دورية أكاديمية
Exploring Raloxifene-Based Metallodrugs: A Versatile Vector Combined with Platinum(II), Palladium(II) and Nickel(II) Dichlorides and Carborates against Triple-Negative Breast Cancer.
العنوان: | Exploring Raloxifene-Based Metallodrugs: A Versatile Vector Combined with Platinum(II), Palladium(II) and Nickel(II) Dichlorides and Carborates against Triple-Negative Breast Cancer. |
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المؤلفون: | Kazimir A; new address, Institute for Drug Discovery, Leipzig University, Leipzig, Brüderstraße 34, 04103, Germany.; Faculty of Chemistry and Mineralogy, Leipzig University, Johannisallee 29, Leipzig, 04103, Germany., Götze T; Faculty of Chemistry and Mineralogy, Leipzig University, Johannisallee 29, Leipzig, 04103, Germany., Lönnecke P; Faculty of Chemistry and Mineralogy, Leipzig University, Johannisallee 29, Leipzig, 04103, Germany., Murganić B; Institute of Nuclear Sciences 'Vinča', University of Belgrade, 12-14 Mike Petrovića Street, Belgrade, 11351, Serbia., Mijatović S; Department of Immunology, Institute for Biological Research 'Siniša Stanković', National Institute of Republic of Serbia, Belgrade University, Bul. despota Stefana 142, Belgrade, 11060, Serbia., Maksimović-Ivanić D; Department of Immunology, Institute for Biological Research 'Siniša Stanković', National Institute of Republic of Serbia, Belgrade University, Bul. despota Stefana 142, Belgrade, 11060, Serbia., Hey-Hawkins E; Faculty of Chemistry and Mineralogy, Leipzig University, Johannisallee 29, Leipzig, 04103, Germany. |
المصدر: | ChemMedChem [ChemMedChem] 2024 Jul 15; Vol. 19 (14), pp. e202400006. Date of Electronic Publication: 2024 Jun 05. |
نوع المنشور: | Journal Article |
اللغة: | English |
بيانات الدورية: | Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101259013 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1860-7187 (Electronic) Linking ISSN: 18607179 NLM ISO Abbreviation: ChemMedChem Subsets: MEDLINE |
أسماء مطبوعة: | Original Publication: Weinheim, Germany : Wiley-VCH, c2006- |
مواضيع طبية MeSH: | Palladium*/chemistry , Palladium*/pharmacology , Nickel*/chemistry , Nickel*/pharmacology , Triple Negative Breast Neoplasms*/drug therapy , Triple Negative Breast Neoplasms*/pathology , Antineoplastic Agents*/pharmacology , Antineoplastic Agents*/chemistry , Antineoplastic Agents*/chemical synthesis , Platinum*/chemistry , Platinum*/pharmacology , Coordination Complexes*/chemistry , Coordination Complexes*/pharmacology , Coordination Complexes*/chemical synthesis , Cell Proliferation*/drug effects , Raloxifene Hydrochloride*/chemistry , Raloxifene Hydrochloride*/pharmacology , Drug Screening Assays, Antitumor*, Humans ; Cell Line, Tumor ; Structure-Activity Relationship ; Molecular Structure ; Dose-Response Relationship, Drug ; Female |
