Preparation and application of novel cysteine and homocysteine fluorescence probe

A technology of homocysteine ​​and cysteine, which is used in the detection of sulfite ions, the preparation of new cysteine ​​and homocysteine ​​fluorescent probes, and can solve the problem of poor water solubility, etc. problem, to achieve the effect of low cost, good selectivity and simple synthesis

Active Publication Date: 2015-03-25
SUZHOU ROWLAND BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these fluorescent probes have poor water solubility, and cysteine ​​and homocysteine ​​can only be monitored in organic solvents or mixed solvents of organic solvents and water, so that they can be detected in biological samples or in vivo The application in , is limited, so it is meaningful to develop such probes that can be used in aqueous solution or require a small amount of organic solvent

Method used

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  • Preparation and application of novel cysteine and homocysteine fluorescence probe
  • Preparation and application of novel cysteine and homocysteine fluorescence probe
  • Preparation and application of novel cysteine and homocysteine fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the synthesis of 2-compound 2-hydroxyl-6-acetylnaphthalene

[0019] Dissolve 2-methoxy-6-acetylnaphthalene (1.5170g, 7.58mmol) in 6mL of dichloromethane, then add 36% concentrated hydrochloric acid (100mL) in parts by mass, heat to 85°C and reflux for 4h, stop heating and cooling After reaching room temperature, the pH was adjusted to neutral with 50% sodium hydroxide solution, and a solid was precipitated. After filtration, the filter cake was obtained as the product, washed with distilled water three times, and dried in vacuum for 24 hours to obtain a white solid. Yield: 1.3552 g. Yield: 96%

Embodiment 2

[0020] Embodiment 2: the synthesis of probe molecule

[0021] 2-Hydroxy-6-acetylnaphthalene (0.0930g, 0.5mmol) was dissolved in 7mL of anhydrous dichloromethane, then triethylamine (0.1011g, 1mmol) was added, and 2,4-dinitrobenzenesulfonyl chloride (0.1333g, 0.5mmol) was dissolved in 3mL of anhydrous dichloromethane, slowly added dropwise to the reaction solution under an ice-water bath, continued to stir for 1h, stopped the reaction, and evaporated the solvent by column chromatography (eluent, V 二氯甲烷 / V 石油醚 =1 / 1) to obtain the product, dried in vacuo for 24h to obtain a pale yellow solid. Yield: 0.0882 g. Yield: 42.3%. The structure of the probe molecule is characterized as follows: 1 H NMR (400MHz, DMSO) δ9.15(d, J=2.3Hz, 1H), 8.74(s, 1H), 8.59(dd, J=8.7, 2.3Hz, 1H), 8.26(dd, J=14.2, 8.9Hz, 2H), 8.10-8.00(m, 2H), 7.90(d, J=2.4Hz, 1H), 7.43(dd, J=9.0, 2.5Hz, 1H), 2.71(s, 3H). 13 C NMR (126MHz, DMSO) δ198.17, 152.05, 148.63, 148.27, 135.79, 135.47, 134.12, 133.04, 131.70...

Embodiment 3

[0022] Embodiment 3: The present invention: the application of fluorescent probe

[0023] Dissolve the probe in the buffer solution (V 乙腈 / V HEPES =1 / 9, pH=7.4) to prepare 1.0×10 -5mol / L solution, adding amino acids (Asn, Ala, Val, Phe, His, Leu, Ser, Ile, Trp, Lys, Arg, Pro, Gly, Met, Tyr, Glu, Thr) to the solution did not cause fluorescence The addition of amino acids (Cys, Hcy) causes changes in fluorescence, and the fluorescent probe shows high sensitivity and high selectivity for cysteine ​​and homocysteine. When cysteine ​​and homocysteine ​​coexist with interfering substances (Asn, Ala, Val, Phe, His, Leu, Ser, Ile, Trp, Lys, Arg, Pro, Gly, Met, Tyr, Glu, Thr) When , the probe is not affected by interference factors and shows a good anti-interference ability. The probe molecule reacts quickly with sulfite, and the change of fluorescence can be observed within 30 seconds. The probe molecule can selectively recognize sulfite in the pH range of 3 to 10, showing a wide...

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Abstract

The invention discloses a novel compound capable of being applied to fluorescent recognition of cysteine and homocysteine, particularly relates to a preparation method and an application of a novel fluorescence probe, and belongs to the technical field of chemical analysis detection. The molecular structural formula of the novel fluorescence probe is as shown in the description. The fluorescence probe can be applied to fluorescent sensing analysis of cysteine and homocysteine in an environment or a biological sample, and has good selectivity on the cysteine and the homocysteine, high anti-jamming capability, and a good application prospect; and the cysteine and the homocysteine can be sensitively and rapidly distinguished out from a plurality of amino acids.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a novel cysteine ​​and homocysteine ​​fluorescent probe and the application of the fluorescent probe in detecting sulfite ions. 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) and homocysteine ​​(Homocysteine, Hcy) are two amino acids that contain thiol (-SH) and have very little structural difference. They play an important role in physiological processes. Medical research has shown that they It is related to many diseases, such as renal failure, Alzheimer's disease, Parkinson's disease, cardiovascular disease, coronary heart disease, and their content changes in organisms can be used as the basis for the diagnosis of these diseases. Therefore, people have invested a lot of energy to study rapid, sensitive and sel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/28C07C309/73C09K11/06G01N21/64
Inventor 宋相志刘兴江
Owner SUZHOU ROWLAND BIOTECH
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