A review on the chemistry of novel platinum chelates based on azo-azomethine ligands

References

Abildgaard, J.; Hansen, E. P.; Josephsen, J.; Hansen, V. K. B.; Sørensen, O. H.; Larsen, S. Synthesis and characterization of nickel-palladium- and platinum(II) complexes of three o, o′-dihydroxydiarylazo dyes: determination of the coordination geometry of this comprehensive series of tridentate diaryl dye complexes by combining results from NMR and X-ray experiments with theoretical ab initio calculations. Inorg. Chim. Acta 2006, 359, 4493–4502; https://doi.org/10.1016/j.ica.2006.05.027.Search in Google Scholar

Alaghaz, A. M. A. -N.; Zayed, E. M.; Alharbi, A. S. Synthesis, spectral characterization, molecular modeling and antimicrobial studies of tridentate azo-dye Schiff base metal complexes. J. Mol. Struct. 2015, 1084, 36–45; https://doi.org/10.1016/j.molstruc.2014.12.013.Search in Google Scholar

Al-Adilee, J. K.; Hessoon, M. H. Synthesis, identification, structural, studies and biological activity of some transition metal complexes with novel heterocyclic azo-Schiff base ligand derived from benzimidazole. J. Chem. Pharmaceut. Res. 2015, 7, 89–103.Search in Google Scholar

Al-Adilee, J. K.; Dakheel, K. H. Synthesis, spectral and biological studies of Ni(II), Pd(II), and Pt(IV) complexes with new heterocyclic ligand derived from azo-Schiff bases dye. Eurasian J. Anal. Chem. 2018, 13(5); https://doi.org/10.29333/ejac/97267.Search in Google Scholar

Aldrich-Wright, R. J.; Deo, M. K.; Ang, L. D.; McGhie, B.; Rajamanickam, A.; Dhiman, A.; Khoury, A.; Holland, J.; Bjelosevic, A.; Pages, B.; Gordon, C. Platinum coordination compounds with potent anticancer activity. Coord. Chem. Rev. 2018, 375, 148–163; https://doi.org/10.1016/j.ccr.2017.11.014.Search in Google Scholar

Bandyopadhyay, P.; Acharya, S.; Kejriwal, A.; Biswas, N. A.; Das, P.; Neogi, N. D. Synthesis, characterization, X-ray structure and spectroscopic study of platinum(II) complexes with tridentate diazene ligands having O, N, S donor set. Inorg. Chim. Acta. 2013, 394, 757–764; https://doi.org/10.1016/j.ica.2012.09.041.Search in Google Scholar

Bednarsk, J. P.; Lemmerhirt, H.; Behnisch, S.; Bodtke, A.; Lillig, H. C. Effects of cytotoxic cis- and trans-diamminemonochlorido platinum(II) complexes on selenium-dependent redox enzymes and DNA. J. Inorg. Biochem. 2018, 178, 94–105; https://doi.org/10.1016/j.jinorgbio.2017.10.011.Search in Google Scholar PubMed

Brabec, V.; Hrabina, O.; Kasparkova, J. Cytotoxic platinum coordination compounds. DNA binding agents. Coord. Chem. Rev. 2017, 351, 2–31; https://doi.org/10.1016/j.ccr.2017.04.013.Search in Google Scholar

Chai, K.; Jiang, Y.; Han, T.; Niu, J.; Zhang, H.; Zeng, M.; Zhang, L.; Duan, X.; Wang, J. Synthesis, DNA binding, topoisomerase I inhibition and antiproliferation activities of three new binuclear terpyridine platinum(II) complexes. Polyhedron 2019, 157, 124–130; https://doi.org/10.1016/j.poly.2018.09.053.Search in Google Scholar

Chakravarty, R. A.; Mitra, K.; Patil, S.; Kondaiah, P. 2-(Phenylazo)pyridineplatinum(II) catecholates showing photocytotoxicity, nuclear uptake, and glutathione-triggered ligand release. Inorg. Chem. 2015, 54, 253–264.10.1021/ic502317zSearch in Google Scholar PubMed