مستخلص: | Triple-negative breast cancer (TNBC) poses challenges in therapy due to the absence of target expression such as estrogen receptor (ER), progesterone receptor (PR), and human epidermal growth factor receptor 2 (HER2). Frequently, the treatment of TNBC involves the combination of several therapeutics. However, an enhanced therapeutic effect can be also achieved within a single molecule. The efficacy of raloxifene can be improved by designing a raloxifene-based hybrid drug bearing a 2,2'-bipyridine moiety (2). Integration of platinum(II), palladium(II), and nickel(II) complexes into this structure dramatically changed the cytotoxicity. The platinum(II) dichloride complex 3 did not demonstrate any activity, while palladium(II) and nickel(II) dichloride complexes 4 and 5 exhibited various cytotoxic behavior towards different types of hormone-receptor positive (HR+) cancer and TNBC cell lines. The replacement of the two chlorido ligands in 3-5 with a dicarbollide (carborate) ion [C (© 2024 The Authors. ChemMedChem published by Wiley-VCH GmbH.) |
References: | N. M. Almansour, Front. Mol. Biosci. 2022, 9, 836417. E. M. Grasset, M. Dunworth, G. Sharma, M. Loth, J. Tandurella, A. Cimino-Mathews, M. Gentz, S. Bracht, M. Haynes, E. J. Fertig, A. J. Ewald, Sci. Transl. Med. 2022, 14, eabn7571. A. K. Shiau, D. Barstad, P. M. Loria, L. Cheng, P. J. Kushner, D. A. Agard, G. L. Greene, Cell 1998, 95, 927–937. B. M. Jacobsen, K. B. Horwitz, Mol. Cell. Endocrinol. 2012, 357, 18–29. N. Iqbal, N. Iqbal, Mol. Biol. Int. 2014, 2014, 852748. A. Schneeweiss, C. Denkert, P. A. Fasching, C. Fremd, O. Gluz, C. Kolberg-Liedtke, S. Loibl, H.-J. Lück, Geburtshilfe Frauenheilkd. 2019, 79, 605–617. O. Treeck, S. Schüler-Toprak, O. Ortmann, Cells 2020, 9, 2358. A. Sellitto, Y. D'Agostino, E. Alexandrova, J. Lamberti, G. Pecoraro, D. Memoli, D. Rocco, E. Coviello, G. Giurato, G. Nassa, R. Tarallo, A. Weisz, F. Rizzo, Cancers 2020, 12, 1477. P. Y. Maximov, B. Abderrahman, S. W. Fanning, S. Sengupta, P. Fan, R. F. Curpan, D. M. Q. Rincon, J. A. Greenland, S. S. Rajan, G. L. Greene, V. C. Jordan, Mol. Pharmacol. 2018, 94, 812–822. L. Scarpetti, C. C. Oturkar, D. Juric, M. Shellock, G. Malvarosa, K. Post, S. Isakoff, N. Wang, B. Nahed, K. Oh, G. M. Das, A. Bardia, Oncologist 2023, 28, 358–363. C. M. Abdelmalek, Z. Hu, T. Kronenberger, J. Küblbeck, F. J. M. Kinnen, S. S. Hesse, A. Malik, M. Kudolo, R. Niess, M. Gehringer, L. Zender, P. A. Witt-Enderby, D. P. Zlotos, S. A. Laufer, J. Med. Chem. 2022, 65, 4616–4632. F. Acconcia, M. Fiocchetti, C. Busonero, V. S. Fernandez, E. Montalesi, M. Cipolletti, V. Pallottini, M. Marino, Mol. Cell. Endocrinol. 2021, 538, 111452. S. Taurin, K. M. Allen, M. J. Scandlyn, R. J. Rosengren, Int. J. Oncol. 