Dinuclear ruthenium complex as well as preparation method and application thereof as living cell fluorescent dye

A dual-nuclear ruthenium complex and fluorescent dye technology, which is applied in the field of cell imaging reagents, can solve the problems of unfavorable differentiation of endogenous fluorescent dyes, self-quenching, unfavorable imaging stability, low photostability, etc., and achieves good cell membrane permeability and cell permeability. Strong ability, simple structure and stable effect

Inactive Publication Date: 2014-04-09
SUN YAT SEN UNIV
View PDF4 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these organic molecules have some disadvantages: low water solubility, easy to produce precipitation or precipitate out immediately after interacting with cells, affecting the dyeing effect; relatively high cytotoxicity, after the dye interacts with cells, it will cause cell death and affect the effect on cells. Observation in normal state; low photostability, due to the action of active agent groups (singlet oxygen, etc.) in the air or in the medium, the fluorescence of the dye is continuously weakened after the excitation wavelength is irradiated, and the photobleaching phenomenon is serious, which is not conducive to stable imaging The intersection of excitation and emission spectra is serious (stoke shift is small), generally around tens of nanometers, which is not conducive to distinguishing endogenous fluorescence and reducing the s

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
  • Dinuclear ruthenium complex as well as preparation method and application thereof as living cell fluorescent dye
  • Dinuclear ruthenium complex as well as preparation method and application thereof as living cell fluorescent dye
  • Dinuclear ruthenium complex as well as preparation method and application thereof as living cell fluorescent dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Binuclear ruthenium complex RuL 1 preparation of

[0043] (1) Using 1,10-phenanthroline-5,6-dione, ammonium acetate, m-phenylacetaldehyde, aniline, and glacial acetic acid as raw materials, mix and heat to reflux for 24 hours under the protection of argon. After the mixture was cooled to room temperature, water was added, neutralized with 25% ammonia water, filtered with suction to obtain a yellow precipitate, washed with water and ether, and the product was recrystallized with methanol to obtain a yellow powder 1,3-bis(1-phenyl-1H-imidazo[4 ,5-f][1,10]phenanthrolin-2-yl)benzene (ie L 1 ). Yield: 85%. Anal. Calcd for (elemental analysis) C 44 h 26 N 8 : C, 79.26; H, 3.93; N, 16.81. Found: C, 79.12; H, 3.45; N, 24.39%. 1 H NMR (500 MHz, DMSO-d 6 ) ppm: 9.11 (d, J = 5.0 Hz, 2H), 9.03 (d, J = 5.0 Hz, 2H), 8.97 (d, J = 5.0 Hz, 2H), 8.17 (s, 1H), 7.93 (m, 2H), 7.76 (m, 8H), 7.66 (m, 2H), 7.56 (d, J = 5.0 Hz, 2H), 7.48 (d, J = 5.0 Hz, 2H), 7.36 (t, J ...

Embodiment 2

[0045] Example 2 Binuclear ruthenium complex RuL 2 preparation of

[0046] Preparation steps are the same as RuL in embodiment 1 1 The difference is that the aniline in step (1) is replaced by p-methylaniline, and the remaining steps and operations remain unchanged.

[0047] The intermediate product 1,3-bis(1-p-tolyl-1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzene (ie L 2 ) Yield: 83%. Anal. Calcd for C 46 h 30 N 8 : C, 79.52; H, 4.35; N, 16.13. Found: C, 79.48; H, 4.42; N, 16.10%. 1 H NMR (500 MHz, DMSO-d 6 ) ppm: 9.10 (d, J = 5.0 Hz, 2H), 9.01 (d, J = 5.0 Hz, 2H), 8.96 (d, J = 5.0 Hz, 2H), 8.25 (s, 1H), 7.91 (m, 2H), 7.63 (d, J =5.0 Hz, 4H), 7.53 (d, J =5.0 Hz, 4H), 7.51 (m, 2H), 7.47 (d, J = 5.0 Hz, 2H), 7.40 (d, J = 5.0 Hz, 2H), 7.30 (t, J 1 =J 2 =5.0 Hz, 1H) , 2.52 (s, 6H). FAB-MS: m / z = 695 [M+1].

