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Dipyridyl Thiosemicarbazone Chelators with Potent and Selective Antitumor Activity Form Iron Complexes with Redox Activity

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Iron Metabolism and Chelation Program, Department of Pathology, University of Sydney, Sydney, New South Wales 2006, Australia, Iron Metabolism and Chelation Program, Children's Cancer Institute Australia for Medical Research, Randwick, Sydney, New South Wales 2031, Australia, and Centre for Metals in Biology, Department of Chemistry, University of Queensland, Brisbane 4072, Australia
Cite this: J. Med. Chem. 2006, 49, 22, 6510–6521
Publication Date (Web):September 29, 2006
https://doi.org/10.1021/jm0606342
Copyright © 2006 American Chemical Society
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    Abstract

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    There has been much interest in the development of iron (Fe) chelators for the treatment of cancer. We developed a series of di-2-pyridyl ketone thiosemicarbazone (HDpT) ligands which show marked and selective antitumor activity in vitro and in vivo. In this study, we assessed chemical and biological properties of these ligands and their Fe complexes in order to understand their marked activity. This included examination of their solution chemistry, electrochemistry, ability to mediate redox reactions, and antiproliferative activity against tumor cells. The higher antiproliferative efficacy of the HDpT series of chelators relative to the related di-2-pyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues can be ascribed, in part, to the redox potentials of their Fe complexes which lead to the generation of reactive oxygen species. The most effective HDpT ligands as antiproliferative agents possess considerable lipophilicity and were shown to be charge neutral at physiological pH, allowing access to intracellular Fe pools.

    *

     Authors for correspondence. D.R.R. (biology):  phone, +61-2-9036-6548; fax, +61-2-9036-6549; e-mail, [email protected]. P.V.B. (chemistry):  phone, +61-7-3365-4266; fax, +61-7-3365-4299; e-mail, [email protected].

    †

     University of Sydney.

    §

     Children's Cancer Institute Australia for Medical Research.

    ‡

     University of Queensland.

    Abbreviations:  3-AP, 3-aminopyridine-2-carboxaldehyde-thiosemicarbazone; DFO, desferrioxamine; DOX, doxorubicin; HDpT, di-2-pyridyl ketone thiosemicarbazone; HDp4aT, di-2-pyridyl ketone 4-allyl-3-thiosemicarbazone; HDp4eT, di-2-pyridyl ketone 4-ethyl-3-thiosemicarbazone; HDp4mT, di-2-pyridyl ketone 4-methyl-3-thiosemicarbazone; HDp44mT, di-2-pyridyl ketone 4,4-dimethyl-3-thiosemicarbazone; HDp4pT, di-2-pyridyl ketone 4-phenyl-3-thiosemicarbazone; H2NIH, 2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone; H2NT, 2-hydroxy-1-naphthylaldehyde thiosemicarbazone; HPKIH, di-2-pyridyl ketone isonicotinoyl hydrazone; H2PIH, pyridoxal isonicotinoyl hydrazone; IBE, iron-binding equivalent; OC, open-circular; ROS, reactive oxygen species; SC, supercoiled; Tf, transferrin; TfR1, transferrin receptor 1.