Chakravorty, A.; Bandyopadhyay, D.; Bandyopadhyay, P.; Albert Cotton, F.; Falvello, L. R. Isomeric bis[(phenylazo)acetaldoximato]platinum(11) compounds. Inorg. Chem. 1983, 22, 1315–1321; https://doi.org/10.1021/ic00151a010.Search in Google Scholar

Chakravorty, A.; Pal, C. K.; Chattopadhyay, S.; Sinha, C. Synthesis, structure, and solution equilibria of diamagnetic and paramagnetic azooximates of bivalent platinum. Geometrical change associated with ligand-based electroprotic reactions. Inorg. Chem 1994, 33, 6140–6147; https://doi.org/10.1021/ic00104a026.Search in Google Scholar

Chattopadhyay, S.; Maiti, N.; Pal, S. Reaction of 2-(phenylazo)aniline with Na2PdCl4: formation of a 2-(phenylazo)imino complex of bivalent palladium. Inorg. Chem 2001, 40, 2204–2205; https://doi.org/10.1021/ic000369p.Search in Google Scholar PubMed

Chattopadhyay, S.; Maiti, N. New azoiminato complexes of bivalent platinum: syntheses, characterization and structure. Int. J. Chem. 2003, 42, 2327–2331.Search in Google Scholar

Chattopadhyay, S.; Patra, D.; Pratihar, L. J.; Shee, B.; Pattanayak, P. Syntheses, characterisation and structure of new diazoketiminato chelates of palladium(II) incorporating a tridentate (N, N,N) azo ligand. Polyhedron 2006, 25, 2637–2642.10.1016/j.poly.2006.03.019Search in Google Scholar

Chattopadhyay, S.; Patra, D.; Pattanayak, P.; Pratihar, L. J. Synthesis, structure and properties of delocalized transition metal chelates: diazoketiminato chelates of Co(III) and Pt(II). Polyhedron 2007, 26, 5484–5490.10.1016/j.poly.2007.08.029Search in Google Scholar

Chattopadhyay, S.; Pattanayak, P.; Parua, P. S.; Patra, D.; Pratihar, L. J.; Brandão, P.; Felix, , V. Synthesis, characterizations and structure of orthometallated Pt(II) and Pt(IV) complexes: oxidative addition to C, N, N, O coordinated Pt(II) complexes. Polyhedron 2014, 70, 1–5; https://doi.org/10.1016/j.poly.2013.12.014.Search in Google Scholar

Coban, B.; Yıldız, U.; Şengül, A.; Irfan Kandemir, I.; Cömert, F. The comparative study of the DNA binding and biological activities of the quaternizeddicnq as a dicationic form and its platinum(II) heteroleptic cationic complex. Bioorg. Chem. 2019, 87, 70–77; https://doi.org/10.1016/j.bioorg.2019.03.009.Search in Google Scholar PubMed

Cope, C. A.; Siekman, W. R. Formation of covalent bonds from platinum or palladium to carbon by direct substitution. J. Am. Chem. Soc. 1965, 87, 3272–3273; https://doi.org/10.1021/ja01092a063.Search in Google Scholar

Farrell, P. N. Multi-platinum anti-cancer agents. Substitution-inert compounds for tumor selectivity and new targets. Chem. Soc. Rev. 2015, 44, 8773–8785; https://doi.org/10.1039/c5cs00201j.Search in Google Scholar PubMed

Goswami, S. Design and synthesis of a new binucleating ligand via cobalt-promoted C-N bond fusion reaction. Ligand isolation and its coordination to nickel, palladium, and platinum. Inorg. Chem 2003, 42, 5367–5375; https://doi.org/10.1021/ic034313h.Search in Google Scholar PubMed

Goswami, S.; Panda, M.; Das, S.; Mostafa, G.; Casti˜neiras, A. Platinum complexes of diazo ligands. Studies of regioselective aromatic ring amination, oxidative halogen addition and reductive halogen elimination reactions. Dalton Trans. 2005, 1249–1255; https://doi.org/10.1039/b418470j.Search in Google Scholar PubMed

Gümüş, F.; Gozelle, M.; Süloğlu, K. A.; Selmanoğlu, G.; Ramazanoğlu, N. Studies on the synthesis, characterization, cytotoxic activities and plasmid DNA binding of platinum(II) complexes having 2-subsituted benzimidazole ligands. Polyhedron 2019, 161, 298–308; https://doi.org/10.1016/j.poly.2019.01.028.Search in Google Scholar

