Application of mon-carbonyl curcumin compound-based visual PH fluorescent probe

A single carbonyl turmeric and fluorescent probe technology, applied in the field of detection, can solve problems such as mechanical wear, and achieve the effects of good selectivity, little fluorescence background interference, and good stability

Inactive Publication Date: 2011-08-17
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The electrode method is not used in the pH measurement of the living body due to the existence of electrochemical interference, possible mechanical wear and other defects

Method used

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  • Application of mon-carbonyl curcumin compound-based visual PH fluorescent probe
  • Application of mon-carbonyl curcumin compound-based visual PH fluorescent probe
  • Application of mon-carbonyl curcumin compound-based visual PH fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Put 0.01 mol of 4-hydroxy-3-methoxy-benzaldehyde and 0.005 mol of acetone in a round bottom flask, add 20 mL of saturated HCl in glacial acetic acid solution, and stir at room temperature (25-30 ℃) for 30 min Leave it for 2 days. After the reaction was complete, 20 mL of water was added to the reaction flask, and the precipitate was filtered to obtain a crude product, which was recrystallized with ethanol and dried in vacuo to obtain an orange-yellow powder. 1,5-Bis(4-hydroxy-3-methoxy)-1,4-pentadien-3-one Yield 98%. mp 99–100 °C. 1 H NMR (DMSO-d6, 300 MHz) δ (ppm): 9.60 (brs, 2H, –OH), 7.63 (d, J = 15.9 Hz, 2H, –CH=C–), 7.35 (s, 2H, ArH ), 7.18 (d, J = 8.1 Hz, 2H, ArH), 7.12 (d, J = 15.9 Hz, 2H, –C=CH–), 6.81 (d, J = 8.1 Hz, 2H, ArH), 3.84 ( s, 6H, –OCH 3 ). ESI–MS (m / z): 325[M-1] - . Anal. Calc. for C 19 h 18 o 5 : C 69.93, H 5.56. Found: C 69.79, H 5.67.

Embodiment 2

[0030] Put 0.01 mol of 4-hydroxy-3-methoxy-benzaldehyde and 0.005 mol of cyclopentanone in a round-bottomed flask, add 20 mL of saturated HCl in glacial acetic acid, and stir at room temperature (25-30 °C) for 30 Leave it for 2 days after min. After the reaction was complete, 20 mL of water was added to the reaction flask, and the precipitate was filtered to obtain a crude product, which was recrystallized with ethanol. 2,5-Bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone Yield 94%. mp 212–214 °C. 1H NMR (DMSO-d6, 300 MHz) δ (ppm): 9.64 (brs, 2H, –OH), 7.34 (s, 2H, –CH=), 7.23 (s, 2H, aroma), 7.15 (d, J = 8.1 Hz, 2H, ArH), 6.87 (d, J = 8.1 Hz, 2H, ArH), 3.83 (s, 6H, –OCH 3 ), 3.06 (s, 4H, –H 2 C–CH 2 –). ESI–MS (m / z): 351[M-1] - . Anal. Calc. for C 21 h 2 0O 5 : C 71.58, H 5.72. Found: C 71.50, H 5.88.

Embodiment 3

[0032] Put 0.01 mol of 4-hydroxy-3-methoxy-benzaldehyde and 0.005 mol of cyclopentanone in a round-bottomed flask, add 20 mL of saturated HCl in glacial acetic acid, and stir at room temperature (25-30 °C) for 30 Leave it for 2 days after min. After the reaction was complete, 20 mL of water was added to the reaction flask, and the precipitate was filtered to obtain a crude product, which was recrystallized with ethanol. Yield 98%. mp 178–179 °C. 1 H NMR (DMSO-d6, 300 MHz) δ (ppm): 9.48 (brs, 2H, –OH), 7.53 (s, 2H, –CH=), 7.08 (s, 2H, ArH), 7.01 (d, J = 8.1 Hz, 2H, ArH), 6.82 (d, J = 8.1 Hz, 2H, ArH), 3.79 (s, 6H, –OCH 3 ), 2.87 (t, J = 6.7 Hz, 4H, –H 2 C–C–CH 2 –), 1.71 (q, J = 6.7 Hz, 2H, –C–CH 2 –C–). ESI–MS (m / z): 365[M-1] - . Anal. Calc. for C 22 h 22 o 5 : C72.12, H 6.05. Found: C 72.03.48, H 6.02.

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Abstract

The invention discloses an application of a mon-carbonyl curcumin compound-based visual PH fluorescent probe. The visual PH fluorescent probe has a structure as shown in the formula I. The fluorescent characteristic of a series of mon-carbonyl curcumins is very high in the sensitivity to the PH detection, is very high in the selectivity to hydrogen ions, and is very small in the interference to the other metal ions. The probes have wide prospect as being used as an reagent for the PH detection; the groups represented by R1, R2, R3 and R4 in the formula I are respectively to be one of substituent groups such as OH, H, OCHO3, Br; X is one of CH2, CH2-O-CH2, CH2-S-CH2; and n=0-2.

Description

technical field [0001] The invention belongs to the technical field of detection, and in particular relates to the application of a monocarbonyl curcumin-based compound as a visualized pH fluorescent probe. Background technique [0002] The pH value is an important parameter in systems such as physiology, pharmacology, and environment. The progress or completion of chemical reactions, and many important physiological processes of cells and organelles are closely related to its changes. Therefore, the determination of pH value is of great significance. The existing pH testing methods mainly include spectroscopic method, electrode method and indicator method. The electrode method is not used in the pH measurement of the living body due to the existence of electrochemical interference, possible mechanical wear and other defects. Fluorescence spectroscopy is a detection method based on optical signals, which has the advantages of high sensitivity, high selectivity, fast reflex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06G01N21/64
Inventor 张焜徐学涛杜志云卢宇靖张瑞瑞方岩雄赵肃清黄宝华黄华容谭伟郑杰
Owner GUANGDONG UNIV OF TECH
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