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    56. Elżbieta U. Stolarczyk, Weronika Strzempek, Marta Łaszcz, Andrzej Leś, Elżbieta Menaszek, Krzysztof Stolarczyk. Thiogenistein—Antioxidant Chemistry, Antitumor Activity, and Structure Elucidation of New Oxidation Products. International Journal of Molecular Sciences 2022, 23 (14) , 7816. https://doi.org/10.3390/ijms23147816
    57. Jaehee Kim, Areum Park, Jieon Hwang, Xianghua Zhao, Jaesung Kwak, Hyun Woo Kim, Minhee Ku, Jaemoon Yang, Tae Il Kim, Kyu-Sung Jeong, Uyeong Choi, Hyuk Lee, Sang Joon Shin. KS10076, a chelator for redox-active metal ions, induces ROS-mediated STAT3 degradation in autophagic cell death and eliminates ALDH1+ stem cells. Cell Reports 2022, 40 (3) , 111077. https://doi.org/10.1016/j.celrep.2022.111077
    58. Yunyun Zheng, Bin Li, Yu Ai, Mengyao Chen, Xinhua Zheng, Jinxu Qi. Synthesis, crystal structures and anti-cancer mechanism of Cu(II) complex derived from 2-acetylpyrazine thiosemicarbazone. Journal of Coordination Chemistry 2022, 75 (9-10) , 1325-1340. https://doi.org/10.1080/00958972.2022.2111660
    59. O.Yu. Selyutina, P.A. Kononova, V.E. Koshman, E.A. Shelepova, M. Gholam Azad, R. Afroz, M. Dharmasivam, Paul V. Bernhardt, N.E. Polyakov, D.R. Richardson. Ascorbate-and iron-driven redox activity of Dp44mT and Emodin facilitates peroxidation of micelles and bicelles. Biochimica et Biophysica Acta (BBA) - General Subjects 2022, 1866 (4) , 130078. https://doi.org/10.1016/j.bbagen.2021.130078
    60. Ming Jiang, Tongfu Yang, Yong Chu, Zhenlei Zhang, Hongbin Sun, Hong Liang, Feng Yang. Design of a novel Pt( ii ) complex to reverse cisplatin-induced resistance in lung cancer via a multi-mechanism. Dalton Transactions 2022, 51 (13) , 5257-5270. https://doi.org/10.1039/D1DT03964D
    61. Bekesho Geleta, Faten S. Tout, Syer Choon Lim, Sumit Sahni, Patric J. Jansson, Minoti V. Apte, Des R. Richardson, Žaklina Kovačević. Targeting Wnt/tenascin C-mediated cross talk between pancreatic cancer cells and stellate cells via activation of the metastasis suppressor NDRG1. Journal of Biological Chemistry 2022, 298 (3) , 101608. https://doi.org/10.1016/j.jbc.2022.101608
    62. Viktor A. Timoshnikov, Olga Yu. Selyutina, Nikolay E. Polyakov, Victoria Didichenko, George J. Kontoghiorghes. Mechanistic Insights of Chelator Complexes with Essential Transition Metals: Antioxidant/Pro-Oxidant Activity and Applications in Medicine. International Journal of Molecular Sciences 2022, 23 (3) , 1247. https://doi.org/10.3390/ijms23031247
    63. Touba Eslaminejad, Yaghoub Pourshojaei, Mahmood Naghizadeh, Hoda Eslami, Mohammad Daneshpajouh, Abdolreza Hassanzadeh. Synthesis of some benzylidene thiosemicarbazide derivatives and evaluation of their cytotoxicity on U87, MCF-7, A549, 3T3 and HUVEC cell lines. Journal of the Serbian Chemical Society 2022, 87 (10) , 1125-1142. https://doi.org/10.2298/JSC210630016E
    64. Tharushi P. Wijesinghe, Mahendiran Dharmasivam, Charles C. Dai, Des R. Richardson. Innovative therapies for neuroblastoma: The surprisingly potent role of iron chelation in up-regulating metastasis and tumor suppressors and down-regulating the key oncogene, N-myc. Pharmacological Research 2021, 173 , 105889. https://doi.org/10.1016/j.phrs.2021.105889
    65. Jia Shao, Qiang Zhang, Jing Wei, Zhiguang Yuchi, Peng Cao, Shao-Qing Li, Shan Wang, Jing-Yuan Xu, Shuang Yang, Yi Zhang, Jin-Xia Wei, Jin-Lei Tian. Synthesis, crystal structures, anticancer activities and molecular docking studies of novel thiazolidinone Cu( ii ) and Fe( iii ) complexes targeting lysosomes: special emphasis on their binding to DNA/BSA. Dalton Transactions 2021, 50 (38) , 13387-13398. https://doi.org/10.1039/D1DT02180J
