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Second near-infrared window nano photosensitizer based on NDI molecules, and preparation method thereof

A photosensitizer, near-infrared technology, applied in medical preparations containing active ingredients, photodynamic therapy, chemical instruments and methods, etc., can solve the problems of lack of research and reports, reduce side effects of treatment, enhance penetration, The effect of reducing the chance of recurrence

Inactive Publication Date: 2020-09-08
NANJING STOMATOLOGICAL HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these fluorescent probes have effective fluorescence emission properties above 1000 nm, there are almost no organic small molecule fluorescent dyes that can have good absorption properties above 1000 nm.
In addition, there are basically no related studies and reports on NIR-II phototherapy based on small organic molecule photosensitizers.

Method used

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  • Second near-infrared window nano photosensitizer based on NDI molecules, and preparation method thereof
  • Second near-infrared window nano photosensitizer based on NDI molecules, and preparation method thereof
  • Second near-infrared window nano photosensitizer based on NDI molecules, and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 4.99 millimoles of 1,4,5,8-naphthalene tetracarboxylic anhydride (compound 1) and 12.5 millimoles of dibromoisocyanuric acid were catalyzed by 40 milliliters of oleum, stirred at room temperature for 3 hours, and then poured into 400 grams of In ice water, add 600 ml of water to filter to obtain a yellow precipitate, wash with 100 ml of water, and dry on potassium hydroxide to obtain tetrabromo-substituted naphthalene tetracarboxylic anhydride (compound 2).

[0036] Add 0.343 mmoles of compound 2 to 5 ml of glacial acetic acid, add 2.4 mmoles of dodecylamine, heat up to 120°C and stir for 6 hours, then cool down to room temperature and add 50 ml of water, then neutralize with saturated sodium bicarbonate, It was extracted with chloroform, dried with anhydrous sodium sulfate, rotary evaporated, and passed through a column (petroleum ether:dichloromethane=2:1) ​​to obtain compound 3.

[0037] Under nitrogen protection, 1.2 mmoles of compound 3, 0.4 mmoles of 1,5-diaminona...

Embodiment 2

[0048] This embodiment is improved on the basis of Embodiment 1. During the reflux reaction, 0.15 mmol of N-phenylglycine was added; in the water washing process after the reflux reaction, 0.15 wt % diisopropanolamine aqueous solution was used for water washing operation. Through the above improvements, the reaction rate between compound 3 and 1,5-diaminonaphthalene can be increased without affecting the purity of the finished NDI photosensitizer.

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Abstract

The invention discloses a preparation method of a second near-infrared window nano photosensitizer based on NDI molecules. The method comprises the following steps: A, reacting 1,4,5,8-naphthalene tetracarboxylic anhydride with dibromoisocyanuric acid under the catalysis of fuming sulfuric acid to generate tetrabromo-substituted naphthalene tetracarboxylic anhydride; B, performing an alkylation reaction on the tetrabromo-substituted naphthalene tetracarboxylic anhydride and dodecylamine, and performing cyclization with 1,5-diaminonaphthalene to obtain an NDI photosensitizer; and C, dissolvingthe NDI photosensitizer prepared in the step A into tetrahydrofuran, then slowly dropwise adding into rapidly stirred pure water, carrying out rotary evaporation on tetrahydrofuran, and then centrifuging to obtain the multifunctional NDI nano photosensitizer. According to the invention, the defects in the prior art can be overcome, the biological tissue penetrating power can be effectively enhanced, the fluorescence imaging signal-to-noise ratio is reduced, and high-resolution and high-contrast oral squamous cell carcinoma tissue optical imaging real-time monitoring is achieved.

Description

technical field [0001] The invention relates to the technical field of cancer photodiagnosis and treatment reagents, in particular to a second near-infrared window nano-photosensitizer based on NDI molecules and a preparation method thereof. Background technique [0002] Oral squamous cell carcinoma is a common malignant epithelial tumor, and the incidence rate of patients ranks sixth in malignant tumors. It is an increasingly serious problem worldwide. Although the diagnosis and treatment of oral squamous cell carcinoma have developed rapidly in the past few decades, the 5-year survival rate of oral squamous cell carcinoma patients has not improved significantly, staying between 40% and 60%. Conventional medical imaging techniques used clinically (such as X-ray imaging, computerized tomography imaging, and magnetic resonance imaging) are often difficult to accurately locate tumor tissue margins, resulting in local recurrence (recurrence The rate is 6.9%-22%), which is an i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16C09K11/06A61K41/00A61P35/00A61K49/00A61K49/22
CPCC07D471/16C09K11/06A61K41/0057A61K41/0052A61P35/00A61K49/0002A61K49/0021A61K49/22C09K2211/1059
Inventor 蔡宇韩伟汤传超宋传慧
Owner NANJING STOMATOLOGICAL HOSPITAL
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