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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. B 2013, 117, 21, 6421-6429
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Polymorphism in Cisplatin Anticancer Drug

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† Research Unit “Molecular Physical Chemistry”, Faculty of Science and Technology, University of Coimbra, 3004-535 Coimbra, Portugal
‡ ISIS Facility, SFTC Rutherford Appleton Laboratory, Chilton, Didcot OX 11 0QX, United Kingdom
§ Departament of Life Sciences, Faculty of Science and Technology, University of Coimbra, 3001-401 Coimbra, Portugal
*E-mail: [email protected], [email protected]
Cite this: J. Phys. Chem. B 2013, 117, 21, 6421–6429
Publication Date (Web):May 3, 2013
https://doi.org/10.1021/jp403486z
Copyright © 2013 American Chemical Society
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Abstract

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This study reports a combined experimental and theoretical study of the solid-state polymorphism of the anticancer agent cisplatin. A complete assignment was performed for the inelastic neutron scattering (INS) and Raman spectra collected simultaneously for cisplatin, at different temperatures, with a view to obtain reliable and definitive evidence of the relative thermal stability of its α and β polymorphic species. A marked temperature-dependent hysteresis was observed, as previously reported in the literature. Theoretical calculations were carried out at the density functional theory level, using a plane-wave basis set approach and pseudopotentials. A detailed comparison with the experimental Raman and INS data showed that the α polymorph is present at the lowest temperatures, whereas the β form occurs near room temperature. Furthermore, regions of coexistence of both forms are identified, which depend on the working mode (heating or cooling). These findings imply that Raman spectroscopy allows clear identification of the α and β polymorphs at a given temperature and can unambiguously discriminate between them. Elucidation of the polymorphic equilibrium of this widely used anticancer drug is paramount for its pharmaceutical preparation and storage conditions.

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Crystal cell parameters and Raman spectra for α- and β-cisplatin. This material is available free of charge via the Internet at http://pubs.acs.org.

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Cited By

This article is cited by 24 publications.