    66. Burcu Saygıdeğer Demir, Ghodrat Mahmoudi, Aycan Sezan, Ezgi Derinöz, Eylem Nas, Yasemin Saygideger, Fedor I. Zubkov, Ennio Zangrando, Damir A. Safin. Evaluation of the antitumor activity of a series of the pincer-type metallocomplexes produced from isonicotinohydrazide derivative. Journal of Inorganic Biochemistry 2021, 223 , 111525. https://doi.org/10.1016/j.jinorgbio.2021.111525
    67. , Qianqian Fu. Di-2-pyridylketone 4, 4-dimethyl-3-thiosemicarbazone effectively induces human colorectal carcinoma cell apoptosis via mTOR pathway. Aging Pathobiology and Therapeutics 2021, 3 (3) , 56-62. https://doi.org/10.31491/APT.2021.09.063
    68. Yu‐Shien Sung, Wangbin Wu, Megan A. Ewbank, Rachel D. Utterback, Michael T. Marty, Elisa Tomat. Albumin Conjugates of Thiosemicarbazone and Imidazole‐2‐thione Prochelators: Iron Coordination and Antiproliferative Activity. ChemMedChem 2021, 16 (18) , 2764-2768. https://doi.org/10.1002/cmdc.202100278
    69. Jason Chekmarev, Mahan Gholam Azad, Des R. Richardson. The Oncogenic Signaling Disruptor, NDRG1: Molecular and Cellular Mechanisms of Activity. Cells 2021, 10 (9) , 2382. https://doi.org/10.3390/cells10092382
    70. Marcelo Melotti, Matheus S. S. Paqui, André L. Amorim, Carla P. de Paula, Marina C. Rocha, Iran Malavazi, Anderson Cunha, Francielli S. Santana, Ronny R. Ribeiro, Rogério A. Gariani, Samuel R. Mendes, Fernando R. Xavier. Polypyridyl iron( iii ) complexes containing long alkyl chains: synthesis, characterization, DFT calculations and biological activity. New Journal of Chemistry 2021, 45 (29) , 12902-12914. https://doi.org/10.1039/D0NJ00895H
    71. Maryam Hosseinkhah, Reza Ghasemian, Faezeh Shokrollahi, Samira Rezaei Mojdehi, Mahboubeh Jahani Sayyad Noveiri, Mohammad Hedayati, Marjan Rezaei, Ali Salehzadeh. Cytotoxic Potential of Nickel Oxide Nanoparticles Functionalized with Glutamic Acid and Conjugated with Thiosemicarbazide (NiO@Glu/TSC) Against Human Gastric Cancer Cells. Journal of Cluster Science 2021, 47 https://doi.org/10.1007/s10876-021-02124-2
    72. Jia-Qi Li, Han Gao, Le Zhai, Le-Yun Sun, Cheng Chen, Jia-Zhu Chigan, Huan-Huan Ding, Ke-Wu Yang. Dipyridyl-substituted thiosemicarbazone as a potent broad-spectrum inhibitor of metallo-β-lactamases. Bioorganic & Medicinal Chemistry 2021, 38 , 116128. https://doi.org/10.1016/j.bmc.2021.116128
    73. Erendra Manandhar, Ashley D. G. Johnson, William M. Watson, Shelby D. Dickerson, Gyan S. Sahukhal, Mohamed O. Elasri, Frank R. Fronczek, Peter J. Cragg, Karl J. Wallace. Detection of ferric ions in a gram-positive bacterial cell: Staphylococcus aureus. Journal of Coordination Chemistry 2021, 74 (1-3) , 380-401. https://doi.org/10.1080/00958972.2020.1868042
    74. Zhang-Xu He, Jin-Ling Huo, Yun-Peng Gong, Qi An, Xin Zhang, Hui Qiao, Fei-Fei Yang, Xin-Hui Zhang, Le-Min Jiao, Hong-Min Liu, Li-Ying Ma, Wen Zhao. Design, synthesis and biological evaluation of novel thiosemicarbazone-indole derivatives targeting prostate cancer cells. European Journal of Medicinal Chemistry 2021, 210 , 112970. https://doi.org/10.1016/j.ejmech.2020.112970
    75. Hai-Yan Wang, Li Weng, Hong-Yan Yang, Xi Yang, Xiao-Ling Dong, Xiao-Mei Tan, Yan Wang. Heterometallic coordination polymers: Treatment activity on diabetic foot by reducing the excess inflammatory response in the plantar tissue. Journal of Chemical Research 2021, 45 (1-2) , 49-55. https://doi.org/10.1177/1747519820923277
    76. Junmiao Wu, Tongfu Yang, Xiaojun Wang, Wenjuan Li, Min Pang, Hongbin Sun, Hong Liang, Feng Yang. Development of a multi-target anticancer Sn( ii ) pyridine-2-carboxaldehyde thiosemicarbazone complex. Dalton Transactions 2021, 88 https://doi.org/10.1039/D1DT01272J
    77. Éva A. Enyedy, Nóra V. May, Veronika F. S. Pape, Petra Heffeter, Gergely Szakács, Bernhard K. Keppler, Christian R. Kowol. Complex formation and cytotoxicity of Triapine derivatives: a comparative solution study on the effect of the chalcogen atom and NH-methylation. Dalton Transactions 2020, 49 (46) , 16887-16902. https://doi.org/10.1039/D0DT03465G
