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Supramolecular photothermal agent compound with stimuli responsiveness and composition and application of supramolecular photothermal agent compound

A stimuli-responsive, compound technology, used in drug combinations, medical preparations containing active ingredients, organic chemistry, etc., can solve problems such as damage, reduce treatment efficiency, damage, etc., and achieve broad economic prospects and high photothermal conversion efficiency. , easily degradable effect

Active Publication Date: 2021-08-31
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Photothermal therapy has gradually become a research hotspot due to its accuracy and controllability, but similar to chemotherapy, normal tissues will inevitably absorb photothermal materials non-specifically, which will reduce their therapeutic efficiency and cause unwanted damage. Great challenges remain in accurately distinguishing cancerous from normal tissue and in achieving controlled elimination of tumor tissue while avoiding damage to surrounding normal tissue

Method used

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  • Supramolecular photothermal agent compound with stimuli responsiveness and composition and application of supramolecular photothermal agent compound
  • Supramolecular photothermal agent compound with stimuli responsiveness and composition and application of supramolecular photothermal agent compound
  • Supramolecular photothermal agent compound with stimuli responsiveness and composition and application of supramolecular photothermal agent compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Example 1 Synthesis of compound Ⅱ-1 and its fluorescence properties

[0123] Such as figure 1 As shown, the synthesis of compound II-1 includes the following steps:

[0124] 1) Synthesis of compound 1:

[0125] 5 mL of trifluoroacetic acid (TFA) was added to the mixture of 3-mercaptopropionate and acetone, stirred at room temperature for 12 hours, and quenched by placing the mixture in an ice bath to obtain compound 1 as a colorless oil.

[0126] 1 HNMR (400MHz, CDCl 3 ): δ(ppm): 3.70(s,6H), 2.87(t,4H), 2.63(t,4H), 1.60(s,6H).

[0127] 2) Synthesis of compound 2:

[0128] Slowly add 5mL of anhydrous tetrahydrofuran (THF) to the reaction flask to dissolve LⅠAlH 4 500 mg of the oily compound 1 was slowly added dropwise under ice bath conditions, the ice bath was removed and the reaction was stirred at room temperature for 6 hours. After the reaction was completed, the reaction system was first placed in an ice-water mixture at 0°C, and then a small amount of water wa...

Embodiment 2

[0150] The synthesis of embodiment 2 compound Ⅱ-2 to Ⅱ-15

[0151] Compounds II-2 to II-15 can be prepared in a similar manner to Example 1.

[0152] 1. Synthesis of Compound Ⅱ-2

[0153]

[0154] Compound 17 was used to replace compound 4 in Example 1, and the remaining reagents and preparation methods were the same as Steps 1-9 in Example 1) to prepare Compound II-2;

[0155] 1 H NMR (400MHz, CDCl 3 )δ:7.79(d,2H),7.68(d,2H),7.40(d,1H),7.34(d,1H),7.22(t,2H),7.11(d,1H),7.06(d,1H ),6.84(d,2H),6.72(q,1H),6.70(t,1H),6.64(t,1H),6.51(m,2H),6.36(s,1H),6.23(s,1H) ,5.64(s,1H),4.71(m,1H),4.37(t,1H),4.13(m,4H),3.81(t,3H),3.77(m,2H),3.59(m,2H), 2.85(t,1H),2.42(d,4H),2.36(d,2H),2.32(d,2H),2.26(s,3H),2.11(m,2H),1.94(m,4H),1.79 (s,6H),1.59(s,6H),1.58(s,2H),1.49(m,2H),1.33(m,2H),1.16(s,6H).

[0156] 2. Synthesis of Compound Ⅱ-3

[0157]

[0158] Compound 19 was used to replace compound 5 in Example 1, and the remaining reagents and preparation methods were the same as Steps 1-9...

Embodiment 3

[0208] The preparation method of embodiment 3 micro-nano structure

[0209] Taking the self-assembled micro-nano structure of compound Ⅱ-1 as an example, dissolve Ⅱ-1 in DMSO (or organic solvents such as ethanol) to make a 2mM storage solution, and add a small amount of the storage solution to deionized water to make it 20μM working solution; take 10 μL dropwise onto a silicon wafer, observe and take pictures under a transmission electron microscope (TEM) and an atomic force microscope (AFM), the micro-nano structure in the form of vesicles can be clearly observed, and the attached Figure 4 That is the result of transmission electron microscope photographing, Figure 5 That is the particle size test distribution of DLS. From the observation results, it is found that the particle size of the micro-nano structure self-assembled by compound II-1 is about 30-150 nm.

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Abstract

The invention relates to a supramolecular photothermal agent compound with stimuli-responsiveness as well as a composition and application thereof, and provides a micro-nano structure which is formed by self-assembling a structure shown in a formula (I), a formula (II) or a formula (III) or an isomer, a pharmaceutically acceptable salt, a hydrate or a solvate of the structure in a water solution. The invention also relates to a pharmaceutical composition thereof and application of the pharmaceutical composition in preparation of double-targeted light treatment drugs, preparation of drugs for diagnosing and / or treating cancers and stimuli-responsive release drugs. The compound provided by the invention can be enriched in tumor tissues through passive and active dual targeting, and can release a photo-thermal agent under pathological stimulation response of a tumor microenvironment; the compound has the advantages of higher photothermal conversion efficiency, excellent photothermal stability and fluorescence imaging, and has a good effect and small trauma when being used for in-vivo cancer phototherapy. The compound has great market value and wide economic prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, and relates to a class of compounds containing stimuli-responsive linking bonds and active targeting groups, in particular to a stimuli-responsive supramolecular photothermal agent compound and its composition and application. Background technique [0002] At present, existing cancer treatment technologies such as surgery and chemotherapy have certain limitations. Therefore, laser photothermal therapy, which has the advantages of non-invasive / minimally invasive and can greatly reduce the pain of patients, has gradually entered people's field of vision. . The method is to irradiate tumor tissue with a beam of near-infrared light, and the fluorescent compound will generate heat while emitting light, and the temperature rise can kill cancer cells to achieve the therapeutic effect. The method has few side effects and high selectivity. Because conventional organic small molecule fluorescent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D417/14A61K41/00A61P35/00
CPCC07D405/14C07D417/14A61K41/0052A61P35/00
Inventor 周现锋马慧慧卢迎习牟雪璐尔李志波
Owner QINGDAO UNIV OF SCI & TECH
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