ACS Publications. Most Trusted. Most Cited. Most Read
Cytotoxicity, Hydrophobicity, Uptake, and Distribution of Osmium(II) Anticancer Complexes in Ovarian Cancer Cells
My Activity
    Article

    Cytotoxicity, Hydrophobicity, Uptake, and Distribution of Osmium(II) Anticancer Complexes in Ovarian Cancer Cells
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, U.K.
    *To whom correspondence should be addressed. Phone: (+44) 024 7652 3818. Fax: (+44) 024 76523819. E-mail: [email protected]
    Other Access OptionsSupporting Information (1)

    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2010, 53, 2, 840–849
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm901556u
    Published December 15, 2009
    Copyright © 2009 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The cytotoxicity, hydrophobicity (log P), cellular uptake, aqueous reactivity, and extent of DNA adduct formation in the A2780 ovarian carcinoma cells for four osmium(II) arene complexes [(η6-arene)Os(4-methyl-picolinate)Cl] that differ only in their arene ligands as benzene (1), p-cymene (2), biphenyl (3), or tetrahydroanthracene (4) are reported. There is a correlation between hydrophobicity (log P), cellular uptake, nucleus uptake, and cytotoxicity of the complexes, following the order 34 > 2 > 1, suggesting that the arene plays an important role in the biological activity of these types of compounds. Cell distribution studies using fractionation showed that all four compounds distribute similarly within cells. DNA binding of osmium did not correlate with cytotoxicity, indicating that the nature of the DNA lesion may also be crucial to activity. TEM images of ovarian cells treated with 3 revealed morphological changes associated with apoptosis with possible involvement of mitochondria.

    Copyright © 2009 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Spectroscopic data and ESI-MS and CHN analysis data for complexes 1, 2, and 4; instrumental settings for ICP-MS (Table S1); time dependence for formation of the aqua complexes of 1, 2, and 4 (Figure S1); TEM images of A2780 cells exposed to complex 3, showing the different stages of cell apoptosis (Figures S2 and S3); TEM images of A2780 cells only stained with 2% uranyl acetate (controls) (Figure S4); TEM images of A2780 cells exposed to 5 μM complex 3 (Figure S5); TEM images of A2780 cells exposed to 20 μM complex 3 (Figure S6). This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 126 publications.

    1. Atin Chatterjee, Sandip Sarkar, Sangheeta Bhattacharjee, Arpan Bhattacharyya, Surajit Barman, Uttam Pal, Raviranjan Pandey, Anitha Ethirajan, Batakrishna Jana, Benu Brata Das, Amitava Das. Microtubule-Targeting NAP Peptide-Ru(II)-polypyridyl Conjugate As a Bimodal Therapeutic Agent for Triple Negative Breast Carcinoma. Journal of the American Chemical Society 2025, 147 (1) , 532-547. https://doi.org/10.1021/jacs.4c11820
    2. Pratikshya Das Pattanayak, Atanu Banerjee, Gurunath Sahu, Sanchita Das, Sudhir Lima, Oluseun Akintola, Axel Buchholz, Helmar Görls, Winfried Plass, Hans Reuter, Rupam Dinda. Insights into the Theranostic Activity of Nonoxido VIV: Lysosome-Targeted Anticancer Metallodrugs. Inorganic Chemistry 2024, 63 (41) , 19418-19438. https://doi.org/10.1021/acs.inorgchem.4c03389
    3. Cuiyan Lin, Huiling Wang, Keyu Chen, Shuangqiang Liu, Zhichen Mao, Zuyu Mo, Rizhen Huang, Ye Zhang, Wei Xie, Jianhua Wei, Junfei Jin. A Cyclometalated Iridium(III) Complex Exerts High Anticancer Efficacy via Fatty Acid Beta-Oxidation Inhibition and Sphingolipid Metabolism Reprogramming. Journal of Medicinal Chemistry 2024, 67 (17) , 14912-14926. https://doi.org/10.1021/acs.jmedchem.4c00280
    4. Sathiya Kamatchi Thangavel, Mohamed Subarkhan Mohamed Kasim, Ramesh Rengan. Promoting the Anticancer Activity with Multidentate Furan-2-Carboxamide Functionalized Aroyl Thiourea Chelation in Binuclear Half-Sandwich Ruthenium(II) Complexes. Inorganic Chemistry 2024, 63 (16) , 7520-7539. https://doi.org/10.1021/acs.inorgchem.4c01265
    5. Sushree Aradhana Patra, Gurunath Sahu, Deepika Mohapatra, Pratikshya Das Pattanayak, Rupam Dinda. Fluorescent Diorganotin(IV) Complexes as Anticancer Agents: Study of Cytotoxicity, Cellular Localization, and Mechanism of Cell Death. Organometallics 2023, 42 (15) , 1934-1950. https://doi.org/10.1021/acs.organomet.3c00182