Herrera, M. J.; Mendes, F.; Gama, S.; Santos, I.; Ranninger, N. C.; Cabrera, S.; Quiroga, G. A. Design and biological evaluation of new platinum(II) complexes bearing ligands with DNA-targeting ability. Inorg. Chem. 2014, 53, 12627–12634; https://doi.org/10.1021/ic502373n.Search in Google Scholar PubMed

Hao, Z.; Liu, Y.; Huang, Y.; Meng, F.; Wang, Y.; Tan, H.; Su, S.; Zhu, W. Synthesis and optoelectronic properties of dinuclear cyclometalated platinum (II) complexes containing naphthalene-functionalized carbazole groups in the single-emissive-layer WPLEDs. J. Organomet. Chem. 2017, 835, 52–59; https://doi.org/10.1016/j.jorganchem.2017.02.018.Search in Google Scholar

Hashemi, M.; Solati, Z.; Ghodsi, A.; Ahmadian, S. Azo-substituted Schiff base complex of Pt(II): synthesis, characterization, DFT and TD-DFT study. Synth. Met. 2015, 210, 398–403; https://doi.org/10.1016/j.synthmet.2015.10.029.Search in Google Scholar

Hussein, A-K. K.; Khalid, J. Al-A. Synthesis, spectral characterization, antimicrobial evaluation studies and cytotoxic activity of some transition metal complexes with tridentate (N, N, O) donor azo dye ligand. Res. Chem. 2021, 3, 100245; https://doi.org/10.1016/j.rechem.2021.100245.Search in Google Scholar

Kasparkova, J.; Pracharova, J.; Zerzankova, L.; Stepankova, J.; Novakova, O.; Farrer, J. N.; Sadler, J. P.; Brabec, V. Interactions of DNA with a new platinum(IV) azide dipyridine complex activated by UVA and visible light: relationship to toxicity in tumor cells. J. Chem. Res. Toxicol 2012, 25, 099–1111.10.1021/tx300057ySearch in Google Scholar PubMed

Kelland, L. The resurgence of platinum-based cancer chemotherapy. Nat. Rev. 2007, 7, 573–584; https://doi.org/10.1038/nrc2167.Search in Google Scholar PubMed

K-Terajima, C.; Mutoh, N.; Sasada, Y.; Anjo, K. Cyclometalation reactions of platinum complexes with azo- and imine-based ligands: ligand-dependent and water-induced C–H activation. J. Organomet. Chem. 2020, 928, 121548; https://doi.org/10.1016/j.jorganchem.2020.121548.Search in Google Scholar

Lalinde, E.; Diez, A.; Moreno, T. M. Heteropolynuclearcycloplatinated complexes: structural and photophysical properties. Coord. Chem. Rev. 2011, 255, 2426–2447; https://doi.org/10.1016/j.ccr.2010.12.024.Search in Google Scholar

Laskar, R. I.; Pasha, S. S.; Das, P.; Rath, P. N.; Bandyopadhyay, D. Water soluble luminescent cyclometalated platinum (II) complex—a suitable probe for bio-imaging applications. Inorg. Chem. Commun. 2016, 67, 107–111; https://doi.org/10.1016/j.inoche.2016.03.017.Search in Google Scholar

Lippard, J. S.; Graf, N. Redox activation of metal-based prodrugs as a strategy for drug delivery. Adv. Drug Deliv. Rev. 2012, 64, 993–1004; https://doi.org/10.1016/j.addr.2012.01.007.Search in Google Scholar PubMed PubMed Central

Lippard, J. S.; Johnstone, C. T.; Suntharalingam, K. The next generation of platinum drugs: targeted Pt(II) agents, nanoparticle delivery, and Pt(IV) prodrugs. Chem. Rev 2016, 116, 3436–3486; https://doi.org/10.1021/acs.chemrev.5b00597.Search in Google Scholar PubMed PubMed Central

Mandal, S.; Paul, N.; Banerjee, P.; Mondal, T. K.; Goswami, S. 1,4-Alkyl migration associated with simultaneous S–C bond cleavage and N–C bond formation in platinum complexes of 2-aminothioethers. Characterization of intramolecular interligand charge transfer phenomenon. Dalton Trans. 2010, 39, 2717–2726.10.1039/b918336aSearch in Google Scholar PubMed

