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Photosensitive dye osmium complex and its preparation method, rapid detection kit and detection method for DNA oxidative damage in the early stage of canceration

A technology of photosensitizing dyes and complexes, which is applied in the field of rapid detection of DNA oxidative damage in the early stage of cancer, can solve the problems of cumbersome operation and unsuitable for routine detection, and achieves the effect of wide application prospect and easy operation.

Active Publication Date: 2015-10-28
DALIAN UNIV OF TECH
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  • Description
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Problems solved by technology

[0006] However, this electrochemical detection method requires the Os(bpy) 3 2+ The probe molecules are grafted to the 5' end of the DNA segment, or the probe molecules and DNA are evenly coated on the surface of the electrode to form a thin film, and the coating is repeated until the uniformity and thickness of the film meet the requirements. Quite cumbersome and not suitable for routine testing

Method used

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  • Photosensitive dye osmium complex and its preparation method, rapid detection kit and detection method for DNA oxidative damage in the early stage of canceration
  • Photosensitive dye osmium complex and its preparation method, rapid detection kit and detection method for DNA oxidative damage in the early stage of canceration
  • Photosensitive dye osmium complex and its preparation method, rapid detection kit and detection method for DNA oxidative damage in the early stage of canceration

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Experimental program
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preparation example Construction

[0078]

[0079] The method for preparing the above-mentioned photosensitizing dye osmium complex comprises the steps:

[0080] (1) Preparation of osmium complex intermediates with L and L' as ligands

[0081] Ligand L, L'(R) independently selected from the following compounds 1 , R 2 The meaning is the same as above) and the metal osmium salt with Y' as the negative ion are simultaneously or sequentially coordinated to obtain the osmium complex intermediate of the general formula LL'Os-Y', the reaction temperature is 20-200 ° C, and the reaction time is 1 -24h, the reaction solvent is selected from methanol, ethanol, ethylene glycol, acetonitrile, water, DMF, DMSO and a mixed solvent composed of any two or more of them in any proportion.

[0082]

[0083] In the above reaction, L and L' may be the same or different. When L and L' are the same, it is preferable to react the ligand for the reaction with the metal osmium salt at the same time, and the molar ratio of metal o...

Embodiment 1

[0151] The synthesis of embodiment 1Os-C3-MV

[0152]

[0153] (1) Os(bpy) 2 Cl 2 Synthesis:

[0154] Will (NH 4 ) 2 [OsCl 6 ] (1.0g, 2.3mmol) and 2,2'-bipyridine (0.72g, 4.6mmol) were dissolved in 30ml of ethylene glycol, heated to reflux with magnetic stirring under nitrogen protection for 1h. After the reaction mixture was cooled to room temperature, 1M Na 2 S 2 o 4 (60mL) in an ice-water bath for 30min. After filtration, the obtained purple-black precipitate was thoroughly washed with water and diethyl ether successively, and dried in vacuo to obtain 0.92 g of a black solid, with a yield of 70%.

[0155] (2) Synthesis of intermediate 1:

[0156] 4-Methyl-2,2′-bipyridine (2.5g, 13.5mmol) was dissolved in dry THF (50mL), the solution was placed in an ice-water bath, and fresh LDA (2.0mL diisopropylamine, 1.6 M n-butyllithium 8.1mL, 10mL THF) was added dropwise, the solution turned black, and continued to stir for 1h, and 1,2-dibromoethane (50mmol, 4.3mL) was ad...

Embodiment 2

[0163] The synthesis of embodiment 2Os-C4-MV

[0164] The synthesis of this compound can refer to the synthesis route of the above-mentioned Os-C3-MV, except that dibromopropane is used instead of dibromoethane, the others are the same as above. 1 H NMR (400MHz, Acetone-d 6 ): δ1.92-1.99 (m,2H,-CH 2 -),2.27-2.33(m,2H,-CH 2 -),3.03(t,2H,-CH 2 -,J=7.8Hz),4.76(s,3H,N + -CH 3 ), 4.98 (t,2H,N + -CH 2 -, J=7.4Hz), 7.37 (d, 1H, bpy′-H, J=5.6Hz), 7.45-7.48 (m, 5H, bpy-H and bpy′-H), 7.81 (d, 1H, bpy ′-H, J=5.9Hz), 7.92-8.03 (m, 10H, bpy-H and bpy′-H), 8.66 (s, 1H, bpy′-H), 8.75 (d, 1H, bpy′-H , J=8.1Hz), 8.78-8.82 (m, 8H, bpy-H and MV 2+ -H β ), 9.33 (d,2H,MV 2+ -H α ,J=6.6Hz),9.37(d,2H,MV 2+ -H α ,J=6.4Hz).HRMS(ESI,m / z):[(M-4PF 6 - )] 4+ calculated for C 45 h 42 N 8 Os221.5781,found221.5775.

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Abstract

The invention provides a photosensitive dye osmium complex and a preparation method thereof, and a kit and a method for performing quick canceration early stage deoxyribonucleic acid (DNA) oxidative damage detection. The photosensitive dye osmium complex has the structural general formula of LL'L''Os-Y4, wherein Y is a halide ion, ClO<4->, BF<4->, PF<6-> or OTs<->; L and L' are independently selected from 2,2'-dipyridyl and a derivative thereof, phenanthroline and a derivative thereof and DPPZ; and L'' is a precursor with 2,2'-dipyridyl and 4,4'-dipyridyl. The kit at least comprises a main body compound 8-element cucurbit urils (a component A), the photosensitive dye osmium complex (a component B) and pure water or phosphate and borate buffering solution (a component D). By adopting the kit, even under the condition of no instrumental equipment, a user can individually and quickly detect 8-oxoG under visible light with eyes only by one drop of blood.

Description

technical field [0001] The invention specifically relates to a photosensitive dye osmium complex and a preparation method thereof, a kit and a detection method for rapidly detecting DNA oxidative damage in the early stage of carcinogenesis using the photosensitive dye osmium complex. Background technique [0002] Once cancer is discovered, most of it is already at an advanced stage, and it is impossible for doctors to recover. Only early diagnosis can prevent problems before they happen. Chemical reactions, radiation, and by-products of aerobic metabolism such as singlet oxygen, superoxide radicals, and hydroxyl radicals can all cause oxidative damage to DNA, generate gene mutations, induce tumors, aging of body cells, and certain degenerative diseases. Among the four bases in DNA, guanine G is most easily oxidized, and its main oxidation product is 8-oxo-7,8-dihydrodeoxyguanine (8-hydroxyguanine, 8-oxoG), which is formed in the body It is relatively stable and is an import...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/10C09K11/06G01N33/52G01N21/78G01N21/25G01N21/31
Inventor 孙世国慕道洲彭孝军蔡明珠王继涛
Owner DALIAN UNIV OF TECH
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