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Contrast agent based on iopamidol lipid derivative and its preparation method and use

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

Active Publication Date: 2019-01-15
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 agent based on iopamidol lipid derivative and its preparation method and use
  • Contrast agent based on iopamidol lipid derivative and its preparation method and use
  • Contrast agent based on iopamidol lipid derivative and its preparation method and use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Dissolve 20 mmol of compound 1 in 70 mL of toluene, then add 1.2 mmol of compound 2 and 0.1 mmol of concentrated sulfuric acid in sequence, stir at 105°C for 48 hours, spin off the solvent, and separate and purify the resulting crude product by column chromatography to obtain compound 3. , The yield is 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). MS theoretical value: 356.29, experimental value[M] + :357.3.

Embodiment 2

[0026] Under the protection of nitrogen, dissolve 1mmol of compound 3 in 50mL of anhydrous toluene, then slowly add 5mmol of thionyl chloride dropwise, stir at 80℃ for 36 hours, spin dry the solvent, and the resulting crude product is mixed with petroleum ether / acetone The compound 4 was purified by solvent recrystallization and the yield was 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

[0028] Under the protection of nitrogen, 1mmol of compound 4 was mixed with 1.3mmol of compound 5, dissolved in 40mL of DMA, stirred at 50°C for 60 hours, and the solvent was evaporated under reduced pressure. The crude product obtained was separated and purified by column chromatography to obtain the compound 6. The yield is 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

Technical field [0001] The present invention belongs to the field of biomedical materials, and relates to non-ionic X-ray contrast agents. More specifically, it relates to a preparation method of a class of novel structurally novel lipid derivatives containing iopamidol groups and intermediates thereof, and Used as a functional material in contrast agents and various carriers. technical background [0002] Computed tomography (CT) is an imaging mode with high spatial and temporal resolution. The ability of CT to distinguish tissue is based on the basis 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. The significant differences in absorption between bone, fat, air and water can produce high-contrast images of anatomical structures. However, in the absence of a contrast agent, not all tissues are fully identified, and the use of a t...

Claims

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Application Information

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Patent Type & Authority Patents(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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