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A Class of Small Molecule Fluorescent Probes and Their Applications

A fluorescent probe and small molecule technology, applied in the direction of fluorescence/phosphorescence, analytical materials, luminescent materials, etc., to achieve good selectivity, good selectivity, and good biological application prospects

Active Publication Date: 2018-06-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is still a challenge to find fluorescent probes with good fluorescent properties (such as high quantum yield, long wavelength and stable properties, etc.), easy synthesis, and detection of albumin at low concentrations.

Method used

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  • A Class of Small Molecule Fluorescent Probes and Their Applications
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  • A Class of Small Molecule Fluorescent Probes and Their Applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Synthesis of fluorescent probe compound ES1:

[0059]

[0060] Add p-dimethylaminobenzaldehyde (1.49g, 10mmol) and rhodanine (1.33g, 10mmol) into a round bottom flask filled with 10mL of toluene, then add 200mg of ammonium acetate and 1mL of glacial acetic acid as catalysts, and heat up to 115°C Reflux reaction. After reacting for 24 hours, the solvent was evaporated under reduced pressure, and the red solid ES1 (78.25%) was obtained by column separation. 1 H NMR (500MHz, DMSO-D6), δ: 3.04(s, 6H), 4.27(s, 1H), 6.82(t, J=10Hz, 2H), 7.42(t, J=10Hz, 2H), 7.53( s,1H); 13 CNMR(500MHz,DMSO-D6),δ:112.172,117.313,119.757,132.872,133.253,151.759,169.371,176.645,194.973,105.280ppm; TOF MS:m / zcalcd for[M+H] + :265.0469,found:265.0458.

Embodiment 2

[0062] Synthesis of fluorescent probe compound ES2:

[0063]

[0064] Add 4-dimethylaminocinnamaldehyde (1.75g, 10mmol) and rhodanine (1.33g, 10mmol) into a round-bottomed flask with 12mL of toluene, then add 200mg of ammonium acetate and 1mL of glacial acetic acid as catalysts, and heat up to 115 ℃ reflux reaction. After reacting for 24 hours, the solvent was evaporated under reduced pressure and separated by chromatography to obtain dark brown solid ES2 (65.46%). 1 H NMR (500MHz, DMSO-D6), δ: 2.99(s, 6H), 3.10(q, J=25Hz, 1H), 6.72(d, J=5Hz, 3H), 7.21(q, J=45Hz, 2H ),7.51(d,J=10Hz,2H); 13 C NMR(500MHz,DMSO-D6),δ:45.75,111.89,112.10,118.48,123.31,129.41,129.73,130.97,145.41,151.45ppm; TOFMS:m / z calcd for[M+H] + :291.0626,found:291.0618.

Embodiment 3

[0066] Synthesis of fluorescent probe compound ES3:

[0067]

[0068] Add p-dimethylaminobenzaldehyde (1.49g, 10mmol) and 2,4-thiazolidinedione (1.17g, 10mmol) into a round-bottomed flask filled with 10mL of toluene, then add 200mg of ammonium acetate and 1mL of glacial acetic acid as Catalyst, heated to 115 ° C reflux reaction. After reacting for 24 hours, the solvent was evaporated under reduced pressure, and the yellow solid ES3 (85.60%) was obtained by column separation. 1 H NMR (500MHz, DMSO-D6), δ: 3.01(s, 6H), 6.83(d, J=10Hz,

[0069] 2H), 7.42(d, J=5Hz, 2H), 7.67(s, 1H), 12.31(s, 1H); 13 C NMR (500MHz, DMSO-D6), δ: 110.79, 110.91, 111.95, 120.02, 115.63, 119.79, 132.10, 132.91, 133.82, 139.29, 151.44,

[0070] 167.48,168.11ppm; TOF MS:m / z calcd for[M-H] - :247.0541,found:247.0545.

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Abstract

The invention discloses a micromolecule fluorescent probe and application thereof .The fluorescent probe is of the structure shown in the general formula I based on the TICT mechanism .Background fluorescence of the micromolecule fluorescent probe is weak in PBS buffer liquid, and the fluorescence intensity is obviously increased after the probe enters a hydrophobic cavity of human serum albumin HSA .The micromolecule fluorescent probe is good in selectivity and not disturbed by other common amino acid and protein molecules .In addition, response time is short after the probe interacts with HSA, and the probe can achieve specific binding of a FA1 locus of HSA .In the PBS buffer liquid, the fluorescence intensity and the HSA concentration show the good linear relation, and accurate detection can be achieved for human serum albumin HSA .In the real urine testing environment, the fluorescence intensity of the micromolecule fluorescent probe and albumin concentration in urine have the good linear relation, and therefore the micromolecule fluorescent probe has the good biological application prospect.

Description

technical field [0001] The present invention relates to a class of fluorescent probes in the field of fine chemical industry, its preparation method and application, in particular to a class of small molecule fluorescent probes based on TICT mechanism, its preparation method and its application in albumin labeling and quantitative detection. Background technique [0002] Fluorescence detection technology has the advantages of high sensitivity, good selectivity, simple method, in situ and real-time detection, etc., and has become an indispensable detection method in modern biotechnology and life science research. Among protein labeling techniques, fluorescent labeling has obvious advantages over other traditional labeling methods, and has attracted more and more attention from researchers. [0003] Human serum albumin (HSA) is the most abundant protein in serum, and its content in serum is about 30-50 g / L. Due to the dialysis of the kidneys, the albumin content in the urine ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D277/34C07D277/32G01N21/64
CPCC07D277/32C07D277/34C09K11/06C09K2211/1037G01N21/6486
Inventor 杜健军朱涛彭孝军樊江莉
Owner DALIAN UNIV OF TECH
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