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Preparation method of two-photon absorption type ruthenium complex and application of ruthenium complex as tumor probe

A two-photon absorption and ruthenium complex technology, applied in the field of medicine, can solve the problems of difficult deep tissue imaging, difficult tumor tissue imaging, poor penetration of phosphorescent probes, etc., and achieve the effect of reducing synthesis time and consumption

Active Publication Date: 2018-08-07
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, phosphorescent probes for single-photon luminescence imaging have poor tissue penetration, making it difficult to image deep tissue interiors.
In addition, in in vivo imaging, small molecule probes often have low selectivity for tumor tissue, making it difficult to image tumor tissue.

Method used

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  • Preparation method of two-photon absorption type ruthenium complex and application of ruthenium complex as tumor probe
  • Preparation method of two-photon absorption type ruthenium complex and application of ruthenium complex as tumor probe
  • Preparation method of two-photon absorption type ruthenium complex and application of ruthenium complex as tumor probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Preparation and characterization of embodiment 1 ruthenium complex

[0088] (1) Synthesis of product 1: as figure 2 As shown in a, take 4.56g (30mmol) of 3,4-diaminobenzoic acid and suspend it in 50mL of absolute ethanol in a single-necked flask. After dissolving 5.5 g (30 mmol) of copper acetate powder in 50 mL of pure water, it was added to the above-mentioned flask and fully stirred until it became a dark brown solid. After 2.68 g (25 mmol) of pyridine-2-carboxaldehyde was added dropwise within 20 min using a separatory funnel, the reaction temperature was heated to 80° C. under reflux and stirred for 2 h. The obtained dark brown solid was suction filtered, washed with pure water and dispersed in 100 mL of ethanol. To remove copper ions, add 7.20 g (30 mmol) of Na 2 S·9H 2The O solid was reacted with the above solution for 2 h, and then the black solid was removed by suction filtration. The obtained filtrate was concentrated to 30 mL, then hydrochloric acid sol...

Embodiment 2

[0094] Example 2 Application of two-photon luminescence imaging of ruthenium complexes

[0095] In this example, the relevant optical properties of the ruthenium complex synthesized in Example 1 were measured, as the basis for its application in the field of bioluminescent imaging. Such as image 3 Shown: image 3 In a, the UV-Vis absorption spectrum of the ruthenium(II) complex in PBS solution shows two absorption peaks, and the stronger absorption peak at 270-382nm is the ligand interior (IL) π→π * transition, and the absorption peak at 407~547nm is the metal center-ligand transition (MLCT) dπ(Ru)→π * (ligand). When the PBS solution of the ruthenium(II) complex is excited at λmax=500nm at the MLCT absorption section, a deep red phosphorescence of 3MLCT is emitted at λmax=670nm (Fig. 3b). We further determined the fluorescence lifetime of the ruthenium complex ( image 3 c), the fluorescence lifetimes of the synthesized polypyridine ruthenium (II) complexes Ru-1 and Ru-R...

Embodiment 3

[0108] The antitumor mechanism of embodiment 3 ruthenium complexes

[0109] 1. The cell viability was determined by MTT method:

[0110] The cell culture method refers to Example 2.

[0111] Take the logarithmic growth of the above-mentioned various cells (CaSki, SiHa, HeLa, MCF-7 tumor cells, Ect1 / E6E7 normal human cervical immortalized squamous cells, and L02 normal liver cells), and divide them into 2×10 4 The concentration of cells / mL was inoculated in a 96-well plate, and the cells were placed in a 37°C cell culture incubator in DMEM medium. After incubating for 24 hours until the cells grow attached to the wall, the drug to be tested (Ru-1, Ru-RGD or cisplatin) was added at a concentration gradient of 5-80 μM. After incubation for 72 hours, 20 μL of 5 mg / mL MTT solution was added to continue incubation for 4 hours. After the end, aspirate the medium, add 150 μL dimethyl sulfoxide (DMSO), measure the absorbance with 570 nm, and calculate the half inhibitory concentratio...

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Abstract

The invention discloses a preparation method of a two-photon absorption type ruthenium complex and application of the ruthenium complex as a tumor probe. The two-photon absorption type ruthenium complex is at least one of Ru-1 and Ru-RGD, wherein the structural formulae of cations of Ru-1 and Ru-RGD are represented by a formula I and a formula II (shown in the description). The two-photon absorption type ruthenium complex is synthesized by virtue of a microwave radiation method, and the ruthenium complex with a tumor targeting property is synthesized by linking a complex with a substituent group with molecules with targeting RGD polypeptides. According to the preparation method, the ruthenium complex is efficiently synthesized, the consumption amount of an organic solvent is reduced, and the synthesis time is shortened; the synthesized ruthenium complex has good single and two-photon cell imaging capacities and a cervical cancer cell targeting function, the diagnosis and treatment of tumors can be simultaneously realized, and the preparation method has great clinical application potential.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a preparation method of a two-photon absorbing ruthenium complex and its application as a tumor probe. Background technique [0002] Due to factors such as population aging and environmental pollution, tumors are now threatening human health around the world. Timely diagnosis and treatment plan can effectively reduce cancer mortality and become an important means to overcome cancer. Diagnosis and therapy is a new type of tumor treatment, and the synthesis of tumor diagnostic and therapeutic agents with both tumor diagnosis and anti-tumor activities has become a research hotspot. [0003] Among many clinically applied antineoplastic drugs, cisplatin is the first clinically applied metal antineoplastic drug. The broad-spectrum antitumor activity and high cure rate of cisplatin make it still widely used at present (N.J.Farrer, P.J.Sadler, Medicinal Inorganic Chemistry (Ed.: E.Ale...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00C09K11/06A61K49/00
CPCA61K49/0056A61P35/00C07F15/0053C09K11/06C09K2211/185
Inventor 陈填烽招振楠
Owner JINAN UNIVERSITY
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