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Membrane permeability dye with large two-photon fluorescence active cross section and application of membrane permeability dye

A two-photon fluorescence and permeability technology, applied in the direction of luminescent materials, fluorescence/phosphorescence, styrene-based dyes, etc., can solve the problems that restrict two-photon three-dimensional imaging technology for cell biological imaging and observation, and achieve excellent cell membrane permeability , low excitation energy, and large two-photon fluorescence active absorption cross-section

Inactive Publication Date: 2015-12-16
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This largely restricts the use of two-photon 3D imaging technology for cell biological imaging and observation.

Method used

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  • Membrane permeability dye with large two-photon fluorescence active cross section and application of membrane permeability dye
  • Membrane permeability dye with large two-photon fluorescence active cross section and application of membrane permeability dye
  • Membrane permeability dye with large two-photon fluorescence active cross section and application of membrane permeability dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of 4,4-2 formyl triphenylamine

[0028] 20ml of DMF was added to the one-necked flask. Under stirring in an ice-water bath, 20 ml of phosphorus oxychloride was slowly added dropwise to the above solution, and stirred at room temperature for 1 h to obtain a yellow turbid solution. Weigh 5 g (20.4 mmol) of triphenylamine, dissolve it with 10 ml of chloroform, and then gradually add it into the above stirred solution, and heat to reflux for 10 hours. The reaction solution was poured into 1000 mL of water, and the 2 Cl 2 extraction. The organic layer was washed with saturated NaCl solution, anhydrous MgSO 4 Dry, filter and evaporate the solvent. The crude product was separated by column chromatography with petroleum ether / ethyl acetate (10:1) as the eluent to obtain a light yellow solid, namely 4,4-2 formyltriphenylamine. Yield: 55%.

[0029] 1 HNMR (400MHz, d6-DMSO): δ (ppm) 9.88 (s, 2H), 7.85 (d, J = 8.64Hz, 4H), 7.49 (t, J = 7.84Hz, 2H), 7.33 (t, J = 7...

Embodiment 2

[0037] 4-[(E)-2-(1H-benzimidazol-2-yl)vinyl]-N-{4-[(E)-2-(1H-benzimidazol-2-yl)ethenyl] Synthesis of phenyl}-N-phenylaniline

[0038] The synthesis process is the same as in Example 1, and 4-[(E)-2-(1H-benzimidazol-2-yl)vinyl]-N-{4-[(E)-2-(1H-benzo Imidazol-2-yl)vinyl]phenyl}-N-phenylaniline, yield: 17%.

[0039] 1H NMR (400MHz, d6-DMSO): δ (ppm): 12.55 (s, 2H), 7.65 (m, J = 7.67Hz, 6H), 7.55 (d, J = 7.64Hz, 4H), 7.41 (t, J =7.84Hz, 2H), 7.16(t, J=7.76Hz, 5H), 7.11(d, J=7.68Hz, 4H), 7.07(d, J=8.24Hz, 4H).

Embodiment 3

[0041] RBL-2H3 and Hela cell culture

[0042] Adherent culture of RBL-2H3 or HeLa cell line in 10% fetal bovine serum medium, at 37°C, 5% CO 2 Cultured in a saturated humidity incubator, and subcultured once every 2-3 days. After the cells grow to the logarithmic phase, the splicing culture: ① Soak the coverslips in absolute ethanol for 30 minutes, dry them with an alcohol lamp, and put them into a disposable 35mm culture dish; ② Wash the cells in the 100ml cell bottle with PBS. Three times, digest with 1ml 0.25% trypsin for 3-5 minutes, pour out the medium carefully, add a small amount of fresh medium and pipette evenly, after counting the cells, leave cells with a suitable density, and add the medium to the required volume (The final concentration of control cells was 1x10 5 ), inoculated into a petri dish containing a coverslip, and placed in CO 2 Cultured in an incubator to allow the cells to grow on the sheet.

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Abstract

The invention discloses membrane permeability dye with a large two-photon fluorescence active cross section. The dye adopts triphenylamine heterocyclic chemical compounds, and the chemical structure of the dye is shown in the formula (I). The invention further discloses an application of the dye in displaying two-photon imaging of cytoplasm in a living cell. Experiments show that the dye has characteristics of larger two-photon fluorescence active absorption cross section, excellent cell membrane permeability, low toxicity and the like, also has the characteristics of wide application range, low price and good bio-compatibility with known probe DAPI (4',6-diamidino-2-phenylindole) and has wide application prospect in the field of laser excitation fluorescence biomarkers.

Description

technical field [0001] The invention relates to a two-photon dye and its application, in particular to a membrane-permeable dye with a large two-photon fluorescence active cross section and its application. Background technique [0002] The development of two-photon microscopy has revolutionized the observation of organs and tissues, especially thick or highly scattering specimens. Compared with single-photon laser confocal microscopy, two-photon microscopy has characteristics such as near-infrared light excitation, avoidance of fluorescence bleaching and phototoxicity, high resolution, reduced tissue light absorption, and reduced tissue autofluorescence interference. However, if the fluorescent probe used has a small two-photon absorption cross-section (similar to the endogenous luminescent substances of biological samples), the advantages of two-photon microscopy will be greatly reduced. Because the single-photon and two-photon absorption of dyes obey different selection ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/14C09K11/06C07D277/64C07D235/14G01N21/64
Inventor 于晓强冯瑞卿孙渝明李学晨
Owner SHANDONG UNIV
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