CN117551136A - 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex, synthesis method and application - Google Patents
4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex, synthesis method and application Download PDFInfo
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 31
- IVVMDDKEBBOTSV-UHFFFAOYSA-N 2-(4-phenyl-6-pyrazin-2-ylpyridin-2-yl)pyrazine Chemical compound C1=CC=C(C=C1)C1=CC(=NC(=C1)C1=NC=CN=C1)C1=CN=CC=N1 IVVMDDKEBBOTSV-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000001308 synthesis method Methods 0.000 title abstract description 6
- 206010033128 Ovarian cancer Diseases 0.000 claims abstract description 18
- 206010061535 Ovarian neoplasm Diseases 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 16
- 229940079593 drug Drugs 0.000 claims abstract description 10
- 239000003446 ligand Substances 0.000 claims abstract description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000008685 targeting Effects 0.000 abstract description 9
- 239000003560 cancer drug Substances 0.000 abstract description 8
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 abstract description 8
- 229960004316 cisplatin Drugs 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 7
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 230000001093 anti-cancer Effects 0.000 abstract description 5
- 230000012010 growth Effects 0.000 abstract description 5
- 206010028980 Neoplasm Diseases 0.000 abstract description 4
- 230000005917 in vivo anti-tumor Effects 0.000 abstract description 4
- 238000000338 in vitro Methods 0.000 abstract description 3
- 230000005918 in vitro anti-tumor Effects 0.000 abstract description 3
- 206010059866 Drug resistance Diseases 0.000 abstract description 2
- 239000002246 antineoplastic agent Substances 0.000 abstract 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract 2
- 229940121657 clinical drug Drugs 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004113 cell culture Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 108010087230 Sincalide Proteins 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010609 cell counting kit-8 assay Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 210000005260 human cell Anatomy 0.000 description 3
- 150000003057 platinum Chemical class 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical class N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention discloses a 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex, a synthesis method and application. The invention synthesizes binuclear platinum complex by taking 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine as an active ligand. The binuclear platinum complex of the targeted ovarian cancer drug-resistant cells has better inhibition effect on the ovarian cancer drug-resistant strain cells SK-OV-3CR, is higher than that of cisplatin drugs, overcomes the drug resistance of clinical drugs, has potential medicinal value, and is expected to be used for preparing various antitumor drugs. The binuclear platinum complex of the targeted ovarian cancer drug-resistant cells can inhibit the growth of SKO3cisR in a targeted manner, has good anticancer activity and tumor targeting, shows excellent in-vitro and in-vivo antitumor activity, has potential medicinal value, and is expected to be used for preparing various antitumor drugs.
Description
Technical Field
The invention relates to the technical field of medicines, in particular to a binuclear platinum complex for targeting ovarian cancer drug-resistant cells, and a synthesis method and application thereof.
Background
Cancer is generally treated by various methods such as radiation therapy, operation, chemotherapy and the like, but only the operation therapy and the radiation therapy are one of the important means of local treatment, while platinum drugs inhibit the growth of tumor cells during the chemotherapy, and simultaneously have toxic effects to various cells which normally proliferate in the organism to different degrees. Therefore, development and treatment of the targeting non-platinum drugs have shown a better prospect (Guo, Z.; et al chem. Soc. Rev.; 2013,42: 202-224.) in recent years, but at present, clinical application needs further deep observation and accumulation in the clinical trial stage, so that the development and treatment have a larger gap from large-scale clinical popularization and application.
At present, clinical cisplatin and derivatives generate serious adverse reactions, including nephrotoxicity, drug resistance and the like. Therefore, researchers are urgently required to develop a targeted, efficient and low-toxicity platinum anticancer complex.
In recent years, a large number of terpyridine derivative metal complexes are reported successively, and the complexes have good anticancer activity, but the complexes with targeting property are still deficient.
Disclosure of Invention
It is an object of the present invention to provide binuclear platinum complexes that target ovarian cancer resistant cells.
The invention provides a binuclear platinum complex for targeting ovarian cancer drug-resistant cells, which has the chemical formula of [ Pt (tpy 2) Cl ]][Pt(DMSO)Cl 3 ]·CH 3 COCH 3 (tpy 2 Pt) having a chemical formula shown in the following formula:
it is another object of the present invention to provide a method for synthesizing the above binuclear platinum complex targeted to ovarian cancer resistant cells.
Specifically, the synthesis method of the binuclear platinum complex tpy2Pt comprises the following steps: ligand 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine (tpy 2), metal salt cis-Pt (DMSO) 2 Cl 2 Anhydrous CH 3 And (3) carrying out coordination reaction on OH and acetone at 45-80 ℃ for 3 days, filtering, and drying in a vacuum drying oven at 45 ℃ to obtain the binuclear platinum complex tpy2Pt.