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  2. Maria Paula M. Marques, Ana L. M. Batista de Carvalho, Adriana P. Mamede, Inês P. Santos, Victoria García Sakai, Asha Dopplapudi, Gianfelice Cinque, Magda Wolna, Peter Gardner, Luís A. E. Batista de Carvalho. Chemotherapeutic Targets in Osteosarcoma: Insights from Synchrotron-MicroFTIR and Quasi-Elastic Neutron Scattering. The Journal of Physical Chemistry B 2019, 123 (32) , 6968-6979. https://doi.org/10.1021/acs.jpcb.9b05596
  3. Nicolas Bélanger-Desmarais, Max Schütz, Christian Reber. Remarkably Intricate Raman Spectra of Platinum(II)–Ligand Skeletal Modes in Diamminedihalido Complexes. The Journal of Physical Chemistry A 2019, 123 (26) , 5574-5579. https://doi.org/10.1021/acs.jpca.9b03893
  4. Marjorie Torres, Sidrah Khan, Michael Duplanty, Hannah C. Lozano, Tyree J. Morris, Trang Nguyen, Yuri V. Rostovtsev, Nathan J. DeYonker, Nasrin Mirsaleh-Kohan. Raman and Infrared Studies of Platinum-Based Drugs: Cisplatin, Carboplatin, Oxaliplatin, Nedaplatin, and Heptaplatin. The Journal of Physical Chemistry A 2018, 122 (34) , 6934-6952. https://doi.org/10.1021/acs.jpca.8b04023
  5. Wen-Ting Deng, Ze-Bin Shen, Li-Jie Su, Yu-Hui Hua, Zhi-Xin Chen, and Jun Tao . Ring-Opening Polymeric Single-Crystal-to-Single-Crystal Transformation in a Co(II) Compound. Crystal Growth & Design 2018, 18 (2) , 587-591. https://doi.org/10.1021/acs.cgd.7b01584
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  8. Ana S. Martins, Ana L.M. Batista de Carvalho, Inês Lamego, M.▪ Paula. M. Marques, Ana M. Gil. Cytotoxicity of Platinum and Palladium Chelates against Osteosarcoma. ChemistrySelect 2020, 5 (20) , 5993-6000. https://doi.org/10.1002/slct.202001361
  9. M. P. M. Marques, A. L. M. Batista de Carvalho, A. P. Mamede, S. Rudić, A. Dopplapudi, V. García Sakai, L. A. E. Batista de Carvalho. Intracellular water as a mediator of anticancer drug action. International Reviews in Physical Chemistry 2020, 39 (1) , 67-81. https://doi.org/10.1080/0144235X.2020.1700083
  10. Karolína M. Šišková. Cisplatin interacting with buffering media and cysteine: Molecular insight due to Raman microspectroscopy. Journal of Raman Spectroscopy 2019, 50 (4) , 528-536. https://doi.org/10.1002/jrs.5545
  11. Ana L. M. Batista de Carvalho, Adriana P. Mamede, Asha Dopplapudi, Victoria Garcia Sakai, James Doherty, Mark Frogley, Gianfelice Cinque, Peter Gardner, Diego Gianolio, Luís A. E. Batista de Carvalho, M. Paula M. Marques. Anticancer drug impact on DNA – a study by neutron spectroscopy coupled with synchrotron-based FTIR and EXAFS. Physical Chemistry Chemical Physics 2019, 21 (8) , 4162-4175. https://doi.org/10.1039/C8CP05881D
  12. Jean M.F. Custodio, Wesley F. Vaz, Mirian R.C. de Castro, Aline Bernardes, Raquel F. Naves, Andrea F. Moura, Manoel O. de Moraes, Cameron C. da Silva, Felipe T. Martins, Caridad N. Perez, Hamilton B. Napolitano. Solvent-driven structural adaptation in a novel anticancer sulfonamide chalcone. Journal of Molecular Structure 2019, 1175 , 389-397. https://doi.org/10.1016/j.molstruc.2018.07.059
  13. Peter W. Albers, David Lennon, Stewart F. Parker. Catalysis. 2017,,, 279-348. https://doi.org/10.1016/B978-0-12-805324-9.00005-4
  14. M. P. M. Marques, A. L. M. Batista de Carvalho, V. Garcia Sakai, L. Hatter, L. A. E. Batista de Carvalho. Intracellular water – an overlooked drug target? Cisplatin impact in cancer cells probed by neutrons. Physical Chemistry Chemical Physics 2017, 19 (4) , 2702-2713. https://doi.org/10.1039/C6CP05198G
  15. Vincent Levet, Rémi Rosière, Romain Merlos, Luca Fusaro, Gilles Berger, Karim Amighi, Nathalie Wauthoz. Development of controlled-release cisplatin dry powders for inhalation against lung cancers. International Journal of Pharmaceutics 2016, 515 (1-2) , 209-220. https://doi.org/10.1016/j.ijpharm.2016.10.019
  16. Poornima Sharma, Debraj Gangopadhyay, Sima Umrao, Shiv Kumar, A. K. Ghosh, P. C. Mishra, Ranjan K. Singh. A novel Raman spectroscopic approach to identify polymorphism in leflunomide: a combined experimental and theoretical study. Journal of Raman Spectroscopy 2016, 47 (4) , 468-475. https://doi.org/10.1002/jrs.4834
  17. T.M. Silva, S.M. Fiuza, M.P.M. Marques, L.A.E. Batista de Carvalho, A.M. Amado. Conformational study and reassessment of the vibrational assignments for Norspermidine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2016, 157 , 227-237. https://doi.org/10.1016/j.saa.2016.01.003
  18. A. L. M. Batista de Carvalho, M. Pilling, P. Gardner, J. Doherty, G. Cinque, K. Wehbe, C. Kelley, L. A. E. Batista de Carvalho, M. P. M. Marques. Chemotherapeutic response to cisplatin-like drugs in human breast cancer cells probed by vibrational microspectroscopy. Faraday Discussions 2016, 187 , 273-298. https://doi.org/10.1039/C5FD00148J
  19. S. M. Fiuza, T. M. Silva, M. P. M. Marques, L. A. E. Batista de Carvalho, A. M. Amado. On the correction of calculated vibrational frequencies for the effects of the counterions — α,ω-diamine dihydrochlorides. Journal of Molecular Modeling 2015, 21 (10) https://doi.org/10.1007/s00894-015-2818-7
  20. Amrit Paudel, Dhara Raijada, Jukka Rantanen. Raman spectroscopy in pharmaceutical product design. Advanced Drug Delivery Reviews 2015, 89 , 3-20. https://doi.org/10.1016/j.addr.2015.04.003
  21. Maria Paula M. Marques, Luis A.E. Batista de Carvalho, Stewart F. Parker. Comment on “Assessment of new DFT methods for predicting vibrational spectra and structure of cisplatin: Which density functional should we choose for studying platinum(II) complexes?” [Spectrochim. Acta A125 (2014) 431–439]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015, 136 , 347. https://doi.org/10.1016/j.saa.2014.08.154
  22. M. Paula M. Marques, Diego Gianolio, Giannantonio Cibin, John Tomkinson, Stewart F. Parker, Rosendo Valero, R. Pedro Lopes, Luis A. E. Batista de Carvalho. A molecular view of cisplatin's mode of action: interplay with DNA bases and acquired resistance. Physical Chemistry Chemical Physics 2015, 17 (7) , 5155-5171. https://doi.org/10.1039/C4CP05183A
  23. Sónia M. Fiuza, Ana M. Amado, Stewart F. Parker, Maria Paula M. Marques, Luís A. E. Batista de Carvalho. Conformational insights and vibrational study of a promising anticancer agent: the role of the ligand in Pd( ii )–amine complexes. New Journal of Chemistry 2015, 39 (8) , 6274-6283. https://doi.org/10.1039/C5NJ01088H
  24. Samuel Tetteh, David K. Dodoo, Regina Appiah-Opong, Isaac Tuffour. Spectroscopic Characterization, In Vitro Cytotoxicity, and Antioxidant Activity of Mixed Ligand Palladium(II) Chloride Complexes Bearing Nucleobases. Journal of Inorganic Chemistry 2014, 2014 , 1-7. https://doi.org/10.1155/2014/586131

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