Near-infrared fluorescent dye and synthesis method thereof, and application of near-infrared fluorescent dye in parasite fluorescence labeling

A technology of fluorescent dyes and synthesis methods, applied in the field of biological optical labeling, can solve the problems of inability to observe fluorescence for a long time, poor stability, and interference of biological spontaneous background fluorescence.

Active Publication Date: 2017-01-04
GANNAN NORMAL UNIV
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  • Application Information

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Problems solved by technology

[0005] The above-mentioned use of traditional organic fluorescent dyes as fluorescent probes for the study of Schistosoma adult worms has the following disadvantages: (1) There is biological background fluorescence interference in short-wavelength excitation and emission
(2) Most of the fluorescent probes have poor photostability, resulting in the inability to observe fluorescence for a long time
(3) Most organic small molecule fluorescent dyes have poor hydrophilicity, which limits their biological applications
In view of the shortage of current fluorescent dyes and the contradiction between the physiological and structural characteristics of Schistosoma adult worms, it is a challenge to develop fluorescent dyes with good fluorescent labeling effect on Schistosoma adult worms

Method used

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  • Near-infrared fluorescent dye and synthesis method thereof, and application of near-infrared fluorescent dye in parasite fluorescence labeling
  • Near-infrared fluorescent dye and synthesis method thereof, and application of near-infrared fluorescent dye in parasite fluorescence labeling
  • Near-infrared fluorescent dye and synthesis method thereof, and application of near-infrared fluorescent dye in parasite fluorescence labeling

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Fluorescent dye NIR-COOH-SO 3 Synthesis of H:

[0029]

[0030] (1) Synthesis of M-1: Add 1mmol of 1,1,2-trimethyl-1H-benzindole and 1.2mmol of 3-bromopropionic acid into a three-necked flask, then add 30mL of toluene as solvent. Under the protection of nitrogen, the reaction system was reacted at 110° C. for 24 hours. After cooling to room temperature, the reaction solution was extracted with dichloromethane (10 mL×3), the organic layers were combined, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain M-1. NMR characterization data: 1 H NMR (400MHz, CDCl 3 )δ8.07(dd, J=13.6,8.3Hz,5H),7.80–7.54(m,2H),4.05(d,J=7.0Hz,2H),3.26(s,5H),1.87(s,6H ), 1.19 (t, J=6.9Hz, 3H).

[0031](2) Synthesis of M-2: 1 mmol of M-1 and 1 mmol of N,N'-diphenylformamidine were dissolved in 25 mL of acetic anhydride, and reacted at 110°C for 2 hours. Cool to room temperature, neutralize by adding aqueous sodium bicarbonate solution, extract the reacti...

Embodiment 2

[0034] Fluorescent dye NIR-COOH-SO 3 Absorption spectrum and fluorescence spectrum test of H:

[0035] Fluorescent dye NIR-COOH-SO 3 H made into 1mmol·L -1 The ethanol stock solution was then diluted for testing. Ultraviolet Spectrum Measurement: The scanning range is 500nm-850nm, and the ultraviolet absorption spectrum characteristics are recorded. The solution determined above was then used to measure the fluorescence spectrum. Fluorescence spectrum measurement: the excitation wavelength is 620nm, and the emission spectrum range is 640nm-850nm. Absorption and fluorescence spectra such as figure 1 As shown, the test results show that the emission peak of the fluorescent dye is located in the near-infrared region of 650-850nm.

Embodiment 3

[0037] Fluorescent dye NIR-COOH-SO 3 Cell fluorescence imaging of H:

[0038] (1) Reagents and materials

[0039] Dimethyl sulfoxide (AR) was purchased from Aladdin Chemical Reagent Co., Ltd., RPMI 1640 culture medium was purchased from Thermo Fisher Scientific, and human cervical cancer cell HeLa was purchased from Shanghai Institute of Biochemistry and Cell Biology, Chinese Academy of Sciences.

[0040] (2) Cell fluorescence imaging

[0041] Human cervical cancer cells HeLa were cultured in RPMI 1640 medium containing 10% fetal bovine serum at 37°C, 5% CO 2 And 95% air atmosphere adherent growth. Fluorescent dye NIR-COOH-SO 3 The cell fluorescence imaging of H was tested on OLYMPUSFV1000 laser confocal fluorescence microscope, the excitation wavelength was 635nm, and the fluorescence signal of 650-750nm was received. Cell fluorescence imaging results such as figure 2 As shown, the experimental results show that the dye NIR-COOH-SO 3 H is good for fluorescently labeli...

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Abstract

The invention belongs to the field of biological optical labeling of verminosis, mainly synthesis of a near-infrared fluorescent dye and application of the near-infrared fluorescent dye in adult schistosoma fluorescence labeling. The near-infrared fluorescent dye has the conjugated diene bond structure, and more particularly, the molecular structure is connected through three olefinic bonds; the hydrophilic groups are sulfo (-SO3H) and carboxyl (-COOH); and the near-infrared fluorescent dye can be used for adult schistosoma fluorescence labeling imaging. The invention implements design, synthesis and fluorescence labeling on adult schistosoma by using the near-infrared fluorescent dye. By using the conjugated system, the emitted light of the near-infrared fluorescent dye is in the near-infrared region; and the hydrophilic sulfo and carboxyl are combined for water solubility modification. The near-infrared fluorescent dye is used for adult schistosoma fluorescence labeling, and effectively solves the problems of poor fluorescent dyeing effect, background fluorescence interference and poor light penetrability in the adult schistosoma fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of bio-optical labeling for the prevention and treatment of parasitic diseases. Specifically, the invention relates to the synthesis of a near-infrared organic fluorescent dye and its application to the fluorescent labeling of schistosomiasis adults. According to a novel method, the near-infrared fluorescent dye has excellent fluorescent labeling effect on Schistosoma adult worms. [0002] technical background [0003] Schistosomiasis is an infectious disease that is prevalent in tropical and subtropical regions, seriously endangering people's health and affecting social and economic development. Schistosomiasis is endemic in 74 countries and regions. There are currently about 652 million people in the world at risk, 193 million infected people, and about 120 million symptomatic cases, of which 20 million are severe cases. my country is the main endemic area of ​​schistosomiasis. Schistosomiasis is a typical zoonotic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C09K11/06C07D209/60G01N21/64
CPCC07D209/60C09B23/083C09K11/06C09K2211/1029G01N21/6428
Inventor 吴勇权范小林江天宇曾冠杰曾红李勋
Owner GANNAN NORMAL UNIV
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