Mitra, K. Platinum complexes as light promoted anticancer agents: a redefined strategy for controlled activation. Dalton Trans. 2016, 45, 19157–19171; https://doi.org/10.1039/c6dt03665a.Search in Google Scholar PubMed

Pratihar, J. L.; Mandal, P.; Lin, C-H.; Brandão, P.; Mal, D.; Felix, V. Synthesis, characterization, structure and catalytic activity of (NNN) tridentate azo-imine nickel(II), palladium(II) and platinum(II) complexes. Polyhedron 2016, 106, 171–177; https://doi.org/10.1016/j.poly.2015.12.050.Search in Google Scholar

Pratihar, L. J.; Mandal, P.; Lin, C-H.; Lai, C.-K.; Mal, D. Azo-amide palladium(II) complexes: synthesis, characterization and application in C–C cross-coupling reactions. Polyhedron 2017, 135, 224–230; https://doi.org/10.1016/j.poly.2017.06.055.Search in Google Scholar

Pratihar, L. J.; Mandal, P.; Lin, C. -H. Synthesis, characterization, structure and redox property of azo-amido and orthometallated azo-imine platinum(II) complexes. Polyhedron 2019, 173, 114102; https://doi.org/10.1016/j.poly.2019.07.047.Search in Google Scholar

Puddephatt, J. P.; Mohamed, E. M.; McCready, M. S. Switching by photochemical trans–cis isomerization of azobenzene substituents in organoplatinum complexes. Organometallics 2012, 31, 6262–6269; https://doi.org/10.1021/om3005405.Search in Google Scholar

Puddephatt, R. J.; Mohamed, E. M.; Paul, D. B. Photoswitchable organoplatinum complexes containing an azobenzene derivative of 3,6-di(2-pyridyl)pyridazine. Can. J. Chem. 2014, 92, 706–715.10.1139/cjc-2013-0588Search in Google Scholar

Puddephatt, R. J.; Moustafa, M. E.; Boyle, P. D. Photoswitchable organoplatinum complexes with an azobenzene derivative of di-2-pyridylamine. New J. Chem. 2020, 44, 2882–2889.10.1039/C9NJ05313ASearch in Google Scholar

Richard, J. P.; Mohamed, E. M.; McCready, M. S. Switching by photochemical trans−cis isomerization of AzobenzeneSubstituents in organoplatinum complexes. Organometallics 2012, 31, 6262–6269; https://doi.org/10.1021/om3005405.Search in Google Scholar

Rimoldi, I.; Facchetti, G. Anticancer platinum(II) complexes bearing N-heterocycle rings. Bioorg. Med. Chem. Lett. 2019, 29, 1257–1263; https://doi.org/10.1016/j.bmcl.2019.03.045.Search in Google Scholar PubMed

Sadler, J. P.; Farrer, J. N.; Woods, J.; Salassa, L.; Zhao, Y.; Robinson, K. S.; Clarkson, G.; Mackay, S. F. A potent trans-diimine platinum anticancer complex photoactivated by visible light. Angew. Chem. Int. Ed. 2010, 49, 8905–8908; https://doi.org/10.1002/anie.201003399.Search in Google Scholar PubMed

Sarkar, B.; Roy, S.; Hartenbach, I. Structures, redox and spectroscopic properties of PdII and PtII complexes containing an azo functionality. Eur. J. Inorg. Chem. 2009a, 17, 2553–2558; https://doi.org/10.1002/ejic.200900419.Search in Google Scholar

Sarkar, B.; Hubner, R.; Pattacini, R.; Hartenbach, I. Combining two non-innocent ligands in isomeric complexes [Pt(pap)mQn]0 (pap = phenylazopyridine, Q = 3, 5-di-tert-butyl-benzoquinone. Dalton Trans. 2009b, 24, 4653–4655; https://doi.org/10.1039/b902645b.Search in Google Scholar PubMed

Sarkar, B.; Deibel, N.; Schweinfurth, D.; Fiedler, J.; Zalis, S. Isomeric separation in donor-acceptor systems of Pd(II) and Pt(II) and a combined structural, electrochemical and spectroelectrochemical study. Dalton Trans. 2011, 40, 9925–9934; https://doi.org/10.1039/c1dt10856e.Search in Google Scholar PubMed

