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Current Bioactive Compounds

Editor-in-Chief

ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

Review Article

Pt(IV) Complexes with Biologically Active and Physicochemical Properties Modifier Ligands

Author(s): Sainath Aher*, Jinhua Zhu, Xiuhua Liu and Laxmikant Borse

Volume 20, Issue 9, 2024

Published on: 24 January, 2024

Article ID: e240124226118 Pages: 19

DOI: 10.2174/0115734072277494231213044339

Price: $65

Abstract

The octahedral Pt(IV) complexes contain either inert or biologically active ligands where the nature of these axial ligands provides additional stability and synergistic biological activity. There are many literature reports from each of the classes mentioning the varied nature of these axial ligands. The targeting, as well as the non-targeting nature of these moieties, exerts additive or synergistic effects of anticancer activity of Pt(II) moieties. Herein, we have discussed the effects of these axially oriented ligands, changes in the non-leaving am(m)ine groups, and changes in the leaving groups on the biological activity. In this review, we have discussed the axial ligands with a focus on the nature of the ligands and alterations in biological activities.

Graphical Abstract

[1]
Rosenberg, B.; VanCamp, L. The successful regression of large solid sarcoma 180 tumors by platinum compounds. Cancer Res., 1970, 30(6), 1799-1802.
[PMID: 5457941]
[2]
Wiltshaw, E. Cisplatin in the treatment of cancer. Platin. Met. Rev., 1979, 23, 90-98.
[3]
Kauffman, G.B.; Pentimalli, R.; Doldi, S.; Hall, M.D. Michele peyrone (1813‐1883), discoverer of cisplatin. Platin. Met. Rev., 2010, 54(4), 250-256.
[http://dx.doi.org/10.1595/147106710X534326]
[4]
Alderden, R.A.; Hall, M.D.; Hambley, T.W. The discovery and development of cisplatin. J. Chem. Educ., 2006, 83(5), 728.
[http://dx.doi.org/10.1021/ed083p728]
[5]
Rosenberg, B.; Vancamp, L.; Trosko, J.; Mansour, V.H. Platinum compounds: A new class of potent antitumour agents. Nature, 1969, 222(5191), 385-386.
[http://dx.doi.org/10.1038/222385a0] [PMID: 5782119]
[6]
Beyerle-Pfnür, R.; Jaworski, S.; Lippert, B.; Schöllhorn, H.; Thewalt, U. Preparation and characterization of (9-methyladenine)triammineplatinum(II) and trans-dihydroxo(9-methyladenine)triammineplatinum(IV) complexes. Inorg. Chim. Acta, 1985, 107(3), 217-222.
[http://dx.doi.org/10.1016/S0020-1693(00)80706-9]
[7]
Vollano, J.F.; Al-Baker, S.; Dabrowiak, J.C.; Schurig, J.E. Comparative antitumor studies on platinum(II) and platinum(IV) complexes containing 1,2-diaminocyclohexane. J. Med. Chem., 1987, 30(4), 716-719.
[http://dx.doi.org/10.1021/jm00387a023] [PMID: 3560163]
[8]
Rose, W.C.; Crosswell, A.R.; Schurig, J.E.; Casazza, A.M. Preclinical antitumor activity of orally administered platinum (IV) complexes. Cancer Chemother. Pharmacol., 1993, 32(3), 197-203.
[http://dx.doi.org/10.1007/BF00685835] [PMID: 8500224]
[9]
Roche, V.F. Foye’s principles of medicinal chemistry; Lippincott Williams & Wilkins Inc: Baltimore, 2013.
[10]
Johnstone, T.C. The crystal structure of oxaliplatin: A case of overlooked pseudo symmetry. Polyhedron, 2014, 67, 429-435.
[http://dx.doi.org/10.1016/j.poly.2013.10.003] [PMID: 24415827]
[11]
Satraplatin FDA Approval Status. Available from: https://www.drugs.com/history/satraplatin.html (Accessed April 8, 2022)
[12]
Satraplatin in children and young adults with refractory solid tumors including brain tumors. NCT01259479, 2022.
[13]
Figg, W.D.; Chau, C.H.; Madan, R.A.; Gulley, J.L.; Gao, R.; Sissung, T.M.; Spencer, S.; Beatson, M.; Aragon-Ching, J.; Steinberg, S.M.; Dahut, W.L. Phase II study of satraplatin and prednisone in patients with metastatic castration-resistant prostate cancer: a pharmacogenetic assessment of outcome and toxicity. Clin. Genitourin. Cancer, 2013, 11(3), 229-237.
[http://dx.doi.org/10.1016/j.clgc.2013.04.007] [PMID: 23684781]
[14]
Wilson, J.J.; Lippard, S.J. Synthetic methods for the preparation of platinum anticancer complexes. Chem. Rev., 2014, 114(8), 4470-4495.
[http://dx.doi.org/10.1021/cr4004314] [PMID: 24283498]
[15]
Johnstone, T.C.; Suntharalingam, K.; Lippard, S.J. The next generation of platinum drugs: targeted Pt(II) agents, nanoparticle delivery, and Pt(IV) prodrugs. Chem. Rev., 2016, 116(5), 3436-3486.
[http://dx.doi.org/10.1021/acs.chemrev.5b00597] [PMID: 26865551]
[16]
Ravera, M.; Gabano, E.; McGlinchey, M.J.; Osella, D. A view on multi-action Pt(IV) antitumor prodrugs. Inorg. Chim. Acta, 2019, 492, 32-47.
[http://dx.doi.org/10.1016/j.ica.2019.04.025]
[17]
