Synthesis, Characterization, and Antitumor Activity of Ruthenium(Ⅱ) Complexes Based on Schiff Base Ligand
- Corresponding author: Yan ZHANG, yanzhang872010@163.com
Citation: Shi-Fang JIA, Xiu-Li HAO, Yan-Zhen WEN, Yan ZHANG. Synthesis, Characterization, and Antitumor Activity of Ruthenium(Ⅱ) Complexes Based on Schiff Base Ligand[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(10): 1919-1926. doi: 10.11862/CJIC.2022.191
Rosenberg B, Vancamp L. Platinum Compounds: A New Class of Potent Antitumour Agents[J]. Nature, 1969,222:385-386. doi: 10.1038/222385a0
Esref Alkis M, Kelestemür Ü, Alan Y, Turan N, Buldurun K. Cobalt and Ruthenium Complexes with Pyrimidine Based Schiff Base: Synthesis, Characterization, Anticancer Activities and Electrochemotherapy Efficiency[J]. J. Mol. Struct., 2021,1226129402. doi: 10.1016/j.molstruc.2020.129402
Jiang G B, Zhang W Y, He M, Gu Y Y, Bai L, Wang Y J, Qiao Y, Du F. Anticancer Activity of Two Ruthenium (Ⅱ) Polypyridyl Complexes toward Hepatocellular Carcinoma HepG - 2 Cells[J]. Polyhedron, 2019,169:209-218. doi: 10.1016/j.poly.2019.05.017
Małecka M, Skoczynska A, Goodman D M, Hartinger C G, Budzisz E. Biological Properties of Ruthenium (Ⅱ)/(Ⅲ) Complexes with Flavonoids as Ligands[J]. Coord. Chem. Rev., 2021,436213849. doi: 10.1016/j.ccr.2021.213849
Jiang G B, Zhang W Y, He M, Gu Y Y, Bai L, Wang Y J, Yi Q Y, Du F. Systematic Evaluation of the Antitumor Activity of Three Ruthenium Polypyridyl Complexes[J]. J. Inorg. Biochem., 2021,225111616. doi: 10.1016/j.jinorgbio.2021.111616
Savić A, Gligorijević N, Aranđelović S. Antitumor Activity of Organoruthenium Complexes with Chelate Aromatic Ligands, Derived from 1, 10 - Phenantroline: Synthesis and Biological Activity[J]. J. Inorg. Biochem., 2020,202110869. doi: 10.1016/j.jinorgbio.2019.110869
Jana D, Zhao Y L. Strategies for Enhancing Cancer Chemodynamic Therapy Performance[J]. Exploration, 2022(2)20210238.
Hartinger C G, Jakupeca M A, Zorbas S, Groessl M, Egger A, Berger W, Zorbas H, Dyson P J, Keppler B K. KP1019, A New Redox-Active Anticancer Agent-Preclinical Development and Results of a Clinical Phase Ⅰ Study in Tumor Patients[J]. Chem. Biodivers., 2008,5(10):2140-2155. doi: 10.1002/cbdv.200890195
Leigen S, Burgers S A, Baas P, Pluim D, Tibben M, Werkhoven E, Alessio E, Sava G, Beijnen J H, Schellens J H M. Phase Ⅰ/Ⅱ Study with Ruthenium Compound NAMI - A and Gemcitabine in Patients with Non - small Cell Lung Cancer after First Line Therapy[J]. Invest. New Drugs, 2015,33(1):201-214. doi: 10.1007/s10637-014-0179-1
Schatzschneider U, Niesel J, Ott I, Gust R, Alborzinia H, Wölfl S. Cellular Uptake, Cytotoxicity, and Metabolic Profiling of Human Cancer Cells Treated with Ruthenium (Ⅱ) Polypyridyl Complexes[J]. ChemMedChem, 2008,3(7):1104-1109. doi: 10.1002/cmdc.200800039
Lentz F, Drescher A, Lindauer A, Henke M, Hilger R A, Hartinger C G, Scheulen M E, Dittrich C, Keppler B K, Jaehde U. Pharmacokinetics of a Novel Anticancer Ruthenium Complex (KP1019, FFC14A) in a Phase Ⅰ Dose-Escalation Study[J]. Anti-Cancer Drugs, 2009,20(2):97-103. doi: 10.1097/CAD.0b013e328322fbc5
Zhong Y W, Wu S H, Burkhardt S E, Yao C J, Abruña H D. Mononuclear and Dinuclear Ruthenium Complexes of 2, 3-Di-2-pyridyl-5, 6-diphenylpyrazine: Synthesis and Spectroscopic and Electrochemical Studies[J]. Inorg. Chem., 2011,50(2):517-524. doi: 10.1021/ic101629w
Huang W K, Cheng C W, Chang S M, Lee Y P, Eric W G. Synthesis and Electron - Transfer Properties of Benzimidazole - Functionalized Ruthenium Complexes for Highly Efficient Dye - Sensitized Solar Cells[J]. Chem. Commun., 2010,46(47):8992-8994. doi: 10.1039/c0cc03517c
Garza-Ortiz A, Maheswari P U, Lutz M, Siegler M A, Reedijk J. Tuning the Cytotoxic Properties of New Ruthenium(Ⅲ) and Ruthenium(Ⅱ) Complexes with a Modified Bis(arylimino)pyridine Schiff Base Ligand Using Bidentate Pyridine - Based Ligands[J]. J. Biol. Inorg. Chem., 2014,19:675-689. doi: 10.1007/s00775-013-1083-4