Sengupta, D.; Goswami, S.; Banerjee, R.; Guberman-Pfeffer, M. J.; Patra, A.; Dutta, A.; Pramanick, R.; Narasimhan, S.; Pradhan, N.; Batista, V.; Venkatesan, T.; Goswami, S. Size-selective Pt siderophores based on redox-active azo-aromatic ligands. Chem. Sci. 2020, 11, 9226–9236; https://doi.org/10.1039/d0sc02683b.Search in Google Scholar PubMed PubMed Central

Sinha, C.; Misra, K. T.; Das, D.; Ghosh, P.; Pal, K. C. Chemistry of azoimidazoles: synthesis, spectral characterization, electrochemical studies, and X-ray crystal structures of isomeric dichloro bis[1-alkyl-2-(arylazo)imidazole] complexes of ruthenium(II). Inorg. Chem 1998, 37, 1672–1678; https://doi.org/10.1021/ic970446p.Search in Google Scholar

Sinha, C.; Santra, K. P.; Das, D.; Misra.Roy R., K. T.; Peng, S-M. Chemistry of azopyrimidines, synthesis, spectral characterization, electrochemistry and X-ray crystal structure of bis[2-(arylazo)pyrimidine] complexes of copper(I). Polyhedron 1999, 18, 1909–1915; https://doi.org/10.1016/s0277-5387(99)00085-6.Search in Google Scholar

Sinha, C.; Pal, S.; Das, D.; Chattopadhyay, P.; Panneerselvam, K.; Lu, T-H. Synthesis, spectral and electrochemical properties of 1-alkyl-2-(naphthyl-β-azo)imidazole complexes of platinum(II) and the reaction with pyridine bases. Single-crystal X-ray structure of dichloro-[1-ethyl-2-(naphthyl-β-azo)imidazole]platinum(II). Polyhedron. 2000, 19, 1263–1270.10.1016/S0277-5387(00)00385-5Search in Google Scholar

Sinha, C.; Rauth, K. G.; Pal, S.; Das, D.; Slawin, Z. M. A.; Woollins, D. J. Synthesis, spectral characterization and electrochemical studies of mixed-ligand complexes of platinum(II) with 2-(arylazo)pyridines and catechols. Single-crystal X-ray structure of dichloro{2-(phenylazo) pyridine}platinum(II). Polyhedron 2001, 20, 363–372; https://doi.org/10.1016/s0277-5387(00)00530-1.Search in Google Scholar

Sinha, C.; Senapoti, S.; Jasimuddin, Sk.; Mostafa, G.; Lu, H. T. Coupling of arylamine with coordinated arylazopyrimidine in platinum(II) complexes. Single crystal X-ray structure, spectra and electrochemistry. Polyhedron 2006, 25, 1571–1578; https://doi.org/10.1016/j.poly.2005.10.035.Search in Google Scholar

Sinha, C.; Sen, C.; Patra, C.; Mondol, S.; Datta, A.; Mallick, D.; Mondal, K. T.; Askun, T.; Celikboyun, P.; Cantürk, Z. Platinum(II)-azoimidazole drugs against TB and cancer: structural studies, cytotoxicity and anti-mycobacterial activity. Polyhedron 2018, 152, 1–10; https://doi.org/10.1016/j.poly.2018.05.062.Search in Google Scholar

Taylor, A.; Branch, S.; Day, P. M.; Patriarcac, M.; Whited, M. Atomic spectrometry update. Clinical and biological materials, foods and beverages. J. Anal. A Spectrom. 2009, 24, 535–579; https://doi.org/10.1039/b901500k.Search in Google Scholar

Teets, S. T.; Mu, G.; Cong, L.; Wen, Z.; Wu, I-Chia J.; Kadish, M. K. Homoleptic platinum azo-iminate complexes via hydrogenative cleavage of formazans. Inorg. Chem 2018, 57, 9468–9477; https://doi.org/10.1021/acs.inorgchem.8b01456.Search in Google Scholar PubMed

