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Multifunctional near infrared fluorescent probe and preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of multifunctional near-infrared fluorescent probes and their preparation, to achieve the effects of less background interference, elimination of interference and low toxicity

Active Publication Date: 2017-07-07
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are very few reports on near-infrared fluorescent probes that can detect both thiols and pH

Method used

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  • Multifunctional near infrared fluorescent probe and preparation method and application thereof
  • Multifunctional near infrared fluorescent probe and preparation method and application thereof
  • Multifunctional near infrared fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] A method for preparing a multifunctional near-infrared fluorescent probe, comprising the following steps:

[0090] (1) The first compound S 1 Synthesis:

[0091] S 1 The synthetic route of:

[0092]

[0093] S 1 The synthesis steps are as follows:

[0094] At room temperature, add cystamine dihydrochloride (162mg, 0.72mmol), 1.5mL methanol, 416μL triethylamine (3mmol) into a 25mL round bottom flask, then add 2mL acetonitrile, and stir rapidly for about 0.5 hours, the solution becomes transparent , cystamine dihydrochloride is completely dissolved to obtain the first mixed solution;

[0095] then put (abbreviated as Cy.7.Cl, 383mg, 0.6mmol) was dissolved in 4mL of acetonitrile to obtain the second mixed solution, which was then added dropwise to the above-mentioned first mixed solution with a dropping funnel at a rate of about 1 drop / 20s, heat, and react at 35°C for 4 hours under the protection of nitrogen. After the reaction is completed, the reaction solut...

Embodiment 2

[0111] A method for preparing a multifunctional near-infrared fluorescent probe, comprising the following steps:

[0112] (1) The first compound S 1 Synthesis:

[0113] S 1 The synthesis steps are as follows:

[0114]At room temperature, add cystamine dihydrochloride (135mg, 0.6mmol), 1.5mL methanol, 166.4μL triethylamine (1.2mmol) into a 25mL round bottom flask, then add 2mL acetonitrile, and stir rapidly for about 0.5 hours, the solution Become transparent, cystamine dihydrochloride all dissolves, obtains the first mixed solution;

[0115] then put (abbreviated as Cy.7.Cl, 383.1mg, 0.6mmol) was dissolved in 4mL of acetonitrile to obtain the second mixed solution, which was then added dropwise to the above-mentioned first mixed solution with a dropping funnel at a rate of about 1 drop / 20s, heat, and react at 30°C for 6 hours under the protection of nitrogen. After the reaction is completed, the reaction solution after the reaction is rotary evaporated to remove the sol...

Embodiment 3

[0124] A method for preparing a multifunctional near-infrared fluorescent probe, comprising the following steps:

[0125] (1) The first compound S 1 Synthesis:

[0126] S 1 The synthesis steps are as follows:

[0127] At room temperature, add cystamine dihydrochloride (135mg, 0.6mmol), 1.5mL methanol, 332.8μL triethylamine (2.4mmol) into a 25mL round bottom flask, then add 2mL acetonitrile, and stir rapidly for about 0.5 hours, the solution Become transparent, cystamine dihydrochloride all dissolves, obtains the first mixed solution;

[0128] then put (abbreviated as Cy.7.Cl, 383.1mg, 0.6mmol) was dissolved in 4mL of acetonitrile to obtain the second mixed solution, which was then added dropwise to the above-mentioned first mixed solution with a dropping funnel at a rate of about 1 drop / 20s, heat, and react at 40°C for 5 hours under the protection of nitrogen. After the reaction is completed, the reaction solution after the reaction is rotary evaporated to remove the so...

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Abstract

The invention provides a multifunctional near infrared fluorescent probe. The chemical formula of the multifunctional near infrared fluorescent probe is as shown in formula (I), wherein X<1> is -S- or -Se-, R' is C1-12 alkylene, X<2> is -C(CH3)2-, -O- or -Se-, each of R1 and R2 is independently selected from H atoms, C1-18 alkyl or groups as shown in SO3R9, R9 is C1-18 alkyl or benzyl, each R3 and R4 is independently selected from C1-18 alkyl or benzyl, each of R5, R6, R7 and R8 is independently selected from C1-18 alkyl or C1-18 alkyl containing at least one of F, Cl, Br, I, O and S, and each of Y1 and Y2 is independently selected from F, Cl, Br or I. The multifunctional near infrared fluorescent probe can simultaneously detect pH and mercaptan, is a double-response ratio type near infrared fluorescent probe and can be used for the photodynamic therapy of tumors. The invention further provides a preparation method and application of the probe.

Description

technical field [0001] The invention relates to the technical field of organic probe molecules, in particular to a multifunctional near-infrared fluorescent probe and its preparation method and application. Background technique [0002] Thiols (that is, compounds containing sulfhydryl groups) play a very important role in living systems, for example, glutathione (GSH) can maintain intracellular redox, intracellular signal conversion, etc., cysteine ​​( Cys) can be used as an extracellular reducing agent, a decisive substrate for protein synthesis, etc. Levels of certain thiols are directly linked to many diseases (eg, psoriasis, liver damage, AIDS) and cancer. [0003] 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. For example, intracellular pH changes when tumors develop. The delicate relationship between cell function an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D405/14G01N21/64A61K41/00
CPCA61K41/0057C07D405/14C09K11/06C09K2211/1088G01N21/6402
Inventor 蔡林涛孟晓青龚萍杨月婷张利吕亚琳吴亚运郑明彬盛宗海陈驰
Owner SHENZHEN INST OF ADVANCED TECH
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