Wexselblatt, E.; Gibson, D. What do we know about the reduction of Pt(IV) pro-drugs? J. Inorg. Biochem., 2012, 117, 220-229.
[http://dx.doi.org/10.1016/j.jinorgbio.2012.06.013] [PMID: 22877926]
[18]
Johnstone, T.C.; Alexander, S.M.; Wilson, J.J.; Lippard, S.J. Oxidative halogenation of cisplatin and carboplatin: synthesis, spectroscopy, and crystal and molecular structures of Pt(IV) prodrugs. Dalton Trans., 2015, 44(1), 119-129.
[http://dx.doi.org/10.1039/C4DT02627F] [PMID: 25367395]
[19]
Khattib, D.; Ishan, M.; Karmakar, S.; Kostrhunova, H.; Brabec, V.; Gibson, D. Oxidation of cis‐diamminediacetato Pt(II) with hydrogen peroxide can give rise to two isomeric Pt(IV) products. Chemistry, 2020, 26(43), 9475-9480.
[http://dx.doi.org/10.1002/chem.202001472] [PMID: 32428256]
[20]
Phadnis, P.P.; Sharma, K.S.; Vimalnath, K.V.; Chakravarty, R.; Chakraborty, S.; Dash, A.; Vatsa, R. Facile synthesis of a Pt(IV) prodrug of cisplatin and its intrinsically 195m Pt labeled analog: A step closer to cancer theranostic. Indian J. Nucl. Med., 2021, 36(2), 140-147.
[http://dx.doi.org/10.4103/ijnm.IJNM_188_20] [PMID: 34385784]
[21]
Feazell, R.P.; Nakayama-Ratchford, N.; Dai, H.; Lippard, S.J. Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design. J. Am. Chem. Soc., 2007, 129(27), 8438-8439.
[http://dx.doi.org/10.1021/ja073231f] [PMID: 17569542]
[22]
Pichler, V.; Heffeter, P.; Valiahdi, S.M.; Kowol, C.R.; Egger, A.; Berger, W.; Jakupec, M.A.; Galanski, M.S.; Keppler, B.K. Unsymmetric mono- and dinuclear platinum(IV) complexes featuring an ethylene glycol moiety: synthesis, characterization, and biological activity. J. Med. Chem., 2012, 55(24), 11052-11061.
[http://dx.doi.org/10.1021/jm301645g] [PMID: 23194425]
[23]
Giandomenico, C.M.; Abrams, M.J.; Murrer, B.A.; Vollano, J.F.; Rheinheimer, M.I.; Wyer, S.B.; Bossard, G.E.; Higgins, J.D. Carboxylation of kinetically inert platinum(IV) hydroxy complexes. an entr.acte.ee into orally active platinum(IV) antitumor agents. Inorg. Chem., 1995, 34(5), 1015-21.
[http://dx.doi.org/10.1021/ic00109a004]
[24]
Zhang, J.Z.; Bonnitcha, P.; Wexselblatt, E.; Klein, A.V.; Najajreh, Y.; Gibson, D.; Hambley, T.W. Facile preparation of mono-, di- and mixed-carboxylato platinum(IV) complexes for versatile anticancer prodrug design. Chemistry, 2013, 19(5), 1672-1676.
[http://dx.doi.org/10.1002/chem.201203159] [PMID: 23255183]
[25]
Hall, M.D.; Hambley, T.W. Platinum(IV) antitumour compounds: their bioinorganic chemistry. Coordination Chemistry Reviews, 2002, 232, 49-67.
[http://dx.doi.org/10.1016/S0010-8545(02)00026-7]
[26]
Gabano, E.; Ravera, M.; Osella, D. Pros and cons of bifunctional platinum(IV) antitumor prodrugs: two are (not always) better than one. Dalton Trans., 2014, 43(26), 9813-9820.
[http://dx.doi.org/10.1039/c4dt00911h] [PMID: 24874896]
[27]
Nováková, O.; Vrána, O.; Kiseleva, V.I.; Brabec, V. DNA interactions of antitumor platinum(IV) complexes. Eur. J. Biochem., 1995, 228(3), 616-624.
[http://dx.doi.org/10.1111/j.1432-1033.1995.tb20301.x] [PMID: 7737155]
[28]
Sinisi, M.; Intini, F.P.; Natile, G. Dependence of the reduction products of platinum(IV) prodrugs upon the configuration of the substrate, bulk of the carrier ligands, and nature of the reducing agent. Inorg. Chem., 2012, 51(18), 9694-9704.
[http://dx.doi.org/10.1021/ic300957v] [PMID: 22921246]
[29]
Nemirovski, A.; Kasherman, Y.; Tzaraf, Y.; Gibson, D. Reduction of cis,trans,cis-[PtCl2(OCOCH3)2(NH3)2] by aqueous extracts of cancer cells. J. Med. Chem., 2007, 50(23), 5554-5556.
[http://dx.doi.org/10.1021/jm070740j] [PMID: 17949066]
[30]
Gibson, D. Multi-action Pt(IV) anticancer agents; do we understand how they work? J. Inorg. Biochem., 2019, 191, 77-84.
[http://dx.doi.org/10.1016/j.jinorgbio.2018.11.008] [PMID: 30471522]
[31]
Gibson, D. Platinum(IV) anticancer agents; are we en route to the holy grail or to a dead end? J. Inorg. Biochem., 2021, 217, 111353.
[http://dx.doi.org/10.1016/j.jinorgbio.2020.111353] [PMID: 33477089]
[32]
Babu, T.; Sarkar, A.; Karmakar, S.; Schmidt, C.; Gibson, D. Multiaction Pt(IV) carbamate complexes can codeliver Pt(II) drugs and amine containing bioactive molecules. Inorg. Chem., 2020, 59(7), 5182-5193.
[http://dx.doi.org/10.1021/acs.inorgchem.0c00445] [PMID: 32207294]
[33]
Marotta, C.; Giorgi, E.; Binacchi, F.; Cirri, D.; Gabbiani, C.; Pratesi, A. An overview of recent advancements in anticancer Pt(IV) prodrugs: New smart drug combinations, activation and delivery strategies. Inorg. Chim. Acta, 2023, 548, 121388.
[http://dx.doi.org/10.1016/j.ica.2023.121388]
[34]
