Automated approach for the evaluation of glutathione-S-transferase P1-1 inhibition by organometallic anticancer compounds

References

• Sau A, Pellizzari Tregno F, Valentino F, et al. Glutathione transferases and development of new principles to overcome drug resistance. Arch Biochem Biophys 2010;500:1527–22.
   Web of Science ®Google Scholar
• Mathew N, Kalyanasundaram M, Balaraman K. Glutathione S-transferase (GST) inhibitors. Expert Opin Therap Pat 2006;16:431–44.
   Web of Science ®Google Scholar
• Di Pietro G, Magno LA, Rios-Santos F. Glutathione S-transferases: an overview in cancer research. Expert Opin Drug Metab Toxicol 2010;6:153–70.
   PubMed Web of Science ®Google Scholar
• Tew KD, et al. Glutathione-associated enzymes in the human cell lines of the national cancer institute drug screening program. Mol Pharmacol 1996;50:149–59.
   PubMed Web of Science ®Google Scholar
• Morrow CS, Smitherman PK, Diah SK, et al. Coordinated action of glutathione S-Transferases (GSTs) and multidrug resistance protein 1 (MRP1) in antineoplastic drug detoxification. Mechanism of GST A1-1- and MRP1-associated resistance to chlorambucil in MCF7 breast carcinoma cells. J Biol Chem 1998;273:20114–20.
   PubMed Web of Science ®Google Scholar
• Ruzza P, Calderan A. Glutathione Transferase (GST)-activated prodrugs. Pharmaceutics 2013;5:220–31.
   PubMedGoogle Scholar
• Singh S. Cytoprotective and regulatory functions of glutathione S-transferases in cancer cell proliferation and cell death. Cancer Chemother Pharmacol 2015;75:1–15.
   PubMed Web of Science ®Google Scholar
• Enache TA, Oliveira-Brett AM. Electrochemical evaluation of glutathione S-transferase kinetic parameters. Bioelectrochemistry 2015;101:46–51.
   PubMed Web of Science ®Google Scholar
• Dirican O, Kaygin P, Oguztuzun S, et al. Immunocytochemical evaluation of glutathione-s-transferase p1 enzyme in patients with rheumatoid arthritis. HLA 2019;93:336.
   Web of Science ®Google Scholar
• Kool J, Eggink M, van Rossum H, et al. Online biochemical detection of glutathione-S-transferase P1-specific inhibitors in complex mixtures. J Biomol Screen 2007;12:396–405.
   PubMedGoogle Scholar
• Hartwell SK, Grudpan K. Flow-based systems for rapid and high-precision enzyme kinetics studies. J Anal Methods Chem 2012;2012:450716.
   PubMed Web of Science ®Google Scholar
• Hansen EH. Flow-injection enzymatic assays. Analytica Chimica Acta 1989;216:257–273.
   Web of Science ®Google Scholar
• Silvestre CIC, Pinto PCAG, Segundo MA, et al. Enzyme based assays in a sequential injection format: a review. Analytica Chimica Acta 2011;689:160–177.
   PubMed Web of Science ®Google Scholar
• Gübeli T, Christian GD, Ruzicka J. Fundamentals of sinusoidal flow sequential injection spectrophotometry. Anal Chem 1991;63:2407–13.
   PubMed Web of Science ®Google Scholar
• Allocati N, Masulli M, Di Ilio C, et al. Glutathione transferases: substrates, inihibitors and pro-drugs in cancer and neurodegenerative diseases. Oncogenesis 2018;7:8.
   PubMed Web of Science ®Google Scholar
• Wani WA, Baig U, Shreaz S, et al. Recent advances in iron complexes as potential anticancer agents. New J Chem 2016;40:1063–1090.
   Web of Science ®Google Scholar
• Sansook S, Hassell-Hart S, Ocasio C, et al. Ferrocenes in medicinal chemistry; a personal perspective. J Organomet Chem 2020;905:121017.
