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Synthesis method of water-soluble squarylium cyanine type near-infrared organic macromolecular photo-thermal agent with high stability

A technology of organic macromolecules and high stability, applied in the field of biomedicine, can solve problems such as chemical instability, hindering application, poor water solubility, etc., and achieve the effects of high light stability, good water solubility, and excellent photothermal properties

Active Publication Date: 2021-11-26
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the inherent chemical instability and poor water solubility of SQ hinder its application in biology and medicine

Method used

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  • Synthesis method of water-soluble squarylium cyanine type near-infrared organic macromolecular photo-thermal agent with high stability
  • Synthesis method of water-soluble squarylium cyanine type near-infrared organic macromolecular photo-thermal agent with high stability
  • Synthesis method of water-soluble squarylium cyanine type near-infrared organic macromolecular photo-thermal agent with high stability

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Embodiment 1

[0041](1) Preparation of SQ1: Step 1: 1,8-Naphtholactam (Compound 1, 5mmol) was dissolved in N,N-Dimethylformamide (20mL), and hydrogenated slowly in an ice-water bath Sodium (25mmol), after stirring for 15min, slowly drop iodoethane (6mmol), after the reaction system slowly rises to room temperature and continue to stir for 2h, add water to quench the reaction, use column chromatography after extraction (eluent sherwood oil, ethyl acetate The volume ratio is 15:1) Compound 2 was separated and purified to obtain 827 mg of a yellow solid with a yield of 84%. The second step: Dissolve compound 2 (2mmol) in ultra-dry tetrahydrofuran (20mL), stir in an ice-water bath for 5min, add methylmagnesium chloride / tetrahydrofuran solution (2mL, 3mol / L) dropwise through a syringe, and then heat the reaction system to 60 After reacting at ℃ for 2 hours, add water to quench the reaction, add potassium iodide solution (2mL, 1mmol / L) to precipitate an orange-red solid, and obtain compound 3 by ...

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Abstract

The invention discloses a synthesis method of a water-soluble squarylium cyanine type near-infrared organic macromolecular photo-thermal agent with high stability, and belongs to the technical field of biomedicine. According to the invention, firstly, a traditional 1, 3-type squarylium cyanine photo-thermal agent (SQ1) is designed and synthesized, the SQ1 has a high molar extinction coefficient, and due to poor water solubility and chemical instability of the SQ1, an amino-modified PEG5000 long chain is connected to the 2' site of a central four-membered ring of the SQ1 through a covalent bond, and a 1, 2, 3-type squarylium cyanine macromolecular photo-thermal agent (PSQ) is obtained. The photo-thermal agent has high light stability, chemical stability and good water solubility in a single molecule state; meanwhile, the PSQ macromolecule is an amphiphilic molecule and can be self-assembled in water to form nano particles (NPs) with uniform particle size and morphology, and the nano particles show excellent photo-thermal properties in in-vitro photo-thermal property research.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a method for synthesizing a water-soluble squaraine-type near-infrared organic macromolecular photothermal agent with high stability. Background technique [0002] Photothermal therapy (PTT) is a typical photon-triggered therapy that kills tumor cells by local hyperthermia generated by photothermal agents (PTAs) under visible or near-infrared (NIR) laser light. It exploits cellular sensitivity to heat to induce apoptosis or increase sensitivity to radiation or chemotherapy. Compared with traditional cancer treatment modalities, such as surgery, radiotherapy, and chemotherapy, PTT is attractive because it may have a high degree of intrinsic specificity and a lower invasive burden. In principle, PTT is also a cancer treatment that causes relatively little damage to surrounding healthy tissue. This is because the thermal effect occurs only when NIR laser light is a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/333C08G83/00
CPCC08G65/33396C08G83/00
Inventor 王红明王怡刚夏国民
Owner NANCHANG UNIV
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