    6. Amit Kumar Pradhan, Abhijit Shyam, Abhijit Dutta, Paritosh Mondal. Quantum Chemical Investigation on Hydrolysis of Orally Active Organometallic Ruthenium(II) and Osmium(II) Anticancer Drugs and Their Interaction with Histidine. The Journal of Physical Chemistry B 2022, 126 (46) , 9516-9527. https://doi.org/10.1021/acs.jpcb.2c05062
    7. Gurunath Sahu, Atanu Banerjee, Rajib Samanta, Monalisa Mohanty, Sudhir Lima, Edward R. T. Tiekink, Rupam Dinda. Water-Soluble Dioxidovanadium(V) Complexes of Aroylhydrazones: DNA/BSA Interactions, Hydrophobicity, and Cell-Selective Anticancer Potential. Inorganic Chemistry 2021, 60 (20) , 15291-15309. https://doi.org/10.1021/acs.inorgchem.1c01899
    8. Gengqi Liu, Zhen Jiang, Jonathan F. Lovell, Lei Zhang, Yumiao Zhang. Design of a Thiol-Responsive, Traceless Prodrug with Rapid Self-Immolation for Cancer Chemotherapy. ACS Applied Bio Materials 2021, 4 (6) , 4982-4989. https://doi.org/10.1021/acsabm.1c00247
    9. Rong Huang, Feng-Ping Feng, Chun-Hua Huang, Li Mao, Miao Tang, Zhu-Ying Yan, Bo Shao, Li Qin, Tao Xu, Yan-Hong Xue, Ben-Zhan Zhu. Chiral Os(II) Polypyridyl Complexes as Enantioselective Nuclear DNA Imaging Agents Especially Suitable for Correlative High-Resolution Light and Electron Microscopy Studies. ACS Applied Materials & Interfaces 2020, 12 (3) , 3465-3473. https://doi.org/10.1021/acsami.9b19776
    10. Adam J. Millett, Abraha Habtemariam, Isolda Romero-Canelón, Guy J. Clarkson, and Peter J. Sadler . Contrasting Anticancer Activity of Half-Sandwich Iridium(III) Complexes Bearing Functionally Diverse 2-Phenylpyridine Ligands. Organometallics 2015, 34 (11) , 2683-2694. https://doi.org/10.1021/acs.organomet.5b00097
    11. Kogularamanan Suntharalingam, Timothy C. Johnstone, Peter M. Bruno, Wei Lin, Michael T. Hemann, and Stephen J. Lippard . Bidentate Ligands on Osmium(VI) Nitrido Complexes Control Intracellular Targeting and Cell Death Pathways. Journal of the American Chemical Society 2013, 135 (38) , 14060-14063. https://doi.org/10.1021/ja4075375
    12. Bastien Boff, Christian Gaiddon, and Michel Pfeffer . Cancer Cell Cytotoxicity of Cyclometalated Compounds Obtained with Osmium(II) Complexes. Inorganic Chemistry 2013, 52 (5) , 2705-2715. https://doi.org/10.1021/ic302779q
    13. Flavia Barragán, Dolors Carrion-Salip, Irene Gómez-Pinto, Alejandro González-Cantó, Peter J. Sadler, Rafael de Llorens, Virtudes Moreno, Carlos González, Anna Massaguer, and Vicente Marchán . Somatostatin Subtype-2 Receptor-Targeted Metal-Based Anticancer Complexes. Bioconjugate Chemistry 2012, 23 (9) , 1838-1855. https://doi.org/10.1021/bc300173h
    14. Miguel A. Esteruelas, Jorge García-Raboso, and Montserrat Oliván . Reactions of an Osmium-Hexahydride Complex with Cytosine, Deoxycytidine, and Cytidine: The Importance of the Minor Tautomers. Inorganic Chemistry 2012, 51 (17) , 9522-9528. https://doi.org/10.1021/ic3013238
    15. Miguel A. Esteruelas, Jorge García-Raboso, Montserrat Oliván, and Enrique Oñate . N–H and N–C Bond Activation of Pyrimidinic Nucleobases and Nucleosides Promoted by an Osmium Polyhydride. Inorganic Chemistry 2012, 51 (10) , 5975-5984. https://doi.org/10.1021/ic300639j
    16. Hong-Ke Liu and Peter J. Sadler . Metal Complexes as DNA Intercalators. Accounts of Chemical Research 2011, 44 (5) , 349-359. https://doi.org/10.1021/ar100140e
    17. Zhe Liu, Abraha Habtemariam, Ana M. Pizarro, Sally A. Fletcher, Anna Kisova, Oldrich Vrana, Luca Salassa, Pieter C. A. Bruijnincx, Guy J. Clarkson, Viktor Brabec, and Peter J. Sadler . Organometallic Half-Sandwich Iridium Anticancer Complexes. Journal of Medicinal Chemistry 2011, 54 (8) , 3011-3026. https://doi.org/10.1021/jm2000932
    18. Sabine H. van Rijt, Hana Kostrhunova, Viktor Brabec, and Peter J. Sadler . Functionalization of Osmium Arene Anticancer Complexes with (Poly)arginine: Effect on Cellular Uptake, Internalization, and Cytotoxicity. Bioconjugate Chemistry 2011, 22 (2) , 218-226. https://doi.org/10.1021/bc100369p
    19. Ying Fu, Abraha Habtemariam, Ana M. Pizarro, Sabine H. van Rijt, David J. Healey, Patricia A. Cooper, Steven D. Shnyder, Guy J. Clarkson, and Peter J. Sadler . Organometallic Osmium Arene Complexes with Potent Cancer Cell Cytotoxicity. Journal of Medicinal Chemistry 2010, 53 (22) , 8192-8196. https://doi.org/10.1021/jm100560f
