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Ring-fused structural near-infrared photosensitizer and preparation method thereof

An infrared photosensitizer and near-infrared light technology, which can be applied in chemical instruments and methods, medical preparations containing active ingredients, and pharmaceutical formulations, and can solve problems such as small wavelengths.

Inactive Publication Date: 2015-11-25
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, BODIPY / aza-BODIPY photosensitizers have received widespread attention, but the problem is that the wavelength is less than 700nm

Method used

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  • Ring-fused structural near-infrared photosensitizer and preparation method thereof
  • Ring-fused structural near-infrared photosensitizer and preparation method thereof
  • Ring-fused structural near-infrared photosensitizer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Preparation of brominated aza-BODIPY photosensitizer I-1 / II-1

[0083]

[0084] (1) Pyrrole containing naphthalene ring V-1 Synthesis.

[0085] (2) Add 150mg of NaH into the round bottom flask, under the protection of nitrogen, wash with dried n-hexane (10ml) three times; drop dry DMSO (5ml), 6-methoxy-2-acetylnaphthalene (200mg , 1 mmol), stirred at room temperature for half an hour, added compound 2-phenylaziridine (175 mg, 1.5 mmol), reacted at room temperature for 2 h, and quenched with ice water. Adjust to neutral with dilute hydrochloric acid, extract with dichloromethane, wash, dry over anhydrous magnesium sulfate, eluent ( n -hexane:CH 2 Cl 2 =1:1) by column chromatography to synthesize off-white pyrrole with ring structure V-1 (89 mg, 30%). 1 HNMR (500MHz, CDCl 3 ): δ (ppm)8.56(brs,1H),7.84(d, 4 J =1.5Hz,1H),7.77(d, 3 J =8.5Hz,1H),7.74(d, 3 J =9.0Hz,1H),7.67(dd, 3 J =9.0Hz, 4 J =2.0Hz,1H),7.60(dd, 3 J =8.5Hz, 4 J =1.5Hz,2H),7.37(t, ...

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Abstract

The invention relates to a kind of ring-fused structural near-infrared photosensitizer and a preparation method thereof, especially relates to a kind of a photosensitizer treating malignant tumor through photodynamic therapy and a preparation method thereof, and concretely provides a kind of a heavy-atom-substituted near-infrared aza-BODIPY-like (aza-boron dipyrromethene-like) photosensitizer, a preparation method thereof, and efficiency of the photosensitizer generating singlet oxygen. The photosensitizer is a series of novel photosensitizers taking heavy-atom-substituted near-infrared fluorescent dye aza-BODIPY developed from azodipyrromethane boron trifluoride as a mother nucleus. The general formula of the phoosensitizer is shown as formulas I / II / III / IV. The aza-BODIPY-like photosensitizer possesses a ring-fused structure, and also possesses advantages of classic traditional dye BODIPY / aza-BODIPOY spectrum performances. The ring-fused structural aza-BODIPY-like photosensitizer has the absorption wavelength more than 700 nm, is capable of deeply penetrating biological issue under irradiation of a long-wavelength monochromatic light source, possesses low toxicity and low side effect, and is high in singlet oxygen generation efficiency, and electron of the photosensitizer is easy for intersystem crossing.

Description

technical field [0001] The invention relates to a photosensitizer for photodynamic therapy for treating malignant tumors and a preparation method thereof, in particular to a near-infrared photosensitizer with a ring structure and a preparation method thereof. Background technique [0002] Non-invasive and real-time imaging of physiological and pathological processes in life or in the body at the molecular and cellular levels can kill tumor or cancer cells while normal Cells are not damaged. [0003] Photodynamic therapy (Photodynamic Therapy, PDT) is widely used in this field. It is a new technology to treat diseases with light and photosensitizer (Photosensitizer, PS). It is mainly used in minimally invasive or non-invasive treatment of modern tumors. The basis of the action is the photodynamic effect, that is, the photosensitizer is excited by irradiating the tissue with light of a specific wavelength, and the photosensitizer in the excited state transfers energy to the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61K41/00A61P35/00
CPCC07F5/022A61K41/00
Inventor 姜新东习东梅苏亚军肖林久赵九丽
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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