Aldehyde-containing metal iridium complexes and their application in the detection and distinction of homocysteine ​​and cysteine

Abstract

The invention discloses an aldehyde group-containing metal iridium complex and an application thereof in detection and distinction of homocysteine and cysteine; the metal iridium complex has the structural formula defined in the specification, wherein R is H, phenyl or C1-C12 alkyl. The aldehyde group in the obtained metal iridium complex can undergo a reaction with homocysteine to generate thiazan, and carboxyl (COOH) on the generated thiazan can form hydrogen bonds with amino (NH2) in the metal iridium complex, so that the complex can give out light to generate a great blue shift and makes light increased, but cysteine does not have the phenomenon; therefore, the metal iridium complex can be made into a fluorescence probe for detection and distinction of homocysteine and cysteine, and has important significance on biological analysis and detection.

Description

technical field

[0001] The invention belongs to the field of chemical materials and biological analysis and detection, and in particular relates to a kind of metal iridium complex containing aldehyde groups and its application in detecting and distinguishing homocysteine ​​and cysteine. Background technique

[0002] Among many amino acids, homocysteine ​​(Hcy) and cysteine ​​(Cys) have very special effects due to their sulfhydryl groups. The level of Hcy in plasma is a symbolic indicator of diseases such as cardiovascular diseases and Alzheimer's disease; and when Cys plays an important role in the folding of proteins, it has a certain detoxification effect, and can participate in preventing cell aging and improving skin quality. It may cause a variety of diseases, so the detection of homocysteine ​​(Hcy) and cysteine ​​(Cys) is very important. Among the existing methods for the determination of homocysteine ​​(Hcy) and cysteine ​​(Cys), the fluorescence detection method ha...

Examples

Embodiment 1

[0014] 1. Under nitrogen protection, add 0.3 g (1 mmol) iridium trichloride and 0.4 g (2.5 mmol) 4-(2-pyridyl)-benzaldehyde (Hpba) into a 50 mL two-necked bottle, and then Add 15 mL of deoxygenated ethylene glycol ether / H 2 O (3:1, v / v), reflux for 24 h, cool to room temperature, filter and wash with ethanol several times, then dissolve the solid with a mixed solution of dichloromethane / methanol (1:1, v / v) and depressurize The solvent was spin-dried to obtain an orange-red solid [(Hpba) 2 IrCl] 2 180 mg, yield 55%. 1 HNMR (400MHz, DMSO, MeSi); δ (ppm): 9.88 (d, 2H J=8 Hz), 9.66 (s, 2H), 9.59 (d, 4HJ=8 Hz), 8.48 (d, 2H J=8 Hz), 8.40 (d, 2H J=8 Hz), 8.26 (m, 2H) , 8.17 (m, 2H), 8.04 (m, 4H) ,7.74 (m, 2H), 7.65 (m, 2H), 7.43 (dd, 4H), 6.76 (s, 2H), 6.15 (s, 2H).

[0015] 2. Add 30 mg of [(Hpba) 2 IrCl] 2 with 10 mg of bpy-NH 2 Dissolve in 8 mL of dichloromethane / methanol mixed solution (1:1, v / v), reflux for 12 h under nitrogen protection, cool to room temperature, and di...

Embodiment 2

[0017] (1) At a concentration of 2.0×10 -5 Add a series of contents of homocysteine ​​and cysteine ​​to the acetonitrile-Tris buffer solution (4:1, v / v) of the complex Ⅰ in mol / L, and measure the concentration of homocysteine ​​and cysteine ​​at 200-600 UV-Vis absorption spectrum in the nm wavelength range, see the results figure 1 , where A is homocysteine ​​and B is cysteine.

[0018] Such as figure 1 As shown, the absorbance value of complex Ⅰ increases with the increase of amino acid content at the wavelength of 255nm; but the difference between the ultraviolet absorption spectra of homocysteine ​​and cysteine ​​is not significant.

[0019] (2) At a concentration of 2.0×10 -5 A series of homocysteine ​​and cysteine ​​were added to the acetonitrile-Tris buffer solution (4:1, v / v) of the complex Ⅰ in mol / L, and the concentrations of homocysteine ​​and cysteine ​​were respectively determined at 400-800 Fluorescence spectra in the nm wavelength range, see results in fi...

technical field

[0001] The invention belongs to the field of chemical materials and biological analysis and detection, and in particular relates to a kind of metal iridium complex containing aldehyde groups and its application in detecting and distinguishing homocysteine ​​and cysteine. Background technique

[0002] Among many amino acids, homocysteine ​​(Hcy) and cysteine ​​(Cys) have very special effects due to their sulfhydryl groups. The level of Hcy in plasma is a symbolic indicator of diseases such as cardiovascular diseases and Alzheimer's disease; and when Cys plays an important role in the folding of proteins, it has a certain detoxification effect, and can participate in preventing cell aging and improving skin quality. It may cause a variety of diseases, so the detection of homocysteine ​​(Hcy) and cysteine ​​(Cys) is very important. Among the existing methods for the determination of homocysteine ​​(Hcy) and cysteine ​​(Cys), the fluorescence detection method ha...

Examples

Embodiment 1

[0014] 1. Under nitrogen protection, add 0.3 g (1 mmol) iridium trichloride and 0.4 g (2.5 mmol) 4-(2-pyridyl)-benzaldehyde (Hpba) into a 50 mL two-necked bottle, and then Add 15 mL of deoxygenated ethylene glycol ether / H 2 O (3:1, v / v), reflux for 24 h, cool to room temperature, filter and wash with ethanol several times, then dissolve the solid with a mixed solution of dichloromethane / methanol (1:1, v / v) and depressurize The solvent was spin-dried to obtain an orange-red solid [(Hpba) 2 IrCl] 2 180 mg, yield 55%. 1 HNMR (400MHz, DMSO, MeSi); δ (ppm): 9.88 (d, 2H J=8 Hz), 9.66 (s, 2H), 9.59 (d, 4HJ=8 Hz), 8.48 (d, 2H J=8 Hz), 8.40 (d, 2H J=8 Hz), 8.26 (m, 2H) , 8.17 (m, 2H), 8.04 (m, 4H) ,7.74 (m, 2H), 7.65 (m, 2H), 7.43 (dd, 4H), 6.76 (s, 2H), 6.15 (s, 2H).

[0015] 2. Add 30 mg of [(Hpba) 2 IrCl] 2 with 10 mg of bpy-NH 2 Dissolve in 8 mL of dichloromethane / methanol mixed solution (1:1, v / v), reflux for 12 h under nitrogen protection, cool to room temperature, and di...

Embodiment 2

[0017] (1) At a concentration of 2.0×10 -5 Add a series of contents of homocysteine ​​and cysteine ​​to the acetonitrile-Tris buffer solution (4:1, v / v) of the complex Ⅰ in mol / L, and measure the concentration of homocysteine ​​and cysteine ​​at 200-600 UV-Vis absorption spectrum in the nm wavelength range, see the results figure 1 , where A is homocysteine ​​and B is cysteine.

[0018] Such as figure 1 As shown, the absorbance value of complex Ⅰ increases with the increase of amino acid content at the wavelength of 255nm; but the difference between the ultraviolet absorption spectra of homocysteine ​​and cysteine ​​is not significant.

[0019] (2) At a concentration of 2.0×10 -5 A series of homocysteine ​​and cysteine ​​were added to the acetonitrile-Tris buffer solution (4:1, v / v) of the complex Ⅰ in mol / L, and the concentrations of homocysteine ​​and cysteine ​​were respectively determined at 400-800 Fluorescence spectra in the nm wavelength range, see results in fi...

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