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Fluorescence identification dye based on nile blue matrix and preparing method and application thereof

A fluorescent recognition and Nile blue technology, applied in the field of fluorescent recognition dyes, can solve the problems of expensive medical treatment, real-time monitoring, and difficult cancer cure, and achieve low biomass background fluorescence, good photostability, and good application prospects Effect

Active Publication Date: 2016-07-27
DALIAN UNIV OF TECH
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  • Abstract
  • Description
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Problems solved by technology

However, the above-mentioned cancer detection techniques have certain disadvantages: high equipment cost and expensive medical treatment; large radiation damage, causing harm to the body; low spatial resolution, easy to cause misdiagnosis; poor time efficiency, and can only be detected in the middle and late stages of cancer. get a valid diagnosis
In addition, during the treatment process, especially during surgical resection, the above-mentioned diagnostic methods cannot monitor in real time and guide doctors to distinguish the tumor boundary, which also makes cancer difficult to cure and easy to repeat.

Method used

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  • Fluorescence identification dye based on nile blue matrix and preparing method and application thereof
  • Fluorescence identification dye based on nile blue matrix and preparing method and application thereof
  • Fluorescence identification dye based on nile blue matrix and preparing method and application thereof

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preparation example Construction

[0047] Another aspect of the present invention provides a class of preparation methods based on Nile blue parent fluorescent recognition dyes, said method comprising the steps of:

[0048] (1) 6-hydroxyl-2-naphthyl methyl ester reacts with a halogenated reagent in a molar ratio of 1:1~2 to prepare the compound of formula II:

[0049]

[0050] The reaction time is 6-36 hours, the reaction temperature is 10-80°C, and the reaction solvent is dichloromethane, ethanol, dimethylformamide, methanol, ethyl acetate or a mixture thereof;

[0051] In a preferred embodiment, the molar ratio of 6-hydroxy-2-naphthylmethyl ester to halogenated reagent is 1:1-1.5, the reaction time is 10-30h, the reaction temperature is 20-60°C, and the reaction solvent is dimethyl Formamide, ethanol, ethyl acetate or mixtures thereof;

[0052] In a more preferred embodiment, the molar ratio of 6-hydroxy-2-naphthylmethyl ester to halogenated reagent is 1:1-1.3, the reaction time is 20-30h, the reaction te...

Embodiment 1

[0080] Synthesis of fluorescent probe compound N1:

[0081]

[0082] (1) Synthesis of Intermediate 2

[0083] Dissolve 6-hydroxy-2-naphthylmethyl ester (10mmol) and NBS (12mmol) in 10ml of dimethylformamide respectively, and add the dimethylformamide solution of 6-hydroxy-2-naphthylmethyl ester into the round bottom flask , NBS was added dropwise into the round bottom flask using a constant pressure dropping funnel. During the reaction process, the reaction temperature was controlled at 28-32° C., the reaction system was filled with nitrogen for protection, and magnetic stirring was accelerated, and the reaction lasted for 24 hours. After the reaction was completed, the reaction solution was poured into ice water, and after standing still, a white precipitate was precipitated, which was dried by suction filtration and separated by chromatographic column to obtain intermediate 1 (60.5%) as a white solid.

[0084] (2) Synthesis of Intermediate 2

[0085] Dissolve Intermedi...

Embodiment 2

[0090] Photophysical Properties of Fluorescent Recognition Dye N1

[0091] Use the fluorescent recognition dye N1 prepared in Example 1 to add Tris-HCl buffer, PBS buffer, HEPES buffer, dimethyl sulfoxide, methanol, acetone, 1,4-dioxane, chloroform, acetic acid Ethyl ester, tetrahydrofuran, test ultraviolet absorption spectrum in dichloromethane ( Figure 2a ), fluorescence emission spectrum ( Figure 2b ), molar extinction coefficient and fluorescence quantum yield ( Figure 2c ), the dye concentration was 5 μM. The instruments used were AgIIlent8453 UV spectrophotometer and AgIIlentCaryEclIIpse fluorescence spectrophotometer. Figure 2 shows that the maximum absorption and emission wavelength of the fluorescent recognition dye N1 is greater than 630nm in the infrared region, has good photophysical properties, and is suitable for biological imaging applications.

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Abstract

The invention discloses a fluorescence identification dye based on a nile blue matrix and a preparing method and application thereof. The fluorescence identification dye has a structure as shown in the general formula I, wherein R1, R2, R3 and R4 are C1-8 alkyl group, C1-6 alkyl sulfonic acid group and C1-6 alkyl carboxylic acid group respectively, X is halogen, and n is an integer from 1 to 4. The fluorescence identification dye can achieve targeted identification of enzyme KIAA1363 in a specific mode, has excellent tissue permeability, light stability and water solubility, low biotoxicity, excellent near infrared fluorescence property, high sensitivity and low background interference degree, and is suitable for biological sample detection. The fluorescence identification dye conducts identification and distinguishing of cancer cells and tissues and non-cancer cells and tissues by means of KIAA1363 expression difference, and the effect of distinguishing in-vitro cancer cell and tissue samples from non-cancer cell and tissue samples is remarkable especially. The fluorescence identification dye can be applied to deep issue imaging and mouse living imaging, and has high application value in imaging assistance and boundary determination during early diagnosis of cancer and operative treatment of cancer.

Description

technical field [0001] The invention relates to a class of fluorescent recognition dyes based on Nile blue precursors, a preparation method thereof, and the application of the fluorescent recognition dyes in identifying cancer cells and tissues. Background technique [0002] Healthcare has always been one of the key issues of global concern. The "World Cancer Report" released by the World Health Organization shows that the incidence of cancer is severe worldwide, and the incidence and mortality rates have increased significantly. Half of the new cases are in Asia, and most are concentrated in China. Cancer has surpassed other diseases to become the disease with the highest fatality rate in our country, so it is particularly important to establish a fast, sensitive and simple method for cancer diagnosis. The current mature cancer diagnosis technologies mainly include nuclear magnetic resonance imaging, infrared imaging, ultrasonic imaging, positron emission tomography, sing...

Claims

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Application Information

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IPC IPC(8): C09B19/00C09K11/06G01N21/64
CPCC09B19/00C09K11/06C09K2211/1033G01N21/6486
Inventor 樊江莉郭士刚康垚彭孝军朱浩
Owner DALIAN UNIV OF TECH
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