Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation and application of mitochondrial targeting photosensitizer based on BODIPY

A photosensitizer and mitochondrial technology, applied in the field of chemical biology, can solve problems such as unclear targeting mechanism

Pending Publication Date: 2022-03-15
NANKAI UNIV
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The photosensitizers targeted by the endoplasmic reticulum are less studied at present, and the relevant targeting mechanism is still unclear, and further exploration is needed

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation and application of mitochondrial targeting photosensitizer based on BODIPY
  • Preparation and application of mitochondrial targeting photosensitizer based on BODIPY
  • Preparation and application of mitochondrial targeting photosensitizer based on BODIPY

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1. Photosensitizer fluoroboron dipyrrole-triphenylphosphine ( mito BD) molecular synthesis, synthetic route see figure 2 : Add 1-ethyl-3-(3-dimethylaminopropyl to a mixed solution of compound BD (0.95g, 1.0mmol) and triphenylphosphine bromobutyric acid (0.42g, 1.0mmol) in dichloromethane ) carbodiimide hydrochloride (EDCI, 0.10 mmol) and 4-dimethylaminopyridine (DMAP, 0.10 mmol), and the mixture was stirred overnight at room temperature in the dark. After the reaction was complete, the reaction was stopped, and the resulting mixture was washed three times with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation under reduced pressure. The crude product was purified and separated on a silica gel column, using dichloromethane / methanol=100 / 4 as the eluent to obtain 0.54 g of a dark green solid, named as mito BD, 40.5% yield. 1 H NMR (400MHz, CDCl 3 )δ (ppm) 8.08 (d, J = 16.5Hz, 2H), 7.93–7.84 (m, 6H), 7.79 (...

Embodiment 2

[0022] Example 2. right mito Research on the absorption and fluorescence properties of BD molecules: through UV-Vis absorption spectrophotometer and fluorescence spectrophotometer (λ Ex=676nm) measurement mito Fluorescence spectra of BD molecules in DMSO. The result is as image 3 with Figure 4 shown.

Embodiment 3

[0023] Example 3. right mito Studies of photosensitivity of BD molecules: Typically, dilute the DPBF probe solution to 2 mL mito BD / DMSO solution and placed in a cuvette, while ensuring that the absorption of the probe at 412nm is 1.0, and then irradiated with a 655nm laser for 90 seconds. The change in the absorbance of the probe at 412 nm was recorded every 15 seconds. mito BD molecules produced in the dark as well as in light 1 o 2 The result is as Figure 5 (A) and 5(B).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides preparation and application of a mitochondrial targeting type photosensitizer based on BODIPY (boron dipyrromethene). A BODIPY dye (BD) with enhanced photosensitivity is introduced on the basis of heavy atoms, and triphenylphosphine cations (TPP) with mitochondrial targeting, which are widely accepted, are derived at the head of a BODIPY core through esterification reaction to obtain mitoBD. By utilizing the electrostatic adsorption effect and fat solubility of TPP and mitochondrial membrane potential, the mitoBD can selectively and accurately target organelle-mitochondria, so that the photodynamic therapy effect on tumor cells is enhanced, and meanwhile, the mitoBD has the application potential of fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of chemical biology, and the research content is based on triphenylphosphine covalently modified boron dipyrrole (BODIPY) dye molecule, which enhances the photodynamic therapy effect on tumor cells by targeting the organelle-mitochondrion, and has fluorescence imaging at the same time application potential. Background technique [0002] Photodynamic therapy (PDT) is a well-known non-invasive therapy widely used in the treatment of various cancers, especially bladder, urinary tract, lung and esophageal cancers. The mechanism of action of PDT is to trigger a photochemical reaction to generate reactive oxygen species (ROS) through the interaction of photosensitizers, light and oxygen, and then trigger a series of reactions to kill cancer cells: (1) reactive oxygen species can oxidize biological macromolecules in cells and directly cause apoptosis. (2) It can also induce a local inflammatory response, activate the immune...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07F9/54C09K11/06A61K41/00A61K49/00A61P35/00G01N21/64
CPCC07F9/5442C09K11/06A61K49/0021A61K41/0057A61P35/00G01N21/6458C09K2211/1014C09K2211/1055
Inventor 李昌华罗培
Owner NANKAI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com