A two-photon fluorescent probe for RNA imaging and its application in living cells

A two-photon fluorescence and imaging technology, applied in the field of fluorescent probes, can solve the lack of two-photon fluorescent probes and other problems, and achieve the effects of good membrane permeability, good photostability, and strong color rendering

Active Publication Date: 2019-05-28
NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, there is still a lack of excellent two-photon fluorescent probes for RNA fluorescence imaging detection in living cells, and this situation needs to be resolved urgently.

Method used

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  • A two-photon fluorescent probe for RNA imaging and its application in living cells
  • A two-photon fluorescent probe for RNA imaging and its application in living cells
  • A two-photon fluorescent probe for RNA imaging and its application in living cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Synthesis of 2-[2-(4-dimethylamino-phenyl)-vinyl]-1,3-dimethyl-3H-benzimidazole iodide (DI)

[0029] Dissolve 1.32g (10mmol) of 2-methylbenzimidazole and 2.83g (20mmol) of methyl iodide in 50ml of toluene, stir for 6 hours, then reflux for 30 minutes, cool to room temperature, filter, and wash with ether to obtain N-formaldehyde Base-2-methylbenzimidazole iodide salt. Dissolve 0.288g (1mmol) of N-methyl-2-methylbenzimidazole iodide salt and 0.149g (1mmol) of p-dimethylaminobenzaldehyde in 20ml of methanol, drop 3 drops of piperidine, and reflux for 6h without Washed with water and ethanol to obtain a brown powder with a yield of 77%.

[0030] 1 H NMR (400MHz, DMSO-d 6 ), δ (ppm): 7.987 (d, J = 3.16Hz, 2H), 7.796 (t, J = 6.6Hz, 2H), 7.721 (s, 1H), 7.650 (dd, J 1 =J 2 =3.08Hz,2H),7.213(d,J=16.48,1H),6.822(d,J=8.84,2H),4.107(s,6H),3.044(s,6H). 13 C NMR (400MHz, DMSO-d 6 ), δ (ppm): 152.79, 149.60, 147.58, 132.46, 131.06, 126.40, 122.19, 112.99, 112.15, 10...

Embodiment 2

[0031] Example 2: Synthesis of 2-[2-(4-dimethylamino-phenyl)-vinyl]-1,3-dibutyl-3H-benzimidazole iodide salt

[0032]1.32g (10mmol) 2-methylbenzimidazole and 3.68g (20mmol) iodobutane were dissolved in 50ml of toluene, stirred for 6 hours, then refluxed for 30 minutes, cooled to room temperature, filtered, and washed with ether to obtain N- Butyl-2-methylbenzimidazole iodide salt. Dissolve 0.372g (1mmol) of N-butyl-2-methylbenzimidazole iodide salt and 0.149g (1mmol) of p-dimethylaminobenzaldehyde in 20ml of methanol, add 3 drops of piperidine dropwise, and reflux for 6h. Washed with water and ethanol to obtain a brown powder with a yield of 70%.

Embodiment 3

[0033] Example 3: Synthesis of 2-[2-(4-dimethylamino-phenyl)-vinyl]-1,3-diethylethyl ether-3H-benzimidazolium bromide

[0034] Dissolve 1.32g (10mmol) 2-methylbenzimidazole and 3.06g (20mmol) 2-bromoethyl ethyl ether in 50ml of toluene, stir for 6 hours, then reflux for 30 minutes, cool to room temperature, filter, diethyl ether After washing, N-ethyl ethyl ether-2-methylbenzimidazolium bromide was obtained. Dissolve 0.404g (1mmol) N-ethyl ethyl ether-2-methylbenzimidazolium bromide and 0.149g (1mmol) p-dimethylaminobenzaldehyde in 20ml methanol, and add 3 drops of piperidine dropwise, and reflux After reacting for 7 hours and washing with absolute ethanol, a brown powder was obtained with a yield of 65%.

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Abstract

The invention relates to a two-photon fluorescence probe for RNA imaging and an application thereof in living cells. A structural general formula of the probe is shown as (I), wherein R is hydrogen, alkyl group, hydroxyalkyl or ether group, and X is bromine or iodine. The two-photon fluorescence probe provided by the invention is a novel RNA selective recognizing two-photon fluorescence probe; the probe has the characteristics of excellent membrane permeability, strong color development and high light stability; and the two-photon fluorescence probe can be developed into a biological detection reagent for RNA related physiological and pathological research.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a two-photon fluorescent probe for RNA imaging in living cells. Background technique [0002] The current fluorescence imaging technology, especially the two-photon fluorescence microscopy imaging technology, has been widely used in real-time monitoring of the morphology and amount of biomolecules in living cells. Compared with laser scanning confocal microscopy, two-photon fluorescence microscopy has the advantages of high detection sensitivity, large penetration depth, high image fidelity, low phototoxicity and photobleaching, and is an important tool for biological tissue imaging. Favored by researchers in biology, life, medicine and other disciplines. At present, most of the commercialized fluorescent probes are single-photon fluorescent probes developed for laser scanning confocal microscopy, which have a small two-photon absorption cross-section, and the required excitation light int...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/14C09K11/06G01N21/64
CPCC07D235/14C09K11/06G01N21/6486
Inventor 赵宁于晓强李龙龙冯瑞卿彭丹李冰李金辉于一涛牟秋红
Owner NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI
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