Multi-mode probe FN, and preparation method and application thereof

A multimodal, probe technology, applied in the fields of hydrazone preparation, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of non-invasive in vivo imaging of the unfavorable nervous system, limited applications, etc., and achieve high sensitivity, specificity, and selection good effect

Pending Publication Date: 2021-07-13
THE FIRST AFFILIATED HOSPITAL OF JINAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned probes only have the function of fluorescence imaging, which is not

Method used

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  • Multi-mode probe FN, and preparation method and application thereof
  • Multi-mode probe FN, and preparation method and application thereof
  • Multi-mode probe FN, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The reaction chemical equation of the multimodal probe FN is as follows:

[0047]

[0048] It was prepared by the following steps: add 0.32mmol compound 1, 0.336mmol compound 2 and 3mL methanol to a 10mL flask, stir the mixture at room temperature for 8 hours, add 10mL water, store at -4°C, refrigerate for 5h, and filter. After filtration, the obtained solid was washed with ice water and ice methanol respectively, and then recrystallized to obtain yellow needle-like crystal 3 (multimodal probe FN), with a yield of 94%. 1 H NMR (400MHz, DMSO-d 6 )δ12.85(s,1H),10.95(s,1H),9.88(s,1H),9.02(s,1H),8.60(d,J=8.4Hz,1H),8.03(d,J=8.9 Hz,1H),7.90(d,J=7.6Hz,1H),7.63–7.54(m,2H),7.47–7.40(m,1H),7.34–7.23(m,2H),7.01(dd,J= 9.0,4.6Hz,1H).HRMS calculated for C 18 h 13 FN 2 o 2 (M+H + ): 308.0956, found 309.1038.

[0049] The multimodal probe FN obtained above is tested as follows:

[0050] Prepare the detection solution: dissolve the multimodal probe FN in tetrahydrofuran to o...

Embodiment 2

[0079] Isotopologue compounds of the multimodal probe FN[ 18 F]FN is prepared by including the following steps: 5- 18 F salicylaldehyde, the 5- 18 F salicylaldehyde and 2-hydroxynaphthaldehyde hydrazone react to obtain compound [ 18 F] FN.

[0080] The reaction chemical equation of the labeling precursor is as follows:

[0081]

[0082] Specifically include the following steps: add 0.81mmol 5-iodosalicylaldehyde (compound 4), 3.42mmol N,N-diisopropylethylamine and 4mL dichloromethane to a dry 25mL flask, add 1.21mmol chloromethyl Methyl ether, reacted at room temperature for 1 hour. Subsequently, the reaction system was quenched with 10 mL of saturated sodium bicarbonate, and then extracted with dichloromethane to obtain the dichloromethane extract phase, which was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered to remove the solid, and removed under reduced pressure. Dichloromethane, and the residue was purified by column chromatography (...

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Abstract

The invention discloses a multi-mode probe FN, and a preparation method and application thereof. The chemical formula of the multi-mode probe FN is C18H13FN2O2, and the structural formula of the multi-mode probe FN is shown as a formula I in the specification. The multi-mode probe FN provided by the invention has strong specificity, good selectivity and high sensitivity on Cu<2+> and S<2->, can detect Cu<2+> and S<2-> in vitro and in cells, and is a very potential fluorescent probe.

Description

Technical field: [0001] The invention relates to the technical field of probe material preparation, in particular to a multimodal probe FN and its preparation method and application. Background technique: [0002] Copper is a common transition metal element, which widely exists in living organisms in the form of ions. As a trace metal element, copper is second only to zinc and iron in abundance in the human body and plays a vital role in various biological processes. Copper ions are a component of many proteins and enzymes and play an important role in the regulation of iron absorption in the body, the synthesis of hemoglobin and the formation of skin, hair and eye pigment. Cu 2+ Metabolic abnormalities in cells can lead to abnormal redox regulation of cells, resulting in oxidative damage to fat, protein and DNA / RNA, and even cancer and neurodegenerative diseases, such as Alzheimer's disease and Parkinson's disease (Nat.Chem.Biol ., 2015, 11, 744). [0003] Hydrogen sulf...

Claims

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Application Information

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IPC IPC(8): C07C249/16C07C251/88C07D319/08C07B59/00C09K11/06G01N21/64A61K51/04A61K101/02
CPCC07C251/88C07D319/08C07B59/001C09K11/06G01N21/6428G01N21/6456A61K51/04C09K2211/1007C09K2211/1011C09K2211/1014C07B2200/05
Inventor叶伟健徐浩魏俊杰黎国聪王璐唐勇进
OwnerTHE FIRST AFFILIATED HOSPITAL OF JINAN UNIV