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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Problems solved by technology

Moreover, generally tumor cells have a high content of copper ions, whic

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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

Example Embodiment

[0024] Example 1 Preparation of rhodamine B thiodihydrazide derivative

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

[0026] Infrared spectroscopy: 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] Hydrogen nuclear magnetic resonance spectroscopy: 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=...

Example Embodiment

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

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

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

[0033] Infrared spectroscopy: IR (KBr), υ: 3209,3077,2967,2929,2897,2869,1720,1614,...

Example Embodiment

[0039] Example 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) ethanol / HEPES buffer solution (20mM HEPES, pH=7.2, 1:1, volume ratio ) Add 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+ Ionic aqueous solutions were tested by ultraviolet-visible spectrophotometry and fluorescence spectrophotometry.

[0041] The result is image 3 , Showing that the 1,2,4-triazole derivative of rhodamine B hydrazide (4) has a positive effect on Cu 2+ It has very good selectivity. The control before and after adding copper ions shows a 120-fold increase in fluorescence, which 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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