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Two-photon fluorescence dye, preparation method thereof and application

A technology of two-photon fluorescence and dye, applied in the field of two-photon fluorescent dye and its preparation

Active Publication Date: 2017-07-28
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Carbazolyl-based two-photon fluorescent dyes with PEG chains as lysosome-targeting groups have not been reported

Method used

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  • Two-photon fluorescence dye, preparation method thereof and application
  • Two-photon fluorescence dye, preparation method thereof and application
  • Two-photon fluorescence dye, preparation method thereof and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the synthesis of compound Lyso-MCO and Lyso-NCO

[0043] 1. Synthesis of Intermediate 1

[0044] Add 2.095g (5mmoL) of 3,6-diiodocarbazole, 0.560g (10mmoL) of KOH, 2.40g (Me(CH 2 CH 2 O) 3 OTs, 7.55mmol) and DMF (30mL), fully stirred and dissolved, and reacted at room temperature for 24 hours, followed by TLC during the reaction; after the reaction was completed, water was added to the reaction solution, then extracted with dichloromethane, and dried over anhydrous sodium sulfate , separated on a silica gel column (eluent: petroleum ether / ethyl acetate=6 / 1, v / v) to obtain 1.695 g of a light yellow solid, namely Intermediate 1, with a yield of 60.0%.

[0045] m.p.72.4-74.6°C. FT-IR (KBr, cm -1 ):2884,1474,1422,1292,1123,798. 1 H NMR (CDCl 3 ,400MHz): δ(ppm)8.29(d,J=1.6Hz,2H),7.70(d,J=1.6Hz,1H),7.68(d,J=1.6Hz,1H),7.22(d,J=1.6Hz,1H) 8.6Hz, 2H), 4.40(t, J=5.6Hz, 2H, CH 2 ), 3.81(t, J=5.6Hz, 2H, CH 2 ),3.52–3.37(m,8H),3.33(s,3H,CH 3 ); 13 C NMR (CDC...

Embodiment 2

[0052] Embodiment 2: Spectral test of two-photon fluorescent dyes Lyso-MCO and Lyso-NCO in DMSO

[0053] The two-photon fluorescent dyes Lyso-MCO and Lyso-NCO of the present invention were respectively dissolved in DMSO to prepare a 1mM mother solution. Take 100 μL of the mother solution in a 10mL volumetric flask, and dilute to volume with different solvents to prepare a 10 μM detection reagent. From figure 1 The maximum ultraviolet absorption peaks of the compounds Lyso-MCO and Lyso-NCO are 318 and 328nm, respectively. When Lyso-MCO and Lyso-NCO were excited at 318nm and 328nm respectively, the single-photon fluorescence emission peaks of Lyso-MCO and Lyso-NCO were located at 403nm and 445nm ( figure 1 and Table 1). The compound Lyso-MCO emits blue light, and the compound Lyso-NCO emits blue-green light. Compared with Lyso-MCO, Lyso-NCO has a red shift of about 42nm. This is consistent with the changing law of the ultraviolet absorption spectrum. With the enhancement of t...

Embodiment 3

[0057] Embodiment 3: Two-photon absorption performance test of Lyso-MCO and Lyso-NCO

[0058] Using a two-photon induced fluorescence measurement technique, a concentration of 10 -3 The two-photon absorption cross section of the target compound at mol / L, from Figure 5 It can be seen that the maximum effective absorption cross sections (δФ) of Lyso-MCO and Lyso-NCO are 20GM and 43GM respectively, and the maximum two-photon excitation wavelengths are 690nm and 700nm respectively. From Figure 5 It can be seen that the two-photon absorption performance of Lyso-NCO is better than that of Lyso-MCO. When the concentrations of Lyso-MCO and Lyso-NCO are in the range of 0.2-1mM and 0.01-1mM respectively, it can be observed that the two-photon fluorescence emission peak intensity of Lyso-MCO and Lyso-NCO at 418nm and 493nm varies linearly with the concentration enhanced ( Figure 4 ).

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Abstract

The invention discloses a two-photon fluorescence dye, a preparation method thereof and an application. The two-photon fluorescence dye takes carbazole as a parent body, and the structure of the two-photon fluorescence dye is as shown in the description. According to the two-photon fluorescence dye, in the wide concentration range, one-photon and two-photon fluorescence signals and the concentration of the fluorescence dye have good linear relationships. Two-photon confocal fluorescence micro-imaging experiments show that the fluorescence dyes Lyso-MCO and Lyso-NCO have good permeability for MCF (macrophage chemotactic factor) cells, lysosomes in the cells can be effectively positioned (positioning coefficients are 0.9475 and 0.9398), and the two-photon fluorescence dye is applicable to two-photon fluorescence imaging of the lysosomes in the cells. Compared with a commercial lysosome dye (Lysosome Tracker Red), the two-photon fluorescence dyes Lyso-MCO and Lyso-NCO are better in photo-stability.

Description

[0001] 1. Technical field [0002] The invention relates to a two-photon fluorescent dye and its preparation method and application, so as to trace and locate lysosomes in cells, and has high single-photon fluorescence quantum yield, large Stokes shift, and effective two-photon absorption cross section Large size, high lysosomal localization coefficient and good photostability. [0003] 2. Background technology [0004] Lysosome is an acidic organelle in eukaryotic cells, which constitutes the terminal degradation "workshop" of mammalian cells, containing a variety of hydrolytic enzymes, which specialize in decomposing various exogenous and endogenous macromolecules. They accept and degrade macromolecules through phagocytosis, endocytosis and autophagy, and play important roles in various physiological processes. To gain insight into their physiological roles, various lysosomal dyes were developed, some of which are commercially available. However, most of these dyes are sing...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B57/00C07D209/86G01N21/64
CPCC07D209/86C09B57/00C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 冯燕刘闯王文娟方国顺黄银亮
Owner ANHUI UNIVERSITY
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