2013, 43, 785–792. A. Kazimir, T. Götze, B. Murganić, S. Mijatović, D. Maksimović-Ivanić, E. Hey-Hawkins, RSC Med. Chem. 2024, DOI: 10.1039/D4MD00051Jin print. M. Kalabay, Z. Szász, O. Láng, E. Lajkó, É. Pállinger, C. Duró, T. Jernei, A. Csámpai, A. Takács, L. Kőhidai, Pharmaceuticals 2022, 15, 314. N. Nayeem, M. Contel, Chem. Eur. J. 2021, 27, 8891–8917. A. P. Ferreira, J. L. F. Da Silva, M. T. Duarte, M. F. M. Da Piedade, M. P. Robalo, S. G. Harjivan, C. Marzano, V. Gandin, M. M. Marques, Organometallics 2009, 28, 5412–5423. B. Köberle, S. Schoch, Cancers 2021, 13, 2073. S. Rottenberg, C. Disler, P. Perego, Nat. Rev. Cancer 2021, 21, 37–50. C. Zhang, C. Xu, X. Gao, Q. Yao, Theranostics 2022, 12, 2115–2132. S. R. Mason, M. L. Willson, S. J. Egger, J. Beith, R. F. Dear, A. Goodwin, Cochrane Database Syst. Rev. 2023, 8, 1–114. The platinum agents: A role in breast cancer treatment? ScienceDirect, https://www.sciencedirect.com/science/article/pii/S0093775401901903, (accessed 22 December 2023). J. Zhou, Y. Kang, L. Chen, H. Wang, J. Liu, S. Zeng, L. Yu, Front. Pharmacol. 2020, 11, 1–17. R. Oun, Y. E. Moussa, N. J. Wheate, Dalton Trans. 2018, 47, 6645–6653. T. Lazarević, A. Rilak, Ž. D. Bugarčić, Eur. J. Med. Chem. 2017, 142, 8–31. T. A. al-Allaf, L. J. Rashan, Boll. Chim. Farm. 2001, 140, 205–210. E. Ulukaya, F. Ari, K. Dimas, E. I. Ikitimur, E. Guney, V. T. Yilmaz, Eur. J. Med. Chem. 2011, 46, 4957–4963. M. Vojtek, M. P. M. Marques, I. M. P. L. V. O. Ferreira, H. Mota-Filipe, C. Diniz, Drug Discovery Today 2019, 24, 1044–1058. G. Genchi, A. Carocci, G. Lauria, M. S. Sinicropi, A. Catalano, Int. J. Environ. Res. Public Health 2020, 17, 679. E. Kahraman, E. Goker, Toxicol. Ind. Health 2023, 39, 94–103. M. Anjomshoa, M. Torkzadeh-Mahani, M. Sahihi, C. Rizzoli, M. Ansari, J. Janczak, S. Sherafat Esfahani, F. Ataei, M. Dehkhodaei, B. Amirheidari, J. Biomol. Struct. Dyn. 2019, 37, 3887–3904. A. F. Armstrong, J. F. Valliant, Dalton Trans. 2007, 38, 4240–4251. M. Gozzi, B. Schwarze, E. Hey-Hawkins, Pure Appl. Chem. 2019, 91, 563–573. D. Sedlák, T. A. Wilson, W. Tjarks, H. S. Radomska, H. Wang, J. N. Kolla, Z. J. Leśnikowski, A. Špičáková, T. Ali, K. Ishita, L. H. Rakotondraibe, S. Vibhute, D. Wang, P. Anzenbacher, C. Bennett, P. Bartunek, C. C. Coss, J. Med. Chem. 2021, 64, 9330–9353. Z. J. Leśnikowski, J. Med. Chem. 2016, 59, 7738–7758. B. Schwarze, S. Jelača, L. Welcke, D. Maksimović-Ivanić, S. Mijatović, E. Hey-Hawkins, ChemMedChem 2019, 14, 2075–2083. A. Kazimir, B. Schwarze, P. Lönnecke, S. Jelača, S. Mijatović, D. Maksimović-Ivanić, E. Hey-Hawkins, Pharmaceutica 2023, 15, 682. A. Kazimir, B. Schwarze, P. Lönnecke, S. Jelača, S. Mijatović, D. Maksimović-Ivanić, E. Hey-Hawkins, RSC Med. Chem. 2023, 14, 2574–2582. P. Mirzapur, M. R. Khazaei, M. T. Moradi, M. Khazaei, Life Sci. 2018, 205, 45–53. H. T. Kim, B. C. Kim, I. Y. Kim, M. Mamura, D. H. Seong, J.-J. Jang, S.-J. Kim, J. Biol. Chem. 2002, 277, 32510–32515. C. W. Yun, J. Jeon, G. Go, J. H. Lee, S. H. Lee, Int. J. Mol. Sci. 2020, 22, 179. S. Mijatović, A. Bramanti, F. Nicoletti, P. Fagone, G. N. Kaluđerović, D. Maksimović-Ivanić, Biotechnol. Adv. 2018, 36,1622–1632. H. Zhao, Z. Darzynkiewicz, Methods Mol. Biol. Clifton NJ 2013, 965, 83–92. L. Bousset, J. Gil, Mol. Oncol. 