Rhodamine derivatives and their preparation method and use

A preparation and compound technology, applied in the field of rhodamine derivatives, can solve the problems of being unsuitable for real-time quantitative research on living cells, short reaction stabilization time, and small concentration range, etc., achieving shortened reaction stabilization time, high sensitivity, and fast stabilization speed Effect

Inactive Publication Date: 2012-06-27
CAPITAL NORMAL UNIVERSITY +1
View PDF2 Cites 25 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the past few years, studies on the synthesis and characterization of neutral particle carriers with high selectivity for specific metal ions have been carried out, but for Fe 3+ The relevant research is not very mature, and some of the currently developed methods for the determination of Fe 3+ Concentration-related products (such as PVC membrane electrodes, sigma company), due to some disadvantages, such as 1. For Fe 3+ 2. Most of the necessary test conditions are acidic (such as pH3.0-4.0), which are not within the normal cell pH range, so it is not suitable for real-time quantitative research on living cells 3. The sensitivity is low, which is mainly manifested in two aspects. On the one hand, the time required for stable reaction is too long (about 1 h), and the reaction reagent used in real-time quantitative research of living cells should be as short as possible. On the one hand, the range of concentration measured by these products is not wide, especially it cannot be directly applied to living cells with little iron content
Therefore, there is no one in the world that can be well applied to the real-time quantitative determination of Fe in living cells. 3+ products, the present invention solves the above three difficult problems to a great extent

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Rhodamine derivatives and their preparation method and use
  • Rhodamine derivatives and their preparation method and use
  • Rhodamine derivatives and their preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of Compound 1, namely (E)-3',6'-bis(diethylamino)-2-(2-(4-oxopent-2-en-2-ylamino)ethyl)spiro[isoind Indoline-1,9'-oxanthene]-3-one.

[0049] Rhodamine B (2.4g, 5mmol) was dissolved in 60mL of ethanol solution into a 250ml round bottom flask, and 0.43mL of ethylenediamine was added dropwise with stirring at room temperature. After the dropwise addition, heat (the boiling temperature of ethanol is 78.5° C.) to reflux for 12 hours, and the reaction system becomes clear until the detection by thin layer chromatography (TLC) shows that the raw materials disappear. After cooling to room temperature, the solvent-ethanol was removed under reduced pressure. Add about 1mol / L 100mL HCl solution to remove unreacted ethylenediamine, then slowly neutralize with NaOH to pH 9-10, extract with dichloromethane, anhydrous Na 2 SO 4 After drying, the resulting solid was washed with CHCl 3 / MeOH (98:2, V:V) column chromatography (the "column" used was a silica gel column) wi...

Embodiment 2

[0056] Embodiment 2, preparation compound RA2, method is the same as embodiment 1, just replaces acetylacetone with ethyl acetoacetate in the reaction raw material, and its nuclear magnetic resonance parameter is:

[0057] 1 H NMR (400MHz, CDCl 3 ): δ1.15-1.19 (m, 15H, CH 2 CH 3 ), 1.76 (s, 3H, CH 3 ), 2.95(t, 2H, J=4.4Hz, CH 2 CH 2 ), 3.18(t, 2H, J=4.4Hz, CH 2 CH 2 ), 3.30-3.36 (m, 4H, NCH 2 CH 3 ), 4.02(q, 2H, J=7.2Hz, OCH 2 CH 3 ), 4.34 (s, 1H, C=CH), 6.24-6.43 (m, 6H, Ar), 7.08-7.10 (m, 1H, Ar), 7.43-7.45 (m, 2H, Ar), 7.89-7.91 ( m, 1H, Ar), 8.38 (t, 1H, J=6.4Hz, NH);

[0058] 13 C NMR (100MHz, CDCl 3 ): 12.5, 18.2, 19.5, 28.6, 40.2, 41.6, 44.5, 64.6, 95.5, 97.6, 105.1, 108.2, 122.6, 123.7, 128.3, 131.1, 132.4, 148.9, 153.2, 153.5, 163.2, 167.6.8, 19

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to rhodamine derivatives and their preparation method and use. The rhodamine derivatives have a general formula I and can be utilized for determination of Fe<3+>. The preparation method of the rhodamine derivatives comprises that an intermediate produced by the reaction of rhodamine B and ethylenediamine is utilized as a raw material and undergoes a condensation reaction with acetylacetone or ethyl acetoacetate in the presence of ceric ammonium nitrate as a catalyst to produce the rhodamine derivatives. Results of an analysis of a mixed-ion interference-resistant iron-ion specific identification capacity of the rhodamine derivatives and an analysis of a living cell condition adaptation capacity of the rhodamine derivatives show that the rhodamine derivatives have strong iron ion specificity, a strong other cation-resistant capacity and a strong living cell condition adaptation capacity, wherein iron ion concentration detection sensitivity is 1*10<-6>; reaction stabilization time is 20 minutes; and a pH value of a Tris-HCl buffer solution is 5.5 or 6.0. The rhodamine derivatives can be utilized as iron ion induction agents for a non-invasive micro-metering system and realizes determination of Fe<3+> concentration, a Fe<3+> flowing speed and a Fe<3+> motion direction.

Description

technical field [0001] The present invention relates to a kind of artificially synthesized rhodamine derivative, and its preparation method and application, especially relate to a kind of for detecting Fe 3+ Rhodamine derivatives of fluorescent dyes, suitable for non-damaging micro-detection of living cells, tissues, and organs. Background technique [0002] Iron is the earliest trace element discovered by people, and it has been discovered for more than two thousand years. Iron has an irreplaceable function in the life activities of prokaryotes and eukaryotes existing on the earth. The study of iron in plants can be traced back to 1843, a century and a half ago, when Gris found that the chlorosis of grape leaves growing on calcareous soil was related to iron deficiency. After research by botanists Sachs and Molisch, it was identified as an essential trace element for plant growth, and iron was also the first plant essential nutrient element discovered. [0003] Fe 3+ Pl...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09B57/00C09K11/06G01N21/64
CPCC09B11/24C09B69/103C09K11/06C09K2211/1011C09K2211/1029C09K2211/1088
Inventor 印莉萍曾程初刘雪静张驰郭长彬赵伟忠何日才刘博文李辉
Owner CAPITAL NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap