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Single-photon and two-photon homocysteine fluorescent probes and use thereof

A fluorescent probe, cysteine ​​technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the constraints of cysteine ​​imaging and observation, the development of two-photon fluorescent probes has not kept up in time, etc. problems, to achieve the effect of intuitive biological detection reagents, large absorption cross-section, and good biocompatibility

Inactive Publication Date: 2011-07-20
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 the two-photon fluorescent probes that specifically recognize cysteine ​​in cells Internationally unreported
This largely restricts the imaging and observation of intracellular cysteine ​​using two-photon 3D imaging technology.

Method used

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  • Single-photon and two-photon homocysteine fluorescent probes and use thereof
  • Single-photon and two-photon homocysteine fluorescent probes and use thereof
  • Single-photon and two-photon homocysteine fluorescent probes and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of 9-ethylcarbazole (1a)

[0027] 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, and stirred at room temperature for 4 h to obtain a brown cloudy liquid. Acetone solution containing 1-bromoethane (9 mL, 120 mmol) was gradually added 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%. 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 can be synthesized with a yield of 82%. 1 H NMR (300MHz, CDCl 3 ), δ(ppm): 8.11(d, J=7.9Hz, 2H), 7...

Embodiment 2

[0033] Synthesis of 3-formyl-9-ethylcarbazole (2a)

[0034] Add 1.86mL DMF into a dry round bottom flask, cool to 0°C with ice water, add 2.3mL redistilled POCl dropwise 3 , to obtain a white solid. and CHCl containing 4.87 g (25 mmol) of compound 1a 3 (15 mL) of the solution was added to the above reaction flask. Remove the ice-water bath, move the reaction bottle to an oil bath, and heat to reflux for 16h. CHCl 3 Evaporate as much as possible, pour the reaction solution into a large amount of ice water, and use NaHCO 3 Adjust the pH to 7-8. use CH 2 Cl 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 light yellow solid with a yield of 87%. 1 H NMR (300MHz, CDCl 3 ), δ(ppm): 10.10(s, 1H), 8.61(s, 1H), 8.16(d, J=7.8Hz, 1H), 8.01(dd, J 1 =8.4Hz,J 2 =1.5Hz, 1H), 7.47-7.57(m, 3H), 7....

Embodiment 3

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

[0041] 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 eluent to obtain a white flocculent solid with a yield of 81%. 1 H NMR (300MHz, CDCl 3 ), δ (ppm): 10.10 (s, 1H), 8.56 (d, J = 1.2Hz, 1H), 8.27 (d, J = 1.8Hz, 1H), 8.05 (dd, J 1 =8.4Hz,J 2 = 1.2Hz, 1H), 7.62(dd, J 1 =8.7Hz,J 2 =1.8Hz, 1H), 7.49(d, J=8.4Hz, 1H), 7.35(d, J=8.7Hz, 1H), 4.4(q, J=7.3Hz, 2H), 1.47(t, J=7.4 Hz, 3H).

[0042] Synthesis of 3-formyl-6-bromo-9-butylcar...

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Abstract

The invention discloses single-photon and two-photon homocysteine fluorescent probes, which are carbazole and pyridine aldehyde compounds. The general formula of the carbazole and pyridine aldehyde compounds is represented by (I), wherein R may be alkyl or hydroxyalkyl. The invention also discloses the use of the fluorescent probes in the observation of the expression and distribution of homocysteine in living cells. The probes have the characteristics of wide application range, low price and specific fluorescently imaging homocysteine in living cells.

Description

technical field [0001] The invention relates to a single- and two-photon fluorescent probe and its application, in particular to a single- and two-photon cysteine ​​fluorescent probe of a carbazole pyridine aldehyde compound and its application. Background technique [0002] As one of the twenty amino acids that make up proteins, cysteine ​​containing sulfhydryl groups plays an irreplaceable role in the physiological process of cells. For example, cysteine ​​is an essential molecule for cell and tissue growth, and cysteine ​​deficiency has been linked to edema, stunted growth in young children, liver damage, and many other diseases. Therefore, it is of great value in life science and medicine to realize the fluorescence imaging of intracellular cysteine ​​and give information on the expression and distribution of intracellular cysteine. [0003] Generally speaking, the instruments for observing intracellular molecular fluorescence imaging include laser scanning confocal mic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C09K11/06C12Q1/02
Inventor 于晓强孙渝明
Owner SHANDONG UNIV
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