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Two-channel lipid droplet fluorescent probe, preparation method and application thereof

A technology of fluorescent probes and channel lipids, which is applied in the field of spectral testing and cell imaging, can solve problems that need to be further developed, and achieve excellent LDs targeting ability, strong anti-interference ability of other ions, and simple post-processing.

Pending Publication Date: 2022-03-08
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some lipid droplet fluorescent probes have been commercialized, the dual-channel lipid droplet-specific imaging fluorescent probes with better specificity and better photostability still need to be further developed

Method used

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  • Two-channel lipid droplet fluorescent probe, preparation method and application thereof
  • Two-channel lipid droplet fluorescent probe, preparation method and application thereof
  • Two-channel lipid droplet fluorescent probe, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the synthesis of compound probe Nap-a, Nap-b, Nap-c:

[0061] (1) Synthesis of probe Nap-a:

[0062]

[0063] Mix 6-bromo-2-(2-hydroxyethyl)-1H-benzo[DE]isoquinoline-1,3(2H)-dione (0.5 mmol, 160.1 mg) and 5-formaldehyde furan-2 - Boronic acid (1.0 mmol, 139.9 mg) was dissolved in dry 4 mL of N,N-dimethylformamide (DMF) and potassium carbonate (K 2 CO 3 , 138.2 mg) as a basic catalyst, and triphenylphosphine palladium dichloride (Pd(pph 3 ) 2 Cl 2 , 73.0 mg) as a catalyst. Under a nitrogen atmosphere, react at room temperature at 25°C for 12 hours to obtain the crude product 5-(2-(2-hydroxyethyl)-1,3-dioxy-2,3-dihydro-1H-benzo[DE]iso Quinolin-6-yl)furan-2-carbaldehyde. The crude product was further purified by flash column chromatography with the corresponding eluent to give 5-(2-(2-hydroxyethyl)-1,3-dioxy-2,3-dihydro-1H-benzo [DE]isoquinolin-6-yl)furan-2-carbaldehyde pure product, the yield was 88%.

[0064] 1 H NMR (400 MHz, DMSO) δ 9.73 (s, ...

Embodiment 2

[0079] Embodiment 2: the absorption spectrum of compound probe Nap-a, Nap-b, Nap-c

[0080] (1) Probe Nap-a:

[0081] The probe Nap-a prepared in Example 1 was dissolved in dimethyl sulfoxide (DMSO) to prepare a 1 mmol / L stock solution. Take eight 30 μL stock solutions and add them to eight 3ml solvents for absorption test. Such as Figure 7 shown. Depend on Figure 7 It can be seen that the absorption of the probe does not change much when added to different solvents, and the maximum absorption is around 420 nm.

[0082] (2) Probe Nap-b:

[0083] The probe Nap-b prepared in Example 1 was dissolved in dimethyl sulfoxide (DMSO) to prepare a 1 mmol / L stock solution. Eight 30 μL stock solutions were taken and added to eight 3 ml solvents for absorption test. Such as Figure 8 shown. Depend on Figure 8 It can be seen that the absorption of the probe does not change much when added to different solvents, and the maximum absorption is around 393 nm.

[0084] (3) Probe Na...

Embodiment 3

[0086] Embodiment 3: the fluorescence intensity of compound probe Nap-a, Nap-b, Nap-c in different solvents

[0087] (1) Probe Nap-a

[0088] The probe Nap-a prepared in Example 1 was dissolved in dimethyl sulfoxide (DMSO) to prepare a 1 mmol / L stock solution. Eight 30 μL stock solutions were taken and added to eight 3 ml solvents for fluorescence testing. Such as Figure 10 shown. Depend on Figure 10 It can be seen that the fluorescence intensity of the probe Nap-a is the lowest in PBS, while the fluorescence intensity is increased many times in other commonly used solvents.

[0089] (2) Probe Nap-b

[0090] The probe Nap-b prepared in Example 1 was dissolved in dimethyl sulfoxide (DMSO) to prepare a 1 mmol / L stock solution. Eight 30 μL stock solutions were taken and added to eight 3 ml solvents for fluorescence testing. Such as Figure 11 shown. Depend on Figure 11 It can be seen that the fluorescence intensity of the probe Nap-b is the lowest in PBS, while the f...

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Abstract

The invention provides a dual-channel lipid droplet fluorescent probe. The structural formula of the fluorescent probe is as shown in NAP-a, NAP-b and NAP-c, the invention also provides a preparation method and application of the fluorescent probe. The probe disclosed by the invention is a novel structural unit responding to the lipid droplets, and dual-channel fluorescence detection on the lipid droplets in a biological system is realized; the synthesis of the probe can be completed by only two steps, and the post-treatment process is simple; the selective rapid detection of the lipid droplet molecular probe is realized, the selectivity is good, and the anti-interference capability of other ions is strong. Based on the specificity and obvious color change, the reagent can be used as a specific indicator for displaying the existence of lipid droplet molecules in an aqueous solution and biological cells, and can be used for real-time qualitative visual colorimetric detection. The method is a simple, rapid and sensitive lipid droplet molecule specific detection probe, and has a wide application prospect in the field of biomolecule detection.

Description

technical field [0001] The invention relates to a class of fluorescent probes for detecting lipid droplets, as well as spectrum testing and cell imaging, and belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Fluorescence imaging provides an intuitive, real-time observation method that can be used to study complex biological structures and physiological processes. As an important carrier for fluorescence imaging, organic fluorescent probes play an important role in the study of organic and cellular physiological processes. Many fluorescent probes targeting mitochondria, lysosomes, and vesicles are commercially available, but few are available for lipid droplet imaging. Moreover, the imaging effects of commercially available lipid droplet fluorescent probes are still unsatisfactory. [0003] Lipid droplets (LDs) are storage sites for neutral lipids, widely present in yeast, bacteria, plant and animal cells. LD has long been rec...

Claims

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Application Information

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IPC IPC(8): C07D405/04C09K11/06G01N21/64
CPCC07D405/04C09K11/06G01N21/6428G01N21/6458C09K2211/1088C09K2211/1029
Inventor 张海涛叶鹏曲建波王建勇
Owner QILU UNIV OF TECH
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