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A kind of pentapeptide modified rhodamine b compound and its preparation method and application

A compound and modified technology, applied in the field of medicine, can solve the problems of poor tumor imaging effect, less research, fast metabolism, etc., and achieve the effects of improving imaging contrast and clarity, good water solubility, and simple process

Active Publication Date: 2021-06-01
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the currently used fluorescent probes such as rhodamines, 5-aminolevulinic acid, and hexaaminolevulinic acid ester are all small molecular compounds, which are distributed in the human body according to the different metabolic needs of various parts in the body. Tissue and organ selectivity or targeting, especially no specific effect on tumors, poor imaging effect on tumors, fast metabolism in vivo, short retention time, low utilization rate, no tumor-targeting fluorescence at home and abroad Probes have entered clinical applications, and there are few studies on tumor-targeted fluorescent probes and cancer imaging detection. Therefore, the development of tumor-targeted fluorescent probes with my country's independent intellectual property rights will improve the early clinical diagnosis of tumors in my country and the difference between benign and malignant tumors. The level of differential diagnosis of tumors has very important significance and far-reaching influence

Method used

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  • A kind of pentapeptide modified rhodamine b compound and its preparation method and application
  • A kind of pentapeptide modified rhodamine b compound and its preparation method and application
  • A kind of pentapeptide modified rhodamine b compound and its preparation method and application

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Effect test

Embodiment 1

[0025] Preparation of pentapeptide modified rhodamine B compound, the steps are as follows:

[0026] 1) Pentapeptide (tyrosyl-isoleucyl-glycyl-seryl-arginine, YIGSR) was prepared by solid-phase peptide synthesis;

[0027] 2) Add 0.5g pentapeptide (tyrosyl-isoleucyl-glycyl-seryl-arginine, YIGSR, 0.84mmol) into the container, add 9-(2-carboxyphenyl)-3 , 6-bis(diethylamino)xanthenium chloride (rhodamine B, 0.4g, 0.84mmol) and diisopropylethylamine (0.11g, 0.84mmol) in DMF (10mL), stirred for 1.5 hours , filtered, and the filtrate and washings were collected, concentrated by rotary evaporation, and added dropwise to cold ether to obtain a red precipitate, which was filtered and washed with suction to obtain 0.51 g of pentapeptide modified rhodamine B compound red solid powder, with a yield of 60%.

[0028] Test the effect of the pentapeptide modified rhodamine B compound prepared in this embodiment as a tracer for fluorescence imaging, and use the same dose of rhodamine B as a co...

Embodiment 2

[0031] Preparation of pentapeptide modified rhodamine B compound, the steps are as follows:

[0032] 1) Pentapeptide (tyrosyl-isoleucyl-glycyl-seryl-arginine, YIGSR) was prepared by solid-phase peptide synthesis;

[0033] 2) Add 1g of pentapeptide (tyrosyl-isoleucyl-glycyl-seryl-arginine, YIGSR, 1.68mmol) into the container, add 9-(2-carboxyphenyl)-3, 6-bis(amino)xanthenium chloride (0.62g, 1.68mmol) and diisopropylethylamine (0.22g, 1.68mmol) in DMF (20mL), stirred for 2 hours, filtered, and the filtrate was collected and washed solution, concentrated by rotary evaporation, and added dropwise into cold ether to obtain a red precipitate, which was filtered and washed to obtain 1.11 g of pentapeptide modified rhodamine B compound red solid powder, with a yield of 70%.

Embodiment 3

[0035] Preparation of pentapeptide modified rhodamine B compound, the steps are as follows:

[0036] 1) Pentapeptide (tyrosyl-isoleucyl-glycyl-seryl-arginine, YIGSR) was prepared by solid-phase peptide synthesis;

[0037]2) 5g pentapeptide (tyrosyl-isoleucyl-glycyl-seryl-arginine, YIGSR, 8.4mmol), 9-(2-carboxyphenyl)-3,6-bis( Hydroxy)xanthenium compound (0.4g, 8.4mmol), dicyclohexylcarbodiimide (DCC, 1.73g, 8.4mmol) and triethylamine (0.85g, 8.4mmol) were dissolved in dimethyl sulfoxide solution ( 100 mL), stirred and reacted in an ice-water bath for 4 hours, precipitated with a mixed solvent of ethanol / ether (volume ratio 1 / 5), and collected the solid by filtration. Then the solid was dissolved with DMF, and then reprecipitated with ethanol / ether mixed solvent (volume ratio 1 / 5), the solid was collected by filtration, and vacuum-dried for 24 hours to obtain 6.16g pentapeptide modified Rhodamine B compound red solid powder, Yield 80%.

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Abstract

The invention relates to a pentapeptide modified rhodamine B compound and its preparation method and application. The pentapeptide modified rhodamine B compound has a chemical structural formula of formula I. The pentapeptide modified rhodamine B compound provided by the present invention has tumor targeting or selectivity, and as a tracer for fluorescence imaging, it can realize tumor targeting imaging and improve imaging contrast and clarity. In addition, the pentapeptide provided by the present invention The dosage of the modified rhodamine B compound can be reduced by half compared with that of rhodamine B, and the water solubility is good, so it is convenient to make a solution for perfusion or injection. Formula I:

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a pentapeptide-modified rhodamine B compound and a preparation method and application thereof. Background technique [0002] At present, the key to the cure of cancer lies in early clinical detection, early diagnosis, and early treatment, that is, whether small lesions can be found earlier and treated in a timely and effective manner. In recent years, with the rapid development of optical imaging and fluorescent labeling technology, in vivo fluorescence imaging has emerged as a biological optical imaging method, and has been widely used in cell tracking, tumor diagnosis and drug development. Show broad application prospects. The basic principle of in vivo fluorescence imaging technology is to use fluorescent probes to label biologically specific tissues, and use high-sensitivity optical detection equipment to realize real-time and in situ detection of fluorescent si...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/04C07K1/113A61K49/00
CPCA61K49/0041A61K49/0056C07K7/06C07K19/00
Inventor 鄢国平刘凡鄢珈睿王玉芳陈思李斌杜飞鹏张云飞
Owner WUHAN INSTITUTE OF TECHNOLOGY
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