Naphthalimide-platinum (II) complex and preparation method and application thereof

A naphthalimide, the technology of the naphthalimide, which is applied in the field of naphthalimide-platinum complex and its preparation, can solve the problem of tumor cell restriction and the like, and achieves a simple synthetic route, good tumor suppressing effect, and reaction conditions. mild effect

Active Publication Date: 2019-05-31
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although cisplatin is widely used as one of the most effective anticancer drugs in chemotherapy, its toxic side effects such as nephrotoxicity, gastrointestinal toxicity, neurotoxi

Method used

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  • Naphthalimide-platinum (II) complex and preparation method and application thereof
  • Naphthalimide-platinum (II) complex and preparation method and application thereof
  • Naphthalimide-platinum (II) complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1.1 Identification of the synthesized naphthalimide derivative ligand c

[0037] The proton nuclear magnetic resonance spectrum of the ligand c obtained is as follows figure 1 as shown, 1 H NMR (400MHz, CDCl3) δ8.48 (d, J = 4.9Hz, 2H), δ8.39 (d, J = 7.2Hz, 1H), δ8.16 (d, J = 2.5Hz, 1H), δ7 .99(d, J=8.2Hz, 1H), δ7.72-7.57(m, 3H), δ7.55-7.48(m, 4H), δ7.39(d, J=2.4Hz, 1H), δ7 .34-7.24(m, 2H), δ7.24-7.18(m, 1H), δ7.14-7.04(m, 2H), δ5.34(s, 2H), δ4.04-4.01(m, 2H ), δ2.63 (t, J=7.0Hz, 2H), δ1.93-1.80 (m, 2H), δ1.78-1.70 (m, 2H).

[0038] The carbon NMR spectrum of ligand c is as follows figure 2 as shown, 13 C NMR (101MHz, CDCl3) δ164.3, δ163.9, δ157.5, δ137.3, δ133.2, δ132.7, δ129.0, δ128.9, δ128.5, δ127.5, δ127.5 ,δ124.1,δ123.7,δ122.8,δ122.5,δ113.9,δ100.0,δ67.6,δ43.6,δ33.3,δ32.6,δ31.0,δ29.3,δ27 .7.

[0039] Therefore, can determine gained yellow ligand c, its structural formula is as follows:

[0040]

[0041] 1.2 Coordination reaction

[0042] Accurately weig...

Embodiment 2

[0059] In order to fully illustrate the use of the naphthalimide-platinum (II) complex described in the present invention in the preparation of antitumor drugs, antitumor activity experiments and toxicity experiments were carried out.

[0060] 1. Cell lines and cell culture

[0061] Five human cell lines were selected in this experiment: human cervical cancer cell HeLa, human lung cancer cell NCI-H460, human ovarian cancer SK-OV-3, human gastric cancer cell BEL-7402 and human normal liver cell HL-7702.

[0062] All human cell lines were cultured in RPMI-1640 medium containing 100U / mL penicillin, 10wt% calf blood, and 100U / mL streptomycin at 37°C with a volume concentration of 5% CO 2 cultured in an incubator.

[0063] 2. Preparation of test compounds

[0064] The purity of used ligand c and naphthalimide-platinum (II) complexes all need ≥ 95%, their DMSO stock solution is diluted into the final solution of 20 μ mol / L with physiological buffer (the final concentration of DMSO...

Embodiment 3

[0080] The complex inhibits the telomerase activity of NCI-H460 cells

[0081] 1. Cell Culture and Compound Formulation

[0082] The human ovarian cancer drug-resistant strain NCI-H460 is a tumor cell line, and the complex has an action time of 10.0 μM for 24 hours. The steps of cell culture and compound preparation are the same as in Example 2.

[0083] 2. Telomerase extraction and inhibition experiments

[0084] The telomerase extraction kit was purchased from Beijing Zhongxi Yuanda Company, item number NKJ15DLM, and stored at -80°C for a long time.

[0085] 2.1 Telomerase extraction

[0086] After the complex (10.0μM) acted on human lung cancer drug-resistant strain NCI-H460 cells (with a blank control group), the following experiments were carried out:

[0087] (1) Collect no less than 1×10 6 Cells (approximately the amount of cells in wells 1-2 of a 6-well plate), centrifuged at a speed of 2000rpm for 5min, collected the cells by centrifugation, washed with pre-cooled...

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Abstract

The invention relates to the field of platinum active ligand complexes, in particular to a naphthalimide-platinum (II) complex, a preparation method thereof and application of the complex in preparation of anti-tumor drugs. The invention provides an efficient, low-toxicity and targeted platinum anti-tumor chemotherapeutic drug. The chemical formula of the complex is I. The preparation method comprises the following steps that 1, a naphthalimide derivative ligand c and dichloro bis(dimethyl sulfoxide)platinum (II) are dissolved in a polar solvent for a coordination reaction; 2, a reaction solution obtained in step 1 is washed and dried to obtain the naphthalimide-platinum (II) complex. The naphthalimide-platinum (II) complex is used for the anti-tumor drugs.

Description

technical field [0001] The invention relates to a platinum active ligand complex and a preparation method, in particular to a naphthalimide-platinum (II) complex, a preparation method and application thereof. Background technique [0002] Lung cancer seriously affects people's life safety and quality of life, and its incidence is rapidly increasing, ranking first in male malignant tumor incidence and second in female incidence (Chen, W., et al. Cancer statistics in China, 2015, 65(1):5-29.). Among them, non-small cell lung cancer (NSCLC) accounts for about 80% of primary lung cancer, and most patients are already in the middle and advanced stages when they are diagnosed. Platinum-based chemotherapy and molecular targeted therapy are the main ways to treat advanced NSCLC. Although cisplatin is widely used as one of the most effective anticancer drugs in chemotherapy, its toxic side effects such as nephrotoxicity, gastrointestinal toxicity, neurotoxicity, bone marrow toxicit...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
Inventor 黄国保杨波李秀英罗金荣刘玉钊马锦湄宋桂兰钟锦萍银玉睿
Owner YULIN NORMAL UNIVERSITY
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