Preparation and application of fluorescent probe capable of being used for distinguishing cysteine/homocysteine and glutathione

A technology for homocysteine ​​and cysteine, which is applied in the field of preparation of fluorescent probes for distinguishing between cysteine/homocysteine ​​and glutathione, achieving fast response, good selectivity, and high resistance to glutathione. The effect of strong interference ability

Inactive Publication Date: 2016-04-27
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Techniques that have been applied so far include high performance liquid chromatography, capillary electrophoresis, electrochem

Method used

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  • Preparation and application of fluorescent probe capable of being used for distinguishing cysteine/homocysteine and glutathione
  • Preparation and application of fluorescent probe capable of being used for distinguishing cysteine/homocysteine and glutathione
  • Preparation and application of fluorescent probe capable of being used for distinguishing cysteine/homocysteine and glutathione

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Experimental program
Comparison scheme
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Embodiment 1

[0027] Embodiment 1: the synthesis of compound 1

[0028] 4-(Dimethylamino)cinnamaldehyde (0.3505g, 2.0mmol), potassium hydroxide (0.2076g, 3.7mmol) and o-hydroxyacetophenone (0.2723g, 2.0mmol) were dissolved in 5 mL of anhydrous methanol, Under the protection of argon, it was heated to reflux for 4h. The reaction was stopped, cooled to room temperature, and the reaction system was poured into 200 g of crushed ice to obtain a brownish-yellow clear solution. Use 4M dilute hydrochloric acid to adjust the pH to about 2-3. A large amount of dark solids precipitate out. Suction filtration, followed by deionized water, 10% sodium bicarbonate solution, and vacuum drying. The crude product was recrystallized from absolute ethanol to obtain 0.3988 g of dark purple needle-like crystals, yield: 68%. The structural characterization of the probe molecule is as follows: 1HNMR (400MHz, CDCl3) δ7.82 (dd, J = 8.0, 1.2Hz, 1H), 7.73 (dd, J = 14.4, 11.2Hz, 1H), 7.47–7.38 (m, 3H), 7.12(d, J=14....

Embodiment 2

[0029] Embodiment 2: the synthesis of compound 2

[0030] Dissolve the product 1 (0.1001 g, 0.3 mmol) obtained in the previous step in 20 mL of methanol and 3 mL of 0.5 M sodium hydroxide solution, stir well to dissolve all the solids, and then add 0.33 mL of 30% hydrogen peroxide solution to it. Raise the temperature to 70°C, react for 3 hours, stop heating, cool to room temperature, filter with suction, wash the crude product twice with cold anhydrous methanol, and dry in vacuo to obtain 0.0544 g of red solid powder, yield: 59%. The structural characterization of the probe molecule is as follows: 1HNMR (400MHz, d6-DMSO) δ7.96 (d, J = 8.3Hz, 1H), 7.42 (dd, J = 17.1, 9.0Hz, 3H), 7.33 (d, J = 8.7Hz, 2H), 7.18(dd, J=7.8, 5.1, 2.8Hz, 1H), 6.98(d, J=16.2Hz, 1H), 6.67(d, J=8.8Hz, 2H), 2.87(s, 6H). HRMS (EI) m / z calculated the molecular weight of [C19H17NO3+H]+: 308.1208, found: 308.1278.

Embodiment 3

[0031] Embodiment 3: the synthesis of probe molecule 3

[0032] Compound 2 (0.0451 g, 0.15 mmol) and 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (NBD-Cl) (0.0307 g, 0.15 mmol) were dissolved in 2 mL of anhydrous Acetonitrile, triethylamine (0.025mL, 0.16mmol) was added, and stirred overnight at room temperature. Stop the reaction, filter with suction, wash twice with absolute ethanol, and dry in vacuo to obtain 0.0371 g of dark brown solid, yield: 56%. The structural characterization of the probe molecule is as follows: 1HNMR (500MHz, d6-DMSO) δ8.61 (d, J = 8.4Hz, 1H), 8.06 (dd, J = 7.9, 1.4Hz, 1H), 7.93–7.81 (m, 3H), 7.60(d, J=8.9Hz, 2H), 7.54(t, J=7.4Hz, 1H), 7.16(d, J=8.4Hz, 1H), 7.00(d, J=15.8Hz, 1H) ,6.71(d,J=9.0Hz,2H),2.99(s,6H).13CNMR(125MHz,d6-DMSO)δ170.06,157.52,155.24,152.67,152.35,145.44,144.83,140.88,138.21,135.81,134.89, 132.66, 130.97, 130.89, 125.77, 125.55, 124.09, 122.53, 118.76, 112.25, 111.44, 109.85, 107.75, 9.27.

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Abstract

The invention discloses a novel compound capable of being used for distinguishing cysteine/homocysteine and glutathione, particularly relates to a preparation method and application of a novel fluorescent probe, and belongs to the technical field of chemical analysis and detection. A molecular structure is shown as the accompanying drawing. The fluorescent probe is used for fluorescent sensing analysis of cysteine, homocysteine and glutathione in environment or biological samples; through the signal differences of output signals after the action with the probe molecules, the cysteine/homocysteine and glutathione can be well distinguished; the selectivity is high; the anti-interference capability is high; the cysteine, the homocysteine and the glutathione can be sensitively and fast distinguished from various amino acids; good application prospects are realized.

Description

technical field [0001] The present invention relates to the technical field of chemical analysis and detection, in particular to a method for preparing a fluorescent probe capable of distinguishing between cysteine / homocysteine ​​and glutathione and the detection of the fluorescent probe in an experimental environment and a cell environment Cysteine, homocysteine ​​and glutathione applications. Background technique [0002] Amino acids are the basic substances that make up proteins and are closely related to the life activities of organisms. Cysteine ​​(Cys), homocysteine ​​(Homocysteine, Hcy) and glutathione (Glutataione, GSH) are common sulfhydryl compounds in organisms, which play an important role in maintaining the normal physiological activities of organisms. effect. Medical research has shown that abnormal physiological concentrations may cause many diseases, such as renal failure, Alzheimer's disease, Parkinson's disease, cardiovascular disease, coronary heart dise...

Claims

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Application Information

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IPC IPC(8): C07D413/12C09K11/06G01N21/64
CPCC07D413/12C09K11/06C09K2211/1007C09K2211/1022C09K2211/1048C09K2211/1088G01N21/6428
Inventor 宋相志刘兴江谌文强齐风佩杨雷杨大雷
Owner CENT SOUTH UNIV
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