Xu, Z.; Tang, W.K.; Zhou, Q.; Chen, S.; Siu, C-K.; Zhu, G. On the hydrolytic stability of unsymmetric platinum(IV) anticancer prodrugs containing axial halogens. Inorg. Chem. Front., 2021, 8(16), 3794-3802.
[http://dx.doi.org/10.1039/D1QI00208B]
[35]
Huang, X.; Huang, R.; Gou, S.; Wang, Z.; Liao, Z.; Wang, H. Combretastatin A-4 analogue: A dual-targeting and tubulin inhibitor containing antitumor Pt(IV) moiety with a unique mode of action. Bioconjug. Chem., 2016, 27(9), 2132-2148.
[http://dx.doi.org/10.1021/acs.bioconjchem.6b00353] [PMID: 27494235]
[36]
Huang, X.; Wang, M.; Wang, C.; Hu, W.; You, Q.; Yang, Y.; Yu, C.; Liao, Z.; Gou, S.; Wang, H. Dual-targeting antitumor conjugates derived from platinum(IV) prodrugs and microtubule inhibitor CA-4 significantly exhibited potent ability to overcome cisplatin resistance. Bioorg. Chem., 2019, 92, 103236.
[http://dx.doi.org/10.1016/j.bioorg.2019.103236] [PMID: 31494328]
[37]
Li, L.; Huang, X.; Huang, R.; Gou, S.; Wang, Z.; Wang, H. Pt(IV) prodrugs containing microtubule inhibitors displayed potent antitumor activity and ability to overcome cisplatin resistance. Eur. J. Med. Chem., 2018, 156, 666-679.
[http://dx.doi.org/10.1016/j.ejmech.2018.07.016] [PMID: 30031977]
[38]
Ma, L.; Wang, N.; Ma, R.; Li, C.; Xu, Z.; Tse, M.K.; Zhu, G. Monochalcoplatin: an actively transported, quickly reducible, and highly potent Pt(IV) anticancer prodrug. Angew. Chem. Int. Ed., 2018, 57(29), 9098-9102.
[http://dx.doi.org/10.1002/anie.201804314] [PMID: 29806087]
[39]
Ma, L.; Ma, R.; Wang, Y.; Zhu, X.; Zhang, J.; Chan, H.C.; Chen, X.; Zhang, W.; Chiu, S.K.; Zhu, G. Chalcoplatin, a dual-targeting and p53 activator-containing anticancer platinum(IV) prodrug with unique mode of action. Chem. Commun. , 2015, 51(29), 6301-6304.
[http://dx.doi.org/10.1039/C4CC10409A] [PMID: 25644651]
[40]
Huang, X.; Liu, Z.; Wang, M.; Yin, X.; Wang, Y.; Dai, L.; Wang, H. Platinum(IV) complexes conjugated with chalcone analogs as dual targeting anticancer agents: In vitro and in vivo studies. Bioorg. Chem., 2020, 105, 104430.
[http://dx.doi.org/10.1016/j.bioorg.2020.104430] [PMID: 33171407]
[41]
Huang, X.; Huang, R.; Wang, Z.; Li, L.; Gou, S.; Liao, Z.; Wang, H. Pt(IV) complexes conjugating with chalcone analogue as inhibitors of microtubule polymerization exhibited selective inhibition in human cancer cells. Eur. J. Med. Chem., 2018, 146, 435-450.
[http://dx.doi.org/10.1016/j.ejmech.2018.01.075] [PMID: 29407969]
[42]
Wang, M.; Liu, Z.; Huang, X.; Chen, Y.; Wang, Y.; Kong, J.; Yang, Y.; Yu, C.; Li, J.; Wang, X.; Wang, H. Dual-target platinum(IV) complexes exhibit antiproliferative activity through DNA damage and induce ER-stress-mediated apoptosis in A549 cells. Bioorg. Chem., 2021, 110, 104741.
[http://dx.doi.org/10.1016/j.bioorg.2021.104741] [PMID: 33647739]
[43]
Li, G.; Zhang, J.; Liu, Z.; Wang, Q.; Chen, Y.; Liu, M.; Li, D.; Han, J.; Wang, B. Development of a series of 4-hydroxycoumarin platinum(IV) hybrids as antitumor agents: Synthesis, biological evaluation and action mechanism investigation. J. Inorg. Biochem., 2019, 194, 34-43.
[http://dx.doi.org/10.1016/j.jinorgbio.2019.02.011] [PMID: 30826588]
[44]
Wang, Q.; Chen, Y.; Li, G.; Liu, Z.; Ma, J.; Liu, M.; Li, D.; Han, J.; Wang, B. Synthesis and evaluation of bi-functional 7-hydroxycoumarin platinum(IV) complexes as antitumor agents. Bioorg. Med. Chem., 2019, 27(10), 2112-2121.
[http://dx.doi.org/10.1016/j.bmc.2019.04.009] [PMID: 30981607]
[45]
Qin, X.; Fang, L.; Zhao, J.; Gou, S. Theranostic Pt(IV) conjugate with target selectivity for androgen receptor. Inorg. Chem., 2018, 57(9), 5019-5029.
[http://dx.doi.org/10.1021/acs.inorgchem.8b00083] [PMID: 29667815]
[46]
Hua, W.; Zhao, J.; Hu, W.; Gou, S. Combination of 7-hydroxycoumarin in a platinum(IV) complex derived from cisplatin enhanced cytotoxicity with multiple mechanisms of action. J. Inorg. Biochem., 2018, 186, 17-23.
[http://dx.doi.org/10.1016/j.jinorgbio.2018.05.015] [PMID: 29807243]
[47]
Yap, S.Q.; Chin, C.F.; Hong Thng, A.H.; Pang, Y.Y.; Ho, H.K.; Ang, W.H. Finely tuned asymmetric platinum(IV) anticancer complexes: Structure-activity relationship and application as orally available prodrugs. ChemMedChem, 2017, 12(4), 300-311.
[http://dx.doi.org/10.1002/cmdc.201600577] [PMID: 28028938]
[48]
Abu Ammar, A.; Raveendran, R.; Gibson, D.; Nassar, T.; Benita, S. A lipophilic Pt(IV) oxaliplatin derivative enhances antitumor activity. J. Med. Chem., 2016, 59(19), 9035-9046.
[http://dx.doi.org/10.1021/acs.jmedchem.6b00955] [PMID: 27603506]
[49]
Kang, X.; Yu, Y.; Chen, Z.; Wu, Y.; Wei, D.; Zhao, Y.; Wang, F.; Xiao, H. A negatively charged Pt(IV) prodrug for electrostatic complexation with polymers to overcome cisplatin resistance. J. Mater. Chem. B Mater. Biol. Med., 2019, 7(21), 3346-3350.
