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A recovery type near-infrared fluorescent probe with pH response and its preparation method and application

A fluorescent probe and near-infrared technology, applied in the field of bioluminescent analysis, can solve the problems of difficult tumor detection, short pH probe wavelength, high signal-to-noise ratio, etc., and achieve simple and easy-to-operate preparation methods and less damage to cells and living bodies , the effect of low signal-to-noise ratio

Active Publication Date: 2017-03-15
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Compared with other pH measurement methods, the use of fluorescent probes for pH detection has the advantages of high sensitivity and good selectivity, but most of the current pH probes have short wavelengths, which cannot avoid tissue self-absorption and autofluorescence, background interference Stronger, some stocks have small displacement, large overlap between ultraviolet absorption spectrum and fluorescence spectrum, high signal-to-noise ratio, high toxicity, and cannot be used for pH detection in cells and living bodies. 4. There is almost no fluorescence change in the tumor environment, and it is difficult to detect the tumor

Method used

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  • A recovery type near-infrared fluorescent probe with pH response and its preparation method and application
  • A recovery type near-infrared fluorescent probe with pH response and its preparation method and application
  • A recovery type near-infrared fluorescent probe with pH response and its preparation method and application

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Embodiment 1

[0065] A preparation method of a recovery type near-infrared fluorescent probe with pH response, comprising the following steps:

[0066] (1) The preparation chemical formula is The switch numerator:

[0067] Dissolve 2.6696mL of ethylenediamine in 10mL of methanol, add it to a 50mL two-necked flask, stir rapidly under ice-bath conditions and dissolve 844.3μL of 4-formaldehyde pyridine in 10mL of methanol and add it dropwise to the above solution, at 0°C N 2 Protection reaction 1h.

[0068] Then, 0.57 g of sodium borohydride was added in batches to the two-necked flask, reacted for 2 h, and 10 mL of distilled water was added and stirred for 20 min to terminate the reaction. Use a rotary evaporator to spin off the solvent and dry it in vacuum for 24h. Then add 20mL of distilled water, extract three times with 50mL of dichloromethane, collect the organic phase, spin off the solvent, pass through the column with basic alumina, and use the volume ratio of dichloromethane and ...

Embodiment 2

[0075] A preparation method of a recovery type near-infrared fluorescent probe with pH response, comprising the following steps:

[0076] (1) The preparation chemical formula is The switch numerator:

[0077] Dissolve 2.6696mL of ethylenediamine in 10mL of methanol, add it to a 50mL two-necked flask, stir rapidly under ice-bath conditions and dissolve 844.3μL of 4-formaldehyde pyridine in 10mL of methanol and add it dropwise to the above solution. 2 Protection reaction 1h.

[0078] Then, 0.57 g of sodium borohydride was added in batches to the two-necked flask, reacted for 2 h, and 10 mL of distilled water was added and stirred for 20 min to terminate the reaction. Use a rotary evaporator to spin off the solvent and dry it in vacuum for 24h. Then add 20 mL of distilled water, extract three times with 50 mL of dichloromethane, collect the organic phase, spin off the solvent, pass through the column with basic alumina, and use the volume ratio of dichloromethane and methanol...

Embodiment 3

[0082] A preparation method of a recovery type near-infrared fluorescent probe with pH response, comprising the following steps:

[0083] (1) The preparation chemical formula is The switch numerator:

[0084] Dissolve 1.3348mL of ethylenediamine in 10mL of methanol, add it to a 50mL two-necked flask, stir rapidly under ice-bath conditions and dissolve 422.15μL of 4-formaldehyde pyridine in 10mL of methanol and add it dropwise to the above solution. 2 Protection reaction 1h.

[0085] Then, 0.29 g of sodium borohydride was added in batches to the two-necked flask, reacted for 2 h, and 10 mL of distilled water was added and stirred for 20 min to terminate the reaction. Use a rotary evaporator to spin off the solvent, and dry in vacuo for 24 hours. Then add 20mL of distilled water, extract three times with 50mL of dichloromethane, collect the organic phase, spin off the solvent, pass through the column with basic alumina, and use the volume ratio of dichloromethane and methano...

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Abstract

The invention provides a restoring-type near infrared fluorescence probe with pH response. The chemical structural formula is shown as a formula (I) in the specification, wherein X refers to C(CH3)2, O, S or Se, Y refers to halogen, Z refers to NH, O or S, R1 and R2 are respectively independently selected from H, C1-18 alkyl or SO3R5, R5 refers to C1-18 alkyl or benzyl, and R3 and R4 are respectively independently selected from C1-18 alkyl or benzyl. When the restoring-type near infrared fluorescence probe with pH response is between pH 5.0 and pH 7.5, the fluorescence intensity is gradually enhanced along with reduction of the pH value, and an excellent linear relation is formed between the fluorescence intensity and the pH value. The stocks displacement is large, the signal to noise ratio is low, the toxicity is low, the damage to cells and living bodies is small, the pKa is 6.4, the probe is very suitable for tumor detection, and the defects of fluorescence probes in the prior art are overcome. The invention also provides a method for preparing the probe. The preparation method is simple.

Description

technical field [0001] The invention relates to the technical field of bioluminescent analysis, in particular to a pH-responsive recovery near-infrared fluorescent probe and a preparation method and application thereof. Background technique [0002] Fluorescence spectroscopy is widely used in biological analysis and imaging because of its high sensitivity, good selectivity, intuitive and accurate information, and the ability to scientifically express the structure, distribution, content, and physiological functions of complex samples. [0003] Many organisms and their tissues emit fluorescence under the excitation of visible light, which seriously interferes with the fluorescence detection and imaging of biological samples. The fluorescence wavelength range of phosphatase (NADPH) and bilirubin is 430-470nm, so the sensitivity and accuracy of fluorescence analysis in the visible light region are greatly affected. The maximum absorption wavelength and emission wavelength of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C09K11/06A61K49/00G01N21/64
Inventor 蔡林涛孟晓青龚萍吕亚琳张利
Owner SHENZHEN INST OF ADVANCED TECH
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