    20. Deepika Mohapatra, Pratikshya Das Pattanayak, Souvik Chatterjee, Werner Kaminsky, Takahiro Sasamori, Takashi Nakamura, Rupam Dinda. Unsymmetrical salen-based oxido VIV: Synthesis, characterization, biomolecular interactions, and anticancer activity. Journal of Inorganic Biochemistry 2025, 264 , 112818. https://doi.org/10.1016/j.jinorgbio.2024.112818
    21. Sofia Sharkawy, Alba Hernández-García, Hana Kostrhunova, Delia Bautista, Lenka Markova, María Dolores Santana, Jana Kasparkova, Viktor Brabec, José Ruiz. A novel benzothiazole-1,2,3-triazole-based arene osmium( ii ) complex as an effective rhabdomyosarcoma cancer stem cell agent. Inorganic Chemistry Frontiers 2025, 12 (4) , 1693-1715. https://doi.org/10.1039/D4QI02737J
    22. Wenting Wang, Yang Xu, Yuqi Tang, Quan Li. Self‐Assembled Metal Complexes in Biomedical Research. Advanced Materials 2024, 112 https://doi.org/10.1002/adma.202416122
    23. Arunachalam Abirami, Umapathy Devan, Rengan Ramesh, Arockiam Antony Joseph Velanganni, Jan Grzegorz Małecki. Exploring the cytotoxicity of dinuclear Ru( ii )  p -cymene complexes appended N , N ′-bis(4-substituted benzoyl)hydrazines: insights into the mechanism of apoptotic cell death. Dalton Transactions 2024, 53 (11) , 5167-5179. https://doi.org/10.1039/D3DT04234K
    24. Daria B. Wojtala, Urszula K. Komarnicka, Agnieszka Kyzioł, Sandra Kozieł, Magdalena Szmitka, Mateusz Słowikowski, Julia Kulczyńska, Grażyna Stochel. Cellular Mechanistic Considerations on Cytotoxic Mode of Action of Phosphino Ru(II) and Ir(III) Complexes. European Journal of Inorganic Chemistry 2023, 26 (33) https://doi.org/10.1002/ejic.202300515
    25. Gurunath Sahu, Sushree Aradhana Patra, Sudhir Lima, Sanchita Das, Helmar Görls, Winfried Plass, Rupam Dinda. Ruthenium(II)‐Dithiocarbazates as Anticancer Agents: Synthesis, Solution Behavior, and Mitochondria‐Targeted Apoptotic Cell Death. Chemistry – A European Journal 2023, 29 (18) https://doi.org/10.1002/chem.202202694
    26. Rizwan Ashraf, Ayesha Sarfraz, Tugba Taskin-Tok, Muhammad Javid Iqbal, Muhammad Adnan Iqbal, Jamshed Iqbal, Haq Nawaz Bhatti, Mohamed El-Naggar, Sumia Akram, Mohammad N. Murshed, Mohamed E. El Sayed, Ahmed Samir. Synthesis, molecular docking and anticancer potential of azolium based salts and their silver complexes: DNA/BSA interaction studies and cell cycle analysis. Journal of Molecular Liquids 2023, 369 , 120921. https://doi.org/10.1016/j.molliq.2022.120921
    27. Pravinkumar Selvam, Sourav De, Priyankar Paira, S. K. Ashok Kumar, Selva Kumar R, Anbalagan Moorthy, Arjita Ghosh, Yung-Chih Kuo, Subhasis Banerjee, Shantha Kumar Jenifer. In vitro studies on the selective cytotoxic effect of luminescent Ru( ii )- p -cymene complexes of imidazo-pyridine and imidazo quinoline ligands. Dalton Transactions 2022, 51 (45) , 17263-17276. https://doi.org/10.1039/D2DT02237K
    28. Minji Wang, Haibo Wang, Xiaohan Xu, Tsz-Pui Lai, Ying Zhou, Quan Hao, Hongyan Li, Hongzhe Sun. Binding of ruthenium and osmium at non‑iron sites of transferrin accounts for their iron-independent cellular uptake. Journal of Inorganic Biochemistry 2022, 234 , 111885. https://doi.org/10.1016/j.jinorgbio.2022.111885
    29. Partha Sarathi Guin, Sanjay Roy. Recently Reported Ru-Metal Organic Coordination Complexes and Their Application (A Review). Russian Journal of General Chemistry 2022, 92 (8) , 1546-1561. https://doi.org/10.1134/S1070363222080242
    30. Nithya Balakrishnan, Jebiti Haribabu, Rahime Eshaghi Malekshah, Srividya Swaminathan, Chandrasekar Balachandran, Nattamai Bhuvanesh, Shin Aoki, Ramasamy Karvembu. Effect of N-benzyl group in indole scaffold of thiosemicarbazones on the biological activity of their Pd(II) complexes: DFT, biomolecular interactions, in silico docking, ADME and cytotoxicity studies. Inorganica Chimica Acta 2022, 534 , 120805. https://doi.org/10.1016/j.ica.2022.120805
    31. Jana Hildebrandt, Norman Häfner, Daniel Kritsch, Helmar Görls, Matthias Dürst, Ingo B. Runnebaum, Wolfgang Weigand. Highly Cytotoxic Osmium(II) Compounds and Their Ruthenium(II) Analogues Targeting Ovarian Carcinoma Cell Lines and Evading Cisplatin Resistance Mechanisms. International Journal of Molecular Sciences 2022, 23 (9) , 4976. https://doi.org/10.3390/ijms23094976
