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Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof

A technology of Schiff base copper and fluorescent probes, applied in the field of applied probes, can solve the problems of long incubation time, low practicability, minutes to 1 hour or even longer

Active Publication Date: 2016-06-15
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One method is molecular probes based on chemodosimetric reactions, but this method requires a long incubation time, usually 20 minutes to 1 hour or even longer, and is less practical

Method used

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  • Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof
  • Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof
  • Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Reagent

[0034] 4-Diethylamino salicylaldehyde, diethyl malonate, piperidine, 80% hydrazine hydrate, 2,6-pyridinedicarbaldehyde, perchlorates of various metal ions (Cr 3+ , Ag + , Fe 3+ ,K + , Na + ,Mg 2+ ,Pb 2+ , Ca 2+ ,Hg 2+ ,Mn 2+ ,Cd 2+ , Fe 2+ ,Zn 2+ , Ni 2+ ,Co 2+ ,Cu 2+ ) in aqueous solution (2.0×10 -2 M), the aqueous solution of various amino acids (2.0×10 -2 M), absolute ethanol, acetonitrile (chromatographically pure), dimethylformamide (analytical pure), HEPES (pH: 7.35-7.45) solution, etc.

[0035] Synthesis

[0036] The synthesis process shown in formula 1: 7-N,N-dimethylamino-2-oxo-2H-3-coumarate (compound 3) and compound 2 were synthesized by prior art. Compound 1 is synthesized by compound 2 and 2,6-pyridinedicarbaldehyde, and is characterized by hydrogen spectrum, carbon spectrum and mass spectrum ( Figure 6 ,7,8). Compound 1-Cu 2+ is composed of compound 1 and Cu(ClO 4 ) 2·6H 2 O prepared.

[0037]

[0038] Compound 1 vs. ...

Embodiment 2

[0048] Synthesis

[0049] Synthesis of Compound 3 (7-N,N-Dimethylamino-2-oxo-2H-3-coumarate)

[0050] 4-Diethylaminosalicylaldehyde (7.72 g, 0.04 mol), diethyl malonate (12.8 g, 12.16 mL, 0.08 mol) and piperidine (4 mL) were mixed in absolute ethanol (120 mL). The mixture was refluxed for 6 hours with stirring. After cooling to room temperature, rotary evaporation until the ethanol solvent was no longer evaporated, a small amount of oily liquid was obtained which was compound 3.

[0051] Synthesis of compound 2 (coumarin hydrazide)

[0052] Weigh 4.3400 g of compound 3 (7-N, N-dimethylamino-2-oxo-2H-3-coumarate, 15 mmol) and dissolve it in 40 ml of ethanol, add 3.6381 ml of 80% hydrazine hydrate ( Density = 1.032 g / ml, 60 mmol). After stirring at room temperature for 12 minutes, it was cooled in ice water for 15 minutes. The resulting precipitate was filtered with suction to obtain the product compound 2 (coumarin hydrazide).

[0053] Synthesis of compound 1

[0054] 0....

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Abstract

The invention discloses a coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as a preparation method and an application thereof. Coumarin hydrazide and 2,6-pyridinedicarboxaldehyde are used as raw materials for synthesis of a coumarin schiff-base derivative (a compound 1), the compound 1 and copper ions are coordinated in order to form the coumarin-copper ion complex with a schiff-base structure, and the compound 1-Cu<2+> is obtained. The probe ensures fluorescence quenching of the compound 1 due to influences of paramagnetism and chelation of Cu<2+>. When thiol-containing amino acids are added, fluorescence of the compound 1-Cu<2+> is enhanced. Other amino acids which do not contain thiols do not influence the fluorescence effects. UV-visible spectrum absorption and fluorescence spectrum show that the compound 1-Cu<2+> has good selectivity and sensitivity for thiol-containing amino acids in a CH3CN:HEPES(3:2,v / v) solution. The probe was successful to be applied to SiHa cells, and was used for carrying out cell imaging experiments of glutathione. The method is hopeful to be applied to detection of thiol compounds in organisms.

Description

technical field [0001] The invention relates to applied probe technology, in particular to a thiol fluorescent probe based on a coumarin Schiff base copper ion complex and a preparation method and application thereof. Background technique [0002] Sulfhydryl (-SH) is a highly active group in cells. There are many protein and non-protein sulfhydryl compounds in organisms, such as reduced glutathione (GSH) and cysteine ​​(CYS), etc., which have important physiological functions. Abnormal levels of these thiols are associated with many diseases. Glutathione is the most abundant thiol in cells. As an important biologically active sulfhydryl compound in the body, glutathione plays an important role in maintaining normal redox reactions in vivo, cell signal transduction, and gene regulation. important role. More importantly, reduced glutathione can remove harmful poisons and metabolites in the body, maintain the integrity of cell membranes, and reduce free radicals' attacks on ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08C07D405/14C09K11/06G01N21/64
CPCC07D405/14C07F1/005C09K11/06C09K2211/188G01N21/6428G01N2021/6432
Inventor 何广杰王中权李静薛爱荣张伟毛光兰何广彦李超英
Owner XINXIANG MEDICAL UNIV
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