[http://dx.doi.org/10.1039/C9TB00155G]
[50]
Ravera, M.; Gabano, E.; Zanellato, I.; Fregonese, F.; Pelosi, G.; Platts, J.A.; Osella, D. Antiproliferative activity of a series of cisplatin-based Pt(IV)-acetylamido/carboxylato prodrugs. Dalton Trans., 2016, 45(12), 5300-5309.
[http://dx.doi.org/10.1039/C5DT04905A] [PMID: 26903367]
[51]
Gramatica, P.; Papa, E.; Luini, M.; Monti, E.; Gariboldi, M.B.; Ravera, M.; Gabano, E.; Gaviglio, L.; Osella, D. Antiproliferative Pt(IV) complexes: synthesis, biological activity, and quantitative structure–activity relationship modeling. J. Biol. Inorg. Chem., 2010, 15(7), 1157-1169.
[http://dx.doi.org/10.1007/s00775-010-0676-4] [PMID: 20526854]
[52]
Lozano-Pérez, A.A.; Gil, A.L.; Pérez, S.A.; Cutillas, N.; Meyer, H.; Pedreño, M.; D Aznar-Cervantes, S.; Janiak, C.; Cenis, J.L.; Ruiz, J. Antitumor properties of platinum(IV) prodrug-loaded silk fibroin nanoparticles. Dalton Trans., 2015, 44(30), 13513-13521.
[http://dx.doi.org/10.1039/C5DT00378D] [PMID: 25799077]
[53]
Schreiber-Brynzak, E.; Pichler, V.; Heffeter, P.; Hanson, B.; Theiner, S.; Lichtscheidl-Schultz, I.; Kornauth, C.; Bamonti, L.; Dhery, V.; Groza, D.; Berry, D.; Berger, W.; Galanski, M.S.; Jakupec, M.A.; Keppler, B.K. Behavior of platinum(IV) complexes in models of tumor hypoxia: cytotoxicity, compound distribution and accumulation. Metallomics, 2016, 8(4), 422-433.
[http://dx.doi.org/10.1039/c5mt00312a] [PMID: 26860208]
[54]
Ravera, M.; Gabano, E.; Zanellato, I.; Bonarrigo, I.; Alessio, M.; Arnesano, F.; Galliani, A.; Natile, G.; Osella, D. Cellular trafficking, accumulation and DNA platination of a series of cisplatin-based dicarboxylato Pt(IV) prodrugs. J. Inorg. Biochem., 2015, 150, 1-8.
[http://dx.doi.org/10.1016/j.jinorgbio.2015.05.012] [PMID: 26042542]
[55]
Wang, Z.; Ma, R.; Yan, L.; Chen, X.; Zhu, G. Combined chemotherapy and photodynamic therapy using a nanohybrid based on layered double hydroxides to conquer cisplatin resistance. Chem. Commun. , 2015, 51(58), 11587-11590.
[http://dx.doi.org/10.1039/C5CC04376J] [PMID: 26096645]
[56]
Kim, W.K.; Kwon, Y.E. Comparative nephrotoxicity of cisplatin and new octahedral Pt(IV) complexes. Cancer Chemother. Pharmacol., 2007, 60(2), 237-243.
[http://dx.doi.org/10.1007/s00280-006-0366-7] [PMID: 17089165]
[57]
Margiotta, N.; Savino, S.; Marzano, C.; Pacifico, C.; Hoeschele, J.D.; Gandin, V.; Natile, G. Cytotoxicity-boosting of kiteplatin by Pt(IV) prodrugs with axial benzoate ligands. J. Inorg. Biochem., 2016, 160, 85-93.
[http://dx.doi.org/10.1016/j.jinorgbio.2015.11.028] [PMID: 26775068]
[58]
Li, J.; Zheng, L.; Xiao, H.; Li, C.; Wu, S.; Xiao, Y.; Liu, J.; Zhang, B. Design of zwitterionic polyester based nano-carriers for platinum(IV) prodrug delivery. Polym. Chem., 2019, 10(39), 5353-5363.
[http://dx.doi.org/10.1039/C9PY00870E]
[59]
Ma, R.; Wang, Y.; Yan, L.; Ma, L.; Wang, Z.; Chan, H.C.; Chiu, S.K.; Chen, X.; Zhu, G. Efficient co-delivery of a Pt(IV) prodrug and a p53 activator to enhance the anticancer activity of cisplatin. Chem. Commun. , 2015, 51(37), 7859-7862.
[http://dx.doi.org/10.1039/C4CC09879J] [PMID: 25854514]
[60]
Margiotta, N.; Savino, S.; Denora, N.; Marzano, C.; Laquintana, V.; Cutrignelli, A.; Hoeschele, J.D.; Gandin, V.; Natile, G. Encapsulation of lipophilic kiteplatin Pt(IV) prodrugs in PLGA-PEG micelles. Dalton Trans., 2016, 45(33), 13070-13081.
[http://dx.doi.org/10.1039/C6DT00763E] [PMID: 27094010]
[61]
Bouché, M.; Bonnefont, A.; Achard, T.; Bellemin-Laponnaz, S. Exploring diversity in platinum(IV) N-heterocyclic carbene complexes: synthesis, characterization, reactivity and biological evaluation. Dalton Trans., 2018, 47(33), 11491-11502.
[http://dx.doi.org/10.1039/C8DT02113A] [PMID: 30074048]
[62]
Xu, Z.; Li, C.; Tong, Z.; Ma, L.; Tse, M.K.; Zhu, G. Halogenated PtIV complexes from n-halosuccinimide oxidation of PtII antitumor drugs: synthesis, mechanistic investigation, and cytotoxicity. Eur. J. Inorg. Chem., 2017, 2017(12), 1706-1712.
[http://dx.doi.org/10.1002/ejic.201601130]
[63]
New, E.J.; Duan, R.; Zhang, J.Z.; Hambley, T.W. Investigations using fluorescent ligands to monitor platinum(iv) reduction and platinum(ii) reactions in cancer cells. Dalton Trans., 2009, 16(16), 3092-3101.
[http://dx.doi.org/10.1039/b821603g] [PMID: 19352538]
[64]
Xu, Z.; Wang, Z.; Yiu, S.M.; Zhu, G. Mono- and di-bromo platinum(IV) prodrugs via oxidative bromination: Synthesis, characterization, and cytotoxicity. Dalton Trans., 2015, 44(46), 19918-19926.
