Proportional near-infrared fluorescent probe as well as preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of probes, can solve problems such as instability, high precursor reactivity, and difficult preparation process, achieve improved selectivity, good photostability, and facilitate cell imaging analysis and measured effect

Active Publication Date: 2013-10-02
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with BODIPY derivatives, there are few studies on aza-bodipy compounds, mainly because the preparation process of aza-bodipy using isoindole as precursor is very difficult. Under normal conditions, such precursors The body is extremely unstable due to its high reactivity 28-30

Method used

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  • Proportional near-infrared fluorescent probe as well as preparation method and application thereof
  • Proportional near-infrared fluorescent probe as well as preparation method and application thereof
  • Proportional near-infrared fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Synthesis of Aza-bodipy-BA.

[0041] The synthetic route of Aza-bodipy-BA is as follows figure 1 shown, including the following steps:

[0042] (1) Dissolve 199.04g1mol of 4-bromoacetophenone in 2.44L of ethanol, add 2.44L of 2.5M sodium hydroxide aqueous solution, add dropwise the ethanol solution of compound 106.12g1mol of benzaldehyde at room temperature, and wait for a large amount of solid after the dropwise addition After precipitation, react at room temperature for 20 h, wash the solid with water, recrystallize with ethanol, wash the solid with ethanol and dry to obtain 229.8 g of yellow solid 1-(4-bromo)-3-propiopropenone (compound 3), yield: 80%.

[0043] Compound 3 detection: 1 H NMR (400MHz, CDCl 3 )δ (ppm): 7.92 (d, 2H, J = 10.8Hz), 7.84 (d, 1H, J = 15.68Hz), 7.67 (d, 4H, J = 14.16Hz), 7.65 (s, 1H), 7.47 (t,3H,J=5.72Hz);

[0044] (2) Compound 3 (216g, 0.75mol, 1eq), diethylamine (274.29g, 3.75mol, 5eq), nitromethane (229.5g, 3.75mol, 5eq) wer...

Embodiment 2

[0051] Example 2: H in homogeneous phase 2 o 2 detection.

[0052] All fluorescence experiments in the homogeneous detection are based on the excitation wavelength of 652nm, the excitation and emission slit widths are both 15nm, the scan rate is 100nm / min, and the attenuation is 1%.

[0053] Photostability experiment: at room temperature, with an optical density of 135.9mWcm -2 , 100W mercury lamp, the wavelength range of 530 ~ 550nm green light continuous irradiation concentration of 20μM aza-bodipy-BA solution, UV absorption stability experiment. The fluorescence photostability experiment was carried out by exciting 10 μM aza-bodipy-BA every 15 minutes with an excitation wavelength of 652 nm. The results show that the quantum yield of aza-bodipy-BA in methanol is 0.60 (with Nile blue as the reference dye), and the extinction coefficient at the maximum absorption wavelength of 655nm is 74540L mol -1 cm -1 , the compound has good photostability (such as figure 2 and i...

Embodiment 3

[0057] Example 3: H in the membrane phase 2 o 2 detection.

[0058] When aza-BODIPY-BA was incorporated into polyvinyl chloride-dioctyl sebacate (PVC-DOS) films (dielectric constant ε=3 of the plasticizer DOS), its response to H 2 o 2 the response to. like Figure 8 As shown, it has an effect on H 2 o 2 The response can range from 10 -7 M to 10 -2 M, the lowest detection limit can reach 10- 8 M and the response time to fluorescence intensity ratio curve follows the first-order kinetic equation, such as Figure 9 to Figure 13 shown. In membrane phase detection, H 2 o 2 Diffusion into the membrane phase reacts with aza-bodipy-BA with a shorter response time than in the homogeneous phase. From the above results, it was suggested that the conversion of phenylboronic acid to phenol in aza-bodipy-BA was environment-related and more suitable for this reaction to occur in the organic phase, probably due to the better solubility of the probe in the organic phase. Such pro...

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Abstract

The invention discloses a proportional near-infrared fluorescent probe. The chemical name of the proportional near-infrared fluorescent probe is aza-bodipy-BA, the structural formula of the proportional near-infrared fluorescent probe is as follows, the light stability is good, the proportional near-infrared fluorescent probe is not sensitive to the pH when the pH value is less than 7.5, and the cell imaging analysis and measurement can be favored. By utilizing the probe, the concentration of H202 in the cell can be detected through the proportional fluorescent method. The reaction principle is as follows: the variation of the fluorescent intensity is caused through the reaction of the H202 and boric acid, so that the selectivity on the H202 also can be greatly improved. The invention also discloses a preparation method of the proportional near-infrared fluorescent probe aza-bodipy-BA and an application of the proportional near-infrared flurosecent probe on the detection of H202.

Description

technical field [0001] The invention belongs to the technical field of probes, and specifically designs a proportional near-infrared fluorescent probe azafluoroboron-dipyrrole-boric acid (aza-bodipy-BA) and its preparation method and application. Background technique [0002] H in the body 2 o 2 It is one of the important reactive oxygen species (ROS), which can regulate the immune system of the human body, and is also closely related to various diseases such as human aging and cancer 1-7 . In recent years, people have begun to pay attention to the development of new chemical methods to study H 2 o 2 And the role played by other ROS in physiology and pathology. One method that has attracted widespread attention is the use of highly selective fluorescent probes to track intracellular H 2 o 2 chemical process 8-16 . [0003] At present, various fluorescent indicators have been used for H 2 o 2 detection of, for example, the dihydro analog 2,7-dichlorodihydrofluoresc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02G01N33/52G01N21/64
Inventor 秦玉翟晶莹徐艳梅朱经伟
Owner NANJING UNIV
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