Synthesis and fluorescence detection imaging application of phosphorescence iridium complex

A phosphorescent iridium complex and iridium complex technology, applied in the field of amino acid detection, can solve the problems of living tissue damage, insufficient tissue penetration depth, low luminescence quantum efficiency of fluorescent probes, etc., and achieve strong tissue penetration and spontaneous background. The effect of less fluorescence interference and less light damage

Active Publication Date: 2016-01-06
GANNAN NORMAL UNIV
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Problems solved by technology

Based on the above advantages, fluorescent probes of iridium complexes have been developed for the fluorescence detection of cysteine ​​and homocysteine, but currently phosphorescent iridium complexes are used for the detection of cysteine ​​and homocysteine. The detection is limited to in vitro detection and fluorescence detection imaging at the cell level, but the in vivo fluorescence imaging detection of small animals has not been realized. The main difficulties lie in the following aspects: (1) The excitation light of most complex fluorescent probes is in the ultraviolet region, while in the ultraviolet region The excitation light in the region has the disadvantages of insufficient tissue penetration depth and photodamage to living tissues in in vivo fluorescence imaging; (2) the luminescent quantum efficiency of the complex fluorescent probe is low, and the application of in vivo fluorescence imaging cannot be well realized

Method used

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  • Synthesis and fluorescence detection imaging application of phosphorescence iridium complex
  • Synthesis and fluorescence detection imaging application of phosphorescence iridium complex
  • Synthesis and fluorescence detection imaging application of phosphorescence iridium complex

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Experimental program
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Effect test

Embodiment 1

[0039] Iridium complex [Ir(CHO-btiq) 2 (bpy)][PF 6 ]Synthesis:

[0040] (a) Weigh 4mmol (766.4mg) 2-chloroquinoline-3-formaldehyde and 4mmol (712.1mg) benzothiophene-2-boronic acid in a 100mL round bottom flask, add 3 molar equivalents of potassium carbonate, add 40mL volume ratio V / V=1:1 mixed solvent of tetrahydrofuran and water, finally add 8% molar equivalent of tetrakis(triphenylphosphine)palladium, heat and reflux at 70°C for 24 hours in a nitrogen protective atmosphere. After the reaction, the reaction liquid was extracted with dichloromethane, and the aqueous phase was extracted three times with dichloromethane (3×10mL). The organic phases were combined, dried overnight with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. After column chromatography separation, the formula The ligand for II, CHO-tbiq. NMR characterization data: 1 HNMR (400MHz, CDCl 3 )δ=10.55(s,1H),8.82(s,1H),8.23(d,J=8.5Hz,1H),8.01(d,J=8.0Hz,1H),7.98–7.92(m,1H), 7....

Embodiment 2

[0044] Response of iridium complexes to cysteine:

[0045] a) The phosphorescent iridium complex was prepared into a 10 μM dilute solution with a mixed solvent of acetonitrile and water at a volume ratio of V / V=4:1.

[0046] b) Prepare 2 mmol of cysteine ​​aqueous solution.

[0047] c) adding 0-40 equivalents of cysteine ​​aqueous solution to the dilute solution of the iridium complex, and reacting at 37° C. for 5 hours.

[0048] d) detect the changes of the ultraviolet absorption spectrum and the fluorescence emission spectrum of the solution with an ultraviolet spectrophotometer and a fluorescence spectrophotometer, such as figure 1 with figure 2 shown. With the increase of cysteine ​​addition, the ultraviolet absorption of the iridium complex at 338nm and 480nm gradually weakened, and the ultraviolet absorption at 495nm increased; the fluorescence signal blue shifted with the increase of cysteine ​​addition , and the signal is enhanced. This is because the aldehyde gr...

Embodiment 3

[0050] Response of iridium complexes to homocysteine:

[0051] a) The phosphorescent iridium complex was prepared into a 10 μM dilute solution with a mixed solvent of acetonitrile and water at a volume ratio of V / V=4:1.

[0052] b) Prepare a 2 mmol homocysteine ​​aqueous solution.

[0053] c) adding 0-40 molar equivalent homocysteine ​​aqueous solution to the dilute solution of the iridium complex, and reacting at 37° C. for 5 hours.

[0054] d) detect the changes of the ultraviolet absorption spectrum and the fluorescence emission spectrum of the solution with an ultraviolet spectrophotometer and a fluorescence spectrophotometer, such as image 3 with Figure 4 shown. With the increase of the addition of cysteine, the ultraviolet absorption of the iridium complex at 338nm and 480nm gradually weakens, and the ultraviolet absorption at 495nm increases; the fluorescence signal blue shifts with the increase of the addition of homocysteine , and the signal is enhanced. This i...

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Abstract

The invention discloses a preparation method and fluorescence detection application of a phosphorescence iridium complex. The phosphorescence complex has a chemical formula [Ir(CHO-btiq)2(bpy)][PF6]. The invention provides the preparation method of the phosphorescence iridium complex, and the application of the phosphorescence iridium complex to the detection of cysteine and homocysteine. The emission spectrum of the phosphorescent iridium complex is in the near-infrared region; biological imaging of the phosphorescent iridium complex has the advantages of little damage small, strong penetrability and little background spontaneous fluorescence; and the phosphorescent iridium complex has good application prospect in small animal in vivo fluorescence imaging. The iridium complex provided by the invention can realize high selectivity detection of cysteine and homocysteine, and provides the possibility for the construction of a simple and high-selectivity fluorescence chemical sensor for determination of cysteine and homocysteine.

Description

technical field [0001] The invention belongs to the field of amino acid detection. More specifically, the invention relates to the synthesis of a phosphorescent iridium complex and its use in the detection of thiol-containing cysteine ​​and homocysteine. The phosphorescent iridium complex has the ability to detect Beneficial effects of cysteine ​​and homocysteine. Background technique [0002] Cysteine ​​(Cys) and homocysteine ​​(Hcy) are sulfhydryl-containing amino acids, which belong to thiols in the human body and can balance redox reactions in organisms. Cysteine ​​and homocysteine ​​in the body The content is closely related to the health status of human body. Studies have shown that the level of cysteine ​​will affect the growth rate of the human body, causing edema, liver damage and other diseases. Homocysteine ​​plays a very important role in metabolism and homeostasis. Hcy is directly related to human cardiovascular disease and progressive Alzheimer's disease. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64G01N21/33
Inventor 吴勇权吴任苗曾冠杰范小林李勋
Owner GANNAN NORMAL UNIV
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