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Synthetic method of cyanine dye and application of cyanine dye as acid-base response fluorescent reagent
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A technology of cyanine dyes and synthesis methods, which is applied in organic dyes, fluorescence/phosphorescence, chemical instruments and methods, etc., and can solve the problems of increased photobleaching, high price, and low yield of cyanine dyes
Active Publication Date: 2020-05-05
CHINA THREE GORGES UNIV
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[0003] However, traditional cyanine dyes increase their excitation and emission wavelengths by adding polymethine chains, which can easily cause problems such as decreased photostability and increased photobleaching of the dye, while functionalized cyanine dyes have multiple modification sites, which can be modified by molecular Design and synthesis of different functionalized cyanine dyes
However, the yield of functionalized cyanine dyes is low and the price is high; especially the asymmetric structure of cyanine dyes with large Stokes shift is more difficult to synthesize, which limits its application
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Embodiment 1
[0020] A kind of synthetic method of cyanine dye, the steps are as follows:
[0021] Step1: Under nitrogen protection, dissolve N-acetylglycine (8.54mmol, 1g) in 10mL of DMF, slowly add phosphorus oxychloride (31.3mmol, 2.92mL) dropwise in an ice-salt bath, react at room temperature for 1h, and then react at 90°C 4 hours. After the reaction, the reaction solution was slowly poured into ice water, neutralized by adding sodiumcarbonate, and extracted with ethyl acetate. Purified by column chromatography (EA:PE=2:1), the intermediate 3,5-dichloro-1H-pyrrole-2,4-dicarbaldehyde was obtained with a yield of 69%.
[0022] Step2: Dissolve indole (2.871g, 0.018mol) and iodomethane (7.69g, 0.054mol) in 20mL of acetonitrile, and stir at 80°C for 2h. After cooling to room temperature, filter and wash with cold diethyl ether. 1,2,3,3-Tetramethyl-3H-indole-1-iodide was obtained with a yield of 60%.
[0023] Step3: Dissolve the compound dialdehyde (0.026mol, 0.5g) and 1,2,3,3,-tetrameth...
Embodiment 2
[0026] Under nitrogen protection, 3,5-dichloro-1H-pyrrole-2,4-dicarbaldehyde (0.05g, 2.6mmol) and 1,2,3,3-tetramethyl-3H-indole-1-iodine Compound (0.165g, 5.5mmol) and sodium acetate (0.067g, 8.1mmol) were added to a reaction flask, 2mL of acetic anhydride was added, and reacted at 80°C for 30min. After the reaction, the solvent was removed by rotary evaporation and purified by column chromatography. A cyanine dye was obtained with a yield of 50%.
Embodiment 3
[0028] 3,5-dichloro-1H-pyrrole-2,4-dicarbaldehyde (0.05g, 2.6mmol) and 1,2,3,3-tetramethyl-3H-indole-1-iodide (0.165g , 5.5mmol) was dissolved in 5mL ethanol, and refluxed for 5h. After the reaction was finished, the solvent was removed by rotary evaporation, and the column chromatography was purified (DCM:CH 3 OH=100:1). Yield 55%.
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Abstract
The invention relates to a synthesis and preparation technology of cyanine dyes, in particular to design and synthesis of cyanine dyes with remarkable response to acid and alkali, which detects absorption spectra and fluorescence spectra of the cyanine dyes in PBS solutions with different pH values. Tests find that the absorption and fluorescence spectra of the compound are obviously changed underacidic and alkaline conditions, and the compound is suitable for detecting cancer cells.
Description
technical field [0001] The invention relates to a method for synthesizing fluorescent dyes, in particular to the synthesis and application of cyanine dyes as acid-base responsive fluorescent dyes. Background technique [0002] Cyanine dye is a near-infrared fluorescent dye composed of a heterocycle containing two nitrogen atoms and a polymethine chain. Its emission and absorption wavelengths are between 600-800nm, which can effectively reduce biological samples due to self-absorption and autofluorescence. Background distractions from the body. In addition, cyanine dye has a large molarextinction coefficient, high fluorescencequantum yield, good water solubility, and good biocompatibility, which make it more suitable for application in the analysis of biological environments. In the biological environment, pH is an important parameter, and its change is closely related to the pathological state, and is an important basis for the diagnosis of certain diseases (for example, ...
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