    78. Silvia Paukovcekova, Jan Skoda, Jakub Neradil, Erika Mikulenkova, Petr Chlapek, Jaroslav Sterba, Des R. Richardson, Renata Veselska. Novel Thiosemicarbazones Sensitize Pediatric Solid Tumor Cell-Types to Conventional Chemotherapeutics through Multiple Molecular Mechanisms. Cancers 2020, 12 (12) , 3781. https://doi.org/10.3390/cancers12123781
    79. S. Krishan, S. Sahni, D.R. Richardson. The anti-tumor agent, Dp44mT, promotes nuclear translocation of TFEB via inhibition of the AMPK-mTORC1 axis. Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease 2020, 1866 (12) , 165970. https://doi.org/10.1016/j.bbadis.2020.165970
    80. Kyung Chan Park, Des R. Richardson. The c-MET oncoprotein: Function, mechanisms of degradation and its targeting by novel anti-cancer agents. Biochimica et Biophysica Acta (BBA) - General Subjects 2020, 1864 (10) , 129650. https://doi.org/10.1016/j.bbagen.2020.129650
    81. Waleska R. P. Costa, Rafael A. C. Souza, Victor M. Deflon, Carolina G. Oliveira. Preparation, structural characterization, voltammetry and Hirshfeld surface analysis of homoleptic iron(III) thiosemicarbazone complexes. Transition Metal Chemistry 2020, 45 (7) , 511-521. https://doi.org/10.1007/s11243-020-00404-w
    82. A.M. Sólimo, M.C. Soraires Santacruz, S. Vanzulli, O. Coggiola, E. Bal de Kier Joffé, L. Finkielsztein, M.A. Callero. Anti-metastatic action of an N4-aryl substituted thiosemicarbazone on advanced triple negative breast cancer.. Heliyon 2020, 6 (10) , e05161. https://doi.org/10.1016/j.heliyon.2020.e05161
    83. Kyung Chan Park, Jasmina Paluncic, Zaklina Kovacevic, Des R. Richardson. Pharmacological targeting and the diverse functions of the metastasis suppressor, NDRG1, in cancer. Free Radical Biology and Medicine 2020, 157 , 154-175. https://doi.org/10.1016/j.freeradbiomed.2019.05.020
    84. S. Chiang, M.L.H. Huang, D.R. Richardson. Treatment of dilated cardiomyopathy in a mouse model of Friedreich’s ataxia using N-acetylcysteine and identification of alterations in microRNA expression that could be involved in its pathogenesis. Pharmacological Research 2020, 159 , 104994. https://doi.org/10.1016/j.phrs.2020.104994
    85. Miljan N. M. Milunović, Oleg Palamarciuc, Angela Sirbu, Sergiu Shova, Dan Dumitrescu, Dana Dvoranová, Peter Rapta, Tatsiana V. Petrasheuskaya, Eva A. Enyedy, Gabriella Spengler, Marija Ilic, Harald H. Sitte, Gert Lubec, Vladimir B. Arion. Insight into the Anticancer Activity of Copper(II) 5-Methylenetrimethylammonium-Thiosemicarbazonates and Their Interaction with Organic Cation Transporters. Biomolecules 2020, 10 (9) , 1213. https://doi.org/10.3390/biom10091213
    86. Kateryna Ohui, Iryna Stepanenko, Iuliana Besleaga, Maria V. Babak, Radu Stafi, Denisa Darvasiova, Gerald Giester, Vivien Pósa, Eva A. Enyedy, Daniel Vegh, Peter Rapta, Wee Han Ang, Ana Popović-Bijelić, Vladimir B. Arion. Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells. Biomolecules 2020, 10 (9) , 1336. https://doi.org/10.3390/biom10091336
    87. Mathilde Bouché, Cécilia Hognon, Stéphanie Grandemange, Antonio Monari, Philippe C. Gros. Recent advances in iron-complexes as drug candidates for cancer therapy: reactivity, mechanism of action and metabolites. Dalton Transactions 2020, 49 (33) , 11451-11466. https://doi.org/10.1039/D0DT02135K
    88. Sumit Sahni, Josef Gillson, Kyung Chan Park, Shannon Chiang, Lionel Yi Wen Leck, Patric J. Jansson, Des R. Richardson. NDRG1 suppresses basal and hypoxia-induced autophagy at both the initiation and degradation stages and sensitizes pancreatic cancer cells to lysosomal membrane permeabilization. Biochimica et Biophysica Acta (BBA) - General Subjects 2020, 1864 (8) , 129625. https://doi.org/10.1016/j.bbagen.2020.129625