    32. Kalaiarasi Giriraj, Mohamed Subarkhan Mohamed Kasim, Keerthana Balasubramaniam, Sathiya Kamatchi Thangavel, Janani Venkatesan, Sharmila Suresh, Pritha Shanmugam, Chiranjeevi Karri. Various coordination modes of new coumarin Schiff bases toward Cobalt (III) ion: Synthesis, spectral characterization, in vitro cytotoxic activity, and investigation of apoptosis. Applied Organometallic Chemistry 2022, 36 (3) https://doi.org/10.1002/aoc.6536
    33. Huiwen Zhang, Xiaofei Liao, Xiaoyun Wu, Chuanling Shi, Yuanyuan Zhang, Yuhan Yuan, Wenlong Li, Jiawen Wang, Yunjun Liu. Iridium(III) complexes entrapped in liposomes trigger mitochondria-mediated apoptosis and GSDME-mediated pyroptosis. Journal of Inorganic Biochemistry 2022, 228 , 111706. https://doi.org/10.1016/j.jinorgbio.2021.111706
    34. A. Byrne, David Cullinane, Karmel S. Gkika, Christopher S. Burke, Tia E. Keyes. Luminescent Metal Complexes in Bioimaging. 2022, 1073-1107. https://doi.org/10.1007/978-3-030-63713-2_37
    35. Artem Osypenko, Adnan Ashraf, Valentyn Pozhydaiev, Maria V. Babak, Muhammad Hanif. Organometallic Chemistry of Anticancer Ruthenium and Osmium Complexes. 2022, 206-225. https://doi.org/10.1016/B978-0-12-820206-7.00045-7
    36. Gizem Selvi, Fethi Ahmet Ozdemir, Gurkan Aykutoglu, Namık Özdemir, Zafer Şerbetçi, Muharrem Dinçer, Osman Dayan. Synthesis, catalytic, cytotoxic, and antibacterial properties of new Ru(II) and Pd(II) complexes bearing bidentate Schiff base ligand. Inorganic and Nano-Metal Chemistry 2021, 51 (12) , 1697-1706. https://doi.org/10.1080/24701556.2020.1852423
    37. Ljiljana E. Mihajlović-Lalić, Jelena Poljarević, Sanja Grgurić-Šipka. Metal complexes with α-picolinic acid frameworks and their antitumor activity. Inorganica Chimica Acta 2021, 527 , 120582. https://doi.org/10.1016/j.ica.2021.120582
    38. Alain C. Jung, Fabien Moinard-Butot, Chloé Thibaudeau, Gilles Gasser, Christian Gaiddon. Antitumor Immune Response Triggered by Metal-Based Photosensitizers for Photodynamic Therapy: Where Are We?. Pharmaceutics 2021, 13 (11) , 1788. https://doi.org/10.3390/pharmaceutics13111788
    39. Jie Zeng, Yu Zhao, Kexun Li, Daoling Long, Wei Li, Liang Liang. A coordinated ruthenium-rifampicin complex reprogramming the colon carcinoma micro-environment mediated by modulation of p53/AkT/mTOR/VEGF pathway. Toxicology and Applied Pharmacology 2021, 426 , 115618. https://doi.org/10.1016/j.taap.2021.115618
    40. Bharat H. Pursuwani, Bhupesh S. Bhatt, Foram U. Vaidya, Chandramani Pathak, Mohan N. Patel. Tetrazolo[1,5-a]quinoline moiety-based Os(IV) complexes: DNA binding/cleavage, bacteriostatic and photocytotoxicity assay. Journal of Biomolecular Structure and Dynamics 2021, 39 (8) , 2894-2903. https://doi.org/10.1080/07391102.2020.1756912
    41. Sourav De, R. Selva Kumar, Ashna Gauthaman, S.K. Ashok Kumar, Priyankar Paira, Anbalagan Moorthy, Subhasis Banerjee. Luminescent ruthenium(II)-para-cymene complexes of aryl substituted imidazo-1,10-phenanthroline as anticancer agents and the effect of remote substituents on cytotoxic activities. Inorganica Chimica Acta 2021, 515 , 120066. https://doi.org/10.1016/j.ica.2020.120066
    42. Kilian R. A. Schneider, Avinash Chettri, Houston D. Cole, Katharina Reglinski, Jannik Brückmann, John A. Roque, Anne Stumper, Djawed Nauroozi, Sylvia Schmid, Christoffer B. Lagerholm, Sven Rau, Peter Bäuerle, Christian Eggeling, Colin G. Cameron, Sherri A. McFarland, Benjamin Dietzek. Intracellular Photophysics of an Osmium Complex bearing an Oligothiophene Extended Ligand. Chemistry – A European Journal 2020, 26 (65) , 14844-14851. https://doi.org/10.1002/chem.202002667
    43. Thangavel Sathiya Kamatchi, Mohamed Kasim Mohamed Subarkhan, Rengan Ramesh, Hangxiang Wang, Jan Grzegorz Małecki. Investigation into antiproliferative activity and apoptosis mechanism of new arene Ru( ii ) carbazole-based hydrazone complexes. Dalton Transactions 2020, 49 (32) , 11385-11395. https://doi.org/10.1039/D0DT01476A
    44. Raul Berrocal‐Martin, Carlos Sanchez‐Cano, Cookson K. C. Chiu, Russell J. Needham, Peter J. Sadler, Steven W. Magennis. Metallation‐Induced Heterogeneous Dynamics of DNA Revealed by Single‐Molecule FRET. Chemistry – A European Journal 2020, 26 (22) , 4980-4987. https://doi.org/10.1002/chem.202000458
    45. José Javier Conesa, Ana C. Carrasco, Vanessa Rodríguez‐Fanjul, Yang Yang, José L. Carrascosa, Peter Cloetens, Eva Pereiro, Ana M. Pizarro. Unambiguous Intracellular Localization and Quantification of a Potent Iridium Anticancer Compound by Correlative 3D Cryo X‐Ray Imaging. Angewandte Chemie 2020, 132 (3) , 1286-1294. https://doi.org/10.1002/ange.201911510
