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A class of aminocyanine fluorescent dyes and its preparation method and application

A fluorescent dye and aminocyanine technology, applied to a class of aminocyanine fluorescent dyes and their preparation and application fields, can solve the problem of rare bifunctional fluorescent dyes, avoid excitation light interference, reduce background interference, and improve application performance Effect

Inactive Publication Date: 2017-06-27
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, it is of great significance to synthesize diagnostic and therapeutic agents that not only have tumor-specific imaging but also can be used for targeted therapy. Currently, such bifunctional fluorescent dyes are still relatively rare.

Method used

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  • A class of aminocyanine fluorescent dyes and its preparation method and application
  • A class of aminocyanine fluorescent dyes and its preparation method and application
  • A class of aminocyanine fluorescent dyes and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1 Synthesis of Cy7-RGD and Cy7-hex-RGD

[0047] 1) Synthesis of condensing agent 2-chloro-1-formyl-3-hydroxymethylcyclohexene, add 40mL DMF and 40mL dichloromethane to a 250mL round bottom flask in an ice bath (0-5°C) , Dissolve 37mL of phosphorus oxychloride in 37mL of dichloromethane, and drop it into the reaction flask drop by drop with a constant pressure dropping funnel for about 1 hour. Then stirred at normal temperature for 1 hour, finally added 10 g of cyclohexanone, and refluxed for 3 hours. After the reaction was complete, the resulting reaction mixture was poured into a large amount of ice water and stored in a refrigerator (4° C.). After standing overnight, a large amount of solid precipitated, which was suction filtered to obtain 15 g of a yellow crude product, with a crude yield of 85.7%. The product can be used in the synthesis of the next intermediate without further purification.

[0048]

[0049] 2) Synthesis of N-ethyl-2,3,3-trimethyl-3H...

Embodiment 2

[0060] Embodiment 2 Purification of Cy7-RGD, Cy7-hex-RGD and reference compound Cy7-hex

[0061] Since the synthesized fluorescent dyes Cy7-RGD, Cy7-hex-RGD and their reference compound Cy7-hex have relatively high polarity and good water solubility, the purpose of separation and purification cannot be achieved by ordinary normal phase silica gel chromatography. , so the reverse C18 silica gel column was selected to optimize the purification conditions of the fluorescent dye and its reference compound for purification, and the selected eluents were water and methanol. In this example, the linear gradient table of eluent component methanol during the purification of the representative dye Cy7-RGD is given, as shown in Table 1 below.

[0062] Table 1 Linear gradient when separating and purifying Cy7-RGD

[0063]

[0064]

[0065] The better water solubility of this kind of dye improves its biological application performance and provides the possibility for intravenous adm...

Embodiment 3

[0066] Embodiment 3 Spectral testing of fluorescent dyes and their reference compounds

[0067] All the dyes used in the present invention are dried overnight in a vacuum drying oven before use, and a vacuum oil pump is used to ensure that the dyes are cooled in a vacuum state during the cooling process, which avoids the dyes from contacting the water vapor in the air during the cooling process. Glass containers that need to be kept dry should be oven dried overnight before use.

[0068] The configuration method of the dye mother liquor used in the present invention is as follows (taking Cy7-RGD as an example): 12.54mg of fluorescent dye Cy7-RGD is added in a 10mL brown volumetric flask, and it is ultrasonically dissolved with a small amount of anhydrous DMSO to make the fluorescent dye Mix well, then bring the solution up to the mark with anhydrous DMSO. After the preparation of the mother solution is completed, the volumetric flask containing the mother solution is sealed a...

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Abstract

The invention discloses a class of aminocyanine fluorescent dyes linked to the cyclic peptide cyclo (RGD) and its preparation method and application. The general structural formula of the compound is as I; it is composed of structural units II and III; the structural unit II is a derived cyanine dye Structure, belonging to water-soluble fluorescent molecules, its spectrum has a large Stokes shift, and is less toxic to normal cells; structural unit III is a cyclic peptide structure of a specific ligand for αvβ3 integrin receptors, which can be used for targeting position. The fluorescent dye has dual functions of tumor imaging diagnosis and targeted therapy.

Description

technical field [0001] The invention relates to a kind of aminocyanine fluorescent dye connected with cyclic peptide cyclo (GD) and its preparation method and application. The compound has dual functions of tumor image diagnosis and targeted therapy. [0002] technical background [0003] Cancer is the most pressing public health problem, and the statistics are staggering. The great challenge of personalized cancer treatment in the future is to explore and improve the early detection methods for localized and scattered tumor cells in patients, which is crucial for the successful treatment of cancer and improving the survival rate of cancer patients. At present, the clinical detection and diagnosis methods of cancer mainly include magnetic resonance imaging, positron emission tomography, computed tomography, X-ray, ultrasound, etc., but they lack specificity and sensitivity, and may also cause radiation risks. Optical imaging method is an emerging non-invasive, real-time, hig...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/06C09K11/06G01N21/64
Inventor 宋锋玲邓君蝶孙亮亮
Owner DALIAN UNIV OF TECH
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