[http://dx.doi.org/10.1039/C5DT03101J] [PMID: 26514681]
[65]
Harringer, S.; Hejl, M.; Enyedy, É.A.; Jakupec, M.A.; Galanski, M.S.; Keppler, B.K.; Dyson, P.J.; Varbanov, H.P. Multifunctional Pt(IV) prodrug candidates featuring the carboplatin core and deferoxamine. Dalton Trans., 2021, 50(23), 8167-8178.
[http://dx.doi.org/10.1039/D1DT00214G] [PMID: 34031671]
[66]
Reithofer, M.R.; Valiahdi, S.M.; Jakupec, M.A.; Arion, V.B.; Egger, A.; Galanski, M.S.; Keppler, B.K. Novel di- and tetracarboxylatoplatinum(IV) complexes. Synthesis, characterization, cytotoxic activity, and DNA platination. J. Med. Chem., 2007, 50(26), 6692-6699.
[http://dx.doi.org/10.1021/jm070897b] [PMID: 18031001]
[67]
Varbanov, H.P.; Valiahdi, S.M.; Kowol, C.R.; Jakupec, M.A.; Galanski, M.S.; Keppler, B.K. Novel tetracarboxylatoplatinum(IV) complexes as carboplatin prodrugs. Dalton Trans., 2012, 41(47), 14404-14415.
[http://dx.doi.org/10.1039/C2DT31366A] [PMID: 22886297]
[68]
Shi, Y.; Liu, S.A.; Kerwood, D.J.; Goodisman, J.; Dabrowiak, J.C. Pt(IV) complexes as prodrugs for cisplatin. J. Inorg. Biochem., 2012, 107(1), 6-14.
[http://dx.doi.org/10.1016/j.jinorgbio.2011.10.012] [PMID: 22169035]
[69]
Zheng, Y.R.; Suntharalingam, K.; Johnstone, T.C.; Yoo, H.; Lin, W.; Brooks, J.G.; Lippard, S.J. Pt(IV) prodrugs designed to bind non-covalently to human serum albumin for drug delivery. J. Am. Chem. Soc., 2014, 136(24), 8790-8798.
[http://dx.doi.org/10.1021/ja5038269] [PMID: 24902769]
[70]
Leal, J.; Santos, L.; Fernández-Aroca, D.M.; Cuevas, J.V.; Martínez, M.A.; Massaguer, A.; Jalón, F.A.; Ruiz-Hidalgo, M.J.; Sánchez-Prieto, R.; Rodríguez, A.M.; Castañeda, G.; Durá, G.; Carrión, M.C.; Barrabés, S.; Manzano, B.R. Effect of the aniline fragment in Pt(II) and Pt(IV) complexes as anti-proliferative agents. Standard reduction potential as a more reliable parameter for Pt(IV) compounds than peak reduction potential. J. Inorg. Biochem., 2021, 218, 111403.
[http://dx.doi.org/10.1016/j.jinorgbio.2021.111403] [PMID: 33730639]
[71]
Choi, H.K.; Bau, R.; Bau, R. Octahedral complexes of anti-cancer Pt(IV)(cyclohexyldiamine) agents with 9-methylguanine. Biochem. Biophys. Res. Commun., 1988, 156(3), 1125-1129.
[http://dx.doi.org/10.1016/S0006-291X(88)80749-6] [PMID: 3190690]
[72]
Ang, W.H.; Pilet, S.; Scopelliti, R.; Bussy, F.; Juillerat-Jeanneret, L.; Dyson, P.J. Synthesis and characterization of platinum(IV) anticancer drugs with functionalized aromatic carboxylate ligands: Influence of the ligands on drug efficacies and uptake. J. Med. Chem., 2005, 48(25), 8060-8069.
[http://dx.doi.org/10.1021/jm0506468] [PMID: 16335930]
[73]
Lorenzo, J.; Delgado, A.; Montaña, Á.M.; Mesas, J.M.; Alegre, M.T.; Rodríguez, M.C.; Avilés, F.X. Synthesis, biological evaluation and SAR studies of novel bicyclic antitumor platinum(IV) complexes. Eur. J. Med. Chem., 2014, 83, 374-388.
[http://dx.doi.org/10.1016/j.ejmech.2014.06.042] [PMID: 24980119]
[74]
Wilson, J.J.; Lippard, S.J. Synthesis, characterization, and cytotoxicity of platinum(IV) carbamate complexes. Inorg. Chem., 2011, 50(7), 3103-3115.
[http://dx.doi.org/10.1021/ic2000816] [PMID: 21361279]
[75]
Utku, S.; Gumus, F.; Tezcan, S.; Serin, M.S.; Ozkul, A. Synthesis, characterization, cytotoxicity, and DNA binding of some new platinum(II) and platinum(IV) complexes with benzimidazole ligands. J. Enzyme Inhib. Med. Chem., 2010, 25(4), 502-508.
[http://dx.doi.org/10.3109/14756360903282858] [PMID: 20233087]
[76]
Chen, S.; Yao, H.; Zhou, Q.; Tse, M.K.; Gunawan, Y.F.; Zhu, G. Stability, reduction, and cytotoxicity of platinum(IV) anticancer prodrugs bearing carbamate axial ligands: Comparison with their carboxylate analogues. Inorg. Chem., 2020, 59(16), 11676-11687.
[http://dx.doi.org/10.1021/acs.inorgchem.0c01541] [PMID: 32799457]
[77]
Alibrahim, K.A.; Al-Saif, F.A.; Alghamdi, M.T.; El-Shahawi, M.S.; Moustafa, Y.M.; Refat, M.S. Synthesis, spectroscopic, thermal, antimicrobial and electrochemical characterization of some novel Ru(III), Pt(IV) and Ir(III) complexes of pipemidic acid. RSC Advances, 2018, 8(40), 22515-22529.
[http://dx.doi.org/10.1039/C8RA03879A] [PMID: 35539728]
[78]
Hall, M.D.; Alderden, R.A.; Zhang, M.; Beale, P.J.; Cai, Z.; Lai, B.; Stampfl, A.P.J.; Hambley, T.W. The fate of platinum(II) and platinum(IV) anti-cancer agents in cancer cells and tumours. J. Struct. Biol., 2006, 155(1), 38-44.
[http://dx.doi.org/10.1016/j.jsb.2006.01.011] [PMID: 16630726]
[79]
Cubo, L.; Hambley, T.W.; Sanz Miguel, P.J.; Carnero, A.; Navarro-Ranninger, C.; Quiroga, A.G. The preparation and characterization of trans-platinum(IV) complexes with unusually high cytotoxicity. Dalton Trans., 2011, 40(2), 344-347.