    46. José Javier Conesa, Ana C. Carrasco, Vanessa Rodríguez‐Fanjul, Yang Yang, José L. Carrascosa, Peter Cloetens, Eva Pereiro, Ana M. Pizarro. Unambiguous Intracellular Localization and Quantification of a Potent Iridium Anticancer Compound by Correlative 3D Cryo X‐Ray Imaging. Angewandte Chemie International Edition 2020, 59 (3) , 1270-1278. https://doi.org/10.1002/anie.201911510
    47. Joanna Wiśniewska, Marzena Fandzloch, Tadeusz Muzioł, Iwona Łakomska. The hydrolysis of a ruthenium(III) complex with triazolopyrimidine ligands and mechanistic insights into its anticancer activity. Inorganic Chemistry Communications 2019, 109 , 107567. https://doi.org/10.1016/j.inoche.2019.107567
    48. Saawan Kumar, Guillaume Gallician, Dennis Weidener, Matthew P. Sullivan, Tilo Söhnel, Muhammad Hanif, Christian G. Hartinger. Design of organoruthenium complexes for nanoparticle functionalization. Journal of Organometallic Chemistry 2019, 891 , 64-71. https://doi.org/10.1016/j.jorganchem.2019.03.020
    49. Qi-Pin Qin, Zhen-Feng Wang, Ming-Xiong Tan, Shu-Long Wang, Bi-Qun Zou, Dong-Mei Luo, Jiao-Lan Qin, Shu-Hua Zhang. Two novel platinum(II) complexes with sorafenib and regorafenib: Synthesis, structural characterization, and evaluation of in vitro antitumor activity. Inorganic Chemistry Communications 2019, 104 , 27-30. https://doi.org/10.1016/j.inoche.2019.03.031
    50. Isolda Romero-Canelón. Ruthenium, Osmium and Iridium in the Fight Against Cancer. 2019, 31-61. https://doi.org/10.1039/9781788016452-00031
    51. Jin-can Chen, Yao Zhang, Xin-ming Jie, Ji She, Guang-zhi Dongye, Yu Zhong, Yuan-yuan Deng, Jie Wang, Bo-yang Guo, Lan-mei Chen. Ruthenium(II) salicylate complexes inducing ROS-mediated apoptosis by targeting thioredoxin reductase. Journal of Inorganic Biochemistry 2019, 193 , 112-123. https://doi.org/10.1016/j.jinorgbio.2019.01.011
    52. Celina Støving Dam, Ian Henry Lambert, Bente Gammelgaard, Stefan Stürup. Distribution of platinum between nuclear and cytosolic fractions – Can subcellular fractionation be performed quantitatively?. Journal of Pharmaceutical and Biomedical Analysis 2019, 165 , 82-89. https://doi.org/10.1016/j.jpba.2018.11.046
    53. Joanna Wiśniewska, Marzena Fandzloch, Iwona Łakomska. The reduction of ruthenium(III) complexes with triazolopyrimidine ligands by ascorbic acid and mechanistic insight into their action in anticancer therapy. Inorganica Chimica Acta 2019, 484 , 305-310. https://doi.org/10.1016/j.ica.2018.09.051
    54. Ting Meng, Qi-Pin Qin, Zhen-Rui Wang, Li-Ting Peng, Hua-Hong Zou, Zhen-Yuan Gan, Ming-Xiong Tan, Kai Wang, Fu-Pei Liang. Synthesis and biological evaluation of substituted 3-(2′-benzimidazolyl)coumarin platinum(II) complexes as new telomerase inhibitors. Journal of Inorganic Biochemistry 2018, 189 , 143-150. https://doi.org/10.1016/j.jinorgbio.2018.09.004
    55. Pingyu Zhang, Huaiyi Huang. Future potential of osmium complexes as anticancer drug candidates, photosensitizers and organelle-targeted probes. Dalton Transactions 2018, 47 (42) , 14841-14854. https://doi.org/10.1039/C8DT03432J
    56. Nanjan Mohan, Mohamed Kasim Mohamed Subarkhan, Rengan Ramesh. Synthesis, antiproliferative activity and apoptosis-promoting effects of arene ruthenium(II) complexes with N, O chelating ligands. Journal of Organometallic Chemistry 2018, 859 , 124-131. https://doi.org/10.1016/j.jorganchem.2018.01.022
    57. Samuel M. Meier-Menches, Christopher Gerner, Walter Berger, Christian G. Hartinger, Bernhard K. Keppler. Structure–activity relationships for ruthenium and osmium anticancer agents – towards clinical development. Chemical Society Reviews 2018, 47 (3) , 909-928. https://doi.org/10.1039/C7CS00332C
    58. Pavel Štarha, Zdeněk Trávníček, Radovan Herchel, Pawel Jewula, Zdeněk Dvořák. A potential method to improve the in vitro cytotoxicity of half-sandwich Os( ii ) complexes against A2780 cells. Dalton Transactions 2018, 47 (16) , 5714-5724. https://doi.org/10.1039/C8DT00193F
    59. Jincan Chen, Fa Peng, Yao Zhang, Baojun Li, Ji She, Xinming Jie, Zhilin Zou, Man Chen, Lanmei Chen. Synthesis, characterization, cellular uptake and apoptosis-inducing properties of two highly cytotoxic cyclometalated ruthenium(II) β-carboline complexes. European Journal of Medicinal Chemistry 2017, 140 , 104-117. https://doi.org/10.1016/j.ejmech.2017.09.007
