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Two-photon fluorescent probe capable of targeting mitochondria and preparation method and application of probe

A reaction and anion technology, applied in the field of biomedicine, can solve the problems of excessive background fluorescence interference, aggregation-induced quenching, shallow penetration depth, etc., and achieve the effects of strong two-photon excitation fluorescence, easy availability of raw materials, and simple method.

Active Publication Date: 2019-07-05
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, there are still many shortcomings in the practical application of traditional organic fluorescent probes: 1) There is aggregation-induced quenching (ACQ) phenomenon in traditional organic fluorescent probes
2) Traditional organic fluorescent probes are mostly single-photon fluorescent probes, which have problems such as shallow penetration depth and excessive background fluorescence interference in the process of in vivo imaging, which limits their further application
Oxygen is relatively scarce in tumor tissue, so it cannot be used as a raw material by the photosensitive machine to generate active oxygen

Method used

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  • Two-photon fluorescent probe capable of targeting mitochondria and preparation method and application of probe
  • Two-photon fluorescent probe capable of targeting mitochondria and preparation method and application of probe
  • Two-photon fluorescent probe capable of targeting mitochondria and preparation method and application of probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The synthesis of formula III compound, wherein Its reaction formula is as follows:

[0042]

[0043] Specifically: under the protection of argon, p-bromoiodobenzene (3.4g, 12mmol), 4-pyridineboronic acid (1.3g, 10mmol), tetrakis (triphenylphosphine) palladium (0.58g, 0.5mol) and sodium carbonate (3.2g, 30mmol) into a 250mL three-neck flask. Toluene (100 mL), ethanol (30 mL) and water (10 mL) were added to deoxygenate and stirred at room temperature for 10 minutes, then heated to reflux to 110° C. and stirred for 24 h. Then, it was filtered, concentrated, extracted with saturated brine, dried, and purified by column chromatography to obtain the product 4-pyridylbromobenzene (58% yield).

Embodiment 2

[0045] The synthesis of formula IV compound, wherein R" is hydrogen; its reaction formula is as follows:

[0046]

[0047] Specifically: under the protection of argon, triphenylamine borate (2.24g, 7mmol), 4-pyridylbromobenzene (1.8g, 7.7mmol), tetrakis (triphenylphosphine) palladium (0.4g, 0.35mol) and carbonic acid Sodium (2.2g, 21mmol) was added into a 250mL three-necked flask. Toluene (70 mL), ethanol (20 mL) and water (7 mL) were added to deoxygenate and stirred at room temperature for 10 minutes, then heated to reflux to 110° C. and stirred for 24 h. Then, it was filtered, concentrated, extracted with saturated brine, dried, and purified by column chromatography to obtain the product 4-pyridinetriphenylaminobenzene (69% yield).

Embodiment 3

[0049] The synthesis of formula V compound, wherein R " is hydrogen, R ' is methyl; Its reaction formula is as follows:

[0050]

[0051] Specifically: under argon protection, 4-pyridinetriphenylaminobenzene (1.4g, 3.6mmol) and methyl iodide (2.3mL, 36mmol) were dissolved in acetone, stirred at room temperature for 24h, and filtered to obtain the product 4-( 1-picoline)trianilinobenzene (74% yield).

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Abstract

The invention discloses a two-photon fluorescent probe capable of targeting mitochondria and a preparation method and application of the probe. The structure of the two-photon fluorescent probe is shown as a formula I, wherein R represents a conjugated structure, R' represents alkyl or aryl, R'' represents hydrogen, methyl or methoxy, X represents halogen anions or bi-trifluoromethane sulfonimideanions or hexafluoro-phosphoric acid anions or tetra-fluoroboric acid anions or trifluoromethanesulfonic acid anions. The compound has stronger two-photon excitation fluorescence, a good aggregation-induced luminescence effect, a great mitochondrial targeting function and excellent photoinduced singlet oxygen generation capability.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a two-photon fluorescent probe capable of targeting mitochondria and its preparation method and application. Background technique [0002] Organelles play an extremely important role in the functional expression of normal cells as well as in the development of diseases. Mitochondria is an important eukaryotic organelle and an important place for cells to carry out aerobic respiration. In addition to supplying energy to cells, mitochondria are also involved in physiological processes such as cell information transmission, cell differentiation, cell apoptosis, and regulation of cell growth and cell cycle. Therefore, developing a class of mitochondria-specific fluorescent probes to track the shape and distribution of mitochondria in cells will help us study some important cellular physiological processes. [0003] Organic fluorescent probes are an important carrier...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07D409/04C09K11/06G01N21/64A61K41/00A61P35/00
CPCA61K41/0057A61P35/00C07D213/38C07D409/04C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1092G01N21/6428
Inventor 李高参王云兵庄伟华杨立
Owner SICHUAN UNIV
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