[http://dx.doi.org/10.1039/C0DT00565G] [PMID: 20936210]
[80]
Chen, C.K.J.; Kappen, P.; Hambley, T.W. The reduction of cis -platinum(IV) complexes by ascorbate and in whole human blood models using 1H NMR and XANES spectroscopy. Metallomics, 2019, 11(3), 686-695.
[http://dx.doi.org/10.1039/c9mt00003h] [PMID: 30839039]
[81]
Reithofer, M.R.; Bytzek, A.K.; Valiahdi, S.M.; Kowol, C.R.; Groessl, M.; Hartinger, C.G.; Jakupec, M.A.; Galanski, M.S.; Keppler, B.K. Tuning of lipophilicity and cytotoxic potency by structural variation of anticancer platinum(IV) complexes. J. Inorg. Biochem., 2011, 105(1), 46-51.
[http://dx.doi.org/10.1016/j.jinorgbio.2010.09.006] [PMID: 21134601]
[82]
Chin, C.F.; Tian, Q.; Setyawati, M.I.; Fang, W.; Tan, E.S.Q.; Leong, D.T.; Ang, W.H. Tuning the activity of platinum(IV) anticancer complexes through asymmetric acylation. J. Med. Chem., 2012, 55(17), 7571-7582.
[http://dx.doi.org/10.1021/jm300580y] [PMID: 22876932]
[83]
Pichler, V.; Valiahdi, S.M.; Jakupec, M.A.; Arion, V.B.; Galanski, M.S.; Keppler, B.K. Mono-carboxylated diaminedichloridoplatinum(IV) complexes – selective synthesis, characterization, and cytotoxicity. Dalton Trans., 2011, 40(32), 8187-8192.
[http://dx.doi.org/10.1039/C1DT10301F] [PMID: 21743934]
[84]
Mihajlović, L.E.; Savić, A.; Poljarević, J.; Vučković, I.; Mojić, M.; Bulatović, M.; Maksimović-Ivanić, D.; Mijatović, S.; Kaluđerović, G.N.; Stošić-Grujičić, S.; Miljković, Đ.; Grgurić-Šipka, S.; Sabo, T.J. Novel methylene modified cyclohexyl ethylenediamine-N,N′-diacetate ligands and their platinum(IV) complexes. Influence on biological activity. J. Inorg. Biochem., 2012, 109, 40-48.
[http://dx.doi.org/10.1016/j.jinorgbio.2012.01.012] [PMID: 22369771]
[85]
Łakomska, I.; Fandzloch, M.; Wojtczak, A.; Szłyk, E. Platinum(IV) coordination compounds containing 5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one as nonleaving ligand. Molecular and cytotoxicity in vitro characterization. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2011, 79(3), 497-501.
[http://dx.doi.org/10.1016/j.saa.2011.03.019] [PMID: 21536486]
[86]
Casas, J.S.; Castiñeiras, A.; Parajó, Y.; Sánchez, A.; Sánchez-González, Á.; Sordo, J. Synthesis and cytotoxicity of new Pt(IV) complexes of 2,2′-biimidazole and derivatives. Polyhedron, 2005, 24(10), 1196-1202.
[http://dx.doi.org/10.1016/j.poly.2005.04.008]
[87]
Lazić, J.M.; Vučićević, L.; Grgurić-Šipka, S.; Janjetović, K.; Kaluđerović, G.N.; Misirkić, M.; Gruden-Pavlović, M.; Popadić, D.; Paschke, R.; Trajković, V.; Sabo, T.J. Synthesis and in vitro anticancer activity of octahedral platinum(IV) complexes with cyclohexyl-functionalized ethylenediamine-N,N′-diacetate-type ligands. ChemMedChem, 2010, 5(6), 881-889.
[http://dx.doi.org/10.1002/cmdc.201000058] [PMID: 20408161]
[88]
Kwon, Y.E.; Whang, K.J.; Park, Y.J.; Kim, K.H. Synthesis, characterization and antitumor activity of novel octahedral Pt(IV) complexes. Bioorg. Med. Chem., 2003, 11(8), 1669-1676.
[http://dx.doi.org/10.1016/S0968-0896(03)00044-0] [PMID: 12659753]
[89]
Varbanov, H.; Valiahdi, S.M.; Legin, A.A.; Jakupec, M.A.; Roller, A.; Galanski, M.S.; Keppler, B.K. Synthesis and characterization of novel bis(carboxylato)dichloridobis(ethylamine)platinum(IV) complexes with higher cytotoxicity than cisplatin. Eur. J. Med. Chem., 2011, 46(11), 5456-5464.
[http://dx.doi.org/10.1016/j.ejmech.2011.09.006] [PMID: 21940073]
[90]
Varbanov, H.P.; Göschl, S.; Heffeter, P.; Theiner, S.; Roller, A.; Jensen, F.; Jakupec, M.A.; Berger, W.; Galanski, M.S.; Keppler, B.K. A novel class of bis- and tris-chelate diam(m)inebis (dicarboxylato)platinum(IV) complexes as potential anticancer prodrugs. J. Med. Chem., 2014, 57(15), 6751-6764.
[http://dx.doi.org/10.1021/jm500791c] [PMID: 25032896]
[91]
Barbanente, A.; Gandin, V.; Ditaranto, N.; Marzano, C.; Hoeschele, J.D.; Suranna, G.P.; Papadia, P.; Natile, G.; Margiotta, N.A. Pt(IV) prodrug of kiteplatin with the bone-targeting pyrophosphate ligand. Inorg. Chim. Acta, 2019, 494, 98-104.
[http://dx.doi.org/10.1016/j.ica.2019.05.011]
[92]
Haputhanthri, R.; Ojha, R.; Izgorodina, E.I.; Guo, S.X.; Deacon, G.B.; McNaughton, D.; Wood, B.R. A spectroscopic investigation into the binding of novel platinum(IV) and platium(II) anticancer drugs with DNA. Vib. Spectrosc., 2017, 92, 82-95.
[http://dx.doi.org/10.1016/j.vibspec.2017.02.006]
[93]
Ionescu, A.; Godbert, N.; Aiello, I.; Ricciardi, L.; La Deda, M.; Crispini, A.; Sicilia, E.; Ghedini, M. Anionic cyclometalated Pt(II) and Pt(IV) complexes respectively bearing one or two 1,2-benzenedithiolate ligands. Dalton Trans., 2018, 47(33), 11645-11657.