    60. Arijit Bag, Pradip Kr. Ghorai. Enhancement of biocompatibility and photoacoustic contrast activity of metal clusters. Journal of Molecular Graphics and Modelling 2017, 75 , 220-232. https://doi.org/10.1016/j.jmgm.2017.05.011
    61. Adnan Ashraf, Muhammad Hanif, Mario Kubanik, Tilo Söhnel, Stephen M.F. Jamieson, Arindam Bhattacharyya, Christian G. Hartinger. Aspirin-inspired organometallic compounds: Structural characterization and cytotoxicity. Journal of Organometallic Chemistry 2017, 839 , 31-37. https://doi.org/10.1016/j.jorganchem.2017.01.016
    62. Ahmed A. Soliman, Amany M. Sayed, Othman I. Alajrawy, Wolfgang Linert. New palladium(II) formamidine complexes: Preparation, characterization, theoretical calculations and cytotoxic activity. Journal of Molecular Structure 2017, 1137 , 453-460. https://doi.org/10.1016/j.molstruc.2017.02.062
    63. MohammadMehdi Haghdoost, Golara Golbaghi, Myriam Létourneau, Shunmoogum A. Patten, Annie Castonguay. Lipophilicity-antiproliferative activity relationship study leads to the preparation of a ruthenium(II) arene complex with considerable in vitro cytotoxicity against cancer cells and a lower in vivo toxicity in zebrafish embryos than clinically approved cis-platin. European Journal of Medicinal Chemistry 2017, 132 , 282-293. https://doi.org/10.1016/j.ejmech.2017.03.029
    64. Ana Zamora, Sergio A. Pérez, Matthias Rothemund, Venancio Rodríguez, Rainer Schobert, Christoph Janiak, José Ruiz. Exploring the Influence of the Aromaticity on the Anticancer and Antivascular Activities of Organoplatinum(II) Complexes. Chemistry – A European Journal 2017, 23 (23) , 5614-5625. https://doi.org/10.1002/chem.201700717
    65. C. Dolan, C.S. Burke, A. Byrne, T.E. Keyes. Cellular Uptake and Sensing Capability of Transition Metal Peptide Conjugates. 2017, 55-89. https://doi.org/10.1016/B978-0-12-803814-7.00002-2
    66. Matthias H. M. Klose, Michaela Hejl, Petra Heffeter, Michael A. Jakupec, Samuel M. Meier-Menches, Walter Berger, Bernhard K. Keppler. Post-digestion stabilization of osmium enables quantification by ICP-MS in cell culture and tissue. The Analyst 2017, 142 (13) , 2327-2332. https://doi.org/10.1039/C7AN00350A
    67. Pingyu Zhang, Yi Wang, Kangqiang Qiu, Zhiqian Zhao, Rentao Hu, Chuanxin He, Qianling Zhang, Hui Chao. A NIR phosphorescent osmium( ii ) complex as a lysosome tracking reagent and photodynamic therapeutic agent. Chemical Communications 2017, 53 (91) , 12341-12344. https://doi.org/10.1039/C7CC07776A
    68. Nuno M. R. Martins, Sellamuthu Anbu, Kamran T. Mahmudov, Rajendran Ravishankaran, M. Fátima C. Guedes da Silva, Luísa M. D. R. S. Martins, Anjali A. Karande, Armando J. L. Pombeiro. DNA and BSA binding and cytotoxic properties of copper( ii ) and iron( iii ) complexes with arylhydrazone of ethyl 2-cyanoacetate or formazan ligands. New Journal of Chemistry 2017, 41 (10) , 4076-4086. https://doi.org/10.1039/C7NJ00420F
    69. Yan-Yih Goh, Yaw-Kai Yan, Nguan Soon Tan, Su-Ann Goh, Shang Li, You-Chuan Teoh, Peter P. F. Lee. Downregulation of oncogenic RAS and c-Myc expression in MOLT-4 leukaemia cells by a salicylaldehyde semicarbazone copper(II) complex. Scientific Reports 2016, 6 (1) https://doi.org/10.1038/srep36868
    70. Lanmei Chen, Guodong Li, Fa Peng, Xinming Jie, Guangzhi Dongye, Kangrong Cai, Ruibing Feng, Baojun Li, Qingwang Zeng, Kaiyi Lun, Jincan Chen, Bilian Xu. The induction of autophagy against mitochondria-mediated apoptosis in lung cancer cells by a ruthenium (II) imidazole complex. Oncotarget 2016, 7 (49) , 80716-80734. https://doi.org/10.18632/oncotarget.13032
    71. Cheng Zhang, Shang-Hai Lai, Chuan-Chuan Zeng, Bing Tang, Dan Wan, De-Gang Xing, Yun-Jun Liu. The induction of apoptosis in SGC-7901 cells through the ROS-mediated mitochondrial dysfunction pathway by a Ir(III) complex. JBIC Journal of Biological Inorganic Chemistry 2016, 21 (8) , 1047-1060. https://doi.org/10.1007/s00775-016-1401-8
    72. Sunil B. Zanje, Arjun N. Kokare, Vishal J. Suryavanshi, Duryodhan P. Waghmode, Sunil S. Joshi, Mansing A. Anuse. Development of a reliable analytical method for the precise extractive spectrophotometric determination of osmium(VIII) with 2-nitrobenzaldehydethiocarbohydrazone: Analysis of alloys and real sample. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2016, 169 , 223-229. https://doi.org/10.1016/j.saa.2016.06.051
