Microwave-assisted solvent-free synthesis and spectral properties of some dimethine cyanine dyes as fluorescent dyes for DNA detection

Zhang, Xianghan; Wang, Lanying; Nan, Zhi-Xiang; Tan, Shi-Huan; Zhang, Zuxun

doi:10.1016/j.dyepig.2008.02.010

Cited by 52 publications

(25 citation statements)

References 21 publications

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“…Over the past decade, fluorescent dyes are used widely in bioimaging, especially for DNA detection [1,2] due to the significant advantages of fluorescent dyes, such as relative stability, low aggregation and high affinity for some biological molecules [3][4][5]. However, in order to decrease the fluorescent background interference caused by the labeled organism, the stronger fluorescent intensity is required [6,7].…”

Section: Introductionmentioning

confidence: 99%

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Fei

Lin

et al. 2015

J Fluoresc

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A novel fluorescent dye, 1-(6-carboxyhexyl)-4-(2-(9-ethyl-carbazole-3-yl) vinyl) quinolizinium bromide, was synthesized, and its structure was characterized by (1)H NMR, (13)C-NMR, IR and HRMS. The spectra properties of this dye in different solvents and under different pH value were invest'igated preliminarily, and the results showed that its fluorescent properties was affected by the polarity and the dipole moment of the solvent. The photostability and thermostability test results showed that its photoreduction rate constant was 1.64 × 10(-5) mol/Min and its fluorescent intensity decreased little after heating at 80 °C for 6 h, suggesting the dye was quite stable. In the labeling experiment of BSA and DNA with the dye, the fluorescent all intensity increased with the addition of BSA and DNA. Specially, the dye showed an excellent turn-on effect upon binding with ctDNA.

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Section: Introductionmentioning

confidence: 99%

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Fei

Lin

et al. 2015

J Fluoresc

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“…Our previous efforts have been devoted to developing the synthesis and applications of cyanine dyes. [13][14][15][16] There are many literatures on the synthesis and applications of benzoindole pentamethine cyanine dyes. [17][18] However, the X-ray single crystal structure, the aggregation behavior of benzoindole pentamethine cyanine dyes in aqueous media and their thermodynamic characteristics have seldom been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, Spectral and Thermodynamic Properties of One Benzoindole Pentamethine Cyanine Dye

Zhang

Zhao

et al. 2013

J Chinese Chemical Soc

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One benzoindole pentamethine cyanine dye was synthesized and characterized by 1 H NMR, IR, MS and UV-Vis spectra. The UV-Vis absorption and fluorescence spectra of the dye in chloroform, dimethyl sulfoxide, acetone, ethanol and methanol were investigated, and the l max of the dye was in the region 682.0-689.0 nm with large molar extinction coefficients (e > 10 5 M -1 cm -1 ) in different solvents. The structure of the dye was also characterized and analyzed by X-ray diffraction. Crystallographic data revealed that the dye belonged to orthorhombic, with space group P2 1 2 1 2 1 , a = 10.059(2) Å, b = 15.098(4) Å, c = 24.989(6) Å, V = 3794.8(15) Å 3 , Z = 4. The C-H ¼ F intermolecular hydrogen bonds were displayed in the molecular system, which were effective in the molecular packing. The aggregation behavior and thermodynamic properties of the dye in aqueous methanol solution were also studied by means of UV-Vis spectroscopy methods. The results indicated that the dye existed monomer-dimer equilibrium in aqueous methanol solutions. The fundamental properties of the dye, such as the dimeric association constant K D , the dimeric free energy DG D , the dimeric entropy DS D , and the dimeric enthalpy DH D were determined. The DH D of the dye was -46.0 kJ mol -1 .

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“…The synthesis of dyes 14e20 followed the procedure [29] with slight modification. Various quaternary salts A (1 mmol), aromatic aldehydes B (1 mmol), 15 temperature in a dried round-bottom flask (50 mL) equipped with a reflux condenser capped with an anhydrous CaCl 2 drying tube.…”

Section: Measurementsmentioning

confidence: 99%

“…In a preceding paper, we reported the synthesis of a series of dimethine cyanine dyes with indole nucleus, and investigated both experimentally and theoretically the absorption and fluorescence properties of these dyes, and their fluorescence maxima were located at 513e549 nm in methanol [28]. We also synthesized and studied a series of dimethine cyanine dyes as fluorescent dyes for DNA or BSA detection, and it was found that significant enhancement of the fluorescent quantum yield was observed for all the dyes in the presence of DNA [29]. Present work is a continuation of researches aimed on the search of cellpermeant dimethine cyanine dyes with attractive spectralluminescent characteristics for biomedical applications, particularly for the usage as fluorescent probes in living cells imaging technology and flow cytometry.…”

Section: Introductionmentioning

confidence: 97%

Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry

et al. 2014

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Microwave-assisted solvent-free synthesis and spectral properties of some dimethine cyanine dyes as fluorescent dyes for DNA detection

Cited by 52 publications

References 21 publications

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Synthesis, Crystal Structure, Spectral and Thermodynamic Properties of One Benzoindole Pentamethine Cyanine Dye

Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry

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