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Polypyridine chiral ruthenium (II) complex and preparation method and application thereof

A technology of ruthenium complexes and polypyridines, applied in the field of polypyridine chiral ruthenium complexes and their preparation, can solve the problems of lack of systematic research

Inactive Publication Date: 2015-09-02
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is a big controversy about whether the ruthenium complex has chiral selection for G4.
There is a lack of systematic research on whether left and right handed chiral ruthenium complexes have the same effect on G-quadruplex DNA due to their different spatial structures

Method used

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  • Polypyridine chiral ruthenium (II) complex and preparation method and application thereof
  • Polypyridine chiral ruthenium (II) complex and preparation method and application thereof
  • Polypyridine chiral ruthenium (II) complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of the main ligand (dppz-idzo)

[0034] Take 0.27g (1.28mmol) of 1,10-phenanthroline-5,6-dione into a 125mL round bottom flask, add 50mL of ethanol, heat and stir to dissolve it completely, stop heating and cool to room temperature. After adding 0.21g (1.28mmol) of 5,6-diaminobenzimidazol-2-one to the above solution under magnetic stirring, a large amount of yellow precipitate was produced immediately, and the reaction was continued for 15 minutes under heating and reflux, and the product was filtered and collected. After drying, it could be The yellow powder dppz-idzo was obtained with a yield of 90.2%.

Embodiment 2

[0036] D-ruthenium (II) complexes (Δ-[Ru(bpy) 2 (dppz-idzo)](PF 6 ) 2 .2H 2 O) Synthesis

[0037] Add Δ-[Ru(bpy) to the pressure bottle 2 (py) 2 ].12H 2 O (130mg, 0.1mmol) and the main ligand (dppz-idzo) (21mg, 0.1mmol), using 20mL of a mixed solution of ethylene glycol and water (9:1, v / v) as a solvent, heated under the protection of argon Reflux 6h. After cooling to room temperature, add 40mL water to dilute, filter, and add saturated NH 4 PF 6 , filtered, washed, and dried to obtain a crude product. Then it was separated by neutral alumina chromatography column with acetonitrile and ethanol (5:1, v / v) as the eluent. Spin dry the eluent to get the product Δ-[Ru(bpy) 2 (dppz-idzo)](PF 6 ) 2 .2H 2 O.

[0038] Yield 73%, 1 H NMR [(CD 3 ) 2 SO]: δ11.73(s, 2H), 9.62(d, J=8.1Hz, 2H), 8.89(dd, J=13.0, 8.2Hz, 4H), 8.28-8.19(m, 4H), 8.14(t , J=7.6Hz, 2H), 8.01(dd, J=8.2, 5.4Hz, 2H), 7.84(d, J=5.3Hz, 2H), 7.76(d, J=5.3Hz, 4H), 7.61(t , J=6.4Hz, 2H), 7.38(t, J=6.4Hz...

Embodiment 3

[0042] L-ruthenium (II) complexes (Λ-[Ru(bpy) 2 (dppz-idzo)](PF 6 ) 2 .2H 2 O) Synthesis

[0043] The synthesis steps are similar to those of the D-ruthenium complex, and the Δ-[Ru(bpy) 2 (py) 2 ].12H 2 O is replaced by Λ-[Ru(bpy) 2 (py) 2 ].12H 2 O can get product product Λ-[Ru(bpy) 2 (dppz-idzo)](PF 6 ) 2 .2H 2 O.

[0044] Yield 75%, 1 H NMR [(CD 3 ) 2 SO]: δ11.71(s, 2H), 9.61(d, J=10.5Hz, 2H), 8.95-8.84(m, 4H), 8.17-8.28(m, 4H), 8.13(t, J=10.0Hz , 2H), 8.00(dd, J=10.5, 7.0Hz, 2H), 7.84(d, J=7.5Hz, 2H), 7.81-7.68(m, 4H), 7.60(t, J=8.0Hz, 2H) , 7.38(t, J=8.0Hz, 2H).Calc.for C 39 h 30 f 12 N 12 OP 2 Ru: C, 43.63; H, 2.82; N, 15.65. Found: C, 43.73; H, 2.83; N, 15.64. MALDI-MS: calcd.For C 39 h 26 N 10 ORu 751.76[M] + ;found 751.1[M] + .

[0045]

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Abstract

The invention relates to a polypyridine chiral ruthenium (II) complex and a preparation method and application thereof. An imidazolone (imidazolone, idzo) is introduced into a main ligand dppz of the ruthenium complex [Ru(bpy)2(dppz)]<2+>, so as to prepare two chiral ruthenium complexes which mutually are geometric isomers. The affinities of the two chiral symmetrical ruthenium complexes on different G-quadruplexes and the recognition capability on the structure are researched by applying means such as fluorescence titration, combination ratio, thermal deformation and circular dichroism spectrum (CD). Compared with the prior art, the chiral ruthenium complex prepared by the method has obvious chiral selectivity on the action of telomere G-quadruplexes of sodium ion-induced antiparallel conformation; and the bonding and stabilizing capabilities of a levorotatory enantiomer on the telomere G-quadruplexes of the sodium ion-induced antiparallel conformation are obviously higher than those of a dextrorotatory ruthenium complex.

Description

technical field [0001] The invention relates to the field of chiral molecules, in particular to a polypyridine chiral ruthenium (II) complex and its preparation method and application. Background technique [0002] Molecular chirality plays an extremely important role in life activities in nature. Macromolecules such as nucleic acids, proteins, and polysaccharides, which are important foundations of life activities, all have chirality. In recent years, the clinical significance of drug chirality has attracted people's attention, and the development of chiral drugs has become an international hot spot. [0003] Studies have found that there are a large number of G-rich (guanine base) repeat sequences in the telomeric region of the human body and many cancer gene promoter regions, and these G-rich sequences will form a four-stranded DNA structure (G-quadruplex structure, Abbreviated as G4). Studies have shown that G-rich sequences can form quadruplex structures of various s...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06G01N21/64
Inventor 徐进红石硕姚天明黄海量
Owner TONGJI UNIV
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