Fluorescence-oriented superoxide enhanced photosensitizer dye based on benzophenothiazine dimer as well as preparation method and application thereof

A benzophenothiazine dimer and oriented technology, which is applied in the field of biochemistry, can solve the problems of conflicts between light dose and scavenging ability, and achieve the goal of enhancing superoxide generation ability, reducing light dose, and effective scavenging effect Effect

Active Publication Date: 2022-02-08
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, current recognition strategies, such as intramolecular charge transfer, light-induced electron transfer, or fluorescence resonance energy transfer, are in conflict with the appeal of light dose and scavenging capacity in this therapeutic modality because of the suppression of therapeutic effects in their inactive states.

Method used

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  • Fluorescence-oriented superoxide enhanced photosensitizer dye based on benzophenothiazine dimer as well as preparation method and application thereof
  • Fluorescence-oriented superoxide enhanced photosensitizer dye based on benzophenothiazine dimer as well as preparation method and application thereof
  • Fluorescence-oriented superoxide enhanced photosensitizer dye based on benzophenothiazine dimer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The preparation method of the fluorescence-guided superoxide-enhanced photosensitizer based on the benzophenothiazine dimer of this embodiment comprises the following steps:

[0052] (1) Synthetic intermediate 1: N-propargyl-1-naphthylamine

[0053] The synthetic route is as follows:

[0054]

[0055] Dissolve 1-naphthylamine (20mmol) and propyne bromide (20mmol) in 20mL of DMF, add potassium carbonate (20mmol) to it with stirring, and heat the reaction at 90°C for 4h with stirring until the reaction is complete, stop the reaction, and use After the solvent was distilled off under reduced pressure, it was redissolved with dichloromethane (50 mL), 100 mL of water was added thereto, and extracted with dichloromethane (200 mL x 3) to obtain an organic layer solution. The organic solvent was dried and removed under reduced pressure to obtain a crude product, which was purified by silica gel chromatography, and the eluent was petroleum ether: dichloromethane=6:1 (v / v) to...

Embodiment 2 2

[0070] Example 2 Comparison of absorption and fluorescence quenching effects of dimers and monomers:

[0071] Prepare dimer structure example 1 and monomeric intermediates 2 and 3 starting mother solutions at 3 mM, and test their absorption and fluorescence spectra at a concentration of 10 μM in acetonitrile. Such as figure 2 As shown in A, the dimer structure of NBS-NBSe exhibits only double the absorbance intensity compared to the monomer, whereas if no dimer quenching occurs, the two-molecule structure can produce nearly double the absorbance, as in the direct Superimposition of NBS+NBSe in solution is shown. Similarly, the fluorescence spectrum shows ( figure 2 B), compared with the highly fluorescent Nile Nile Blue and Nile Selenide structures, the dimer structure NBS-NBSe exhibited a significant fluorescence quenching effect, while the stacked NBS and NBSe in pure solution only Exhibited slightly reduced fluorescence. This experiment confirmed that the dimer strate...

Embodiment 3

[0072] Embodiment 3 The absorption and fluorescence regulation effect of dimer:

[0073] The dimer structure in this example is connected by disulfide bonds, aiming to realize the function of fluorescent indicator that can be regulated by glutathione overexpressed in the tumor. Such as image 3 As shown in A, under the action of 50 equivalents of glutathione, the dimer structure exhibits a process of enhanced absorption over time (double peaks gradually become single peaks). At the same time, along with the disaggregation process of the dimer, the dimer structure NBS-NBSe simultaneously exhibited an obvious fluorescence recovery process (such as image 3 As shown in B), it can recover to about 10 times in 30 minutes (such as image 3 C shown). It is proved that the structure can effectively realize the fluorescence regulation under glutathione, and achieve the function as a tumor fluorescence recognizer.

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Abstract

The invention discloses a benzophenothiazine dimer-based fluorescence-oriented superoxide enhanced photosensitizer dye as well as a preparation method and application thereof. A dimer aggregation quenching mode is adopted to construct a fluorescence-oriented superoxide enhanced photosensitizer dye capable of realizing fluorescence-oriented phototherapy of a local area, and the dye can be used for distinguishing tumor / normal tissue and serving as a fluorescent indicator in optical fiber introduction therapy, and / or used for a superoxide enhanced photosensitizer, and / or used for preparing a photodynamic therapy drug with low light dose, and / or used for preparing a photodynamic therapy drug with combination of type I and type II.

Description

technical field [0001] The present invention relates to the field of biochemistry, in particular to the application of photochemistry in imaging and treatment, and in particular to a class of fluorescence-guided superoxide-enhanced photosensitizer dyes based on benzophenothiazine dimers, and their preparation methods and applications . Background technique [0002] Light-activated therapy for tumors, including photodynamic therapy and photothermal therapy, has been extensively studied and has important application prospects due to its outstanding features such as non-invasiveness, spatial precision, and synergistic effect. In clinical photodynamic therapy, in order to solve the limitation of insufficient penetration of light, the introduction of optical fiber is an effective physical way to solve the problem of light at the tumor location. However, unlike the skin surface or direct photodynamic therapy, the treatment mode introduced by the optical fiber requires imaging as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D421/14C09K11/06C09B21/00A61K41/00A61P35/00
CPCC07D421/14C09K11/06C09B21/00A61K41/0057A61P35/00C09K2211/1037C09K2211/1059C09K2211/104
Inventor 彭孝军熊涛陈颖超樊江莉
Owner DALIAN UNIV OF TECH
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