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Novel pH response fluorescent molecular probe and application thereof

A fluorescent molecular probe, a new technology, applied in the field of new pH-responsive fluorescent molecular probes regulated by intramolecular hydrogen bonds, can solve the problems of inconvenient use, and achieve the effect of simple preparation method and large displacement value

Active Publication Date: 2013-11-20
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the pH value of the living environment is mainly tested by the microelectrode method, which requires electric drive and is inconvenient to use in the living system.

Method used

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  • Novel pH response fluorescent molecular probe and application thereof
  • Novel pH response fluorescent molecular probe and application thereof
  • Novel pH response fluorescent molecular probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A novel pH-responsive fluorescent molecular probe regulated by intramolecular hydrogen bonds has the following molecular structure:

[0029]

[0030] The preparation method is as follows:

[0031] In a 100 mL three-necked flask equipped with a stirring bar, a condenser, and a thermometer, put 50 mL of ethanol, add a small piece of 0.58 g of metallic sodium, and after the sodium is completely dissolved, add 3.51 g of 1-ethyl-2-methyl- 3-sulfopropyl-5,6-dichlorobenzimidazole betaine and 0.74 g chloral, stirred and heated to reflux for 1 hour. Then cooled to room temperature, filtered, washed with ethanol, and vacuum-dried to obtain the crude product . Purified by silica gel column chromatography to obtain purple crystals, that is, the probe : 1,1′-Diethyl-3,3′-disulfopropyl-5,5′,6,6′-tetrachlorocarbamocyanine sodium salt.

[0032] The pH-responsive fluorescence performance of the probe was measured in solution by fluorescence method: the fluorescent molecular probe w...

Embodiment 2

[0034] In this embodiment, the fluorescent molecular probe has the following molecular structural formula:

[0035]

[0036] The pH-responsive fluorescence performance of the probe was measured in solution by fluorescence method: the fluorescent molecular probe was dispersed in dimethyl sulfoxide-water (volume ratio 1:9) at a concentration of 30 μM, and different pH conditions were controlled. Excited with 500 nm light, the fluorescence peak at 605 nm was measured by pH-fluorescence response spectrum. The strong fluorescence region was pH 7.8-8.9, and the fluorescence enhancement factor was 90.

Embodiment 3

[0038] In this embodiment, the fluorescent molecular probe has the following molecular structural formula:

[0039]

[0040] The pH-responsive fluorescence performance of the probe was measured in the solution by the fluorescence method: the fluorescent molecular probe was dispersed in ethanol at a concentration of 20 μM, controlled at different pH conditions, respectively excited by 450 nm light, and the fluorescence at 572 nm The peak was measured by pH-fluorescence response spectrum, the strong fluorescence region was pH 7.7-8.5, and the fluorescence enhancement factor was 82.

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Abstract

The invention discloses a novel pH response fluorescent molecular probe, which has a general formula of the structure as shown in the specification, wherein, n is equal to 1 to 5; R1 is an alkyl chain with 1 to 8 carbon atoms; and R2 is hydrogen, fluorine, chlorine, bromine, iodine, methoxy, ethoxy or nitro connected to the 4th, 5th, 6th, 7th, 4'th, 5'th, 6'th or 7'th site of a benzimidazole ring. The invention also discloses an application of the novel fluorescent molecular probe in the field of pH response fluorescent detection. The novel pH response fluorescent molecular probe has very wide detection wavelength, and can be excited from ultraviolet to visible light (less than 520nm). Fluorescent images of the novel fluorescent molecular probe in different areas of a life system can also be acquired in combination with confocal laser scanning microscopy. Compared with the existing pH response fluorescent molecular probe, the novel pH response fluorescent molecular probe has the advantages that the preparation method is simple and the displacement value with exciting light is large.

Description

technical field [0001] The invention relates to the technical field of fluorescent molecular probes, in particular to a novel pH-responsive fluorescent molecular probe regulated by intramolecular hydrogen bonds and its application. Background technique [0002] The pH value of the living environment is an important physiological parameter, which plays an important indicator role in the activities of cells, enzymes and many human tissues, such as cell proliferation, apoptosis, drug resistance, ion transport, muscle contraction, etc. Therefore Monitoring the pH change of the living environment is of great significance for the study of the behavior of living cells and the study of the nervous system. In general, there are two pH ranges in the living cell environment, one is pH 6.8~7.4, such as cytoplasm; the other is pH 4.5~6.0, which is acidic organelles, such as lysosomes. The normal range of cellular pH environment is It is beneficial to cell growth, and the abnormal pH env...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D235/20G01N21/64
Inventor 孟庆华向德成刘恒谢少艾郑少瑜
Owner SHANGHAI JIAO TONG UNIV
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