The synthetic route is as follows:
the synthesis temperature of the binuclear platinum complex of the invention must be 45-80 ℃, if the synthesis temperature exceeds 80 ℃, the pipe is burnt completely, the yield is low, if the synthesis temperature is lower than 45 ℃, almost no product is produced, the yield is extremely low, the separation is difficult, after the optimized condition, the reaction system reacts at 80 ℃, and the yield of the target product obtained by the system is highest.
The reaction of the present invention must contain a mixed solution of acetone and methanol in a total volume of 1.5-10.0mL, too low impurities, too high yields, and very low yields, and wherein the mixed solution contains 3.5mL of anhydrous CH 3 OH and 0.5mL of acetone are the reaction conditions at which the yield is highest. Without acetone, little product is produced; without methanol, the byproducts are relatively large, and the separation and the treatment are difficult.
The reaction days are 3 days, and the product is relatively pure and easy to separate. Over 3 days, the quality of the product is not increased any more.
A third object of the present invention provides the use of the above dinuclear platinum complex tpy2Pt.
In particular to application of binuclear platinum complex tpy2Pt in preparing a drug for targeted treatment of ovarian cancer. Further relates to application of the binuclear platinum complex tpy2Pt in preparing a drug for targeted treatment of ovarian cancer of drug-resistant strains.
Compared with the prior art, the invention synthesizes three binuclear platinum complexes [ Pt (tpy 2) Cl targeted to ovarian cancer drug-resistant cells by taking the terpyridine derivative tpy2 as an active ligand][Pt(DMSO)Cl 3 ]·CH 3 COCH 3 (tpy 2 Pt) and examined its activity and toxicity against human ovarian carcinoma SK-OV-3 (SKO 3) and cisplatin-resistant strain SK-OV-3/DDP (SKO 3 cisR) and normal HL-7702 cells. Experimental results show that tpy2Pt targets inhibit proliferation of human ovarian cancer SKO3cisR and IC thereof 50 The value is 1.95+/-0.50 mu M, and the activity is far greater than that of the ligand tpy2, cis-Pt (DMSO) 2 Cl 2 And clinical medicine cisplatin, and their inhibition to normal HL-7702 cell is very small>45.0 mu M), the binuclear platinum complex tpy2Pt can inhibit the growth of SKO3cisR in a targeted manner, and has good anticancer activity and tumor targeting. In a word, the binuclear platinum complex tpy2Pt shows excellent in-vitro and in-vivo anti-tumor activity, has the capability of overcoming cisplatin resistance, has potential medicinal value, and is expected to be used for preparing various anti-tumor medicaments.
Drawings
FIG. 1 is a diagram showing the structure of an X-ray single crystal of a binuclear platinum complex tpy2Pt prepared in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of a binuclear platinum complex tpy2Pt prepared in example 1 of the present invention.
Detailed Description
The present invention will be further illustrated by the following specific examples, but the present invention is not limited to these examples.
The metal salt cis-Pt (DMSO) involved in the synthesis method of the invention 2 Cl 2 Can refer to nowPreparation is carried out in the literature (Al-Allaf, T.A.K.; et Al Transit.Met.chem.,1998, 23:403-406.). The ligand tpy2 was synthesized by the synthetic method of the reference (K.Czerwi ń ska, B.Machura, S.Kula, S.Krompiec, K.Erfurt, C.Roma-Rodrigues, A.R.Fernandes, L.S.Shul 'pina, N.S. Ikonnikov and G.B. Shul' pin, dalton Trans.,2017,46,9591-9604.).
Example 1
Into a 15.0mL high temperature pressure tube, 0.1mmol of ligand tpy2 and 0.2mmol of metal salt cis-Pt (DMSO) were added 2 Cl 2 3.5mL of anhydrous CH 3 OH and 0.5mL acetone, carrying out coordination reaction for 3.0 days at 80 ℃, filtering, and drying in a vacuum drying oven at 45 ℃ to obtain massive crystals tpy2Pt. Wherein, the yield of tpy2Pt was 92.9%.
The product obtained was identified:
(1) The X-ray single crystal structure diagram of the complex tpy2Pt is shown in figure 1.
(2) The nuclear magnetic resonance hydrogen spectrum of the complex tpy2Pt is shown in figure 2.
1 H NMR(400MHz,DMSO-d 6 )δ10.05(s,2H),9.21(d,J＝2.8Hz,4H),8.93(d,J＝2.3Hz,2H),8.25-8.21(m,2H),7.75-7.70(m,3H),2.54(s,6H).
(3) Infrared spectrum results of the complex tpy2Pt.
IR(KBr):3935,3844,3467,3079,3008,2918,1607,1585,1523,1470,1433,1417,1402,1376,1316,1299,1252,1179,1144,1075,1058,1027,981,920,893,855,772,731,689,647,635,621,587,532,461,439cm -1 .
