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Two-photon fluorescent probe as well as preparation method and application thereof

A two-photon fluorescence and probe technology, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of low sensitivity and detection concentration, and achieve the effects of low detection concentration, easy synthesis, and simple operation

Inactive Publication Date: 2014-03-05
ANHUI UNIVERSITY
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  • Abstract
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  • Claims
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Problems solved by technology

[0006] The present invention aims to provide a two-photon fluorescent probe and its preparation method and application. The technical problem to be solved is to select a suitable fluorescent probe structure through molecular design to realize the qualitative detection of cysteine ​​or cysteine ​​in cells by two-photon imaging. Homocysteine ​​has the advantages of specific selectivity, high sensitivity, and low detection concentration. Cytotoxicity tests show that the present invention has almost no toxic effect on cells

Method used

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  • Two-photon fluorescent probe as well as preparation method and application thereof
  • Two-photon fluorescent probe as well as preparation method and application thereof
  • Two-photon fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of fluorescent probe molecule NQ

[0029] 1. Synthesis of Intermediate 1

[0030] Weigh 15g (68.49mmol) of p-iodoaniline and 100mL of 6mol / L hydrochloric acid in a three-neck flask, install a condenser, heat to 105°C, until the solid is completely dissolved, slowly add 12g (171mmol) of crotonaldehyde dropwise, and track with TLC After the reaction of the raw materials is completed, stop the reaction, cool to room temperature, pour the reaction solution into 200mL water, extract with ethyl acetate (100mL×2) to remove unreacted crotonaldehyde, and neutralize the aqueous solution with ammonia water to a pH value of 8. Extract with ethyl acetate (50mL×2), combine the organic phases, dry the organic phase with anhydrous sodium sulfate, and spin dry to obtain the crude product, which is reconstituted in a mixed solvent of ethyl acetate and petroleum ether (volume ratio 1:20). Crystallization gave 14.45 g (53.72 mmol) of intermediate 1, with a yiel...

Embodiment 2

[0038] Example 2: Two-photon testing of fluorescent probe molecules

[0039] Using the two-photon measurement technique, the two-photon absorption cross section of the fluorescent probe molecule (NQ) and the fluorescent probe molecule reacted with cysteine ​​(MQ-Cys) was tested, from Figure 4 It can be seen that the maximum absorption cross-sections of fluorescent probe molecules reacted with cysteine ​​or homocysteine ​​(NQ-Cys or NQ-Hcy) are 587 and 693 GM respectively, and the two-photon excitation wavelengths are both at 800 nm. Example 3: Cytotoxicity Test

Embodiment 3

[0040] The MTT (3-(4,5-dimethylthiazole-2)-2,5-diphenyltetrazolium bromide) experiment was based on the reported articles to do some cytotoxicity tests. Add 0, 10, 30, and 80 μM fluorescent probe molecules to the same batch of cells, and the conditions are at 37 ° C, containing 5% CO 2 According to the formula of cell viability: cell viability %=OD570 (sample) / OD570 (control group) × 100, the cell viability can be calculated ( Figure 5 ). from Figure 5 We can see that when the concentration is 10 μM, the cell survival rate is still about 98%, which shows that the fluorescent probe molecule of the present invention has no toxic effect on cells, so it can be used for cell detection and tracking amino acid small molecules.

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Abstract

The invention discloses a two-photon fluorescent probe as well as a preparation method and an application thereof. The structure of the two-photon fluorescent probe is as shown in the specification. The two-photon fluorescent probe presents relatively high selectivity and high sensitivity in a coexisting system of aminothiopropionic acid or homocysteine and other amino acids. The cytotoxicity test shows that the two-photon fluorescent probe almost has no toxicity on cells. The two-photon fluorescent microscopic imaging experiment shows that the two-photon fluorescent probe is good in permeability on 293FT cells. The two-photon fluorescent probe is suitable for detecting the distribution of amino acid micromolecules in the cells.

Description

1. Technical field [0001] The invention relates to a two-photon fluorescent probe, its preparation method and application, which can qualitatively detect cysteine ​​or homocysteine ​​in cells through two-photon imaging. 2. Background technology [0002] Amino acids such as cysteine, homocysteine ​​and glutathione play important roles in biological systems. They have the same structural formula, and when the concentration of these amino acids reaches a certain level, it can cause a series of diseases, such as growth slowdown, hair fading, edema, lethargy, liver damage, muscle and fat loss, skin lesions and Alzheimer's disease. Syndrome. How to detect them is very important and attracts the interest of many scientists. However, it is still rare to qualitatively detect amino acid molecules in cells, so it is particularly important to detect small amino acid molecules in vivo and in vitro. [0003] Fluorescent probes are molecules that can change the fluorescent signal accord...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D215/14G01N21/64
Inventor 孟祥明叶维鹏蔡玉磊汪恕欣朱满洲冯燕
Owner ANHUI UNIVERSITY
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