2022, 16, 3855–3880. S. Braun, S. Jelača, M. Laube, S. George, B. Hofmann, P. Lönnecke, D. Steinhilber, J. Pietzsch, S. Mijatović, D. Maksimović-Ivanić, E. Hey-Hawkins, Molecules 2023, 28, 4547. A. B. C. Simas, V. L. P. Pereira, C. B. Barreto Jr., D. L. De Sales, L. L. De Carvalho, Quim. Nova 2009, 32, 2473–2475. D. B. G. Williams, M. Lawton, J. Org. Chem. 2010, 75, 8351–8354. P. Van Thong, D. T. Thom, N. T. T. Chi, Vietnam J. Chem. 2018, 56, 146–151. J. L. Spencer, M. Green, F. G. A. Stone, J. Chem. Soc. Chem. Commun., 1972, 1178. E. C. Taylor, A. McKillop, Acc. Chem. Res. 1970, 3, 338–346. R. K. Harris, E. D. Becker, S. M. Cabral De Menezes, R. Goodfellow, P. Granger, Concepts Magn. Reson. 2002, 14, 326–346. W. Kohn, in Density Functional Methods In Physics, Springer US, Boston, MA, 1985, pp. 1–9. F. Neese, WIREs Comput. Mol. Sci. 2012, 2, 73–78. C. J. Cramer, D. G. Truhlar, Phys. Chem. Chem. Phys. 2009, 11, 10757–10816. T. Weymuth, E. P. A. Couzijn, P. Chen, M. Reiher, J. Chem. Theory Comput. 2014, 10, 3092–3103. H. Schröder, A. Creon, T. Schwabe, J. Chem. Theory Comput. 2015, 11, 3163–3170. S. Kossmann, F. Neese, J. Chem. Theory Comput. 2010, 6, 2325–2338. A. Hellweg, D. Rappoport, Phys. Chem. Chem. Phys. 2014, 17, 1010–1017. E. van Lenthe, J. G. Snijders, E. J. Baerends, J. Chem. Phys. 1996, 105, 6505–6516. A. Kazimir, B. Schwarze, P. Lönnecke, S. Jelača, S. Mijatović, D. Maksimović-Ivanić, E. Hey-Hawkins, Pharmaceutica 2023, 15, 682. R. F. W. Bader, T. T. Nguyen-Dang, in Advances in Quantum Chemistry, Academic Press, 1981, pp. 63–124. R. Hilal, S. G. Aziz, A. O. Alyoubi, S. Elroby, Procedia Comput. Sci. 2015, 51, 1872–1877. M. Palusiak, T. M. Krygowski, Chem. Eur. J. 2007, 13, 7996–8006. Rigaku Oxford Diffraction, (1995-2023), CrysAlisPro Software system, Rigaku Corporation, Wroclaw, Poland. G. M. Sheldrick, Acta Crystallogr. Sect. Found., Adv. 2015, A71, 3–8. G. M. Sheldrick, Acta Crystallogr. Sect. Struct. Chem. 2015, C71, 3–8. K. Brandenburg, DIAMOND 4 (Version 4.6.8), Crystal Impact GbR, Bonn, Germany, 2022. |
معلومات مُعتمدة: | 451-03-66/2024-03/200007 Ministry of Science, Technological Development and Innovation of the Republic of Serbia; 57440919 DAAD; Research Grants Bi-national; Projekt DEAL |
فهرسة مساهمة: | Keywords: TNBC; metallacarborane; metallodrugs; nickel; palladium; platinum; raloxifene; senescence |
المشرفين على المادة: | 5TWQ1V240M (Palladium) 7OV03QG267 (Nickel) 0 (Antineoplastic Agents) 49DFR088MY (Platinum) 0 (Coordination Complexes) 4F86W47BR6 (Raloxifene Hydrochloride) |
تواريخ الأحداث: | Date Created: 20240420 Date Completed: 20240715 Latest Revision: 20240715 |
رمز التحديث: | 20240715 |
DOI: | 10.1002/cmdc.202400006 |
PMID: | 38642018 |
قاعدة البيانات: | MEDLINE |
تدمد: | 1860-7187 |
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DOI: | 10.1002/cmdc.202400006 |