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Phenylboronic acid modified near-infrared squaraine dyes as well as preparation method and application thereof

An infrared method and phenylboronic acid technology, applied in the field of analytical chemistry, can solve the problems of inability to realize real-time and in-situ detection

Inactive Publication Date: 2018-10-19
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, some of the analytical methods developed for measuring intracellular ATP concentration are mostly offline, and the cell extracts are obtained by breaking the cells for analysis, which cannot realize real-time and in situ detection (Manfredi, G.; Yang, L.; Gajewski, C. D.; et al. Measurements of ATP in mammalian cells. Methods ,2002, 26(4), 317-326. Li, M.; Zhang, J.; Suri, S.; et al. Detection of adenosine triphosphate with an aptamer biosensor based on surface-enhanced Raman scattering. Analytical Chemistry , 2012 , 84, 2837-2842.)

Method used

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  • Phenylboronic acid modified near-infrared squaraine dyes as well as preparation method and application thereof
  • Phenylboronic acid modified near-infrared squaraine dyes as well as preparation method and application thereof
  • Phenylboronic acid modified near-infrared squaraine dyes as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of:

[0048] First add 20 mL of ethanol to a 50 mL round-bottomed flask, then add 2.00 g of squaraine (17.6 mmol), and reflux at 80°C for 3 hours. After the squaraine is completely dissolved, remove the ethanol by rotary evaporation under reduced pressure. After repeating this operation three times Reflux reaction again 24 hours, after reaction finishes, adopt sherwood oil: ethyl acetate is 2:1 (v / v) to carry out silica gel column chromatography separation as eluent, obtain light yellow oily liquid product 2.09 g, productive rate is 70 %. 1 H NMR (400 MHz, CDCl 3 ) δ 4.74 (q, J = 7.1Hz, 4H), 1.48 (t, J = 7.1 Hz, 6H).

Embodiment 2

[0050] Dicyanovinyl squaraine derivatives Preparation of:

[0051] Dissolve 1.77 g of malononitrile (26.8 mmol) in 35 mL of dry benzene, place in a 100 mL round-bottomed flask, and drop into 5 g of the (29.4 mmol), then slowly added 2.98 g triethylamine (29.4 mmol) into the above reaction solution, and stirred at room temperature for 6 h. After the reaction was completed, the reaction bottle was placed in the refrigerator to cool for 24 hours, and the 2 Cl 2 After extraction, the organic layer was concentrated in vacuo to obtain 5.28 g of a yellow solid product with a yield of 62%. 1 H NMR (400 MHz, CDCl 3 )δ 9.19 (brs, 1H), 4.76 (q, J = 7.0 Hz, 2H), 3.32-3.25 (m, 6H), 1.99 (s, 1H), 1.49 (t, J = 7.1 Hz, 3H), 1.38 (t, J = 7.3 Hz, 9H).

Embodiment 3

[0053] 2,3,3-Trimethylindole preparation of

[0054] Add 20 mL of absolute ethanol containing 500 mg of phenylhydrazine (4.62 mmol) into a 50 mL round bottom flask, then slowly add 438 mg of methyl isopropyl ketone (5.09 mmol) into the above solution dropwise, the solution becomes light Then 0.25 mL of concentrated sulfuric acid was added dropwise within 0.5 h. At this time, the reaction system turned into a yellow turbid liquid again, and the reaction was refluxed at 80°C for 3 h. As the reaction temperature increased, the color of the reaction system gradually changed from yellow to orange, and then to an orange-red turbid solution. It was detected by TLC that the reaction was complete. After the reaction solution was cooled to room temperature, NaOH solution was added dropwise to adjust the pH to 8. use CH 2 Cl 2 Extracted three times, removed the solvent under reduced pressure, and purified by silica gel column chromatography using petroleum ether:ethyl acetate 3:1 (v...

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Abstract

The invention discloses phenylboronic acid modified near-infrared squaraine dyes as well as a preparation method and application thereof. The preparation method comprises the following steps: mixing an indole-modified phenylboronic acid derivative with a dicyanyl vinyl squaraine derivative; carrying out dissolution, backflow, pressure-reduction evaporation-removal on a solvent and silica gel column chromatography purification to obtain the near-infrared squaraine dyes. The squaraine dyes have the advantages of better stability and excellent optical performance, in particular to contraposition-substituted phenylboronic acid groups; the squaraine dyes can be partially combined with cis-glycol in an ATP (adenosinetriphosphate) molecule, so that change of absorption spectrum and fluorescence spectrum of the dyes is induced through multiple electrostatic interactions among the dyes, the ATP and CTAB (Cetyl Trimethyl Ammonium Bromide), so that the dyes can be used as fluorescent probes for ATP detection, and the fluorescent probes are used for carrying out fluorescent imaging detection on the ATP in cells; moreover, the probes have the advantages of better biocompatibility and cellular permeability and lower biotoxicity, and has better detection sensitivity on ATP.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and in particular relates to a near-infrared squaraine dye modified by phenylboronic acid, a preparation method thereof and its application in fluorescence imaging detection of intracellular ATP. Background technique [0002] Adenosine 5'-triphosphate (ATP) consists of adenine, ribose, and three phosphate groups. ATP is not only a universal energy currency in living cells, but also a signaling mediator involved in various biological processes such as the triphosphate cycle, ion channels, neurotransmission, cell division, and DNA synthesis (Xu, Z.; Singh, N. J.; Lim, J. . et al. Unique sandwichstacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH. Journal of the American Chemical Society ,2009, 131(42), 15528-15533. Ashcroft, F. M.; Gribble, F. M. ATP-sensitive K + channels and insulin secretion: their role in health and disease. Diab...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B23/04G01N21/64
Inventor 傅南雁王桂美
Owner FUZHOU UNIV
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