   Web of Science ®Google Scholar
• Hwang E, Jung HS. Metal-organic complex-based chemodynamic therapy agents for cancer therapy. Chem Commun 2020;56:8332–8341.
   PubMed Web of Science ®Google Scholar
• Murray BS, Babak MV, Hartinger CG, et al. The development of RAPTA compounds for the treatment of tumors. Coord Chem Rev 2016;306:86–114.
   Web of Science ®Google Scholar
• Riedel T, Demaria O, Zava O, et al. Drug repurposing approach identifies a synergistic drug combination of an antifungal agent and an experimental organometallic drug for melanoma treatment. Mol Pharm 2018;15:116–126.
   PubMedGoogle Scholar
• Riedel T, Cavin S, van den Bergh H, et al. Chemo-manipulation of tumor blood vessels by a metal-based anticancer complex enhances antitumor therapy. Sci Rep 2018;8:10263–10263.
   PubMed Web of Science ®Google Scholar
• Švorc Ľ, Tomčík P, Durdiak J, et al. Analytical methods for the detection of osmium tetroxide: a review. Pol J Environ Stud 2012;21:7–13.
   Web of Science ®Google Scholar
• Liu Z, Sadler PJ. Organoiridium complexes: anticancer agents and catalysts. Acc Chem Res 2014;47:1174–1185.
   PubMed Web of Science ®Google Scholar
• Kilpin KJ, Dyson PJ. Enzyme inhibition by metal complexes: concepts, strategies and applications. Chem Sci 2013;4:1410–1419.
   Web of Science ®Google Scholar
• Ang WH, De Luca A, Chapuis-Bernasconi C, et al. Organometallic ruthenium inhibitors of glutathione-S-transferase P1-1 as anticancer drugs. ChemMedChem 2007;2:1799–806.
   PubMed Web of Science ®Google Scholar
• Ang WH, Parker LJ, De Luca A, et al. Rational design of an organometallic glutathione transferase inhibitor. Angew Chem Int Ed Engl 2009;48:3854–7.
   PubMed Web of Science ®Google Scholar
• Păunescu E, Soudani M, Martin P, et al. Organometallic glutathione S-transferase inhibitors. Organometallics 2017;36:3313–3321.
   Web of Science ®Google Scholar
• Scolaro C, Bergamo A, Brescacin L, et al. In vitro and in vivo evaluation of ruthenium(II)-arene PTA complexes. J Med Chem 2005;48:4161–4171.
   PubMed Web of Science ®Google Scholar
• Biancalana L, Batchelor LK, Funaioli T, et al. α-diimines as versatile, derivatizable ligands in ruthenium(II) p-cymene anticancer complexes. Inorganic Chem 2018;57:6669–6685.
   Google Scholar
• Agonigi G, Biancalana L, Lupo MG, et al. Exploring the anticancer potential of diiron bis-cyclopentadienyl complexes with bridging hydrocarbyl ligands: behavior in aqueous media and in vitro cytotoxicity. Organometallics 2020;39:645–657.
   Web of Science ®Google Scholar
• Biancalana L, De Franco M, Ciancaleoni G, et al. Easily available, amphiphilic diiron cyclopentadienyl complexes exhibit in vitro anticancer activity in 2D and 3D human cancer cells through redox modulation triggered by CO release. Chem Eur J 2021;27:10169–10185.
   PubMed Web of Science ®Google Scholar
• Braccini S, Rizzi G, Biancalana L, et al. Anticancer diiron vinyliminium complexes: a structure–activity relationship study. Pharmaceutics 2021;13:1158.
   PubMed Web of Science ®Google Scholar
• Rocco D, Batchelor LK, Agonigi G, et al. Anticancer potential of diiron vinyliminium complexes. Chem Eur J 2019;25:14801–14816.
   PubMedGoogle Scholar
• Rocco D, Busto N, Pérez‐Arnaiz C, et al. Antiproliferative and bactericidal activity of diiron and monoiron cyclopentadienyl carbonyl complexes comprising a vinyl-aminoalkylidene unit. Appl Organomet Chem 2020;34:e5923.
