Carbazole-based two-photon fluorescent probe as well as preparation method and application thereof

A two-photon fluorescence and probe technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high cell phototoxicity, large fluorescence interference, and small excitation wavelength, and achieve low detection concentration and high sensitivity. High, easy-to-operate effect

Active Publication Date: 2017-10-24
ANHUI UNIVERSITY
View PDF2 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the detection of HSO in cells 3 - All fluorescent probes are single-photon fluorescent probes. Single-photon fluorescent probes generally

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Carbazole-based two-photon fluorescent probe as well as preparation method and application thereof
  • Carbazole-based two-photon fluorescent probe as well as preparation method and application thereof
  • Carbazole-based two-photon fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of fluorescent probe molecule MBCB

[0025]Add 3-benzothiazole-6-formyl-N-methylcarbazole (0.53g, 1.5mmol) into a 100mL round bottom flask, add 15mL of methanol, heat and stir until the raw material is dissolved, then add 2,3-di Tolylbenzothiazol-3-ium iodide (0.44g, 1.5mmol), and 2-3 drops of piperidine were added dropwise, and the reaction was refluxed at 70°C for 4h; after the reaction was completed, it was left to cool, and after separation, it was filtered to obtain a red crude The product was recrystallized twice with a mixed solvent of dichloromethane:methanol=4:1 (v / v) to obtain 0.63 g of the target product with a yield of 67%.

[0026] 1 H NMR (400MHz, DMSO-d 6 ): δ9.22(s,1H),9.04(s,1H),8.42(m,2H),8.30–8.19(m,3H),8.15(t,J=12.6Hz,2H),8.07(d, J=8.1Hz, 1H), 7.89(m, 3H), 7.79(t, J=7.6Hz, 1H), 7.57(t, J=7.4Hz, 1H), 7.47(t, J=7.4Hz, 1H) ,4.60(q,J=6.6Hz,2H),4.41(s,3H),1.42(t,J=7.0Hz,3H).δ171.87,167.93,150.04,142.82,142.02,141.94,134.29,...

Embodiment 2

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

[0028] Dissolve the two-photon fluorescent probe of the present invention in DMSO to prepare 1 mM mother solution, take 100 μL of the mother solution in a 10 mL volumetric flask, and then use glycerol:PBS=2:8 solvent to make up a 10 μM detection reagent. The detection reagents have absorption peaks at 316nm and 480nm respectively; add 20 times the equivalent of HSO 3 - After that, the absorption peaks of MBCB at 316nm and 480nm decreased gradually, and two new absorption peaks appeared at 306nm and 351nm ( figure 1 ). After adding 20 times the equivalent of various anions, reactive oxygen species and amino acids to 10 μM detection reagent ( figure 2 a), detection of fluorescence spectrum changes in the range of 375-675nm, it can be seen that MBCB is only for HSO 3 - and SO 3 2- There is an obvious fluorescence enhancement phenomenon, with a specific response; when accompanied by HSO 3 - (0-50...

Embodiment 3

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

[0030] Using the two-photon induced fluorescence measurement technique, the two-photon absorption cross section of the fluorescent probe molecule (MBCB) was tested, from Figure 4 It can be seen that when the two-photon excitation wavelength is 740nm, the maximum absorption cross section of the fluorescent probe molecule is 138GM. It shows that the probe can be applied to two-photon bioimaging.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a carbazole-based two-photon fluorescent probe as well as a preparation method and application thereof. The carbazole-based two-photon fluorescent probe has the following structural formula, wherein the structural formula is as shown in the specification. The two-photon fluorescent probe disclosed by the invention shows specific response and high sensitivity in a system with coexistence of bisulfite (HSO3-) and other interference reagents. The cytotoxicity assay shows that the probe hardly has any toxic or side effect on cells. The two-photon confocal fluorescence microscopic imaging experiment shows that the probe has high permeability on MCF-7 cells. The probe is applicable to two-photon fluorescence imaging and qualitative detection of the HSO3- in cell mitochondria.

Description

1. Technical field [0001] The present invention relates to a two-photon fluorescent probe and its preparation method and use, specifically a carbazole-based two-photon fluorescent probe and its preparation method and use, so as to realize two-photon imaging qualitative detection of HSO 3 - , has the advantages of specific selectivity, high sensitivity and low detection concentration. 2. Background technology [0002] SO 2 It is one of the important sources of air pollution and also produces biological effects at physiological concentrations. Gaseous SO 2 Can be converted into its sulfite / bisulfite (SO 3 2- / HSO 3 - =1:3) derivatives. endogenous SO 2 It and its derivatives are involved in almost various physiological processes, including vasodilation, antihypertensive effect, inhibition of vascular smooth muscle and regulation of cardiac channel function. However, the biological role of sulfite is poorly understood because SO 2 and its derivatives cannot be direct...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D417/14C09K11/06G01N21/64
CPCC07D417/14C09K11/06C09K2211/1029C09K2211/1037G01N21/6428G01N21/6447G01N21/6486
Inventor 冯燕张婉王文娟孙新方国顺黄银亮
Owner ANHUI UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap