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O-phenanthroline ruthenium complex photosensitive dye and its preparation method and use

A technology of o-phenanthroline ruthenium and photosensitizing dye, which is applied in the field of ruthenium complex photosensitizer to achieve strong therapeutic effect and increase the effect of treatment depth

Active Publication Date: 2020-09-29
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 dye and its preparation method and use
  • O-phenanthroline ruthenium complex photosensitive dye and its preparation method and use
  • O-phenanthroline ruthenium complex photosensitive dye and its preparation method and use

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Embodiment 1

[0053] The synthesis of embodiment 1. photosensitive molecule Ru-tmxf:

[0054]

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

[0056] Ruthenium complex intermediate 1 (0.106g, 0.2mmol) was added to a 100mL single-necked flask containing 20mL ethanol and 10mL water, intermediate 2 (0.1g, 0.21mmol) was added, and refluxed for 24h under nitrogen protection. The solvent was evaporated under reduced pressure. Neutral alumina column separation (dichloromethane:methanol=15:1) gave an 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–2PF 6 ] 2+ :...

Embodiment 2

[0060] Embodiment 2. Singlet oxygen performance test of photosensitive molecule Ru-tmxf

[0061] 10 μM reference [Ru(bpy) 3 ] 2+ Add the photosensitive molecule Ru-tmxf to the test quartz dish containing 3mL methanol solution, adjust the absorbance at 415nm to about 1 through the DPBF solution, place the dish at 450nm, 2mW / cm 2 The solution was irradiated under a xenon light source, and the absorption spectrum of the solution was recorded every two minutes. The test results are shown in figure 1 In Figures A and B, the absorption of the solution decays at a certain value as the irradiation time increases, indicating that the solution produces singlet oxygen under the irradiation of the light source of this wavelength, and as the irradiation time increases, the absorption spectrum of the solution The absorption at 460nm did not change, which to some extent shows that the photosensitive molecule Ru-tmxf has good photostability. Similarly, 10 μM of photosensitive molecule Ru...

Embodiment 3

[0062] Example 3. Target competition experiment

[0063] MCF-7 and COS-7 cells were cultured in DMEM (invitrogen) with 10% FCS (invitrogen). 17β-estradiol was used as a competitive inhibitor of Ru-tmxf entry into MCF-7 cells. 0, 25, and 50 μM 17β-estradiol were pre-added to the dish containing MCF-7 cells for 24 hours, and then 3 μM compound Ru-tmxf was added and incubated for 2 hours, and then laser confocal imaging was used. The excitation wavelength of the photosensitive molecule is 488nm, and the acceptance wavelength range is 570nm-620nm. from figure 2 It can be seen in A, B and C (D, E and F are the mixed images of bright field and fluorescent field) that the cellular uptake of competitive inhibitors is reduced, and the inhibitory strength increases with the increase of 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 present invention relates to a class of photosensitizers in the field of fine chemicals and their preparation methods and uses, in particular to a class of ruthenium complex photosensitizers, their preparation methods and uses. Background technique [0002] Photodynamic therapy (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. It shows great application potential in malignant diseases such as cancer and various benign diseases. [0003] The three elements of photodynamic therapy are: light source, photosensitizer and oxygen. The photosensitizer is the most important component among the three elements of PDT. At present, commercialized photosensitizers such as porphyrin derivative chlorin (ce6), cyanine dye IR-780, and ICG all play an important role in photodynamic and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K41/00A61P35/00C09B57/10
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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