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O-phenanthroline ruthenium complex photosensitive dyes, and preparation method and application thereof

A technology of o-phenanthroline ruthenium and photosensitizing dyes, which is applied in the field of photosensitizers of ruthenium complexes, to achieve the effect of increasing treatment depth and strong treatment effect

Active Publication Date: 2018-08-03
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Among the numerous photosensitizer precursors, bipyridyl ruthenium complexes and their derivatives have the advantages of excellent two-photon performance, moderate fluorescence quantum yield, stable spectral properties, good photothermal and chemical stability, and low cytotoxicity. Photosensitizers and imaging fluorescent reagents have been widely used, and currently no ruthenium complexes have been developed as photosensitizers with targeted properties

Method used

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  • O-phenanthroline ruthenium complex photosensitive dyes, and preparation method and application thereof
  • O-phenanthroline ruthenium complex photosensitive dyes, and preparation method and application thereof
  • O-phenanthroline ruthenium complex photosensitive dyes, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1. Synthesis of photosensitive molecule Ru-tmxf:

[0054]

[0055] (1) Synthesis of intermediate compound 3:

[0056] The ruthenium complex intermediate 1 (0.106 g, 0.2 mmol) was added to a 100 mL one-neck flask containing 20 mL of ethanol and 10 mL of water, and intermediate 2 (0.1 g, 0.21 mmol) was added, and refluxed for 24 h under nitrogen protection. The solvent was evaporated under reduced pressure. Neutral alumina column separation (dichloromethane:methanol=15:1) to obtain orange-red solid, finally the solid was dissolved in water, and saturated ammonium hexafluorophosphate solution was added to precipitate a red solid intermediate 3 (70%). 1 H NMR (500MHz, CD 3 SOCD 3 ), δ: 3.66(t, J=10Hz, 2H), 4.2(t, 10H, 2H), 7.00(d, J=10Hz, 2H), 7.38(d, J=10Hz, 1H), 7.49(t, J=8Hz, 1H), 7.58(d, J=10Hz, 2H), 7.79(m, 10H), 7.96(d, J=5Hz, 1H), 8.09(m, 4H); 8.39(d, J=10Hz) , 4H), 8.77(m, 4H), 9.18(d, J=10Hz, 1H); ES-MS: m / z calcd for C 51 H 35 N 11 ORu 2+ [M–2P...

Embodiment 2

[0059] Example 2. Singlet oxygen performance test of photosensitive molecule Ru-tmxf

[0060] The 10 μM reference [Ru(bpy) 3 ] 2+ and photosensitive molecule Ru-tmxf were added to a test quartz dish containing 3 mL methanol solution, the absorbance at 415 nm was adjusted to about 1 by DPBF solution, and the dish was placed at 450 nm, 2 mW / cm 2 Under the xenon lamp light source, the absorption spectrum of the solution was recorded every two minutes. The test results are displayed at figure 1 In Figure A and Figure B, the absorption of the solution attenuates at a certain value with the increase of the irradiation time, indicating that the solution produces singlet oxygen under the irradiation of the light source of this wavelength, and with the increase of the irradiation time, the absorption spectrum of the solution The absorption at 460 nm did not change, indicating that the photosensitive molecule Ru-tmxf has good photostability to a certain extent. Similarly, 10 μM of ...

Embodiment 3

[0061] Example 3. Targeted competition experiment

[0062] MCF-7, COS-7 cells were cultured in DMEM (invitrogen) with 10% FCS (invitrogen). 17β-estradiol was employed as a competitive inhibitor of Ru-tmxf entry into MCF-7 cells. 0, 25 and 50 μM of 17β-estradiol were pre-added to the dishes containing MCF-7 cells for 24 h, and then 3 μM of the compound Ru-tmxf was added to the dishes for 2 h, followed by confocal laser imaging. The excitation wavelength of the photosensitive molecule is 488nm, and the acceptance band is 570nm-620nm. from figure 2 As can be seen from the A, B and C panels of (D, E and F are the mixed images of bright field and fluorescence field), the cellular uptake of the competitive inhibitor was reduced, and the inhibitory intensity increased with the increase of the concentration .

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Abstract

The invention provides o-phenanthroline ruthenium complex photosensitive dyes, and a preparation method and an application thereof. The photosensitive dyes have a structure as shown in a general formula I which is described in the specification. The o-phenanthroline ruthenium complex compound provided by the invention can target an estrogen receptor and distinguish cells over-expressed and low-expressed by the estrogen receptor. Under the condition of co-culturing of estrogen receptor over-expressed and low-expressed cells, the ruthenium complex can selectively enter estrogen receptor over-expressed cells, thereby causing a difference of photodynamic cells in killing effects. Meanwhile, the ruthenium complex photosensitizer provided by the invention can also be excited by two photons, so adeeper tumor treatment depth is achieved.

Description

technical field [0001] The invention relates to a class of photosensitizers in the field of fine chemicals, a preparation method and uses thereof, in particular to a class of ruthenium complex photosensitizers, a preparation method and uses thereof. Background technique [0002] Photodynamic therapy (PDT) is a method that applies the principles of photochemistry, photophysics and photobiology to the diagnosis and treatment of diseases. It is the fourth therapy after surgery, chemotherapy and radiotherapy. Cancer and other malignant diseases and a variety of benign diseases have shown great application potential. [0003] The three elements of photodynamic therapy are: light source, photosensitizer and oxygen. Among them, the photosensitizer is the most important component of the three elements of PDT. At present, commercial photosensitizers such as porphyrin derivatives chlorin (ce6), cyanine dyes IR-780, and ICG have all played an important role in photodynamic and photot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K41/00A61P35/00
CPCA61K41/008A61P35/00C07F15/0053
Inventor 樊江莉赵学泽李明乐杜健军彭孝军
Owner DALIAN UNIV OF TECH
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