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Fluorescent probe FAL1 for formaldehyde and pH dual-function detection as well as preparation method and application of fluorescent probe FAL1

A fluorescent probe, FAL1 technology, applied in the field of chemical detection, can solve the problems affecting the uptake and curative effect of pH-sensitive chemotherapy drugs, and achieve the effects of strong photochemical stability, high quantum efficiency, and easy chemical modification

Pending Publication Date: 2022-03-08
河南省农业科学院农业质量标准与检测技术研究所 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, acid-base dysregulation is a common property of cancer cells and may affect the uptake and efficacy of pH-sensitive chemotherapeutic drugs

Method used

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  • Fluorescent probe FAL1 for formaldehyde and pH dual-function detection as well as preparation method and application of fluorescent probe FAL1
  • Fluorescent probe FAL1 for formaldehyde and pH dual-function detection as well as preparation method and application of fluorescent probe FAL1
  • Fluorescent probe FAL1 for formaldehyde and pH dual-function detection as well as preparation method and application of fluorescent probe FAL1

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation method of the fluorescent probe FAL1 for dual-function detection of formaldehyde and pH, the specific steps are:

[0041] (1) Intermediate 1 was prepared by dissolving 4-bromo-1,8-naphthalene anhydride (2.77 g, 10 mmol) and dimethyldiamine (2.644 g, 30 mmol) in ethanol (50 mL) , stirred and reacted for 4 hours under reflux conditions, a large amount of solids were precipitated after cooling to room temperature, and 1.384 g of light yellow solids were obtained by suction filtration, which was intermediate 1, and the yield was 40%;

[0042] (2) The preparation method of probe FAL1 was as follows: intermediate 1 (347.2 mg, 1 mmol) and 80% hydrazine hydrate (363 μL, 6 mmol) were dissolved in ethylene glycol monomethyl ether (15 mL) solution, heated React under reflux conditions for 15 hours. After cooling to room temperature, pour the mixed solution into pure water to precipitate a large amount of solids. Suction filter and wash the obtained solids with ethy...

Embodiment 2

[0047] The preparation method of the fluorescent probe FAL1 for dual-function detection of formaldehyde and pH, the specific steps are:

[0048] (1) Intermediate 1 was prepared by dissolving 4-bromo-1,8-naphthalene anhydride (2.77 g, 10 mmol) and dimethyldiamine (3.525 g, 40 mmol) in ethanol (50 mL) , stirring and reacting for 6 hours under reflux conditions, after cooling to room temperature, a large amount of solids were precipitated, and 1.73 g of light yellow solids were obtained by suction filtration, which was intermediate 1, and the yield was 50%;

[0049] (2) The preparation method of probe FAL1 was as follows: intermediate 1 (347.2 mg, 1 mmol) and 80% hydrazine hydrate (242 μL, 4 mmol) were dissolved in ethylene glycol monomethyl ether (15 mL) solution, heated Reaction under reflux conditions for 12 hours, after cooling to room temperature, pour the mixed solution into pure water to precipitate a large amount of solids, suction filter and wash the obtained solids with...

Embodiment 3

[0054] The preparation method of the fluorescent probe FAL1 for dual-function detection of formaldehyde and pH, the specific steps are:

[0055] (1) Intermediate 1 was prepared by dissolving 4-bromo-1,8-naphthalene anhydride (2.77 g, 10 mmol) and dimethyldiamine (7.05 g, 80 mmol) in ethanol (50 mL) , stirred and reacted for 8 hours under reflux conditions, and a large amount of solids were precipitated after cooling to room temperature, and 2.08 g of light yellow solids were obtained by suction filtration, which was intermediate 1, and the yield was 60%;

[0056] (2) The preparation method of probe FAL1 was as follows: intermediate 1 (347.2 mg, 1 mmol) and 80% hydrazine hydrate (484 μL, 8 mmol) were dissolved in ethylene glycol monomethyl ether (15 mL) solution, heated React under reflux conditions for 10 hours. After cooling to room temperature, pour the mixed solution into pure water to precipitate a large amount of solids. Suction filter and wash the obtained solids with et...

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Abstract

The invention belongs to the field of chemical detection, and relates to a formaldehyde and pH bifunctional detection reagent, in particular to a formaldehyde and pH bifunctional fluorescent molecule based on a naphthalimide derivative as well as a preparation method and application of the formaldehyde and pH bifunctional fluorescent molecule. The recognition performance of the probe FAL1 in various common analytes of DMSO / Tris-HCl is researched through a fluorescence spectrophotometer. Research results show that the probe FAL1 has specific fluorescence recognition performance on formaldehyde, can overcome interference of other common analytes, and has a wide pH value application range. The lowest detection limit of the probe to formaldehyde is 38 nM, and the probe is successfully applied to detection of formaldehyde in tap water through a standard recovery test; the fluorescence emission response of the probe to the pH value is within the pH value range of 3-8, and the probe is suitable for pH marking in a pH-value-sensitive microenvironment in an organism and has high practical application value in the fields of environment detection and biology.

Description

technical field [0001] The invention belongs to the field of chemical detection, and relates to formaldehyde and pH dual-function detection reagents, in particular to formaldehyde and pH dual-function fluorescent molecules based on naphthalimide derivatives, and a preparation method and application thereof. Background technique [0002] Formaldehyde (FA) is a colorless gas widely used as a synthetic material in wood processing, textile, construction, carpet, fresh-keeping paper and chemical industries. Formaldehyde in the environment mainly comes from industrial activities, food preservatives and construction materials. Formaldehyde is one of the ubiquitous pollutants in indoor air. Due to its high reactivity and toxicity, it can easily cause DNA damage, tearing, vomiting, sneezing, coughing, lethargy and coma, Alzheimer's disease, and even death. Based on clear evidence of damage from formaldehyde, the International Agency for Research on Cancer (IARC) classified it as a G...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06G01N21/6428G01N2021/6432G01N2021/6439C09K2211/1029Y02A50/30
Inventor 王铁良张迪郭洁李漫马志伟马莹魏亮亮周晓华刘进玺吴绪金刘冰杰
Owner 河南省农业科学院农业质量标准与检测技术研究所
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