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Preparation method of nucleolus targeting photo-thermal reagent based on perylene bisimide and application thereof

A perylene imide and photothermal reagent technology, applied in the field of chemical synthesis of biopharmaceuticals, can solve problems such as human safety and health threats, large surgical limitations and side effects, and achieve good photothermal conversion efficiency, excellent photothermal killing effect, Good water solubility

Active Publication Date: 2021-09-07
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003]Cancer is currently the second largest death threat to human beings, posing a huge threat to human safety and health. Traditional cancer treatment methods include surgery, chemotherapy, radiotherapy, etc. Major limitations and side effects

Method used

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  • Preparation method of nucleolus targeting photo-thermal reagent based on perylene bisimide and application thereof
  • Preparation method of nucleolus targeting photo-thermal reagent based on perylene bisimide and application thereof
  • Preparation method of nucleolus targeting photo-thermal reagent based on perylene bisimide and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] TPDI of reagent preparation: Example 1

[0032]

[0033] Step 1). The reaction flask was added 1g Compound 1, was added 50mL of concentrated sulfuric acid (H 2 SO 4 ) As solvent dissolved with stirring 2h, the reaction was further added liquid bromine 260μL, 10mg elemental iodine as a catalyst, oxygen, nitrogen protection, the reaction for 16h at 85 ℃. By N 2 The reaction flask was the residual gas remaining bromine was blown into dilute sodium hydroxide (NaOH) solution, the reaction solution was then precipitated into ice water, the precipitate then washed three times with ice, and then filtered off with suction and drying, to give compound yields 2 98%;

[0034] Step 2) and 240 mg of Compound 2 500mg of N, N- dimethylethylenediamine was added to the reaction flask was added 36mL volume ratio of 9: 6: 3 N, N- dimethylformamide (DMF), a mixed solvent of dioxane and propionic acid, N 2 Protected slowly warmed to 70 ℃, the reaction 10min, the reaction was stopped. Again on ...

Embodiment 2

[0038] Application TPDI binding agent (ctDNA, G- quadruplex) as a nucleic acid: Example 2

[0039] UV absorption and fluorescence spectra: in Example 1 TPDI photothermal agent formulated in different solvents (water, dimethyl sulfoxide, ethyl acetate, acetone, methanol, n-hexane, dichloromethane) embodiment will be 10μM test solution, the samples were tested by UV and fluorescence spectroscopy, such as image 3 Shown; in the Example 1, respectively photothermal agent 5μM, 10μM, 15μM, 20μM, 30μM of G- quadruplex ctDNA and are co-incubated overnight, and then tested for UV absorption spectra, various materials and experimental results show low after concentration of the nucleic acid binding spectrum faint red shift of the UV absorption spectrum intensity decreased, this red-shift in the G- quadruplex TPDI group and more obvious than ctDNA and TPDI group, showed bonding strength of different materials may be inconsistent nucleic acid ,like Figure 4 Indicated.

[0040]Circular Two-Colo...

Embodiment 3

[0043] Example 3: TPDI as a photothermal reagent application

[0044] Photoothermal performance test: The photosyic reagents in Example 1 were formed into aqueous solution sample of 10 μm, 30 μm, 50 μm, 100 μm, respectively, and the sample solution was irradiated with a laser having an emission wavelength of 660 nm, so that the temperature was warmed to the maximum stable temperature. A process is approximately 10 min, and the sample is made to cool to room temperature. This process is approximately 20 min, and the sample temperature is recorded in 20S interval, and the entire process is recorded by the thermal imaging, and the TPDI photothermal conversion efficiency is obtained according to the formula. About 50%, the laser power used is 1W / cm 2 ,like Figure 8 Indicated.

[0045] Photoothermal stability test: ICG is an unstable fluctine material that is often used as a control material for light thermal stability. The photothermal temperature reduction test was performed by the...

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Abstract

The invention discloses a preparation method of a nucleolus targeted photo-thermal reagent based on perylene bisimide and an application thereof. The preparation method comprises the following steps: firstly, reacting liquid bromine with perylene anhydride to obtain bromine-substituted perylene bisimide; and then introducing substituent groups into an imide site and a bay site through a reaction between amino and acid anhydride and a nucleophilic substitution reaction between amino and bromine, so as to obtain the perylene bisimide-based nucleolus targeted photo-thermal reagent. The photo-thermal reagent designed and synthesized by the invention is a compound capable of generating strong specific binding with nucleic acid, the binding force enables the photo-thermal reagent to be rapidly taken by cells (within three minutes) and enriched to a nucleolus part with concentrated DNA and RNA, and the targeting effect on the nucleolus is superior to that of a commercial dye nucleolus green. The photothermal reagent designed and synthesized by the invention is good in water solubility, good in light, heat and chemical stability, high in absorbance in a near-infrared region, good in photothermal conversion efficiency and excellent in photothermal killing effect on tumor cells, and can realize photothermal therapy of cancer cells.

Description

Technical field [0001] The present invention belongs to the field of biological pharmaceutical chemistry synthetic techniques, and in particular, relates to the nucleolus based method for the preparation of perylene imide photothermal targeting agent and in vitro and cellular level. Background technique [0002] Perylene and derivatives thereof having excellent light, heat, chemical stability, almost 100% fluorescence quantum yield, narrow emission peak, after a particular modification of perylene was found to have excellent properties of light and heat, the current fluorescent probes have been widely used and the field of cancer diagnosis and treatment. [0003] Cancer is now the second largest human death threats to human health and safety posed a huge threat to traditional cancer treatment methods include serious limitations and side effects of surgery, chemotherapy and radiotherapy. Photothermal therapy using light absorber as an exogenous photothermal agents can effectively ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09B57/08C09K11/06A61K41/00A61P35/00G01N21/64
CPCC07D471/06C09B57/08C09K11/06A61K41/0052A61P35/00G01N21/6428C09K2211/1044
Inventor 尹梅贞柯鑫冀辰东程文玉
Owner BEIJING UNIV OF CHEM TECH
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