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Fluorinated Cy7 compound as well as synthesis method and application thereof

A synthesis method and compound technology, applied in chemical instruments and methods, organic chemistry, pharmaceutical formulations, etc., can solve the problems of low sensitivity and resolution, and achieve the effects of simple synthesis conditions, easy-to-obtain raw materials, and simple preparation methods

Active Publication Date: 2022-05-13
INNOVATION ACAD FOR PRECISION MEASUREMENT SCI & TECH CAS
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Fluorescence imaging is more sensitive and can reach the resolution of organelles; magnetic resonance imaging has no tissue penetration depth limit, but the sensitivity and resolution of traditional 1H MRI are relatively low, and the use of heteronuclear contrast agents (3He, 19F, 129Xe, etc.) can further improve the sensitivity of the contrast agent because there is no background signal interference

Method used

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  • Fluorinated Cy7 compound as well as synthesis method and application thereof
  • Fluorinated Cy7 compound as well as synthesis method and application thereof
  • Fluorinated Cy7 compound as well as synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] 1, the synthesis of formula (I) compound

[0042] Weigh phenylhydrazine-4-sulfonic acid (17.0g, 90.4mmol), anhydrous sodium acetate (7.5g, 90.7mmol) and 3-methyl-2-butanone (17.0g, 190.7mmol) in a 250mL round bottom flask 100mL of glacial acetic acid was added to the round bottom flask, and under the protection of nitrogen, the round bottom flask was heated to 130°C and refluxed for 6h. After the reaction was completed, it was cooled to room temperature, and a large amount of ether was added to the obtained mixed product for precipitation. After the precipitation was complete, Filter, collect filter cake, filter cake is purified by column chromatography (eluent: CH 3 OH:CH 2 Cl 2 =1:5, v / v), a pink solid (16.4g, yield 75.9%) was obtained;

[0043] 1 H NMR (500MHz, MeOD) δ7.92–7.82 (m, 1H), 7.50 (d, J = 8.0Hz, 1H), 2.01 (s, 1H), 1.38 (s, 3H);

[0044] 13 C NMR (126MHz, MeOD) δ192.09(s), 173.88(s), 153.81(s), 145.57(s), 142.42(s), 125.73(s), 119.48(s), 118.31(s), 53...

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Abstract

The invention discloses a fluorinated Cy7 compound as well as a synthesis method and application thereof. The fluorinated Cy7 compound has the following structural formula. The compound is simple in preparation method, cheap and easily available in raw materials, relatively simple in synthesis condition, relatively low in synthesis cost, relatively high in yield and suitable for large-scale production. The compound has a passive targeting capability and can be enriched in a tumor area, so that the tumor area is developed and imaged through a 19F MRI and fluorescence imaging method, the diagnosis of tumors is realized, and therefore, the compound is suitable for being used as a 19F MRI and fluorescence imaging bimodal developing agent.

Description

technical field [0001] The invention belongs to the technical field of multimodal imaging, and in particular relates to a fluorinated Cy7 compound, a synthesis method and application thereof. Background technique [0002] Compared with biomacromolecular drugs or imaging agents, the synthesis of small molecular drugs or imaging agents is simpler, the structure is easier to control, and characteristics such as characterization and purity are easier to determine. Developers are enduring and are constantly being developed. [0003] Integrating multimodal imaging functions on the same small molecule carrier can achieve mass production and complement the advantages of their respective imaging modalities, achieving better results than single imaging modalities. Fluorescence imaging is more sensitive and can achieve resolution at the organelle level; magnetic resonance imaging has no tissue penetration depth limit, but traditional 1 The sensitivity and resolution of H MRI are rela...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/10C09K11/06A61K49/00A61K49/10
CPCC07D209/10C09K11/06A61K49/0002A61K49/0034A61K49/0052A61K49/10C09K2211/1029
Inventor 陈世桢肖龙李昱张磊周欣叶朝辉
Owner INNOVATION ACAD FOR PRECISION MEASUREMENT SCI & TECH CAS
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