Near-infrared and two-photon dual-mode imaging fluorescence probe, as well as preparation and application thereof

A dual-mode imaging and fluorescent probe technology, applied in the field of chemical biology, can solve problems such as unfavorable tumor detection, false positives, and non-targeting Nile red, and achieve good spectral properties and enhanced fluorescence intensity

Inactive Publication Date: 2017-05-31
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when Nile Red is used as a near-infrared fluorescent dye for cell imaging, Nile Red itself is not targeted, and can be imaged

Method used

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  • Near-infrared and two-photon dual-mode imaging fluorescence probe, as well as preparation and application thereof
  • Near-infrared and two-photon dual-mode imaging fluorescence probe, as well as preparation and application thereof
  • Near-infrared and two-photon dual-mode imaging fluorescence probe, as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1 Preparation of fluorescent probe of the present invention

[0038]Compound 2 (1mmol), compound 3 (1mmol), 1-hydroxybenzotriazole (HOBT, 2.5mmol), N,N-diisopropylethylamine (DIEA, 2.5mmol) and N,N-dimethyl Dimethyl formamide (DMF, 5 mL) was added into a 50 mL one-necked flask, and stirred at room temperature in the dark for 24 hours. Separation and purification with a silica gel column yielded a brown product (67% yield). Detect all-color products, see HRMS spectrum figure 1 , whose structural formula is: , which is the fluorescent probe of the present invention. In this embodiment, the structural formula of compound 2: , the structural formula of compound 3: . The CAS number of compound 3 is 58-85-5. The method of compound 2: 2mmol of 3-diethylaminophenol was slowly added to 5mL of hydrochloric acid with a mass concentration of 18% under the condition of ice bath, and then 2.4 mmol of sodium nitrite was added, and the reaction was more than 12h; a...

Embodiment 2

[0039] Embodiment 2 Fluorescence spectra of fluorescent probes of the present invention in different aqueous solutions

[0040] Using Nile Red, compound 2, and the brown product obtained in Example 1 as fluorescent probes, their fluorescence spectra in different buffers were detected.

[0041] Mix the above-mentioned fluorescent probes with Britton-Robinson buffer solution containing 10% DMSO and Britton-Robinson buffer solution containing 10% EtOH to prepare a buffer solution with a fluorescent probe concentration of 10 μmol / L, and adjust the pH of the buffer solution to Adjusted to 7.54. Then take 540nm and 590nm as the excitation wavelength (λ ex =540nm, 590nm) for fluorescence detection; the obtained fluorescence spectrum is as follows figure 2 shown. according to figure 2 It can be drawn that the fluorescence spectrum of the probe obtained with Nile Red, compound 2, and the brown product obtained in Example 1 has a maximum emission wavelength at 660 nm, and the peak...

Embodiment 3

[0042] Embodiment 3 The fluorescence intensity of the fluorescent probe of the present invention in positive and negative cells

[0043] Compound 2 (N-OH for short) and the brown product obtained in Example 1 (N-BN for short) were used as fluorescent probes to detect their fluorescence spectra in positive and negative cells. The positive cells are cell lines with high biotin receptor expression (HeLa); the negative cells are cells with low biotin receptor expression (NIH3T3).

[0044] Cells HeLa (positive cells) with high expression of biotin receptors or NIH3T3 cells (negative cells) with low expression of biotin receptors were inoculated into 35 mm confocal small dishes and cultured for 24 hours, and then replaced with 5 μmol / L fluorescent probe) Cell culture medium was incubated for 15 minutes, washed three times with PBS, and placed under a confocal microscope (equipped with a femtosecond laser) to detect the fluorescence imaging results of positive or negative cells in fl...

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Abstract

The invention relates to preparation and application of a near-infrared and two-photon dual-mode imaging fluorescence probe, and belongs to the technical field of chemicobiology. The near-infrared and two-photon dual-mode imaging fluorescence probe is synthesized by a nile red derivative and biotin which serve as raw materials, and the fluorescence probe is a brown product. The fluorescence probe disclosed by the invention is high in spectral quality, and respectively takes 540 nm and 590 nm as excitation wavelengths; at 660 nm, the maximum emission wavelength appears, and the fluorescence intensity is relatively high. The fluorescence probe further has a targeting effect on tumor cells, and is a targeting infrared fluorescence probe; on one hand, on the premise of not destroying a tissue sample, an in-vivo signal can be detected in real time; on the other hand, enrichment of the signal in a tumor can be enhanced, and the signal-to-noise ratio is increased. The fluorescence probe disclosed by the invention can carry out near infrared imaging and two-photon imaging; by mutual verification of the two modes, the accuracy of a result can be improved.

Description

technical field [0001] The invention relates to the preparation and application of a near-infrared and two-photon dual-mode imaging fluorescent probe, which belongs to the technical field of chemical biology. Background technique [0002] Cancer is one of the most serious diseases that threaten human health and life. According to the latest statistical analysis, there were 4.292 million new cancer cases and 2.814 million deaths in China in 2015. Therefore, timely detection of tumors in situ and residual tumors after surgery, and early control of tumors is a huge challenge at present. Exploring effective and rapid methods to detect tumors is crucial for cancer treatment. [0003] The main methods for clinical diagnosis and detection of tumors include Magnetic Resonance Imaging (MRI), Positron Emission Tomography (PET), and X-rays. To a certain extent, these methods lack certain targeting and sensitivity , and accompanied by certain radiation damage. Optical Tomography is a ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D495/04G01N21/64
CPCC07D495/04C09K11/06C09K2211/1022C09K2211/1033C09K2211/1044C09K2211/1092G01N21/6402G01N21/6486
Inventor 林伟英孔秀琪董宝利张楠王超宋学真
Owner UNIV OF JINAN
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