(4) The elemental analysis results are shown in table 1.
Table 1 results of elemental analysis of Complex tpy2Pt in the examples
Thus, the resulting complex tpy2Pt can be determined to have the following structural formula:
in order to fully illustrate the application of the three binuclear platinum complexes tpy2Pt-tpy4Pt targeting ovarian cancer drug-resistant cells in pharmacy, the inventor performs in-vitro and in-vivo anti-tumor activity experiments.
1. Proliferation inhibition activity experiment of binuclear platinum complex tpy2Pt for targeting ovarian cancer drug-resistant cells on three human cell lines
1. Cell strain and cell culture
The experiment selects 3 human cell lines such as human ovarian cancer SK-OV-3 (SKO 3) and cisplatin-resistant strain SK-OV-3/DDP (SKO 3 cisR) and normal HL-7702 cells.
All the human cell lines are cultured in RPMI-1640 culture solution containing 100U/mL penicillin, 10wt% calf blood and 100U/mL streptomycin, and the culture solution is placed at 37 ℃ and contains CO with the volume concentration of 5% 2 Culturing in incubator.
2. Preparation of test Compounds
All compounds used were required to have a purity of 95.0% or more, their DMSO stock was diluted with physiological buffer to a final solution of 40. Mu. Mol/L (final concentration of DMSO 1.0%) and the extent of inhibition of each compound at this concentration on growth of normal cells or selected tumor cells was tested.
3. Cell growth inhibition experiment (CCK-8 method)
(1) Cell digestion, counting and concentration of 5X 10 4 mu.L of cell suspension was added to each well of a 96-well cell culture plate per mL of cell suspension;
(2) 96-well cell culture plates were placed at 37℃with 5% CO 2 Culturing in an incubator for 24 hours;
(3) Diluting the drug with the complete culture medium to the required concentration, adding 100 mu L of corresponding drug-containing culture medium into each hole, and setting up a negative control group;
(4) 96-well cell culture plates were placed at 37℃with 5% CO 2 Culturing in an incubator for 48 hours;
(5) CCK-8 staining was performed, λ=450 nm, and OD values were determined;
a) 10 mu L of CCK-8 is added into each hole, and the culture is continued for 2 hours in an incubator;
b) Mixing gently for 10 min;
c) The number of living cells was determined by measuring at λ=450 nm, reading the OD value of each well with an enzyme-labeled instrument, and determining the number of living cells based on the measured optical density value (OD value), wherein the higher the OD value, the higher the cell activity. Using the formula:
calculating the inhibition rate of each compound on the growth of the selected cells, and calculating the IC of each tested compound on each selected cell strain by using a Bliss method 50 Values. The results are shown in Table 2 below.
TABLE 2 IC of compounds against various cell lines 50 Value (mu M)
IC from Table 2 50 As can be seen from the results of the activity screening, tpy2Pt targets to inhibit proliferation of SKO3cisR, a human ovarian cancer, IC 50 The value is 1.95+/-0.50 mu M, and the activity is far greater than that of the ligand tpy2 and cis-Pt (DMSO) 2 Cl 2 And clinical medicine cisplatin, and their inhibition to normal HL-7702 cell is very small>45.0 mu M), the binuclear platinum complex tpy2Pt can inhibit the growth of SKO3cisR in a targeted manner, and has good anticancer activity and tumor targeting. In conclusion, the binuclear platinum complex tpy2Pt shows excellent in vivo anti-tumor activity, has the capability of overcoming cisplatin resistance, has potential medicinal value, and is expected to be used for preparing various anti-tumor medicaments.
Claims (6)
1. The 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex is characterized by having the following chemical structural formula:
2. the method for synthesizing 4-phenyl-2, 6-bis (2 '-pyrazinyl) pyridine binuclear platinum complex according to claim 1, wherein the ligand 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine and metal salt cis-Pt (DMSO) are taken 2 Cl 2 Anhydrous CH 3 Carrying out coordination reaction on OH and acetone at 45-80 ℃ for 3 days, filtering, and drying in a vacuum drying oven at 45 ℃ to obtain the product.
3. The method for synthesizing a 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex according to claim 2, wherein the total volume of the mixed solution of anhydrous acetone and methanol is 1.5 to 10.0mL.
4. The method for synthesizing a 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex according to claim 3, wherein the anhydrous CH 3 OH was 3.5mL and acetone was 0.5mL.
5. Use of the 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex according to claim 1 for the preparation of a medicament for targeted treatment of ovarian cancer.
6. The use of the 4-phenyl-2, 6-bis (2' -pyrazinyl) pyridine binuclear platinum complex according to claim 1 for preparing a medicament for targeted treatment of ovarian cancer of drug-resistant plants.
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