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A kind of fluorescent probe and its preparation method and application

A fluorescent probe and selected technology, applied in the field of analytical chemistry, can solve the problems that fluorescent probes are not suitable for detecting high-concentration target molecules, inaccurate fluorescent signal results and false positive results, etc., and achieve detection conditions that are easy to implement and photostable Good performance and fast response time

Active Publication Date: 2021-12-07
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First, the small change in the intensity of the fluorescent signal before and after the detection leads to inaccurate results or usually causes false positive results due to non-specific luminescence due to other reasons
Especially in a complex body fluid environment, it is very challenging to detect formaldehyde accurately, sensitively and specifically under the influence of various factors
Second, traditional fluorescent molecules have the effect of fluorescence quenching caused by aggregation, so their corresponding fluorescent probes are not suitable for detecting high-concentration target molecules
Third, formaldehyde is easily soluble in the aqueous phase system and polymerizes to form paraformaldehyde. None of the existing fluorescent probes can detect these two forms of formaldehyde at the same time.

Method used

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  • A kind of fluorescent probe and its preparation method and application
  • A kind of fluorescent probe and its preparation method and application
  • A kind of fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Synthesis of embodiment 1 fluorescent probe compound HT-C1

[0072]

[0073] (1) Synthesis of Intermediate 2

[0074] Potassium allyltrifluoroborate (65mg, 0.44mmol) was dissolved in 7N NH 3 solution in MeOH (2.0 mL) and stirred at room temperature for 15 min. Compound 1 (93 mg, 0.22 mmol) was dissolved in 7N NH 3 MeOH solution (5.0 mL) and CH 2 Cl 2 (2.0 mL) in the mixed solution. The two reactant solutions were combined and stirred for 12 hours. Pour the reactants into saturated NaHCO 3 aqueous solution (50 mL) and extracted with ethyl acetate. The combined organic fractions were dried (anhydrous Na 2 SO 4 ), filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography using petroleum ether / ethyl acetate (3 / 1, v / v) to afford compound 2 as a yellow powder (96 mg, 95%). 1 H NMR (400MHz, CDCl 3 ,298K),δ(ppm):8.60-7.61(m,2H),7.14-6.80(m,13H),6.62(d,J=8.5Hz,4H),5.41(d,J=53.3Hz,1H) , 5.13 (d, J=66.0Hz, 2H), 4.22-3...

Embodiment 2

[0077] Synthesis of embodiment 2 fluorescent probe compound HT-C2

[0078]

[0079] Synthesis of Probe Molecule HT-C2

[0080] Compound 2 (23 mg, 0.050 mmol) was dissolved in MeOH (1.0 mL). To this solution, compound 10 (3.3mg, 0.017mmol) and sodium cyanoborohydride (NaBH 3 CN, 1.1 mg, 0.017 mmol). After reacting at room temperature for 12 hours, the reactant was poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic fractions were washed with anhydrous Na 2 SO 4 Dry, filter and concentrate under reduced pressure. The crude residue was purified by high performance liquid chromatography (HPLC) to yield the target compound HT-C2. 1 H NMR (600MHz, (CD 3 ) 2SO,298K),δ(ppm):9.50(d,J=52.3Hz,1H),7.89(s,1H),7.39(s,1H),7.24(s,1H),7.16(t,J=7.4 Hz,1H),7.11(t,J=7.3Hz,1H),7.04(s,1H),7.00-6.95(m,1H),6.87(t,J=5.7Hz,1H),6.83(t,J =5.7Hz,1H),6.70(d,J=8.8Hz,1H),6.65(d,J=8.8Hz,1H),6.54(s,1H),5.41(s,1H),4.97(t,J =14.1Hz,1H),4....

Embodiment 3

[0081] Synthesis of embodiment 3 fluorescent probe HT-1:

[0082]

[0083] Synthesis of fluorescent probe HT-1

[0084] Compound 2 (45 mg, 0.097 mmol) was dissolved in MeOH (1.0 mL). To this solution, compound 3 (7.0mg, 0.020mmol) and sodium cyanoborohydride (NaBH 3 CN, 1.3 mg, 0.020 mmol). After reacting for 12 hours, the reactant was poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic fractions were dried (anhydrous Na 2 SO 4 ), filtered and concentrated under reduced pressure. The crude residue was purified by high performance liquid chromatography (HPLC) to give the target compound HT-1 (11 mg, 71%). 1 H NMR (600MHz, (CD 3 ) 2 SO,298K),δ(ppm):9.72(d,J=98.6Hz,1H),7.97(d,J=6.4Hz,1H),7.50(s,1H),7.23(d,J=20.8Hz, 1H), 7.14(dt, J=16.8, 7.2Hz, 1H), 7.07-6.96(m, 1H), 6.85(dd, J=24.9, 8.7Hz, 1H), 6.67(dd, J=31.9, 8.7Hz ,1H),6.56(s,1H),5.41(s,1H),4.97(t,J=15.1Hz,1H),4.58(s,1H),4.32-4.08(m,1H),3.89(d, J=49.5Hz...

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Abstract

A fluorescent probe and its preparation method and application relate to a formaldehyde detection fluorescent probe and its preparation method and application, belonging to the technical field of analytical chemistry. This kind of fluorescent probe is based on aggregation-induced luminescent dyes and has a double quenching mechanism, which makes the detection background lower, the signal-to-noise ratio is enhanced, and the simultaneous detection of free and polymerized formaldehyde is realized for the first time. The formaldehyde fluorescent probe of the present invention can resist aceglyoxal, glutathione, benzaldehyde, D-glutamic acid, L-alanine, L-cysteine, hydrogen peroxide, acetaldehyde, glyoxal, Glycine and other molecular interference, good selectivity, high accuracy. In addition, the formaldehyde fluorescent probe of the present invention can also detect biological samples (serum, urine), which embodies formaldehyde fluorescence imaging in the complex environment of body fluids, and has potential practical application value in the fields of environmental monitoring and biomedicine.

Description

technical field [0001] The invention relates to a class of fluorescent probes and a preparation method and application thereof, belonging to the technical field of analytical chemistry. Background technique [0002] Formaldehyde is an active carbonyl compound that can react with amino groups at the ends of proteins and DNA to destroy their original biological activity. Exposure to exogenous formaldehyde is mostly through inhalation or ingestion. Endogenous formaldehyde is a product of human physiological activities, which is mediated by enzyme systems, such as semicarbazide-sensitive amine oxidase (SSAO) and lysine Specific histone demethylase 1 (LSD1). In a healthy human brain, an appropriate amount of formaldehyde plays an important role in human memory storage, retention and long-term memory retrieval. However, excessive formaldehyde will not only damage the central nervous system, weaken people's memory and cognitive ability, cause neuron degeneration, such as Alzheime...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/64C07C217/58C07C213/02C09K11/06G01N21/64
CPCC07C217/58C07C217/64C09K11/06G01N21/6428G01N2021/6432
Inventor 张崇敬王福嘉杨海涛
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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