   Web of Science ®Google Scholar
• Marchetti F, Zacchini S, Zanotti V. C–N coupling of isocyanide ligands promoted by acetylide addition to diiron aminocarbyne complexes. Organometallics 2015;34:3658–3664.
   Web of Science ®Google Scholar
• Schroeder NC, Funchess R, Jacobson RA, et al. Reactions of Cp2Fe2(CO)2(.mu.-CO)(.mu.-CSR)+ bridging-carbyne complexes with nucleophiles. Organometallics 1989;8:521–529.
   Google Scholar
• Biancalana L, Kostrhunova H, Batchelor LK, et al. Hetero-bis-conjugation of bioactive molecules to half-sandwich ruthenium(II) and iridium(III) complexes provides synergic effects in cancer cell cytotoxicity. Inorganic Chem 2021;60:9529–9541.
   Google Scholar
• Agonigi G, Riedel T, Gay MP, et al. Arene osmium complexes with ethacrynic acid-modified ligands: synthesis, characterization, and evaluation of intracellular glutathione S-transferase inhibition and antiproliferative activity. Organometallics 2016;35:1046–1056.
   Web of Science ®Google Scholar
• Biancalana L, Pratesi A, Chiellini F, et al. Ruthenium arene complexes with triphenylphosphane ligands: cytotoxicity towards pancreatic cancer cells, interaction with model proteins, and effect of ethacrynic acid substitution. New J Chem 2017;41:14574–14588.
   Web of Science ®Google Scholar
• Biancalana L, Batchelor LK, De Palo A, et al. A general strategy to add diversity to ruthenium arene complexes with bioactive organic compounds via a coordinated (4-hydroxyphenyl)diphenylphosphine ligand. Dalton Transactions 2017;46:12001–12004.
   PubMed Web of Science ®Google Scholar
• Biancalana L, Batchelor LK, Pereira SAP, et al. Bis-conjugation of bioactive molecules to cisplatin-like complexes through (2,2'-Bipyridine)-4,4'-dicarboxylic acid with optimal cytotoxicity profile provided by the combination ethacrynic acid/flurbiprofen. Chem Eur J 2020;26:17525–17535.
   PubMed Web of Science ®Google Scholar
• Fulci C, Rotili D, De Luca A, et al. A new nitrobenzoxadiazole-based GSTP1-1 inhibitor with a previously unheard of mechanism of action and high stability. J Enzyme Inhib Med Chem 2017;32:240–247.
   PubMed Web of Science ®Google Scholar
• Bräutigam M, Teusch N, Schenk T, et al. Selective inhibitors of glutathione transferase P1 with trioxane structure as anticancer agents. ChemMedChem 2015;10:629–39.
   PubMed Web of Science ®Google Scholar
• Musdal Y, Hegazy UM, Aksoy Y, et al. FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. Chem Biol Interact 2013;205:53–62.
   PubMed Web of Science ®Google Scholar
• Pereira SAP, Biancalana L, Marchetti F, et al. Assessment of metal-based dihydrofolate reductase inhibitors on a novel mesofluidic platform. Sens Actuators B Chem. 2022;366:131978.
   Google Scholar
• Miller JC, JN, Miller. Estadística para Química Analítica. Wilmington, NC: Adisson Wesley Ibroamerican; 1993.
   Google Scholar
• McIlwain CC, Townsend DM, Tew KD. Glutathione S-transferase polymorphisms: cancer incidence and therapy. Oncogene 2006;25:1639–1648.
   PubMed Web of Science ®Google Scholar
• Singh RR, Reindl KM. Glutathione S-transferases in cancer. Antioxidants 2021;10:701.
   Web of Science ®Google Scholar
• Huang G, Mills L, Worth LL. Expression of human glutathione S-transferase P1 mediates the chemosensitivity of osteosarcoma cells. Mol Cancer Ther 2007;6:1610–9.
   PubMed Web of Science ®Google Scholar