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Triphenylamine-benzopyranium salt derivative NIR-BT-P as well as synthesis method and application thereof

A technology of NIR-BT-P and benzopyrylium salt, which is applied in the field of triphenylamine-benzopyrylium salt derivatives, can solve problems such as measurement difficulties, and achieves low cost, efficient targeting, and simple synthesis. Effect

Pending Publication Date: 2022-05-24
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polarity is a complex factor that involves a range of non-covalent interactions, including dipolarity / polarizability and hydrogen bonding, so measuring it in living cells is difficult and researchers urgently need to develop Effective and convenient tool to accurately detect polarity in mitochondria

Method used

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  • Triphenylamine-benzopyranium salt derivative NIR-BT-P as well as synthesis method and application thereof
  • Triphenylamine-benzopyranium salt derivative NIR-BT-P as well as synthesis method and application thereof
  • Triphenylamine-benzopyranium salt derivative NIR-BT-P as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation and Characterization of NIR-BT-P

[0036] Synthetic route of NIR-BT-P:

[0037]

[0038] The synthetic method of NIR-BT-P, the steps are:

[0039] (1) At 0°C, cyclohexanone (3.1 mL, 30 mmol) was added dropwise to concentrated H 2 SO 4 (40 ml), keeping the solution stirring, then 4-(diethylamino)-2-hydroxybenzaldehyde (2.9 g, 15 mmol) was added. The mixture was further heated at 90°C for 2 hours, and after cooling to room temperature, the mixture was slowly poured into ice water (300 ml), followed by the addition of 4 ml of HClO 4 , the mixture was filtered, washed with water, and dried in vacuo, the obtained brown solid was 6-(diethylamino)-1,2,3,4-tetrahydrooxopyrimidine (5.2 g, yield 97%), which was obtained without further purification. available for the next step.

[0040] (2) 6-(Diethylamino)-1,2,3,4-tetrahydrooxopyrimidine (1.8g, 5mmol) and 4-(diphenylamino)benzaldehyde (2.7g, 10mmol) were dissolved in CH 3 in COOH. The mixture was heated at ...

Embodiment 2

[0042] To prepare a DMSO solution of 2mMNIR-BT-P, add 1,4 dioxane with volumes of 2, 1.9, 1.8, 1.7, 1.6, 1.5, 1.4, 1.3, 1.2, 1.1, 1, 0.9ml to 12 In the fluorescence cuvette, add distilled water in volumes of 0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, and 1.1 mL of distilled water to the cuvette, and add 10 μL NIR-BT to it. The DMSO solution of -P was detected on a fluorescence spectrophotometer at the same time. With the increase of the volume ratio of distilled water in the system, the fluorescence intensity at 830 nm gradually decreased. Fluorescence emission map see Figure 4 .

Embodiment 3

[0044] Prepare 2mM NIR-BT-P DMSO solution, prepare 2mM sulfur dioxide aqueous solution; add 1,4 dioxygen with volumes of 1.7, 1.6, 1.5, 1.4, 1.3, 1.2, 1.1, 1, 0.9ml to 9 cuvettes respectively Six rings, and then add distilled water in volumes of 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1 mL, and measure the maximum fluorescence intensity F on a fluorescence spectrometer. max are 556.1, 464.4, 394.4, 314.2, 260.2, 191.9, 142.1, 94.4, 41.1, with the polarity (Δf) as the abscissa, with the fluorescence intensity F max Draw a graph for the ordinate to get the polar working curve; the linear regression equation is: F max =3297.0-10830.5Δf, see Figure 5 .

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Abstract

The invention provides a triphenylamine-benzopyran onium salt derivative NIR-BT-P as well as a synthesis method and application thereof. The derivative NIR-BT-P has a Chinese name of (E)-6-(diethylamino)-4-(4 (diphenylamino) benzylidene)-1, 2, 3, 4 tetraoxypyrimidine, and the derivative NIR-BT-P has a structural formula shown in the description. The invention relates to a preparation method of a diethylene glycol dimer, which is characterized in that the diethylene glycol dimer has an English name of (E)-6-(diethylene glycol dimer)-4-(4 (diethylene glycol dimer)-1, 2, 3, 4 tetraethylene glycol dimer, and the English name of the diethylene glycol dimer is (E)-6-(diethylene glycol dimer)-4 (4)-1, 2, 3, 4 tetraethylene glycol dimer. The derivative NIR-BT-P is used as a fluorescent probe, and in different organic solvents, detection of polarity by different fluorescence intensity signals is realized through a fluorospectro photometer. According to the method, the difference of polarities in cancer cells and normal cells in a living body is utilized, so that the near-infrared fluorescence imaging is used for distinguishing and detecting tumor tissues and normal tissues in the living body.

Description

technical field [0001] The invention relates to triphenylamine-benzopyrylium salt derivatives, in particular to the application of a triphenylamine-benzopyrylium salt derivative NIR-BT-P in near-infrared detection of polarity. Background technique [0002] As an important indicator, polarity plays a pivotal role in chemistry and biology. In biological systems, especially at the cellular level, polarity determines the interaction activity of a large number of proteins and enzymes and reflects the permeability of membrane compartments. Furthermore, polarity is closely related to a variety of physiological processes, such as membrane fusion, protein denaturation, conformational changes in enzymes, and peptide aggregation. In particular, abnormal changes in polarity are closely related to a variety of diseases, including Alzheimer's disease, diabetes, liver cirrhosis, and cancer. In addition, the polarities and roles of different subcellular compartments are also different. M...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64A61K49/00
CPCC07D311/82C09K11/06G01N21/6428G01N21/6456A61K49/0041C09K2211/1088C09K2211/1007C09K2211/1014
Inventor 张涛阴彩霞霍方俊
Owner SHANXI UNIV
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