[http://dx.doi.org/10.1039/C8DT02444H] [PMID: 30095835]
[94]
Hambley, T.W.; Battle, A.R.; Deacon, G.B.; Lawrenz, E.T.; Fallon, G.D.; Gatehouse, B.M.; Webster, L.K.; Rainone, S. Modifying the properties of platinum(IV) complexes in order to increase biological effectiveness. J. Inorg. Biochem., 1999, 77(1-2), 3-12.
[http://dx.doi.org/10.1016/S0162-0134(99)00133-6] [PMID: 10626347]
[95]
Bouché, M.; Vincent, B.; Achard, T.; Bellemin-Laponnaz, S. N-heterocyclic carbene platinum(IV) as metallodrug candidates: Synthesis and 195Pt NMR chemical shift trend. Molecules, 2020, 25(14), 3148.
[http://dx.doi.org/10.3390/molecules25143148] [PMID: 32660104]
[96]
Bakalova, A.; Varbanov, H.; Buyukliev, R.; Stanchev, S.; Momekov, G.; Ivanov, D. Novel Pt(II) and Pt(IV) complexes with 3-amino-5-methyl-5-(4-pyridyl)-2,4-imidazolidenedione. Synthesis, physicochemical, chemometric and pharmacological investigation. Inorg. Chim. Acta, 2010, 363(7), 1568-1576.
[http://dx.doi.org/10.1016/j.ica.2010.01.008]
[97]
Bakalova, A.; Varbanov, H.; Buyukliev, R.; Momekov, G.; Ferdinandov, D.; Konstantinov, S.; Ivanov, D. Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione. Eur. J. Med. Chem., 2008, 43(5), 958-965.
[http://dx.doi.org/10.1016/j.ejmech.2007.06.025] [PMID: 17707952]
[98]
Escolà, A.; Crespo, M.; López, C.; Quirante, J.; Jayaraman, A.; Polat, I.H.; Badía, J.; Baldomà, L.; Cascante, M. On the stability and biological behavior of cyclometallated Pt(IV) complexes with halido and aryl ligands in the axial positions. Bioorg. Med. Chem., 2016, 24(22), 5804-5815.
[http://dx.doi.org/10.1016/j.bmc.2016.09.037] [PMID: 27670096]
[99]
Łakomska, I.; Wojtczak, A.; Sitkowski, J.; Kozerski, L.; Szłyk, E. Platinum(IV) complexes with purine analogs. Studies of molecular structure and antiproliferative activity in vitro. Polyhedron, 2008, 27(13), 2765-2770.
[http://dx.doi.org/10.1016/j.poly.2008.05.032]
[100]
Kelly, M.E.; Dietrich, A.; Gómez-Ruiz, S.; Kalinowski, B.; Kaluderović, G.N.; Müller, T.; Paschke, R.; Schmidt, J.; Steinborn, D.; Wagner, C.; Schmidt, H. Platinum(IV) metallacrown ethers: Synthesis, structures, host properties and anticancer evaluation. Organometallics, 2008, 27(19), 4917-4927.
[http://dx.doi.org/10.1021/om800323z]
[101]
Perfahl, S.; Bodtke, A.; Pracharova, J.; Kasparkova, J.; Brabec, V.; Cuadrado, J.; Stürup, S.; Schulzke, C.; Bednarski, P.J. Preparation of bis(5-phenyltetrazolato) Pt(II) and Pt(IV) analogues of transplatin and in vitro evaluation for antitumor activity. Inorg. Chim. Acta, 2017, 456, 86-94.
[http://dx.doi.org/10.1016/j.ica.2016.11.017]
[102]
Jolley, J.N.; Yanovsky, A.I.; Kelland, L.R.; Nolan, K.B. Synthesis and antitumour activity of platinum(II) and platinum(IV) complexes containing ethylenediamine-derived ligands having alcohol, carboxylic acid and acetate substituents. J. Inorg. Biochem., 2001, 83(2-3), 91-100.
[http://dx.doi.org/10.1016/S0162-0134(00)00190-2] [PMID: 11237267]
[103]
McGhie, B.S.; Sakoff, J.; Gilbert, J.; Aldrich-Wright, J.R. Synthesis and characterisation of platinum(IV) polypyridyl complexes with halide axial ligands. Inorg. Chim. Acta, 2019, 495, 118964.
[http://dx.doi.org/10.1016/j.ica.2019.118964]
[104]
Song, R.; Park, S.Y.; Kim, Y.S.; Kim, Y.; Kim, S.J.; Ahn, B.T.; Sohn, Y.S. Synthesis and cytotoxicity of new platinum(IV) complexes of mixed carboxylates. J. Inorg. Biochem., 2003, 96(2-3), 339-345.
[http://dx.doi.org/10.1016/S0162-0134(03)00149-1] [PMID: 12888269]
[105]
Garnuszek, P.; Maurin, M.; Skierski, J.S.; Koronkiewicz, M.; Witowska-Jarosz, J. Synthesis and preliminary evaluation of the new water-soluble radioactive platinum(IV) complexes. J. Inorg. Biochem., 2004, 98(3), 553-559.
[http://dx.doi.org/10.1016/j.jinorgbio.2003.12.021] [PMID: 14987857]
[106]
Ameta, R.K.; Singh, M.; Kale, R.K. Synthesis and structure-activity relationship of benzylamine supported platinum(iv) complexes. New J. Chem., 2013, 37(5), 1501-1508.
[http://dx.doi.org/10.1039/c3nj41141a]
[107]
Deo, K.M.; Sakoff, J.; Gilbert, J.; Zhang, Y.; Aldrich Wright, J.R. Synthesis, characterisation and influence of lipophilicity on cellular accumulation and cytotoxicity of unconventional platinum(IV) prodrugs as potent anticancer agents. Dalton Trans., 2019, 48(46), 17228-17240.
[http://dx.doi.org/10.1039/C9DT04049H] [PMID: 31728483]
[108]
Deo, K.M.; Sakoff, J.; Gilbert, J.; Zhang, Y.; Aldrich Wright, J.R. Synthesis, characterisation and potent cytotoxicity of unconventional platinum(IV) complexes with modified lipophilicity. Dalton Trans., 2019, 48(46), 17217-17227.
