Near-infrared fluorescent small-molecule probe as well as synthesis method and application thereof

A technology of small molecule probes and synthesis methods, which is applied in the field of near-infrared fluorescent small molecule probes and their synthesis, can solve the problems of limiting the clinical transformation of nano-photothermal materials, the difficulty of further clinical transformation, and the need to improve the photothermal performance. Achieve good tumor photothermal therapy effect, excellent photothermal agent performance, and enhance the effect of photothermal conversion efficiency

Pending Publication Date: 2022-02-01
LINYI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although nanoparticles have good photothermal conversion efficiency, they are not easily degraded in the body. The complex preparation process, potential long-term toxicity, and uneven size greatly limit the further clinical transformation of nanophotothermal materials. Thermal agents have natural advantages in the above aspects
[0006] Most of the organic small-molecule photothermal agents reported in the current literature need the help of "nano-based" strategies to assist in their photothermal therapeutic performance. However, this makes the drug system face the common limitations of "nanomaterial" systems, making it difficult to further develop carry out clinical translation
IR-780 has a natural tumor-targeting function, but its photothermal performance needs to be improved, and the administration method in the tumor-bearing mouse model is intratumoral injection

Method used

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  • Near-infrared fluorescent small-molecule probe as well as synthesis method and application thereof
  • Near-infrared fluorescent small-molecule probe as well as synthesis method and application thereof
  • Near-infrared fluorescent small-molecule probe as well as synthesis method and application thereof

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preparation example Construction

[0044] Such as figure 1 As shown, the synthetic method of the near-infrared fluorescent small molecule probe provided by the embodiment of the present invention comprises the following steps:

[0045] S101, add carbon tetrabromide CBr in a 100mL three-necked bottle 4 and triphenylphosphine PPh 3 , placed in a mixture of ice and water, and when the temperature of the solution dropped to 0°C, slowly add 3,3,3-trifluoro-1-propanol reagent dropwise;

[0046] S102, after the dropwise addition, the reaction solution turns into a yellow viscous liquid; after moving the reaction device to room temperature, heat and reflux at 60°C for 1 hour; lower the temperature and set up a distillation device, heat up to evaporate the product, and when the temperature rises to 100°C, the liquid evaporates. Continue to heat up until no liquid evaporates to obtain a colorless liquid compound 1;

[0047] S103, the compound 1,2,3,3-trimethyl-3H indole and potassium iodide KI were dissolved in aceton...

Embodiment 1

[0053] 1. Overview of the invention

[0054] The invention relates to a near-infrared fluorescent small molecule probe for targeted breast cancer therapy and its dual-modal imaging and photothermal therapy. The near-infrared small molecule probes for dual-mode imaging and treatment provided by the present invention are derived on the basis of IR-780 molecules, retain the basic structure of IR-780 molecules, and change the alkyl group connected to the N atom carbon chain end, add -CF at the end 3 The group can be used to target tumor tissue, in vivo near-infrared fluorescence imaging, tumor photothermal therapy, and enhance photothermal conversion efficiency.

[0055] 2. Design ideas

[0056] Experience has shown that in medicine, when fluorine atoms or fluorine-containing groups (especially CF 3 group) into the compound, its electrical effect and simulation effect change the distribution of electron density inside the molecule, affect the acidity and alkalinity of the inter...

Embodiment 2

[0095] Tumor-bearing nude mice whose tumor models were successfully established were subjected to 18F-FDG micro-PET and CT scans after injecting 0.1mL IR-780-F solution into the tail vein for 96 hours. Nude mice were fasted for 12 h before scanning and drank water normally. On the day of scanning, 400uCi18F-FDG was rapidly injected from the tail vein of nude mice. After metabolism for 30 minutes, nude mice were anesthetized with 2% isoflurane, fixed on the small animal examination bed, and the position of nude mice was adjusted to ensure that they were in the middle of the scanning coil, and then scanned for 10 minutes. Anesthesia was maintained with 1.5% isoflurane during the scan. Experimental results such as Figures 9 to 15 shown.

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Abstract

The invention belongs to the technical field of biomedicine, and discloses a near-infrared fluorescent small-molecule probe as well as a synthesis method and application thereof, and the near-infrared fluorescent small-molecule probe is IR-780-F. The near-infrared fluorescent small-molecule probe is derived on the basis of an IR-780 molecule, the basic structure of the IR-780 molecule is reserved, the tail end of an alkyl carbon chain connected with an N atom is changed, and a -CF3 group is added to the tail end. The IR-780-F shows excellent performance in the aspects of light stability, cancer cell targeting, fluorescence imaging and the like, is low in toxicity, can be used for tumor tissue targeting, in-vivo near-infrared fluorescence imaging, photo-thermal therapy and the like, and realizes diagnosis and treatment integration.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, in particular to a near-infrared fluorescent small molecule probe and its synthesis method and application. Background technique [0002] At present, surgical resection, radiotherapy, and chemotherapy are important methods for clinical treatment of cancer, but these methods have certain limitations, and the curative effect still needs to be improved. There is an urgent need to develop new methods and new drugs for the treatment of cancer. [0003] In recent years, emerging cancer treatment strategies include immunotherapy, gene therapy, photodynamic therapy, photothermal therapy, etc. Among them, photothermal therapy (PTT) has become a research hotspot in the field of tumor treatment due to its advantages of non-invasiveness, precise spatiotemporal control, strong specificity, and high tumor destruction efficiency. Near infrared light (Near infrared, NIR) has good tissue penetration ability,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/10C09K11/06A61K41/00A61K47/54A61K49/00A61P35/00
CPCC07D209/10C09K11/06A61K41/0052A61K47/54A61P35/00A61K49/0034A61K49/0052C09K2211/1029C09K2211/1007A61N5/0625A61N5/062A61N2005/0659A61K49/0032A61B5/0071A61B5/015C09B67/0071C09B67/0092
Inventor 曲宗金李函王振孟梓娟张书圣
Owner LINYI UNIVERSITY
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