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Near infrared fluorescence probe with extremely acid pH response as well as preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of bioluminescent analysis, can solve problems such as large overlap between ultraviolet absorption spectrum and fluorescence spectrum, inability to avoid tissue self-absorption and autofluorescence, and inability to detect pH in cells and living bodies. Achieve the effect of obvious color change, convenient naked eye recognition, and little damage to cells and living bodies

Active Publication Date: 2016-04-20
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 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 Strong, small displacement of some stocks, large overlap of ultraviolet absorption spectrum and fluorescence spectrum, low signal-to-noise ratio, high toxicity, and cannot be used for pH detection of cells and living bodies

Method used

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  • Near infrared fluorescence probe with extremely acid pH response as well as preparation method and application thereof
  • Near infrared fluorescence probe with extremely acid pH response as well as preparation method and application thereof
  • Near infrared fluorescence probe with extremely acid pH response as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] A preparation method of a near-infrared fluorescent probe with an extremely acidic pH response, comprising the following steps:

[0071] (1) Preparation

[0072] 25.8mg (0.3mmol) of and 63.8 mg (0.1 mmol, molecular weight 638.19) of the compound Dissolve in 2ml of anhydrous DMF solvent, react at 80°C for 1h under argon gas atmosphere, remove the solvent by rotary evaporation, dry in vacuum for 12h, pass through a silica gel column, and carry out gradient elution with a mixed solution of dichloromethane and methanol , the volume ratio of eluent dichloromethane and methyl alcohol is changed from 40:1 to 20:1, remove solvent, obtain blue solid product 55mg, productive rate 80%, the structural formula of this blue solid product is

[0073] (2) Preparation of near-infrared fluorescent probes with extremely acidic pH response:

[0074] The chemical formula will be 68.8mg (0.1mmol) and 68.4mg (0.4mmol) of Put it into a three-necked flask, add 3mL of anhydrous DMF ...

Embodiment 2

[0078] A preparation method of a near-infrared fluorescent probe with an extremely acidic pH response, comprising the following steps:

[0079] (1) Preparation

[0080] The chemical formula will be Dissolve 1.02g (5mmol) of the compound in 15ml of 1,4-dioxane, add 1.05g of Fmoc-Cl, and then add 10% aqueous sodium carbonate solution to control the pH value of the reaction solution between 8.0-9.0 in real time room temperature, stirring overnight. Then add 10mL of distilled water, extract with ethyl acetate several times, collect the organic phase, spin off the solvent, and dry in vacuum for 12h to obtain the chemical formula: white flocculent product.

[0081] (2) The preparation is with embodiment 1;

[0082] (3) The chemical formula is 34.4mg (0.05mmol) and 41mg (0.2mmol) of Put it into a three-necked flask, add 2 mL of anhydrous DMF as a solvent, and add 14 μL of triethylamine (0.1 mmol) as an acid-binding agent. Under the protection of argon, react at a temperat...

Embodiment 3

[0085] A preparation method of a near-infrared fluorescent probe with an extremely acidic pH response, comprising the following steps:

[0086] (1) Preparation

[0087] 52mg (0.6mmol) of and 63.8 mg (0.1 mmol) of the compound Dissolve in 3ml of anhydrous DMF solvent, react at 70°C for 1.5h under an argon gas atmosphere, remove the solvent by rotary evaporation, dry in vacuum for 12h, pass through a silica gel column, and carry out gradient washing with a mixed solution of dichloromethane and methanol Remove, the volume ratio of eluent dichloromethane and methanol is changed from 40:1 to 20:1, remove solvent, obtain blue solid product 55mg, productive rate 80%, the structural formula of this blue solid product is

[0088] (2) Preparation of near-infrared fluorescent probes with extremely acidic pH response:

[0089] The chemical formula will be 68.8mg (0.1mmol) and 102mg (0.6mmol) Put it into a three-necked flask, add 3mL of anhydrous DMF as a solvent, and add 35μL...

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Abstract

The invention provides a near infrared fluorescence probe with extremely acid pH response. The chemical structural formula is shown by a formula (I), wherein X is -C(CH3)2-, -O-, -S- or -Se-; Z is -CH2-Ph or a group shown by -R'NH2; R' is C1-12 alkylene; R1 and R2 are separately selected from H atom, C1-18 alkyl or a group shown by -SO3R5; R5 is C1-18 alkyl or benzyl; R3 and R4 are separately selected from C1-18 alkyl or benzyl; and Y is F, Cl, Br or I. The near infrared fluorescence probe has the advantages of relatively low pKa value, relatively high sensitivity to H<+>, high selectivity, relatively large stocks displacement, little background interference and relatively low harm to cells and living body and is very suitable for detecting pH in an extremely acid environment and overcomes the defects of the fluorescence probes of the prior art. The invention also provides a preparation method and an application of the probe.

Description

technical field [0001] The invention relates to the technical field of biological fluorescence analysis, in particular to a near-infrared fluorescent probe with an extremely acidic pH response, a preparation method and an application thereof. Background technique [0002] Intracellular pH plays a crucial role in a series of tissue activities such as enzyme activity, cell proliferation and apoptosis, drug resistance, ion transport, endocytosis, and muscle contraction. Small changes in pH can cause cellular dysfunction, causing diseases such as cancer and Alzheimer's disease. Excessive acidity and alkalinity can lead to heart, lung disease or neurological diseases, and even life-threatening in severe cases. Under normal physiological conditions, the concentration of H+ in the cell fluid is about 7.40, and its fluctuation range is generally 0.1-0.2 pH units. Some acidic organelles, such as lysosomes, have a pH range of 4.5-5.5. Extremely acidic environments (pH<4) are let...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D209/14C09K11/06G01N21/64G01N21/359A61K49/00
CPCA61K49/0032C07D209/14C07D401/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/359G01N21/64
Inventor 蔡林涛吕亚琳龚萍张利孟晓青李三朋周理华
Owner SHENZHEN INST OF ADVANCED TECH
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