    89. C.K. Holley, S. Majd. Examining the Anti-Tumor Activity of Dp44mT-Loaded Nanoparticles In Vitro. 2020, 5029-5032. https://doi.org/10.1109/EMBC44109.2020.9176197
    90. Bhushan Shakya, Paras Nath Yadav. Thiosemicarbazones as Potent Anticancer Agents and their Modes of Action. Mini-Reviews in Medicinal Chemistry 2020, 20 (8) , 638-661. https://doi.org/10.2174/1389557519666191029130310
    91. Bi-Qun Zou, Xiao-Ling Huang, Qi-Pin Qin, Zhen-Feng Wang, Xue-Yu Wu, Ming-Xiong Tan, Hong Liang. Transition metal complexes with 6,7-dichloro-5,8-quinolinedione as mitochondria-targeted anticancer agents. Polyhedron 2020, 181 , 114482. https://doi.org/10.1016/j.poly.2020.114482
    92. S. Krishan, S. Sahni, L.Y.W. Leck, P.J. Jansson, D.R. Richardson. Regulation of autophagy and apoptosis by Dp44mT-mediated activation of AMPK in pancreatic cancer cells. Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease 2020, 1866 (5) , 165657. https://doi.org/10.1016/j.bbadis.2019.165657
    93. Zhixuan Wu, Duraippandi Palanimuthu, Nady Braidy, Nor Hawani Salikin, Suhelen Egan, Michael L.H. Huang, Des R. Richardson. Novel multifunctional iron chelators of the aroyl nicotinoyl hydrazone class that markedly enhance cellular NAD + /NADH ratios. British Journal of Pharmacology 2020, 177 (9) , 1967-1987. https://doi.org/10.1111/bph.14963
    94. Winaki P. Sohtun, Themmila Khamrang, Arunachalam Kannan, Gowdhami Balakrishnan, Dhandayutham Saravanan, Mohammad Abdulkader Akhbarsha, Marappan Velusamy, Mallayan Palaniandavar. Iron(III) bis‐complexes of Schiff bases of S ‐methyldithiocarbazates: Synthesis, structure, spectral and redox properties and cytotoxicity. Applied Organometallic Chemistry 2020, 34 (5) https://doi.org/10.1002/aoc.5593
    95. B. Amritha, O. Manaf, M. Nethaji, A. Sujith, M.R. Prathapachandra Kurup, Suni Vasudevan. Mn(II) complex of a di-2-pyridyl ketone-N(4)-substituted thiosemicarbazone: Versatile biological properties and naked-eye detection of Fe2+ and Ru3+ ions. Polyhedron 2020, 178 , 114333. https://doi.org/10.1016/j.poly.2019.114333
    96. Kyung Chan Park, Bekesho Geleta, Lionel Yi Wen Leck, Jasmina Paluncic, Shannon Chiang, Patric J. Jansson, Zaklina Kovacevic, Des R. Richardson. Thiosemicarbazones suppress expression of the c-Met oncogene by mechanisms involving lysosomal degradation and intracellular shedding. Journal of Biological Chemistry 2020, 295 (2) , 481-503. https://doi.org/10.1074/jbc.RA119.011341
    97. Soheila Jenabi Sardroud, Seyed Abolfazl Hosseini-Yazdi, Majid Mahdavi, Morgane Poupon, Eliska Skorepova. Synthesis, characterization and in vitro evaluation of anticancer activity of a new water-soluble thiosemicarbazone ligand and its complexes. Polyhedron 2020, 175 , 114218. https://doi.org/10.1016/j.poly.2019.114218
    98. Miguel A. Gonzálvez, Andrés G. Algarra, Manuel G. Basallote, Paul V. Bernhardt, María J. Fernández-Trujillo, Manuel Martínez. Proton-assisted air oxidation mechanisms of iron( ii ) bis-thiosemicarbazone complexes at physiological pH: a kinetico-mechanistic study. Dalton Transactions 2019, 48 (44) , 16578-16587. https://doi.org/10.1039/C9DT03557E
    99. Merve Ertas, Zafer Sahin, Emre F. Bulbul, Ceysu Bender, Sevde N. Biltekin, Barkin Berk, Leyla Yurttas, Aysu M. Nalbur, Hayati Celik, Şeref Demirayak. Potent ribonucleotide reductase inhibitors: Thiazole‐containing thiosemicarbazone derivatives. Archiv der Pharmazie 2019, 352 (11) https://doi.org/10.1002/ardp.201900033
    100. Christopher J Parkinson, Geoffrey W Birrell, Marina Chavchich, Donna Mackenzie, Richard K Haynes, Carmen de Kock, Des R Richardson, Michael D Edstein. Development of pyridyl thiosemicarbazones as highly potent agents for the treatment of malaria after oral administration. Journal of Antimicrobial Chemotherapy 2019, 74 (10) , 2965-2973. https://doi.org/10.1093/jac/dkz290
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