    73. Mickaël Marloye, Gilles Berger, Michel Gelbcke, François Dufrasne. A Survey of the Mechanisms of Action of Anticancer Transition Metal Complexes. Future Medicinal Chemistry 2016, 8 (18) , 2263-2286. https://doi.org/10.4155/fmc-2016-0153
    74. Leli Zeng, Yu Chen, Jiangping Liu, Huaiyi Huang, Ruilin Guan, Liangnian Ji, Hui Chao. Ruthenium(II) Complexes with 2-Phenylimidazo[4,5-f][1,10]phenanthroline Derivatives that Strongly Combat Cisplatin-Resistant Tumor Cells. Scientific Reports 2016, 6 (1) https://doi.org/10.1038/srep19449
    75. Andrea Kurzwernhart, Stephan Mokesch, Erik Klapproth, Mahsa S. Adib‐Ravazi, Michael A. Jakupec, Christian G. Hartinger, Wolfgang Kandioller, Bernhard K. Keppler. Flavonoid‐Based Organometallics with Different Metal Centers – Investigations of the Effects on Reactivity and Cytotoxicity. European Journal of Inorganic Chemistry 2016, 2016 (2) , 240-246. https://doi.org/10.1002/ejic.201501020
    76. Amit Kumar, Ashish Kumar, Rakesh Kumar Gupta, Rajendra Prasad Paitandi, Krishna Beer Singh, Surendra Kumar Trigun, Maninder Singh Hundal, Daya Shankar Pandey. Cationic Ru(II), Rh(III) and Ir(III) complexes containing cyclic -perimeter and 2-aminophenyl benzimidazole ligands: Synthesis, molecular structure, DNA and protein binding, cytotoxicity and anticancer activity. Journal of Organometallic Chemistry 2016, 801 , 68-79. https://doi.org/10.1016/j.jorganchem.2015.10.008
    77. Huaiyi Huang, Pingyu Zhang, Yu Chen, Kangqiang Qiu, Chengzhi Jin, Liangnian Ji, Hui Chao. Synthesis, characterization and biological evaluation of labile intercalative ruthenium( ii ) complexes for anticancer drug screening. Dalton Transactions 2016, 45 (33) , 13135-13145. https://doi.org/10.1039/C6DT01270A
    78. Emilia Păunescu, Patrycja Nowak‐Sliwinska, Catherine M. Clavel, Rosario Scopelliti, Arjan W. Griffioen, Paul J. Dyson. Anticancer Organometallic Osmium(II)‐ p ‐cymene Complexes. ChemMedChem 2015, 10 (9) , 1539-1547. https://doi.org/10.1002/cmdc.201500221
    79. S. V. Zaitseva, S. A. Zdanovich, O. I. Koifman. Intermolecular interaction of osmium and ruthenium porphyrinates with organic bases. Russian Journal of Inorganic Chemistry 2015, 60 (6) , 759-764. https://doi.org/10.1134/S0036023615060182
    80. Lara C. Sudding, Prinessa Chellan, Preshendren Govender, Gregory S. Smith. Cyclometalated Benzaldimine-Terminated Rhodium and Iridium Dendrimers: Synthesis, Characterization and Molecular Structures of Mononuclear Analogues. Journal of Inorganic and Organometallic Polymers and Materials 2015, 25 (3) , 457-465. https://doi.org/10.1007/s10904-015-0184-7
    81. Serenella Medici, Massimiliano Peana, Valeria Marina Nurchi, Joanna I. Lachowicz, Guido Crisponi, Maria Antonietta Zoroddu. Noble metals in medicine: Latest advances. Coordination Chemistry Reviews 2015, 284 , 329-350. https://doi.org/10.1016/j.ccr.2014.08.002
    82. Aisling Byrne, Ciarán Dolan, Roisin D. Moriarty, Aaron Martin, Ute Neugebauer, Robert J. Forster, Anthony Davies, Yuri Volkov, Tia E. Keyes. Osmium( ii ) polypyridyl polyarginine conjugate as a probe for live cell imaging; a comparison of uptake, localization and cytotoxicity with its ruthenium( ii ) analogue. Dalton Transactions 2015, 44 (32) , 14323-14332. https://doi.org/10.1039/C5DT01833A
    83. Huaiyi Huang, Pingyu Zhang, Yu Chen, Liangnian Ji, Hui Chao. Labile ruthenium( ii ) complexes with extended phenyl-substituted terpyridyl ligands: synthesis, aquation and anticancer evaluation. Dalton Transactions 2015, 44 (35) , 15602-15610. https://doi.org/10.1039/C5DT02446C
    84. Lara C. Sudding, Richard Payne, Preshendren Govender, Fabio Edafe, Catherine M. Clavel, Paul J. Dyson, Bruno Therrien, Gregory S. Smith. Evaluation of the in vitro anticancer activity of cyclometalated half-sandwich rhodium and iridium complexes coordinated to naphthaldimine-based poly(propyleneimine) dendritic scaffolds. Journal of Organometallic Chemistry 2014, 774 , 79-85. https://doi.org/10.1016/j.jorganchem.2014.10.003
    85. Gajendra Gupta, Narayana Nagesh, Benjamin S. Murray, Paul J. Dyson, Bruno Therrien. Antiproliferative activities of trithiolato-bridged dinuclear arene osmium complexes. Inorganica Chimica Acta 2014, 423 , 31-35. https://doi.org/10.1016/j.ica.2014.07.050
    86. Muhammad Hanif, Maria V. Babak, Christian G. Hartinger. Development of anticancer agents: wizardry with osmium. Drug Discovery Today 2014, 19 (10) , 1640-1648. https://doi.org/10.1016/j.drudis.2014.06.016
