eu(III) complex (2), with naringenin-2-hydroxy benzoyl hydrazone ligand were synthesized and characterized. The interaction of the two metal complexes and the free ligand with calf thymus DNA (CT DNA) was investigated by electronic absorption spectroscopy, fluorescence spectroscopy and viscosity measurement. All the experimental evidences indicate that these three compounds can strongly bind to CT DNA via an intercalation mechanism. The intrinsic binding constants of the Y(III) complex (1), Eu(III) complex (2) and the free ligand with CT DNA were 2.1 x 10(4), 8.5 x 10(4) and 1.6 x 10(4) M(-1), respectively. Furthermore, the antioxidant activity of the metal complexes was determined by hydroxyl radical scavenging method in vitro.


Subject(s)
Antioxidants/chemical synthesis , DNA/genetics , Flavanones/chemical synthesis , Hydrazones/chemical synthesis , Antioxidants/chemistry , Electrons , Flavanones/chemistry , Hydrazones/chemistry , Hydroxyl Radical/chemistry , Ligands , Metals, Rare Earth , Molecular Structure , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry , Viscosity
14.
Zhong Nan Da Xue Xue Bao Yi Xue Ban ; 32(1): 144-7, 2007 Feb.
Article in Chinese | MEDLINE | ID: mdl-17344605

ABSTRACT

OBJECTIVE: To observe the curative effect of different physical rehabilitation techniques on patients with lumbar disc herniation. METHODS: Eighty-four patients were randomly divided into Group A, Group B and Group C. Group A were treated with the computerized pelvis traction and ultrashort wave, Group B were treated with the computerized pelvis traction only, while Groups C were treated with the computerized pelvis traction, the ultrashort wave and the traditional Chinese medicine iontophoresis. The outcome was measured with the Japanese Orthopaedics Association Score (JOA score) about lower back pain (LBP). RESULTS: Compared with before the treatment, the JOA score of all the 3 groups increase markedly after the treatment (P<0.001). Compared with group B, the JOA score of Groups A and Group C significantly increased (P<0.05). Compared with Group A, the JOA score in Group C significantly increased (P<0.05). CONCLUSION: The curative effect of comprehensive rehabilitation on lumbar disc herniation is better than that of the single rehabilitation.


Subject(s)
Intervertebral Disc Displacement/therapy , Medicine, Chinese Traditional/methods , Physical Therapy Modalities , Traction/methods , Adult , Combined Modality Therapy , Computers , Female , Humans , Intervertebral Disc Displacement/rehabilitation , Iontophoresis , Male , Middle Aged , Pelvis , Treatment Outcome , Ultrasonic Therapy
15.
Chem Pharm Bull (Tokyo) ; 55(1): 26-8, 2007 Jan.
Article in English | MEDLINE | ID: mdl-17202696

ABSTRACT

A new ligand, naringenin-2-hydroxy benzoyl hydrazone (H(5)L), was prepared by condensation of naringenin with 2-hydroxy benzoyl hydrazine. Its Cu(II), Ni(II), Zn(II) complexes have also been synthesized and characterized on the basis of (1)H-NMR, IR, UV-Vis spectra, elemental analyses, molar conductivity and thermal analyses. The general formula of these complexes was M(H(3)L) [M=Cu(II), Ni(II) and Zn(II)]. In addition, the antioxidant activities (superoxide and hydroxyl radical) of the free ligand and its complexes were determined in vitro. These compounds were found to possess potent antioxidant activity and be better than standard antioxidants like vitamin C and mannitol. In particular, the Cu(II) complex displayed excellent activity on the superoxide radical.


Subject(s)
Antioxidants/chemical synthesis , Antioxidants/pharmacology , Copper/chemistry , Flavanones/chemical synthesis , Flavanones/pharmacology , Nickel/chemistry , Schiff Bases/chemistry , Zinc/chemistry , Antioxidants/chemistry , Flavanones/chemistry , Magnetic Resonance Spectroscopy , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet
16.
Bioorg Med Chem ; 14(17): 6012-21, 2006 Sep 01.
Article in English | MEDLINE | ID: mdl-16781158

ABSTRACT

A new ligand, 6-hydroxy chromone-3-carbaldehyde-(2'-hydroxy) benzoyl hydrazone (L), was prepared by condensation of 6-hydroxy-3-carbaldehyde chromone (CDC) with 2-hydroxy benzoyl hydrazine. Its four rare earth complexes have been synthesized and characterized on the basis of elemental analyses, molar conductivities, mass spectra, 1H NMR, thermogravimetry/differential thermal analysis (TG-DTA), UV-vis spectra, fluorescence spectra, and IR spectra. The general formula of the complexes is [LnL2.(NO3)2].NO3 [Ln=La(1), Sm(2), Dy(3), Eu(4)]. Spectrometric titration, ethidium bromide displacement experiments, and viscosity measurements indicate that Eu(III) complex and ligand, especially the Eu(III) complex, strongly bind with calf-thymus DNA, presumably via an intercalation mechanism. The intrinsic binding constants of Eu(III) complex and ligand with DNA were 3.55 x 10(6) and 1.33 x 10(6)M(-1) through fluorescence titration data, respectively. In addition, the suppression ratio for O2-* and OH* of the ligand and its complexes was studied by spectrophotometric methods. The experimental results show that La (1), Sm (2), and Eu (4) complexes are better effective inhibitor for OH* than that of mannitol. It indicates that the complexes have the activity to suppress O2-* and OH* and exhibit more effective antioxidants than ligand alone.


Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/chemical synthesis , Chromones/chemistry , Chromones/chemical synthesis , DNA/chemistry , Hydrazones/chemistry , Hydrazones/chemical synthesis , Lanthanum/chemistry , Binding, Competitive , DNA/metabolism , Dysprosium/chemistry , Europium/chemistry , Models, Chemical , Molecular Structure , Samarium/chemistry
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