183
Views
1
CrossRef citations to date
0
Altmetric
Article

Synthesis, characterization, and biological applications of pyrazole moiety bearing osmium(IV) complexes

, ORCID Icon, , ORCID Icon, , ORCID Icon & ORCID Icon show all
Pages 593-618 | Received 04 Jul 2019, Accepted 21 Apr 2021, Published online: 28 May 2021

References

  • Sun, C.-Y.; Zhang, Q.-Y.; Zheng, G.-J.; Feng, B. Phytochemicals: Current Strategy to Sensitize Cancer Cells to Cisplatin. Biomed. Pharmacother. 2019, 110, 518–527. DOI: 10.1016/j.biopha.2018.12.010.
  • Goettel, J. T.; Braunschweig, H. Recent Advances in Boron-Centered Ligands and Their Transition Metal Complexes. Coord. Chem. Rev. 2019, 380, 184–200. DOI: 10.1016/j.ccr.2018.09.013.
  • Kuthyala, S.; Nagaraja, G. K.; Sheik, S.; Hanumanthappa, M.; Kumar S, M. Synthesis of Imidazo [1, 2-a]Pyridine-Chalcones as Potent Inhibitors against A549 Cell Line and Their Crystal Studies. J. Mol. Struct. 2019, 1177, 381–390. DOI: 10.1016/j.molstruc.2018.09.087.
  • Jastrząb, R.; Nowak, M.; Skrobańska, M.; Tolińska, A.; Zabiszak, M.; Gabryel, M.; Marciniak, Ł.; Kaczmarek, M. T. DNA as a Target for Lanthanide(III) Complexes Influence. Coord. Chem. Rev. 2019, 382, 145–159. DOI: 10.1016/j.ccr.2018.12.018.
  • Nath, A. K.; Shi, X.; Harrison, D. L.; Morningstar, J. E.; Mahon, S.; Chan, A.; Sips, P.; Lee, J.; MacRae, C. A.; Boss, G. R.; et al. Cisplatin Analogs Confer Protection against Cyanide Poisoning. Cell Chem. Biol. 2017, 24, 565–575.e4. DOI: 10.1016/j.chembiol.2017.03.013.
  • Inamdar, P. R.; Sheela, A. Spectroscopic Investigations on Partial Intercalative Binding Behaviour of Terpyridine Based Copper(II) Complexes with DNA. J. Photochem. Photobiol, B. 2016, 159, 133–141. DOI: 10.1016/j.jphotobiol.2016.03.007.
  • Gamov, G. A.; Zavalishin, M. N.; Sharnin, V. A. Comment on the Frequently Used Method of the Metal complex-DNA Binding Constant Determination from UV–Vis Data. Spectrochim. Acta, Part A. 2019, 206, 160–164. DOI: 10.1016/j.saa.2018.08.009.
  • dos Santos Chagas, C.; Fonseca, F. L. A.; Bagatin, I. A. Quinoline-Derivative Coordination Compounds as Potential Applications to Antibacterial and Antineoplasic Drugs. Mater. Sci. Eng. C 2019, 98, 1043–1052. DOI: 10.1016/j.msec.2019.01.058.
  • Takate, S. J.; Shinde, A. D.; Karale, B. K.; Akolkar, H.; Nawale, L.; Sarkar, D.; Mhaske, P. C. Thiazolyl-Pyrazole Derivatives as Potential Antimycobacterial Agents. Bioorg. Med. Chem. Lett. 2019, 29, 1199–1202. DOI: 10.1016/j.bmcl.2019.03.020.
  • Lunagariya, M. V.; Thakor, K. P.; Pursuwani, B. H.; Patel, M. N. Evolution of 1, 3, 5-Trisubstituted Bipyrazole Scaffold Based Platinum(II) Complexes as a Biological Active Agent. Nucleosides Nucleotides Nucleic Acids 2018, 37, 455–483. DOI: 10.1080/15257770.2018.1498510.
  • Wang, Z.; Sun, X.; Fu, W.; Xu, C.; Ji, B. Four-Coordinate Cu(I) complexes Supported by N-Heterocyclic Carbene Ligands Bearing Electron-Donating/Withdrawing Groups: Synthesis, Structures and Photophysical Properties. J. Lumin. 2018, 204, 618–625. DOI: 10.1016/j.jlumin.2018.08.064.
  • Berger, G.; Grauwet, K.; Zhang, H.; Hussey, A. M.; Nowicki, M. O.; Wang, D. I.; Chiocca, E. A.; Lawler, S. E.; Lippard, S. J. Anticancer Activity of Osmium(VI) Nitrido Complexes in Patient-Derived Glioblastoma Initiating Cells and in Vivo Mouse Models. Cancer Lett. 2018, 416, 138–148. DOI: 10.1016/j.canlet.2017.11.041.
