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Rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit, preparation method and application thereof

A technology of hydrazide derivatives and structural units, applied in the field of rhodamine B hydrazide derivatives and its preparation, to achieve good selectivity

Inactive Publication Date: 2012-10-24
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, generally tumor cells have a high content of copper ions, which promotes angiogenesis of tumor cells and leads to tumor proliferation.

Method used

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  • Rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit, preparation method and application thereof
  • Rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit, preparation method and application thereof
  • Rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Preparation of Rhodamine B Thiobishydrazide Derivatives

[0025]Add 4.50g (9.85mmol) rhodamine B hydrazide to 130mL acetonitrile solution containing 2.09g (10.81mmol) p-methoxybenzoyl isothiocyanate, heat the mixture to reflux for 20 minutes, then cool down to room temperature , a large amount of white solids were precipitated, filtered under reduced pressure, the filter cake was washed with cold acetonitrile, and dried to obtain 6.26 g of rhodamine B thiobishydrazide derivative 3 as a white or light pink solid, yield: 97.7%.

[0026] Infrared spectrum measurement: IR(KBr), υ: 3282,3081,2970,2931,2893,2870,1711,1662,1633,1612,1510,1425,1375,1356,1330,1261,1221,1186,1118,1079 ,1023,857,816,785,763,698,635,606,578cm -1 .

[0027] H NMR spectrum determination: 1 H NMR (CDCl 3 ,400MHz),δ(ppm):1.16(t,12H,NCH 2 CH 3 ,J=7.0Hz),3.32(q,8H,NCH 2 CH 3 ,J=7.1Hz),3.84(s,3H,OCH 3 ),6.33(dd,2H,Xanthene–H,J=8.9,2.1Hz),6.36(d,2H,Xanthene–H,J=2.0Hz),6.78(d,2H,Xanthene–...

Embodiment 2

[0030] Example 2 Preparation of rhodamine B hydrazide derivatives containing 1,2,4-triazole structural units

[0031] 1.22g (1.88mmol) of rhodamine B thiobishydrazide derivative 3 was dissolved in 50mL of chloroform, and then 550mg (9.34mmol) of 85wt% hydrazine hydrate was added to the above solution. The reaction mixture was heated to reflux, and the reaction was continued for 1 hour. After the reaction was complete, the system was cooled down, diluted with 50 mL of chloroform, washed with water, left to stand, separated into layers, separated, the organic phase was dried with anhydrous magnesium sulfate, filtered with suction, and the filtrate was concentrated to obtain the crude product .

[0032] Purification by silica gel column chromatography (1:2 petroleum ether-ethyl acetate) yielded 314 mg of light purple compound 4, which is a rhodamine B hydrazide derivative containing a 1,2,4-triazole structural unit.

[0033] Infrared spectrum measurement: IR(KBr), υ: 3209,3077,2...

Embodiment 3

[0039] Embodiment 3 UV-Vis Spectrophotometry and Fluorescence Spectrophotometry Test

[0040] Use a micro-syringe to add 10 mL of the prepared rhodamine B hydrazide 1,2,4-triazole derivative (4) to ethanol / HEPES buffer solution (20 mM HEPES, pH=7.2, 1:1, volume ratio ) solution by adding 10 equivalents of Na + ,Mg 2+ ,Al 3+ ,K + , Ca 2+ ,Cr 3+ ,Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Zn 2+ , Ag + ,Cd 2+ , Ba 2+ ,Pb 2+ ,Hg 2+ and Cu 2+ The ionic water solution was tested by UV-Vis spectrophotometry and fluorescence spectrophotometry respectively.

[0041] The result is as image 3 , showing the effect of the 1,2,4-triazole derivative (4) of rhodamine B hydrazide on Cu 2+ It has very good selectivity, and the contrast before and after adding copper ions shows that the fluorescence is enhanced by 120 times, and has a strong fluorescence enhancement effect.

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Abstract

The invention discloses a preparation method for rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit and an application thereof used as a Cu2+ fluorescent probe. The rhodamine-B hydrazide derivative has a structural formula as shown in formula (I). The rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit does not emit fluorescence. A solution color changes from colorless to purple after the rhodamine-B hydrazide derivative reacts with Cu2+ in a EtOH / HEPES buffer solution (20 mM, pH=7.2, with a volume ratio being 1:1). Cu2+ can be identified by a colorimetric method among seventeen metal ions, and the rhodamine-B hydrazide derivative presents a fluorescence ''open'' effect, can be used as Cu2+ colorimetric analysis and the fluorescent probe at the same time, and has very good selectivity. The rhodamine-B hydrazide derivative has a fluorescent detection limit of 3.4*10<-8> M for Cu2+, and the rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit can be used for fluorescent imaging and positioning detection of Cu2+ in HeLa cells.

Description

technical field [0001] The present invention relates to a rhodamine B hydrazide derivative and its preparation method and application, in particular to a rhodamine B hydrazide derivative containing a 1,2,4-triazole structural unit and its preparation method and its use as Cu 2+ Application of fluorescent probes. Background technique [0002] Rhodamine B has the advantages of large molar extinction coefficient, high quantum yield, and low background interference. After modification, it can be used as a metal ion fluorescent probe for research and as a labeled biomolecule. In recent years, there have been more and more reports on the use of rhodamine B fluorescent probes for the detection of metal ions in living cells. [0003] Copper is a trace element whose content in the human body is second only to iron and zinc. Copper participates in ceruloplasmin, superoxide dismutase (SOD), lysine oxidase, glutamine reductase, cytochrome C oxidase, etc. The composition of several enz...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/07C12Q1/02
Inventor 赵宝祥苗俊英张尚立刘为永
Owner SHANDONG UNIV
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