[http://dx.doi.org/10.1039/C9DT03339D] [PMID: 31729519]
[109]
Bauer, E.; Domingo, X.; Balcells, C.; Polat, I.H.; Crespo, M.; Quirante, J.; Badía, J.; Baldomà, L.; Font-Bardia, M.; Cascante, M. Synthesis, characterization and biological activity of new cyclometallated platinum(IV) iodido complexes. Dalton Trans., 2017, 46(43), 14973-14987.
[http://dx.doi.org/10.1039/C7DT03448B] [PMID: 29048088]
[110]
Harper, B.W.J.; Petruzzella, E.; Sirota, R.; Faccioli, F.F.; Aldrich-Wright, J.R.; Gandin, V.; Gibson, D. Synthesis, characterization and in vitro and in vivo anticancer activity of Pt( IV ) derivatives of [Pt(1S,2S-DACH)(5,6-dimethyl-1,10-phenanthroline)]. Dalton Trans., 2017, 46(21), 7005-7019.
[http://dx.doi.org/10.1039/C7DT01054K] [PMID: 28513693]
[111]
Zhao, X.; Zhang, Y.; Hou, X.; Shi, J.; Shen, S.; Huo, S. Synthesis, characterization, and cytotoxicity of Pt(IV) complexes containing 1,10-phenanthroline and 2,2′-bipyridine and diaminocyclohexane ligands. Trans. Met. Chem., 2017, 42(3), 219-228.
[http://dx.doi.org/10.1007/s11243-017-0125-0]
[112]
Mishra, A.; Mishra, S.; Manav, N.; Saluja, D.; Chandra, R.; Kaushik, N. Synthesis, characterization, antibacterial and cytotoxic study of platinum (IV) complexes. Bioorg. Med. Chem., 2006, 14(18), 6333-6340.
[http://dx.doi.org/10.1016/j.bmc.2006.05.047] [PMID: 16765599]
[113]
Sharma, N.K.; Ameta, R.K.; Singh, M. Spectrophotometric and physicochemical studies of newly synthesized anticancer Pt(IV) complexes and their interactions with CT-DNA. J. Mol. Liq., 2016, 222, 752-761.
[http://dx.doi.org/10.1016/j.molliq.2016.07.101]
[114]
Solé, M.; Balcells, C.; Crespo, M.; Quirante, J.; Badia, J.; Baldomà, L.; Font-Bardia, M.; Cascante, M. Synthesis, characterization and biological activity of new cyclometallated platinum(IV) complexes containing a para -tolyl ligand. Dalton Trans., 2018, 47(27), 8956-8971.
[http://dx.doi.org/10.1039/C8DT01124A] [PMID: 29922789]
[115]
Kaluđerović, G.N.; Kommera, H.; Schwieger, S.; Paethanom, A.; Kunze, M.; Schmidt, H.; Paschke, R.; Steinborn, D. Synthesis, characterization, in vitro antitumoral investigations and interaction with plasmid pBR322 DNA of R2eddp-platinum(iv) complexes (R = Et, n-Pr). Dalton Trans., 2009, 48(48), 10720-10726.
[http://dx.doi.org/10.1039/b911597h]
[116]
Xu, Z.; Chan, H.M.; Li, C.; Wang, Z.; Tse, M.K.; Tong, Z.; Zhu, G. Synthesis, structure, and cytotoxicity of oxaliplatin-based platinum(IV) anticancer prodrugs bearing one axial fluoride. Inorg. Chem., 2018, 57(14), 8227-8235.
[http://dx.doi.org/10.1021/acs.inorgchem.8b00706] [PMID: 29943979]
[117]
Rehm, T.; Rothemund, M.; Dietel, T.; Kempe, R.; Schobert, R. Synthesis, structures and cytotoxic effects in vitro of cis - and trans -[Pt(IV) Cl4 (NHC)2] complexes and their Pt(II) precursors. Dalton Trans., 2019, 48(43), 16358-16365.
[http://dx.doi.org/10.1039/C9DT02438G] [PMID: 31624819]
[118]
Höfer, D.; Varbanov, H.P.; Legin, A.; Jakupec, M.A.; Roller, A.; Galanski, M.S.; Keppler, B.K. Tetracarboxylatoplatinum(IV) complexes featuring monodentate leaving groups - A rational approach toward exploiting the platinum(IV) prodrug strategy. J. Inorg. Biochem., 2015, 153, 259-271.
[http://dx.doi.org/10.1016/j.jinorgbio.2015.08.018] [PMID: 26365319]
[119]
Trávníček, Z.; Popa, I.; Čajan, M.; Herchel, R.; Marek, J. The first platinum(IV) complexes involving aromatic cytokinins or cyclin-dependent kinase inhibitors derived from 6-benzylaminopurine: X-ray structures of (BohH22+) [PtCl6] H2O and (RosH22+) 2 [PtCl6] Cl2 4H2O. Polyhedron, 2007, 26(18), 5271-5282.
[http://dx.doi.org/10.1016/j.poly.2007.07.026]
[120]
Zare Dehnavi, M.; Ostad, S.N.; Abedi, A. The influence of the nonleaving group on the anticancer activity of tetrachlorido platinum(IV) complexes with pyridine/bipyridine derivatives. Inorg. Chim. Acta, 2019, 486, 594-601.
[http://dx.doi.org/10.1016/j.ica.2018.11.023]
[121]
Rakić, G.M.; Grgurić-Šipka, S.; Kaluđerović, G.N.; Bette, M.; Filipović, L.; Aranđelović, S.; Radulović, S.; Tešić, Ž.L. The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines. Eur. J. Med. Chem., 2012, 55, 214-219.
[http://dx.doi.org/10.1016/j.ejmech.2012.07.019] [PMID: 22858225]
[122]
Chen, C.K.J.; Kappen, P.; Gibson, D.; Hambley, T.W. Trans-Platinum(IV) pro-drugs that exhibit unusual resistance to reduction by endogenous reductants and blood serum but are rapidly activated inside cells: 1 H NMR and XANES spectroscopy study. Dalton Trans., 2020, 49(23), 7722-7736.
[http://dx.doi.org/10.1039/D0DT01622E] [PMID: 32469362]

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