  • Gichumbi, J. M.; Friedrich, H. B. Half-Sandwich Complexes of Platinum Group Metals (Ir, Rh, Ru and Os) and Some Recent Biological and Catalytic Applications. J. Organomet. Chem. 2018, 866, 123–143. DOI: 10.1016/j.jorganchem.2018.04.021.
  • Büchel, G. E.; Kossatz, S.; Sadique, A.; Rapta, P.; Zalibera, M.; Bucinsky, L.; Komorovsky, S.; Telser, J.; Eppinger, J.; Reiner, T.; Arion, V. B. Cis-Tetrachlorido-Bis(Indazole)Osmium(IV) and Its Osmium(III) Analogues: paving the Way towards the Cis-Isomer of the Ruthenium Anticancer Drugs KP1019 and/or NKP1339. Dalton Trans. 2017, 46, 11925–11941. DOI: 10.1039/C7DT02194A.
  • Kamecka, A.; Kapturkiewicz, A.; Suwińska, K. Luminescent Osmium(II) Complexes with 2-(2-Pyridyl)-Benzimidazolate Anion. Inorg. Chem. Commun. 2018, 89, 27–31. DOI: 10.1016/j.inoche.2018.01.002.
  • Dong, W.-K.; Zhang, J.; Zhang, Y.; Li, N. Novel Multinuclear Transition Metal(II) Complexes Based on an Asymmetric Salamo-Type Ligand: Syntheses, Structure Characterizations and Fluorescent Properties. Inorg. Chim. Acta 2016, 444, 95–102. DOI: 10.1016/j.ica.2016.01.034.
  • El-Gamal, K. M.; Hagrs, M. S.; Abulkhair, H. S. Synthesis, Characterization and Antimicrobial Evaluation of Some Novel Quinoline Derivatives Bearing Different Heterocyclic Moieties. Bull. Facul. Pharm. Cairo Univ. 2016, 54, 263–273. DOI: 10.1016/j.bfopcu.2016.08.002.
  • Michelini, L. J.; Castro, M. R. C.; Custodio, J. M. F.; Naves, L. F. N.; Vaz, W. F.; Lobón, G. S.; Martins, F. T.; Perez, C. N.; Napolitano, H. B. A Novel Potential Anticancer Chalcone: Synthesis, Crystal Structure and Cytotoxic Assay. J. Mol. Struct. 2018, 1168, 309–315. DOI: 10.1016/j.molstruc.2018.05.010.
  • Lay, P. A.; Sargeson, A. M. Tris(1,2-Ethanediamine) Complexes of Osmium(IV), Osmium(III) and Osmium(II): Oxidative Dehydrogenation Reactions. Inorg. Chim. Acta 1992, 198-200, 449–460. DOI: 10.1016/S0020-1693(00)92389-2.
  • Maruyama, K.; Mishima, Y.; Minagawa, K.; Motonaka, J. Electrochemical and DNA-Binding Properties of Dipyridophenazine Complexes of Osmium(II). J. Electroanal. Chem. 2001, 510, 96–102.
  • Gilewska, A.; Masternak, J.; Kazimierczuk, K.; Trynda, J.; Wietrzyk, J.; Barszcz, B. Synthesis, Structure, DNA Binding and Anticancer Activity of Mixed Ligand Ruthenium(II) Complex. J. Mol. Struct. 2018, 1155, 288–296. DOI: 10.1016/j.molstruc.2017.10.105.
  • Lunagariya, M. V.; Thakor, K. P.; Varma, R. R.; Waghela, B. N.; Pathak, C.; Patel, M. N. Synthesis, Characterization and Biological Application of 5-Quinoline 1,3,5-Trisubstituted Pyrazole Based Platinum(ii) Complexes. Med. Chem. Commun. 2018, 9, 282–298. DOI: 10.1039/C7MD00472A.
  • Mirzaei-Kalar, Z. In Vitro Binding Interaction of Atorvastatin with Calf Thymus DNA: multispectroscopic, Gel Electrophoresis and Molecular Docking Studies. J. Pharm. Biomed. Anal. 2018, 161, 101–109. DOI: 10.1016/j.jpba.2018.08.033.
  • Raman, N.; Pothiraj, K.; Baskaran, T. DNA Interaction, Antimicrobial, Electrochemical and Spectroscopic Studies of Metal(II) Complexes with Tridentate Heterocyclic Schiff Base Derived from 2′-Methylacetoacetanilide. J. Mol. Struct. 2011, 1000, 135–144. DOI: 10.1016/j.molstruc.2011.06.006.
  • Kou, Y.-Y.; Li, M.-L.; Ren, X.-H. Synthesis, Structure, and DNA Binding/Cleavage of Two Novel Binuclear Co(II) Complexes. Spectrochim. Acta, Part A. 2018, 205, 435–441. DOI: 10.1016/j.saa.2018.07.050.
  • Patel, M. N.; Joshi, H. N.; Patel, C. R. Copper(II) Complexes with Norfloxacin and Neutral Terpyridines: Cytotoxic, Antibacterial, Superoxide Dismutase and DNA-Interaction Approach. Polyhedron 2012, 40, 159–167. DOI: 10.1016/j.poly.2012.03.050.