Todd, C. R.; Lippard, J. S. Structure of duplex DNA containing the cisplatin 1, 2-{Pt(NH3)2}2+-d(GpG) cross-link at 1.77 Å resolution. J. Inorg. Biochem. 2010, 104, 902–908; https://doi.org/10.1016/j.jinorgbio.2010.04.005.Search in Google Scholar PubMed PubMed Central

Tümer, M.; Onur, S.; Güngor, S. A.; Tümer, F. The color, photophysical and electrochemical properties of azo-imineligands and their copper(II) and platinium(II) complexes. J. Mol. Struct. 2020, 127135, 1200; https://doi.org/10.1016/j.molstruc.2019.127135.Search in Google Scholar

Wang, J.; Chai, K.; Jiang, Y.; Han, T.; Niu, J.; Zhang, H.; Zeng, M.; Zhang, L.; Duan, X. Synthesis, DNA binding, topoisomerase I inhibition and antiproliferation activities of three new binuclear terpyridine platinum(II) complexes. Polyhedron 2019, 157, 124–130; https://doi.org/10.1016/j.poly.2018.09.053.Search in Google Scholar

Wang, X.; Wang, X.; Guo, Z. Functionalization of platinum complexes for biomedical applications. Acc. Chem. Res. 2015, 48, 2622–2631; https://doi.org/10.1021/acs.accounts.5b00203.Search in Google Scholar PubMed

Wheate, J. N.; Walker, S.; Craig, E. G.; Oun, R. The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Trans. 2010, 39, 8113–8127; https://doi.org/10.1039/c0dt00292e.Search in Google Scholar PubMed

Wang, Q.; Huang, Z.; Ma, J.; Lu, X.; Zhang, L.; Wang, X.; Wang, G. P. Design, synthesis and biological evaluation of a novel series of glycosylated platinum(iv) complexes as antitumor agents. Dalton Trans. 2016, 45, 10366–10374; https://doi.org/10.1039/c6dt01562j.Search in Google Scholar PubMed

Williams, G. A. J.; Develay, S.; Rochester, L. D.; Murphy, L. Optimising the luminescence of platinum(II) complexes and their application in organic light emitting devices (OLEDs). Coord. Chem. Rev. 2008, 252, 2596–2611; https://doi.org/10.1016/j.ccr.2008.03.014.Search in Google Scholar

Xu, X.; Li, -S. Y.; Peng, B.; Ma, L.; Cao, -L. S.; Bai, L. L.; Yang, C-R.; Meng, Y-Y. Synthesis, crystal structures and antitumor activity of two platinum(II) complexes with methyl hydrazinecarbodithioate derivatives of indolin-2-one. Eur. J. Med. Chem. 2017, 127, 137–146; https://doi.org/10.1016/j.ejmech.2016.12.050.Search in Google Scholar PubMed

Yam, W. W. V.; Wong, M. C. K.; Tang, S. W.; LuZhu, X. X. N. Functionalized platinum(II) terpyridyl alkynyl complexes as colorimetric and luminescence pH sensors. Inorg. Chem. 2005, 44, 1492–1498; https://doi.org/10.1021/ic049079p.Search in Google Scholar PubMed

Zhu, W.; Hao, Z.; Liu, Y.; Huang, Y.; Meng, F. Synthesis and optoelectronic properties of dinuclearcyclometalated platinum (II) complexes containing naphthalene-functionalized carbazole groups in the single-emissive-layer WPLEDs. J. Organomet. Chem. 2017, 835, 52–59.10.1016/j.jorganchem.2017.02.018Search in Google Scholar

Zhu, Y.; Luo, K.; Li, X.; Wang, H.; Yang, C.; Ni, H.; Li, Q. Four new binuclear platinum (II) complexes with 2-(1H)-quinolinone as bridging ligands: synthesis, crystal structure and photophysical properties. J. Lumin. 2018, 204, 296–302; https://doi.org/10.1016/j.jlumin.2018.08.010.Search in Google Scholar

Zoubi, A. W.; A-Hamdani, S. A. A.; Ahmed, D. S.; Ko, G. Y. A new azo-Schiff base: synthesis, characterization, biological activity and theoretical studies of its complexes. Appl. Organomet. Chem. 2017, 32, e3895; https://doi.org/10.1002/aoc.3895.Search in Google Scholar