One and two-photon mitochondrion fluorescence probe and application thereof

A fluorescent probe and mitochondrial technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of lack of fluorescent probes and inapplicability of two-photon fluorescence microscopy, etc., and achieve good biocompatibility and two-photon performance Good, low price effect

Active Publication Date: 2013-10-02
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, probes that can be used for one-photon fluorescence imaging are sometimes not suitable for two-photon fluorescence microscopy because the one- and two-photon absorp...

Method used

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  • One and two-photon mitochondrion fluorescence probe and application thereof
  • One and two-photon mitochondrion fluorescence probe and application thereof
  • One and two-photon mitochondrion fluorescence probe and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Synthesis of 9-ethylcarbazole (1a)

[0024] 28 g (500 mmol) of KOH was dissolved in 60 mL of acetone solution, and stirred at room temperature to obtain a yellow solution. Carbazole (13.2 g, 80 mmol) was added to the above solution, stirred at room temperature for 4 h to obtain a brown cloudy liquid. Acetone solution containing 1-bromoethane (9 mL, 120 mmol) was added gradually and reacted overnight. The reaction solution was poured into 1000 mL of water, a yellow precipitate was formed, and a yellow solid was obtained by filtration. The solid was recrystallized from ethanol to obtain a white solid, yield: 83%.

[0025] 1 H NMR (300MHz, CDCl 3 ),δ(ppm):8.10(d,J=7.8Hz,2H),7.39-7.49(m,4H),7.20-7.25(m,2H),4.36(q,J=7.2Hz,2H),1.43 (t, J=7.2Hz, 3H).

[0026] Synthesis of 9-Hydroxyethylcarbazole (1b)

[0027] The process is the same as above, and 9-hydroxyethyl carbazole can be synthesized with a yield of 81%. :

[0028] 1 H NMR (300MHz, CDCl 3 ),δ(ppm):8.79(d,J=7.8...

Embodiment 2

[0030] Synthesis of 3-acetyl-9-ethylcarbazole (2a)

[0031] 3.91g, 20mmol of compound 1a was dissolved in 75mL of anhydrous dichloromethane, and anhydrous AlCl3 (5.2g, 40mmol) was added under vigorous stirring to obtain a black precipitate. The mixture was cooled to 0°C under an ice bath, and acetic anhydride (2.04 g, 20 mmol) dissolved in 15 mL of anhydrous dichloromethane was added slowly. After the addition was complete, the ice bath was removed and stirred vigorously at room temperature overnight. The reaction solution was poured into a large amount of ice water, with NaHCO 3 Adjust the pH to 7-8. use CH 2 C1 2 Extraction, the organic layer was washed with water, 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 white solid with a yield of 87%.

[0032] 1 H NMR (400MHz, CDCl 3 ),δ(ppm):8.75(d,J=1.52Hz,1H),8.11-8.17(m,2H),7.50-7.54(m,1H...

Embodiment 3

[0037] Synthesis of 3-acetyl-6-bromo-9-ethylcarbazole (3a)

[0038] Under the protection of argon, compound 2 (2.2g, 9.85mmol) and NBS (1.9g, 10.67mmol) were added to 60mL of chloroform / glacial acetic acid mixed solution (1:1, v / v), and reacted at room temperature for 15h . After the reaction is complete, the reaction solution is poured into 500mL water, and the 2 Cl 2 extraction. The organic layer was washed with saturated NaCl solution, anhydrous MgSO 4Dry, filter and evaporate the solvent. The crude product was separated by column chromatography, using petroleum ether / ethyl acetate (10:1) as the eluent, to obtain a white flocculent solid, yield: 81%.

[0039] 1 H NMR (400MHz, CDCl 3 ),δ(ppm):8.71(d,J=1.52Hz,1H),8.30(d,J=1.88Hz,1H),8.18(dd,J 1 =8.70Hz,J 2 =1.70Hz,1H),7.62(dd,J 1 =8.64Hz,J 2 =1.92Hz,1H),7.44(d,J=8.68Hz,1H),7.35(d,J=8.64Hz,1H),4.4(q,J=7.25Hz,2H),2.74(s,3H), 1.47(t,J=7.26Hz,3H).

[0040] Synthesis of 6-bromo-9-ethylcarbazole (3b)

[0041] The proc...

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Abstract

The invention discloses a one and two-photon mitochondrion fluorescence probe. The fluorescence probe is a pyridine salt compound, the structure of which is shown by a general formula (I), wherein R1 in the general formula represents alkyl or hydroxyalkyl, and R2 represents acetyl or hydrogen. The invention also discloses the application of the fluorescence probe of marking or displaying the distribution of the mitochondrion in living cells. Experiments prove that compared with mitochondrion fluorescence probes sold in markets, the mitochondrion fluorescence probe has the characteristics of low price, good two-photon property, low excitation energy, strong developing performance, better biocompatibility, and capability of focusing on fluorescence imaging mitochondrion in the living cells, and has potential application value in the field of exciting fluorescence biomarker with laser.

Description

technical field [0001] The invention relates to a mitochondrial fluorescent probe and its application, in particular to a single- and two-photon mitochondrial fluorescent probe of a pyridine cationic compound and its application. Background technique [0002] Mitochondria is one of the organelles with important physiological functions in eukaryotic cells, and it is an important place for cells to produce energy through respiration. At the same time, studies have found that the number and distribution of mitochondria are closely related to the vitality of cell life activities, and play an important role in physiological activities such as cell proliferation, differentiation, intercellular signal transduction, and intracellular free radical generation; and other diseases are closely related. Therefore, it is of great value in life science and medicine to develop new fluorescent probes for intracellular mitochondrial imaging and to provide information on the number and distrib...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/06G01N21/64
Inventor 于晓强孙渝明苗芳
Owner SHANDONG UNIV
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