    87. PIYALI PAUL, SAMARESH BHATTACHARYA. Palladium complexes of pyrrole-2-aldehyde thiosemicarbazone: Synthesis, structure and spectral properties. Journal of Chemical Sciences 2014, 126 (5) , 1547-1555. https://doi.org/10.1007/s12039-014-0699-4
    88. Rajendra Prasad Paitandi, Rakesh Kumar Gupta, Roop Shikha Singh, Gunjan Sharma, Biplob Koch, Daya Shankar Pandey. Interaction of ferrocene appended Ru(II), Rh(III) and Ir(III) dipyrrinato complexes with DNA/protein, molecular docking and antitumor activity. European Journal of Medicinal Chemistry 2014, 84 , 17-29. https://doi.org/10.1016/j.ejmech.2014.06.052
    89. Ana M. Pizarro, Ruth J. McQuitty, Fiona S. Mackay, Yao Zhao, Julie A. Woods, Peter J. Sadler. Cellular Accumulation, Lipophilicity and Photocytotoxicity of Diazido Platinum(IV) Anticancer Complexes. ChemMedChem 2014, 9 (6) , 1169-1175. https://doi.org/10.1002/cmdc.201402066
    90. Guo-dong Li, Lan-mei Chen, Xin-yu Wang, Ling-feng Wu, Xin-ming Jie, Jin-can Chen. Electronic Structures, DNA-binding, SAR, and Spectral Properties of Ruthenium Methylimidazole Complexes [Ru(MeIm)4L]2+ (L=iip, tip, 2ntz). Chinese Journal of Chemical Physics 2014, 27 (2) , 159-167. https://doi.org/10.1063/1674-0068/27/02/159-167
    91. Ruth J. Mcquitty. Metal-based Drugs. Science Progress 2014, 97 (1) , 1-19. https://doi.org/10.3184/003685014X13898980185076
    92. Tânia S. Morais, Filipa C. Santos, Tiago F. Jorge, Leonor Côrte-Real, Paulo J. Amorim Madeira, Fernanda Marques, M. Paula Robalo, António Matos, Isabel Santos, M. Helena Garcia. New water-soluble ruthenium(II) cytotoxic complex: Biological activity and cellular distribution. Journal of Inorganic Biochemistry 2014, 130 , 1-14. https://doi.org/10.1016/j.jinorgbio.2013.09.013
    93. Ashley Wragg, Martin R. Gill, Christopher J. Hill, Xiaodi Su, Anthony J. H. M. Meijer, Carl Smythe, Jim A. Thomas. Dinuclear osmium( ii ) probes for high-resolution visualisation of cellular DNA structure using electron microscopy. Chem. Commun. 2014, 50 (93) , 14494-14497. https://doi.org/10.1039/C4CC05547K
    94. Cai-Ping Tan, Yi-Ying Lu, Liang-Nian Ji, Zong-Wan Mao. Metallomics insights into the programmed cell death induced by metal-based anticancer compounds. Metallomics 2014, 6 (5) , 978. https://doi.org/10.1039/c3mt00225j
    95. Sabine H. van Rijt, Isolda Romero-Canelón, Ying Fu, Steve D. Shnyder, Peter J. Sadler. Potent organometallic osmium compounds induce mitochondria-mediated apoptosis and S-phase cell cycle arrest in A549 non-small cell lung cancer cells. Metallomics 2014, 6 (5) , 1014. https://doi.org/10.1039/c4mt00034j
    96. Surin Hong, Soomin Park, Junsu Park, Jongheop Yi. Effect of end group modification of DNA-functionalized gold nanoparticles on cellular uptake in HepG2 cells. Colloids and Surfaces B: Biointerfaces 2013, 112 , 415-420. https://doi.org/10.1016/j.colsurfb.2013.08.020
    97. Hanlu Wang, Xingye Zeng, Rujin Zhou, Cunyuan Zhao. A comparative DFT study on aquation and nucleobase binding of ruthenium (II) and osmium (II) arene complexes. Journal of Molecular Modeling 2013, 19 (11) , 4849-4856. https://doi.org/10.1007/s00894-013-1987-5
    98. Richard Payne, Preshendren Govender, Bruno Therrien, Catherine M. Clavel, Paul J. Dyson, Gregory S. Smith. Neutral and cationic multinuclear half-sandwich rhodium and iridium complexes coordinated to poly(propyleneimine) dendritic scaffolds: Synthesis and cytotoxicity. Journal of Organometallic Chemistry 2013, 729 , 20-27. https://doi.org/10.1016/j.jorganchem.2013.01.009
    99. Zhenli Zhu, Chunying Huang, Qian He, Qing Xiao, Zhifu Liu, Suicheng Zhang, Shenghong Hu. On line vapor generation of osmium based on solution cathode glow discharge for the determination by ICP-OES. Talanta 2013, 106 , 133-136. https://doi.org/10.1016/j.talanta.2012.12.010
    100. A.M. Pizarro, N.P.E. Barry, P.J. Sadler. Metal–DNA Coordination Complexes. 2013, 751-784. https://doi.org/10.1016/B978-0-08-097774-4.00330-2
    Load all citations

    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2010, 53, 2, 840–849
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm901556u
    Published December 15, 2009
    Copyright © 2009 American Chemical Society

    Article Views

    2904

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.