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A water-soluble heptamethine near-infrared dye with tumor targeting and its application

A tumor-targeting, near-infrared technology, which is applied in the fields of methine/polymethine dyes, organic dyes, organic chemistry, etc., can solve the problems that the imaging effect needs to be improved, and achieve good targeting, stability, and good imaging effect Effect

Active Publication Date: 2021-09-28
NANJING NUOYUAN MEDICAL DEVICES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

ICG-03 has higher stability and targeting than ICG, but its imaging effect still needs to be improved when administered at low doses

Method used

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  • A water-soluble heptamethine near-infrared dye with tumor targeting and its application
  • A water-soluble heptamethine near-infrared dye with tumor targeting and its application
  • A water-soluble heptamethine near-infrared dye with tumor targeting and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of compound I of the present invention

[0034] 1. Take 10g of phenylhydrazine-4-sulfonic acid, 6g of methyl isopropyl ketone, and 70ml of acetic acid, and heat to reflux at 120°C for 6 hours under constant stirring. It can be seen that the raw materials are continuously dissolved and the solution turns brick red. After the reaction, the solution was spin-dried and washed with diethyl ether to obtain brick-red solid 2,3,3-trimethyl-6-sulfonylindole, whose mass spectrum and hydrogen spectrum data are as follows: m / z=238.1, 1 HNMR (400MHz, DMSO-d6) δ7.86 (d, J = 1.5Hz, 1H), 7.70 (dd, J = 8.1, 1.6Hz, 1H), 7.51 (d, J = 8.1Hz, 1H), 2.55 ( s,3H), 1.43(s,6H).

[0035] 2. Take 15g of 2,3,3-trimethyl-6-sulfonylindole, 21g of 1,3-propane sultone, and 240ml of o-dichlorobenzene, and reflux for 12h under constant stirring. The raw materials and products All are insoluble in solvents, but can be uniformly dispersed in a molten state. After the reaction was complet...

Embodiment 2

[0040] Comparison of the imaging effects of ICG, ICG-03 and NIR-04 on human tumor-bearing mouse models of different cell lines

[0041] In order to investigate the tumor targeting ability of NIR-04, five mouse tumor models were constructed in this example, and tumor cells bel7404 (liver cancer), sw1990 (pancreatic cancer), MCF7 (breast cancer) and A549 (lung cancer) were inoculated in the armpit and U87 (glioma), through non-destructive in-situ near-infrared fluorescence imaging technology, real-time detection of NIR-04, ICG-03 (see 201710290191.3 for the preparation method) and ICG in bel7404 (liver cancer), sw1990 (pancreatic cancer), MCF7 ( Breast cancer), A549 (lung cancer) and U87 (glioma) tumor-bearing mice (axillary tumor) in vivo dynamic distribution. In the experiment, a 760nm laser was selected as the light source, and a high-sensitivity near-infrared inductively coupled camera was used to obtain the fluorescent signal in the mouse body. An 800nm ​​long-pass filter w...

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Abstract

The invention discloses a water-soluble heptamethine near-infrared dye with tumor targeting property and application thereof. The near-infrared dye of structural formula I is widely distributed in the tissues of the body along with hemoglobin, and its metabolism in normal tissues is faster than that in tumor tissues, so it can stay in tumor tissues in large quantities, thereby playing the function of in vivo diagnosis. Therefore, the near-infrared fluorescent dye described in the present invention can be used in the preparation of tumor diagnostic reagents.

Description

technical field [0001] The invention belongs to the technical field of non-specific molecular targeting diagnostic reagents, and relates to a water-soluble heptamethine near-infrared dye with tumor targeting and an application thereof. Background technique [0002] With the extension of the average life expectancy of residents and the changes in living environment and eating habits, malignant tumors have become one of the most common diseases with high mortality in the world. In recent years, the morbidity and mortality of malignant tumors in China have also shown an increasing trend year by year. In the current clinical treatment, surgery is a more effective method to treat early tumors. Direct resection of non-metastatic tumors can give patients more chances of survival. [0003] At present, clinicians often use preoperative medical imaging technology to determine the size, location and surrounding environment of tumors. Commonly used preoperative imaging methods includ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/10
CPCA61K49/0032C07D209/10C09B23/105C09K11/06C09K2211/1007C09K2211/1029
Inventor 顾月清李兆伦陶吉
Owner NANJING NUOYUAN MEDICAL DEVICES CO LTD
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