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A class of [1,2,4]-triazolocyclic compounds with fluorescent properties and preparation method and use thereof

A technology of fluorescent properties and heterocyclic compounds is applied in the field of preparation of novel fluorescent molecules, which can solve the problems of low detection limit and inability to distinguish effectively, and achieve the effects of good biocompatibility, low cytotoxicity and good application prospects.

Active Publication Date: 2022-07-29
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The structures of organic small molecules commonly used in fluorescence detection include coumarins, naphthalimides, phenimidazoles, benzothiazoles, rhodamines, fluoropyrroles, etc. Most of these molecules have high fluorescence intensity and detection limits. However, these molecules are still insufficient in terms of biocompatibility and metal ion detection specificity, especially for the detection of iron ions. Most of the above commonly used organic fluorescent probe molecules cannot be effectively detected. Differentiate Fe 3+ and Fe 2+ Therefore, the present invention provides a new class of fluorescent molecules of [1,2,4]-triazole heterocyclic compounds and their application in metal detection. Different metal responsive groups are introduced into the fluorescent molecular structure, which can For the detection of different trace metal elements, especially in the detection of iron ions, the fluorescent molecule can specifically identify Fe 3+ , without recognizing Fe 2+

Method used

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  • A class of [1,2,4]-triazolocyclic compounds with fluorescent properties and preparation method and use thereof
  • A class of [1,2,4]-triazolocyclic compounds with fluorescent properties and preparation method and use thereof
  • A class of [1,2,4]-triazolocyclic compounds with fluorescent properties and preparation method and use thereof

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Embodiment 1

[0044] Embodiment 1 The present invention will be described in more detail below with reference to the accompanying drawings and embodiments. It should be understood that the preferred embodiments described herein are only used to illustrate and explain the present invention, but not to limit the present invention.

[0045]

[0046] Compound I-36a (1 mmol) was dissolved in 15 mL of acetonitrile, phosphorus oxybromide (4 mmol) was added, heated to reflux and reacted at this temperature for 5-6 hours (TLC tracking reaction), after the completion of the reaction, concentrated under reduced pressure to remove the solvent , the obtained residue was extracted with dichloromethane, the organic phase solution was taken and concentrated under reduced pressure to remove the solvent to obtain pure compound I-36b with a yield of 75%.

[0047] (2) Preparation of compound I-36c

[0048] Compound I-36b (0.5 mmol) was dissolved in 15 mL of 1,4-dioxane, phenylboronic acid (0.6 mmol) was add...

Embodiment 2

[0054] Example 2 Fluorescent molecule I-36 to Fe 3+ Detection of ions

[0055] 2.1 Determination of detection limit

[0056] to 1×10 -5 In μmol / L I-36 solution, 0, 20, 40, 60, 80, 100, 120, 140, 160 μmol / L Fe were added respectively 3+ ions to detect changes in fluorescence intensity. The fluorescence intensity at 440nm continued to decrease until the fluorescence disappeared, and the detection limit was calculated to be 0.8×10 -6 mol / L.

[0057] 2.2 Fluorescent molecular probe I-36 to Fe 3+ ion selectivity

[0058] to 1×10 -5 In the I-36 solution of μmol / L, 160 μmol / L of ferric ions, ferrous ions, lithium ions, magnesium ions, aluminum ions, calcium ions, zinc ions, copper ions, nickel ions, and manganese ions were added, respectively. Rapid detection of changes in fluorescence intensity. Test results such as figure 1 As shown, the probe has almost no response to other ions, ferric ions cause significant fluorescence quenching, and the outstanding characteristic of ...

Embodiment 3

[0063] Embodiment 3 Detection of metal palladium by fluorescent molecule I-49

[0064] using similar means, such as image 3 and Figure 4 , the fluorescent probe compound I-49 has good selectivity for metal palladium, and the detection limit is also low to the micromolar level.

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Abstract

The invention relates to the field of heterocyclic compounds, and discloses a preparation method and application of a class of [1,2,4]-triazolo-ring fluorescent molecules. The excitation wavelength of cyclic heterocyclic compounds is between 200-800nm; the emission wavelength is between 400-800nm, and the cytotoxicity is low, the biocompatibility is good, and different metal-responsive groups are connected, which can selectively detect the corresponding of trace metal elements. The fluorescent molecule of the invention can be used for the detection of trace metals in the environment, cells and organisms, and has a good application prospect in biological imaging.

Description

technical field [0001] The invention relates to a preparation method and application of a new type of fluorescent molecules, in particular to a type of [1,2,4]-triazolocyclic fluorescent molecules, and the preparation method and application thereof. Background technique [0002] The relationship between metal elements and life, especially human health, has attracted widespread attention. So far, it is known that trace elements contained in the human body include iron, zinc, copper, manganese, cobalt, molybdenum, chromium, vanadium, nickel and tin. They are all indispensable elements in the human body. Take iron as an example. Iron is a vital element in living organisms, especially Fe 3+ , it participates in the formation of a variety of enzymes and proteins in life, and plays a vital role in the chemical reactions of various organisms. Human Fe 3+ Imbalance can cause metabolic disorders and affect physical health, leading to diseases such as anemia, liver and kidney damage...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06G01N21/64
CPCC07D487/04C09K11/06G01N21/6428G01N21/6456C09K2211/1074C09K2211/1037C09K2211/1088C09K2211/1092G01N2021/6432
Inventor 黄龙江耿延汝廉成锡陈丽平李秀芬赵迎春葛晓萍
Owner QINGDAO UNIV OF SCI & TECH