Contrast medium based on iopamidol lipid derivative as well as preparation method and application of contrast medium

A lipid derivative, iopamidol technology, applied in the field of biomedical materials, can solve the problems of easy and rapid extravasation and removal, large size, and removal, and achieve the effect of cheap raw materials, strong operability, and mild reaction conditions

Active Publication Date: 2017-06-13
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the biggest problem with this type of low-molecular-weight CT contrast agent is that it is easy to extravasate and clear in the body quickly, and the time for blood selectivity enhancement is very short.
In order to solve this problem, researchers have used micro- or nano-sized particles as carriers to carry CT contrast agents and used them in the study of CT imaging [Invest Radiol 1993; 28:1028-1032; Acta Radiot 1996; 37:63-68. ], but its size is still relatively large (0.25-3.50 microns), and it is easy to be quickly cleared by the phagocytic system in the body
In recent years, research on nanoparticle-loaded CT contrast agents is also underway, but the contrast agents inside them are often released and leaked prematurely during circulation, resulting in poor imaging effects

Method used

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  • Contrast medium based on iopamidol lipid derivative as well as preparation method and application of contrast medium
  • Contrast medium based on iopamidol lipid derivative as well as preparation method and application of contrast medium
  • Contrast medium based on iopamidol lipid derivative as well as preparation method and application of contrast medium

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Dissolve 20mmol of compound 1 in 70mL of toluene, then add 1.2mmol of compound 2 and 0.1mmol of concentrated sulfuric acid in sequence, stir at 105°C for 48 hours, and spin the solvent to dry. The obtained crude product is separated and purified by column chromatography to obtain compound 3 , yield 53.5%.C 21 h 40 o 4 1 H NMR (CDCl 3 ,400MHz)δ:0.88(t,3H,CH 3 ),1.26-1.31(m,28H,CH 2 ), 1.49(t,3H,CH 3 ), 1.64(t,2H,CH 2 ),2.35(t,2H,CH 2 ), 5.01-5.03 (m, 1H, CH). Theoretical value of mass spectrum MS: 356.29, experimental value [M] + :357.3.

Embodiment 2

[0030] Under the protection of nitrogen, 1 mmol of compound 3 was dissolved in 50 mL of anhydrous toluene, then slowly added dropwise to 5 mmol of thionyl chloride, stirred at 80 ° C for 36 hours, and the solvent was spin-dried, and the obtained crude product was mixed with petroleum ether / acetone Compound 4 was purified by solvent recrystallization with a yield of 65.2%.C 21 h 39 ClO 3 1 H NMR (CDCl 3 ,400MHz)δ:0.88(t,3H,CH 3 ),1.26-1.32(m,28H,CH 2 ), 1.47(t,3H,CH 3 ),1.62-1.65(m,2H,CH 2 ),2.35(t,2H,CH 2 ),5.00-5.04(m,1H,CH).MS theoretical value: 374.99, experimental value [M] + :375.8.

Embodiment 3

[0032] Under the protection of nitrogen, 1 mmol of compound 4 and 1.3 mmol of compound 5 were mixed, dissolved in 40 mL of DMA, stirred at 50°C for 60 hours, and evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by column chromatography to obtain compound 6, Yield 75%.C 29 h 40 Cl 2 I 3 NO 5 1 H NMR (CDCl 3 ,400MHz)δ:0.88(t,3H,CH 3 ),1.26-1.32(m,28H,CH 2 ),1.53(t,3H,CH 3 ),1.63-1.65(m,2H,CH 2),2.36(t,2H,CH 2 ), 5.07-5.10 (m, 1H, CH). MS theoretical value: 934.25, experimental value [M] + :935.1.

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Abstract

The invention discloses a contrast medium based on an iopamidol lipid derivative, as well as a preparation method and application of the contrast medium. The lipid molecule structure comprises both hydrophobic aliphatic chains and hydrophilic iopamidol groups which can be combined to form nanoparticle structures by selves in a water solution, and in addition, as the aliphatic chains and the iopamidol can be connected through degradable ester bonds, the biocompatibility of the contrast medium can be further improved; moreover, as covalent bonds in the molecule structures of such substances are connected with iopamidol functional groups, the content of iopamidol in nanoparticles can be increased, and meanwhile the problems that the contrast medium is released and leaked too early in the particle circulation process can be effectively avoided. The nanoparticles formed by lipid of the contrast medium can be used as a functional material which is used as a contrast medium and a carrier of various medicines and other contrast mediums, thereby having wide clinical application prospects.

Description

[0001] Dai Zhifei, Liang Xiaolong [0002] Applicant unit: Peking University technical field [0003] The invention belongs to the field of biomedical materials, and relates to a non-ionic X-ray contrast agent, more specifically, to a novel structure-containing lipid derivative containing an iopamidol group and a method for preparing its intermediate, as well as its It is used as a functional material in contrast agents and various carriers. [0004] technical background [0005] Computed tomography (CT) is an imaging modality with high spatial and temporal resolution. The ability of CT to distinguish tissues is based on the fact that different tissues provide different degrees of X-ray attenuation, where the attenuation coefficient depends on the atomic number and electron density of the constituent elements in the tissue. Significant differences in absorption between bone, fat, air, and water produce high-contrast images of anatomy. However, in the absence of contrast ag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/46C07C231/02A61K49/04
CPCC07C231/02C07C237/46
Inventor 戴志飞梁晓龙
Owner PEKING UNIV
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