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Single/double-photon acidic cell organelle fluorescent probe and application thereof

A technology of acidic organelles and fluorescent probes, which is applied in the fields of fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., and can solve the problems of two-photon fluorescent probe development that has not been kept up in time, constraints on imaging and observation, and two-photon fluorescent probes. Less reports and other issues, to achieve good biocompatibility, low price, low excitation energy

Inactive Publication Date: 2014-12-10
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Especially in recent years, two-photon fluorescence three-dimensional imaging technology has developed rapidly, but the development of special two-photon fluorescent probes has not kept up in time, especially in the international market for two-photon fluorescent probes that highly selectively label acidic organelles in cells. Less reported
This largely restricts the imaging and observation of intracellular acidic organelles using two-photon 3D imaging technology.

Method used

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  • Single/double-photon acidic cell organelle fluorescent probe and application thereof
  • Single/double-photon acidic cell organelle fluorescent probe and application thereof
  • Single/double-photon acidic cell organelle fluorescent probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 9-ethylcarbazole (1a)

[0026] 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%.

[0027] 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).

[0028] Synthesis of 9-butylcarbazole (1b)

[0029] The process is the same as above, and 9-butylcarbazole is synthesized with a yield of 82%.

[0030] 1 H NMR (300MHz, CDCl 3 ), δ(ppm): 8.11(d, J=7...

Embodiment 2

[0035] Synthesis of 3-acetyl-9-ethylcarbazole (2a)

[0036] 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 4Dry, 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%.

[0037] 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 8.75(d, J=1.52Hz, 1H), 8.11-8.17(m, 2H), 7.50-7.5...

Embodiment 3

[0045] Synthesis of 3-acetyl-6-bromo-9-ethylcarbazole (3a)

[0046] 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 4 Dry, 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%.

[0047] 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).

[0048] Synthesis of 6-bromo-9-ethylcarbazole (3b)

[0049] The pro...

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Abstract

The invention discloses a single / double-photon acidic cell organelle fluorescent probe. The fluorescent probe is a carbazole pyridine compound, and the fluorescent probe is as shown in a general formula of (I). The invention also discloses an application of the fluorescent probe as the single / double-photon fluorescent probe for marking the acidic cell organelles in the display of the distribution of the acidic cell organelles inside a viable cell. The fluorescent probe disclosed by the invention has the characteristics that application range is wide, price is low and the acidic cell organelles are specially and fluorescently imaged in an active cell; and the fluorescent probe has wide application prospect as a single-photon ratio type and double-photon optical switch type fluorescent probe for the acidic cell organelles.

Description

technical field [0001] The invention relates to a one-photon ratio-type and two-photon optical switch type fluorescent probe and its application, in particular to a single- and two-photon acidic organelle fluorescent probe of a carbazole pyridine compound and its application. Background technique [0002] Acidic organelles such as lysosomes are one of the organelles with important physiological functions in eukaryotic cells, especially playing a key role in physiological activities such as intracellular digestion, apoptosis and autophagy. At the same time, studies have found that abnormal pH values ​​in acidic organelles are closely related to cancer. Therefore, realizing fluorescence imaging of intracellular acidic organelles and giving information on pH distribution in acidic organelles has important life science and medical value. [0003] Generally speaking, the instruments for observing intracellular molecular fluorescence imaging include laser scanning confocal micros...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D401/06G01N21/64
Inventor 于晓强冯瑞卿孙渝明苗芳
Owner SHANDONG UNIV
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