[0048] Final product [(phen) 2 Ru(L 2 )Ru(phen) 2 ] (ClO 4 ) 4 (i.e. RuL 2 ) Yield: 66%. Anal. Calcd for C 94 h 62 Cl 4 N 16 o 16 Ru 2 : C, ...

Embodiment 3

[0049] Example 3 Binuclear ruthenium complex RuL 3 preparation of

[0050] Preparation steps are the same as RuL in embodiment 1 1 The difference is that the aniline in step (1) is replaced by 4-tert-butylaniline, and the remaining steps and operations remain unchanged.

[0051] The intermediate product 1,3-bis(1-(4-tert-butylphenyl)-1H-imidazo[4,5-f][1,10]phenanthrolin- 2-yl)benzene (ie L 3 ) Yield: 80%. Anal. Calcd for C 52 h 42 N 8 : C, 80.18; H, 5.43; N, 14.39. Found: C, 80.09; H, 5.48; N, 14.43%. 1 H NMR (500 MHz, DMSO-d 6 ) ppm: 9.11 (d, J = 5.0 Hz, 2H), 9.03 (d, J = 5.0 Hz, 2H), 8.97 (d, J = 5.0 Hz, 2H), 8.00 (s, 1H), 7.91 (m, 2H), 7.72 (d, J =5.0 Hz, 4H), 7.62 (d, J =5.0 Hz, 2H), 7.52 (m, 2H), 7.46 (d, J = 5.0 Hz, 2H), 7.39 (d, J = 5.0 Hz, 1H), 7.33 (t, J 1 =J 2 =5.0 Hz, 1H), 7.29 (d, J = 5.0 Hz, 3H), 1.25 (s, 18H). FAB-MS: m / z = 779 [M+1].

[0052] Final product [(phen) 2 Ru(L 3 )Ru(phen) 2 ] (ClO 4 ) 4 (i.e. RuL 3 ) Yield: 65%. Anal. Calcd for...

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 discloses a dinuclear ruthenium (II) complex as well as a preparation method and an application thereof as a living cell fluorescent dye. The dinuclear ruthenium (II) complex is characterized in that the cation part of the dinuclear ruthenium (II) complex is [(phen)2Ru(L)Ru(phen)2]<4+> and the structural formula is shown as the formula I in the specification; and the anion part of the dinuclear ruthenium (II) complex is (ClO4)<1-> or Cl<1->. The dinuclear ruthenium (II) complex has excellent fluorescent characteristics and good cell membrane permeability, is a good living cell imaging reagent, simultaneously has bigger two-photon absorption interface, can color cytoplasm in the living cells without cell pretreatment and has good resistance to bleaching and a simple and stable structure. Cell viability experiment results show that the complex has lower cytotoxicity, causes slight cellular damage, has high coloring sensitivity and strong cell permeability and has great application potentials as a long-time single/two-photon cell imaging dye and a biological probe.

Description

technical field [0001] The invention relates to the technical field of cell imaging reagents, in particular to a class of binuclear ruthenium complexes, a preparation method thereof, and an application as a single- and two-photon living cell fluorescent dye. Background technique [0002] In recent years, live cell imaging has become the focus of scientists' attention. With the continuous development of laser confocal fluorescence microscopy technology, people's research on cells has become more and more in-depth. The development of suitable biological imaging reagents has aroused great interest of scientists. At present, most of the commercial fluorescent dyes used in the field of cell imaging are small organic molecules, such as PI, DAPI, Mitotracker Green, etc. However, these organic molecules have some disadvantages: relatively low water solubility, easy to produce precipitation or precipitate out immediately after interacting with cells, affecting the dyeing effect; rela...

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
IPC IPC(8): C07F15/00G01N33/52G01N21/64
Inventor 巢晖许文超左嘉睿计亮年
Owner SUN YAT SEN UNIV
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