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Fluorescent probe based on 1, 8-naphthalimide derivative as well as preparation method and application of fluorescent probe

A fluorescent probe, naphthalimide technology, which is applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of cumbersome preparation methods of fluorescent probes, low yield, and inability to identify hydrogen sulfide with naked eyes.

Pending Publication Date: 2022-08-09
PEOPLES HOSPITAL OF HENAN PROV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its detection range is 0-40μM, but the preparation method of its fluorescent probe is cumbersome, the yield is low, and the naked eye cannot recognize hydrogen sulfide

Method used

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  • Fluorescent probe based on 1, 8-naphthalimide derivative as well as preparation method and application of fluorescent probe
  • Fluorescent probe based on 1, 8-naphthalimide derivative as well as preparation method and application of fluorescent probe
  • Fluorescent probe based on 1, 8-naphthalimide derivative as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] This embodiment is a preparation method of a fluorescent probe SBD based on 1,8-naphthalimide derivatives, and the steps are as follows:

[0045] (1) (Intermediate 1) Preparation of 6-bromo-2-(2-(dimethylamino)ethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione :

[0046] In a 50 mL single-neck flask, commercial 4-bromo-1,8-naphthalene anhydride (276 mg, 1 mmol) and dimethyldiamine (163 μL, 1.5 mmol) were dissolved in ethanol (25 mL), and the reaction was stirred under reflux conditions. After cooling to room temperature for 5 h, a large amount of solid was precipitated, which was filtered by suction and washed with ice ethanol to obtain a light yellow solid, which was Intermediate 1 (173 mg), and the yield was 50%;

[0047] (2) (Intermediate 2) 2-(2-(Dimethylamino)ethyl)-6-(piperazin-1-yl)-1H-benzisoquinoline-1,3(2H)-dione Preparation of:

[0048] In a 50 mL single-necked flask, intermediate 1 (346 mg, 1 mmol) and piperazine (235 μL, 3 mmol) were dissolved in ethylene gl...

Embodiment 2

[0054] This embodiment is a preparation method of a fluorescent probe SBD based on 1,8-naphthalimide derivatives, and the steps are as follows:

[0055] (1) (Intermediate 1) Preparation of 6-bromo-2-(2-(dimethylamino)ethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione :

[0056] In a 50 mL single-neck flask, commercial 4-bromo-1,8-naphthalene anhydride (276 mg, 1 mmol) and dimethyldiamine (326 μL, 3 mmol) were dissolved in ethanol (25 mL), and the reaction was stirred for 6 h under reflux conditions. , after cooling to room temperature, a large amount of solid was precipitated. After suction filtration and washing with ice ethanol, a pale yellow solid was obtained, which was Intermediate 1 (225 mg), and the yield was 65%;

[0057] (2) (Intermediate 2) 2-(2-(Dimethylamino)ethyl)-6-(piperazin-1-yl)-1H-benzisoquinoline-1,3(2H)-dione Preparation of:

[0058] In a 50 mL single-necked flask, intermediate 1 (346 mg, 1 mmol) and piperazine (470 μL, 6 mmol) were dissolved in ethylene gly...

Embodiment 3

[0064] This embodiment is a preparation method of a fluorescent probe SBD based on 1,8-naphthalimide derivatives, and the steps are as follows:

[0065] (1) (Intermediate 1) Preparation of 6-bromo-2-(2-(dimethylamino)ethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione :

[0066] In a 50 mL single-necked flask, commercial 4-bromo-1,8-naphthalene anhydride (276 mg, 1 mmol) and dimethyldiamine (435 μL, 4 mmol) were dissolved in ethanol (25 mL), and the reaction was stirred for 10 h under reflux conditions. , after cooling to room temperature, a large amount of solid was precipitated. After suction filtration and washing with ice ethanol, a pale yellow solid was obtained, which was Intermediate 1 (277 mg), and the yield was 80%;

[0067] (2) 2-(2-(Dimethylamino)ethyl)-6-(piperazin-1-yl)-1H-benzisoquinoline-1,3(2H)-dione (Intermediate 1) Preparation of:

[0068] In a 50 mL single-necked flask, intermediate 1 (346 mg, 1 mmol) and piperazine (775 μL, 10 mmol) were dissolved in ethylene g...

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Abstract

The invention belongs to the field of organic synthesis, and relates to preparation of a fluorescent probe, in particular to a fluorescent probe based on a 1, 8-naphthalimide derivative as well as a preparation method and application of the fluorescent probe. The fluorescent probe based on the 1, 8-naphthalimide derivative prepared by the invention is simple in preparation method and high in yield. The probe is a light yellow solution in a DMSO-PBS buffer system, almost no fluorescence exists, after the probe and hydrogen sulfide are subjected to a specific reaction, the solution becomes pink and has strong yellow fluorescence, and naked eye recognition of hydrogen sulfide can be achieved. The probe has specific selectivity on hydrogen sulfide under the excitation condition of 400nm, is high in anti-interference capability, has the lowest detection limit of 152nM on hydrogen sulfide, and has a relatively wide pH value application range. Experimental results in common kidney cancer cells show that the fluorescent probe has relatively low cytotoxicity, can be applied to exogenous hydrogen sulfide fluorescence imaging in biological living cells, and has a wide application prospect in the field of biomolecular detection.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to the preparation of fluorescent probes, in particular to a fluorescent probe based on 1,8-naphthalimide derivatives and a preparation method and application thereof. Background technique [0002] Hydrogen Sulfide (H 2 S), nitric oxide (NO), and carbon monoxide (CO) are three common gas-active small molecules, and widely exist in living organisms and play an important role. Hydrogen sulfide participates in the regulation of various physiological activities in the nervous system, endocrine system, respiratory system, cardiovascular and cerebrovascular system and kidney, and plays an important role in maintaining the normal physiological activities of the living body. Hydrogen sulfide participates in various renal pathophysiological processes through vascular effects, anti-inflammatory, antioxidant, etc., such as obstructive renal injury, renal fibrosis, diabetic nephropathy and other ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06G01N21/6428G01N21/643G01N21/6486G01N21/6456C09K2211/1029C09K2211/1044C09K2211/1007
Inventor 王雁良王利蒙张迪施佳成李漫张丽娜刘琳
Owner PEOPLES HOSPITAL OF HENAN PROV
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