Selvamurugan S, Viswanathamurthi P, Endo A, Hashimoto T, Natarajan K. Synthesis, Spectral Characterization, Antioxidant, Anticancer In Vitro, and DNA Cleavage Studies of a Series of Ruthenium (Ⅱ) Complexes Bearing Schiff Base Ligands[J]. J. Coord. Chem., 2013,66(22):4052-4066. doi: 10.1080/00958972.2013.858135
Sathiyaraj S, Sampath K, Butcher R J. Designing, Structural Elucidation, Comparison of DNA Binding, Cleavage, Radical Scavenging Activity and Anticancer Activity of Copper (Ⅰ) Complex with 5-Dimethyl-2-phenyl-4-[(pyridin-2-ylmethylene)-amino]-1, 2-dihydropyrazol-3-one Schiff Base Ligand[J]. Eur. J. Med. Chem., 2013,64:81-89. doi: 10.1016/j.ejmech.2013.03.047
Garza-Ortiz A, Maheswari P U, Siegler M, Spek A L, Reedijk J. A New Family of Ru (Ⅱ) Complexes with a Tridentate Pyridine Schiff-Base Ligand and Bidentate Co-ligands: Synthesis, Characterization, Structure and In Vitro Cytotoxicity Studies[J]. New J. Chem., 2013,37:3450-3460. doi: 10.1039/c3nj00415e
Sathiyaraj S, Butcher R J, Jayabalakrishnan C. Synthesis, Characterization, DNA Interaction and In Vitro Cytotoxicity Activities of Ruthenium(Ⅱ) Schiff Base Complexes[J]. J. Mol. Struct., 2012,1030:95-103. doi: 10.1016/j.molstruc.2012.07.021
Raja G, Butcher R J, Jayabalakrishnan C. Studies on Synthesis, Characterization, DNA Interaction and Cytotoxicity of Ruthenium(Ⅱ) Schiff Base Complexes[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2012,94:210-215. doi: 10.1016/j.saa.2012.03.035
Mosmann T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays[J]. J. Immunol. Methods, 1983,65(1/2):55-63.
BAI X F, MA X, XIE X X, SHAO M S, GUO N N, YAN N, YAO L. Synthesis and Anti-tumor Activity of Tubulysins Analogues[J]. Chem. J. Chinese Universities, 2017,38(1):47-55.
Zhang Y, Cai P, Hu P C, Yang F, Cheng G Z. Synthesis, Characterization, Crystal Structure, Cytotoxicity, Apoptosis and Cell Cycle Arrest of Ruthenium (Ⅱ) Complex[Ru(bpy)2(adpa)] (PF6)2 (bpy=2, 2'-Bipyridine, adpa=4-(4-Aminophenyl) diazenyl-N-(pyridin-2-ylmethylene)aniline)[J]. RSC Adv., 2015,5:11591-11598. doi: 10.1039/C4RA12715C
Mendoza-Ferri M G, Hartinger C G, Mendoza M A, Groessl M, Egger A E, Eichinger R E, Mangrum J B, Farrell N P, Maruszak M, Bednarski P J, Klein F, Jakupec M A, Nazarov A A, Severin K, Keppler B K. Transferring the Concept of Multinuclearity to Ruthenium Complexes for Improvement of Anticancer Activity[J]. J. Med. Chem., 2009,52:916-925. doi: 10.1021/jm8013234
Giannini F, Paul L E H, Furrer J, Therrien B, Süss-Fink G. Highly Cytotoxic Diruthenium Trithiolato Complexes of the Type[(η6-p-MeC6H4Pri)2Ru2(μ2 - SR)3]+ : Synthesis, Characterization, Molecular Structure and In Vitro Anticancer Activity[J]. New J. Chem., 2013,37:3503-3511. doi: 10.1039/c3nj00476g
Mulyana Y, Weber D K, Buck D P, Motti C A, Collinsb J G, Keene F R. Oligonuclear Polypyridylruthenium (Ⅱ) Complexes Incorporating Flexible Polar and Non-polar Bridges: Synthesis, DNA-Binding and Cytotoxicity[J]. Dalton Trans., 2011,40:1510-1523. doi: 10.1039/c0dt01250e
Gorle A K, Ammit A J, Wallace L, Keene F R, Collins J G. Multinuclear Ruthenium(Ⅱ) Complexes as Anticancer Agents[J]. New J. Chem., 2014,38:4049-4059. doi: 10.1039/C4NJ00545G
DeBerardinis R J, Lum J J, Hatzivassiliou G, Thompson C B. The Biology of Cancer: Metabolic Reprogramming Fuels Cell Growth and Proliferation[J]. Cell Metab., 2008,7(1):11-20. doi: 10.1016/j.cmet.2007.10.002
Liu H Y, Yuan Y Z, Guo H Y, Mitchelson K, Zhang K, Xie L, Qin W Y, Lu Y, Wang J, Guo Y, Zhou Y X, He F C. Hepatitis B Virus Encoded X Protein Suppresses Apoptosis by Inhibition of the Caspase-Independent Pathway[J]. J. Proteome Res., 2012,11(10):4803-4813. doi: 10.1021/pr2012297
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R=none (Ru1), —C(CH3)2 (Ru2), —SO2 (Ru3)
Black: control; Red: exposed to Rosup as positive control; Yellow: Ru1; Green: Ru2; Blue: Ru3; Incubation time: 24 h