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Two-photon fluorescent probe as well as preparation method and application thereof

A two-photon fluorescence and probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low sensitivity and detection concentration, and achieve the effects of low detection concentration, simple operation and simple structure

Active Publication Date: 2016-08-31
ANHUI UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The present invention aims to provide a two-photon fluorescent probe and its preparation method and application. The technical problem to be solved is to obtain a suitable fluorescent probe structure through molecular design, so as to realize the qualitative detection of Au in cell mitochondria by two-photon imaging. 3+ , has the advantages of specific selectivity, high sensitivity, and low detection concentration, and the cytotoxicity test shows that the fluorescent probe of the present invention has almost no toxic effect on cells

Method used

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  • Two-photon fluorescent probe as well as preparation method and application thereof
  • Two-photon fluorescent probe as well as preparation method and application thereof
  • Two-photon fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0024] Embodiment 1: the synthesis of fluorescent probe molecule PyCM-3

[0025]Add 9-ethyl-6-(4'-(1'-methylpyridinium iodide)ethylene)-3-formylcarbazole (1) (0.1171 g, 0.25 mmol) and anhydrous methanol in a round bottom flask 12mL, stir at 70°C to dissolve, add dropwise 3 drops of glacial acetic acid, then add dropwise 0.0413g (0.25mmol) of anhydrous methanol solution (8mL) of 2-hydrazino-benzothiazole, and reflux at 70°C after dropping React for 4h (TLC tracking reaction), after the reaction, cool to room temperature, let stand, precipitate crystals, filter, wash 3 times with anhydrous methanol, and then recrystallize with anhydrous methanol to obtain the target compound PyCM-3, which is brown-red flake Solid, 0.1188g, yield 75%.

[0026] 1 H NMR (400MHz, DMSO-d 6 ): δ12.14(s,1H),8.82(d,J=6.4Hz,2H),8.66(s,1H),8.49(s,1H),8.33(s,1H),8.22(t,J= 11.7Hz, 3H), 7.91(t, J=9.7Hz, 2H), 7.77(t, J=8.2Hz, 3H), 7.57(d, J=16.2Hz, 1H), 7.44(d, J=7.8Hz ,1H),7.31(t,J=7.2Hz,1H),7.12(t,J=7....

Embodiment 2

[0027] Embodiment 2: the spectroscopic test of fluorescent probe molecule

[0028] Dissolve the fluorescent probe molecules of the present invention in DMSO to prepare a 1 mM mother solution, take 100 μL of the mother solution in a 10 mL volumetric flask, and then use EtOH to make up the volume to prepare a 10 μM detection reagent. The detection reagents have absorption peaks at 344nm and 440nm; add 8 times the equivalent of Au 3+ After that, the absorption peak of PyCM-3 at 344nm disappeared, and a new absorption peak appeared at 420nm ( figure 2 ). After adding 8 times the equivalent of various metal ions, anions, active oxygen species and amino acids to 10μM detection reagent (3a), the fluorescence spectrum changes in the range of 445-750nm were detected. It can be seen that PyCM-3 only detects Au 3+ There is an obvious fluorescence enhancement phenomenon, with a specific response; when with Au 3+ (0-160μM) is continuously added, and it can be observed that the fluoresce...

Embodiment 3

[0029] Example 3: Two-photon testing of fluorescent probe molecules

[0030] Utilizing two-photon-induced fluorescence measurement technique, the fluorescent probe molecule (PyCM-3) and Au 3+ After the two-photon absorption cross section, from Figure 5 a It can be seen that when the two-photon excitation wavelength is 860nm, the fluorescent probe molecules and Au 3+ The maximum absorption cross section after action is 1208GM. from Figure 5 b It can be seen that with Au 3+ (0-80μM) was continuously added, and it can be observed that the intensity of the two-photon fluorescence emission peak at 580nm is gradually enhanced.

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Abstract

The invention discloses a two-photon fluorescent probe as well as a preparation method and application thereof. The two-photon fluorescent probe takes carbazole as matrix. The structure of the two-photon fluorescent probe is described in the specification. Molecules of the two-photon fluorescent probe show specificity response and high sensitivity in a system that trivalent gold ions (Au<3+>) and other interference reagents coexist. Cytotoxicity tests show that the probe almost has no toxic or side effect on cells, and two-photon confocal fluorescence microscopic imaging tests show that the probe has good HeLa cell permeability and is applicable to two-photon fluorescence imaging and qualitative detection on Au<3+> in a cell mitochondrion.

Description

1. Technical field [0001] The invention relates to a two-photon fluorescent probe and its preparation method and application, so as to realize the qualitative detection of Au in cell mitochondria by two-photon imaging 3+ , has the advantages of specific selectivity, high sensitivity and low detection concentration. 2. Background technology [0002] In recent years, due to the biocompatibility of gold, functional gold nanoparticles are mostly used as materials for drugs, gene delivery, biosensors and bioimaging. Although gold is stable and biocompatible, and in its ionic form (Au + and Au 3+ )-based drugs can be used to treat rheumatoid arthritis, tuberculosis, cancer, asthma, and malaria, but the toxicological effects of gold should still be taken seriously. The ionic forms of gold are potentially toxic to humans, especially Au 3+ Can cause severe poisoning of biological systems, because it can bind DNA and the nervous system, and can even cause DNA strand breaks. There...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C09K11/06G01N21/64
CPCC07D417/14C09K11/06C09K2211/1029C09K2211/1037G01N21/6428G01N2021/6443
Inventor 冯燕王文娟王奇孟祥明朱满洲
Owner ANHUI UNIVERSITY
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