  • Mehta, J. V.; Gajera, S. B.; Patel, M. N. Biological Applications of Pyrazoline-Based Half-Sandwich Ruthenium(III) Coordination Compounds. J. Biomol. Struct. Dyn. 2017, 35, 1599–1607. DOI: 10.1080/07391102.2016.1189360.
  • Patra, M.; Wenzel, M.; Prochnow, P.; Pierroz, V.; Gasser, G.; Bandow, J. E.; Metzler-Nolte, N. An Organometallic Structure-Activity Relationship Study Reveals the Essential Role of a Re(CO)3 Moiety in the Activity against Gram-Positive Pathogens Including MRSA. Chem. Sci. 2015, 6, 214. DOI: 10.1039/c4sc02709d.
  • Daryanavard, M.; Jannesari, Z.; Javeri, M.; Abyar, F. A New Mononuclear Zinc(II) Complex: Crystal Structure, DNA- and BSA Binding, and Molecular Modeling; in Vitro Cytotoxicity of the Zn(II) Complex and Its Nanocomplex. Spectrochim. Acta, Part A. 2020, 233, 118175. DOI: 10.1016/j.saa.2020.118175.
  • Ekengard, E.; Glans, L.; Cassells, I.; Fogeron, T.; Govender, P.; Stringer, T.; Chellan, P.; Lisensky, G.; Hersh, W. H.; Doverbratt, I.; et al. Antimalarial Activity of Ruthenium(II) and Osmium(II) Arene Complexes with Mono- and Bidentate Chloroquine Analogue Ligands. Dalton Trans. 2015, 44, 19314–19329. DOI: 10.1039/c5dt02410b.
  • Rudnitskaya, O.; V.; Dobrokhotova, E.; V.; Kultyshkina, E.; K.; Dorovatovskii, P.; V.; Lazarenko, V.; A.; Khrustalev, V. N. A Balance of Redox and Ligand-Exchange Processes in the Reaction of H2[OsCl6] with Thiourea: isolation and Characterization of a Novel Osmium Complex [(NH2)2CSSC(NH2)2]2[OsIVCl6]Cl2•3H2O. Inorg. Chim. Acta 2019, 484, 352–356. DOI: 10.1016/j.ica.2018.09.071.
  • Mehta, J.; V.; Gajera, S.; B.; Thakor, P.; Thakkar, V.; R.; Patel, M.; N. Synthesis of 1,3,5-Trisubstituted Pyrazoline Derivatives and Their Applications. RSC Adv. 2015, 5, 85350–85362. DOI: 10.1039/C5RA17185G.
  • Das, A.; Peng, S.-M.; Bhattacharya, S. Chemistry of 2-(Phenylazo)Pyridine Complexes of Osmium: synthesis, Characterization and Reactivities. Polyhedron 2000, 19, 1227–1232. DOI: 10.1016/S0277-5387(00)00378-8.
  • Ramachandran, E.; Thomas, S.; P.; Poornima, P.; Kalaivani, P.; Prabhakaran, R.; Padma, V.; V.; Natarajan, K. Evaluation of DNA Binding, Antioxidant and Cytotoxic Activity of Mononuclear Co(III) Complexes of 2-Oxo-1,2-Dihydrobenzo[h]Quinoline-3-Carbaldehyde Thiosemicarbazones. Eur. J. Med. Chem. 2012, 50, 405–415. DOI: 10.1016/j.ejmech.2012.02.026
  • Pursuwani, B.; H.; Bhatt, B.; S.; Vaidya, F.; U.; Pathak, C.; Patel, M. N.; Tetrazolo[1,5-a]Quinoline Moiety-Based Os(IV) Complexes: DNA Binding/Cleavage, Bacteriostatic and Photocytotoxicity Assay. J. Biomol. Struct. Dyn. 2020, 39, 2894–2903.
  • Yan, I.; Wang, X.; Wang, Y.; Zhang, Y.; Li, Y.; Guo, Z. Cytotoxic Palladium(II) Complexes of 8-Aminoquinoline Derivatives and the Interaction with Human Serum Albumin. J. Inorg. Biochem. 2012, 106, 46–51. DOI: 10.1016/j.jinorgbio.2011.09.032
  • Kathrotiya, H.; G.; Patel, M.; P. Synthesis and Identification of b-Aryloxyquinoline Based Diversely Fluorine Substituted N-Aryl Quinolone Derivatives as a New Class of Antimicrobial, Antituberculosis and Antioxidant Agents. Eur. J. Med. Chem. 2013, 63, 675–684. DOI: 10.1016/j.ejmech.2013.03.017
  • Chagasa, C.; D.; S.; Fonseca, F.; L.; A.; Bagatin, I.; A. Quinoline-Derivative Coordination Compounds as Potential Applications to Antibacterial and Antineoplasic Drugs. Mater. Sci. Eng. C 2019, 98, 1043–1052. DOI: 10.1016/j.msec.2019.01.058

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.