Dual-emission fluorescent probe for detecting beta-amyloid protein plaque as well as preparation method and application of dual-emission fluorescent probe
A technology of amyloid protein and dual-emission fluorescence, applied in the field of specific molecular recognition materials, can solve the problems of incompletely clear pathogenic mechanism of AD and incurable disease
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Embodiment 1
[0067] Example 1 Synthesis of Organic Small Molecular Probes (I)
[0068] The synthesis of a kind of organic small molecule probe (I) of the present embodiment, the synthetic route diagram is as follows figure 1 The specific synthesis steps are as follows:
[0069] 1. Synthetic intermediate 1
[0070] 4g (26.8mmol) of p-dimethylaminobenzaldehyde, 3.14g (26.8mmol) of N-acetylglycine, 2g (24mmol) of anhydrous sodium acetate and 30ml of acetic anhydride were added to a 100ml pressure bottle, and the mixture was stirred at 100°C The reaction of the product was complete (TLC monitoring). It was cooled to room temperature, extracted with dichloromethane to remove the acid anhydride, and concentrated under reduced pressure to obtain 2.72 g of intermediate 1 with a yield of 44.2%.
[0071] 1H NMR(400MHz, CDCl3)δ8.00(d,J=8.5Hz,2H),7.09(s,1H),6.73(d,J=8.4Hz,2H),3.08(s,6H),2.37(s ,3H).13C NMR(101MHz, CDCl3)δ168.72,163.02,151.92,134.42,132.73,127.82,121.67,111.96,40.22,15.58.HRMS(ESI)...
Embodiment 2
[0084] Example 2 UV absorption and fluorescence spectrum experiments of fluorescent compound (I) in different solvents
[0085] Experimental method: Dissolve the fluorescent compound (ie, the organic small molecule probe (I) synthesized in Example 1) in dimethyl sulfoxide (DMSO) to prepare a 10 mM stock solution; then use different solvents (toluene, dioxane, etc.) , ethyl acetate, chloroform, acetone, acetonitrile, DMSO, isopropanol, ethanol, methanol, PBS buffer solution) was diluted into 10 μM solution to be tested, and its ultraviolet absorption spectrum and fluorescence spectrum were measured.
[0086] The ultraviolet absorption spectra of fluorescent compound (I) in different solvents in this example are shown in Figure 5 , the experimental results show that the fluorescent compound (I) exhibits two absorption peaks in the solvent, which are around 430 nm and 530 nm, respectively. The two absorptions also indicate that the molecule may have two emission bands.
[0087...
Embodiment 3
[0088] Example 3 In vitro binding experiment of fluorescent compound (I) with different proteins
[0089]Experimental method: Dissolve the fluorescent compound (that is, the organic small molecule probe (I) synthesized in Example 1) in dimethyl sulfoxide, prepare a 10 mM stock solution, and then use PBS buffer to prepare 1 μM probe and 10 μM protein (Aβ monomer, Aβ oligomer, Aβ aggregate, human serum albumin (HAS), bovine serum albumin (BSA)) (all proteins were purchased from Shanghai Qiangyao Biotechnology Co., Ltd.). Under the excitation light in the range of 430nm to 530nm, the fluorescence spectrum was detected by excitation at every distance of 10nm.
[0090] In this example, the fluorescence spectra (λex=430nm~540nm) of the response of fluorescent compound (I) and different proteins (10 μM) are shown in Figure 7 (In the figure, C17 represents the probe (I) of the present invention). The experimental results showed that the green light region of the fluorescent compoun...
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