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Interaction of Oxaliplatin, Cisplatin, and Carboplatin with Hemoglobin and the Resulting Release of a Heme Group

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Environmental Health Sciences, Department of Public Health Sciences, Faculty of Medicine and Dentistry, University of Alberta, 10-102 Clinical Sciences Building, Edmonton, Alberta T6G 2G3, Canada
Cite this: Chem. Res. Toxicol. 2004, 17, 10, 1391–1397
Publication Date (Web):September 30, 2004
https://doi.org/10.1021/tx049868j
Copyright © 2004 American Chemical Society
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    Abstract

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    Oxaliplatin, carboplatin, and cisplatin are widely used to treat a number of cancers. While their DNA adducts are believed to cause cell death, the involvement of their protein adducts in the toxicity and action of these drugs is unclear. Here, we report the interactions of hemoglobin (Hb) with the three platinum (Pt) drugs, demonstrating the formation of Hb−Pt complexes and the release of a heme group from Hb. Oxaliplatin (0.05 μM) was able to form three major complexes with Hb (3−10 μM) after 1 h of incubation at room temperature, and these complexes accounted for ∼60% of the total oxaliplatin. Cisplatin and carboplatin formed one major and two minor complexes only after 24 and 96 h of incubation, respectively. Incubation of these Pt drugs (0.05−10 μM) with whole blood of healthy volunteers and the analysis of red blood cells confirmed the relative ability of these Pt drugs binding to Hb. For the whole blood samples incubated with oxaliplatin and cisplatin for 24 h, only protein complexes were detected in red blood cells, indicating a complete binding of oxaliplatin and cisplatin to the protein. In contrast, carboplatin was partially bound; both the free and the protein-bound carboplatin species were detected in red blood cells. The binding of the Pt drugs to Hb was accompanied by the release of a heme group from Hb, which was monitored by size fractionation, chromatographic separation, and selective detection of both Pt- and iron (Fe)-containing molecular species. The released heme was further identified by size fractionation and nanospray mass spectrometry. The findings of the Pt drug interaction with Hb and the dissociation of heme from Hb are potentially useful for a better understanding of the toxicity and side effects of these chemotherapeutic drugs.

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    45. Björn Meermann, Michael Sperling. Hyphenated techniques as tools for speciation analysis of metal-based pharmaceuticals: developments and applications. Analytical and Bioanalytical Chemistry 2012, 403 (6) , 1501-1522. https://doi.org/10.1007/s00216-012-5915-9
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    47. Bente Gammelgaard, Stefan Stürup, Charlotte Møller. Inductively Coupled Plasma Mass Spectrometry for Analysis of Metal‐Containing Pharmaceuticals. 2012, 1-25. https://doi.org/10.1002/9780470921920.edm100
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    51. Tingting Chen, Shajun Zhu, Hui Cao, Yanfang Shang, Miao Wang, Guoqing Jiang, Yujun Shi, Tianhong Lu. Studies on the interaction of salvianolic acid B with human hemoglobin by multi-spectroscopic techniques. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2011, 78 (4) , 1295-1301. https://doi.org/10.1016/j.saa.2010.12.081
    52. Melani Sooriyaarachchi, Aru Narendran, Jürgen Gailer. Comparative hydrolysis and plasma protein binding of cis-platin and carboplatin in human plasma in vitro. Metallomics 2011, 3 (1) , 49-55. https://doi.org/10.1039/C0MT00058B
    53. Gianni Sava, Alberta Bergamo, Paul J. Dyson. Metal-based antitumour drugs in the post-genomic era: what comes next?. Dalton Transactions 2011, 40 (36) , 9069. https://doi.org/10.1039/c1dt10522a
    54. José Luis Gómez-Ariza, Elham Zeini Jahromi, Macarena González-Fernández, Tamara García-Barrera, Jürgen Gailer. Liquid chromatography-inductively coupled plasma-based metallomic approaches to probe health-relevant interactions between xenobiotics and mammalian organisms. Metallomics 2011, 3 (6) , 566. https://doi.org/10.1039/c1mt00037c
    55. . References. 2010, 459-565. https://doi.org/10.1002/9780470872390.refs
    56. Leticia Cubo, Michael Groessl, Paul J. Dyson, Adoración G. Quiroga, Carmen Navarro‐Ranninger, Angela Casini. Proteins as Possible Targets for Cytotoxic trans ‐Platinum(II) Complexes with Aliphatic Amine Ligands: Further Exceptions to the DNA Paradigm. ChemMedChem 2010, 5 (8) , 1335-1343. https://doi.org/10.1002/cmdc.201000104
    57. Yan-Qing Wang, Hong-Mei Zhang, Bo-Ping Tang. The interaction of C.I. acid red 27 with human hemoglobin in solution. Journal of Photochemistry and Photobiology B: Biology 2010, 100 (2) , 76-83. https://doi.org/10.1016/j.jphotobiol.2010.05.004
    58. Qiu-Hua Zhou, Hong-Mei Zhang, Lin Wu, Yan-Qing Wang. Binding of Al(III)-tetracarboxyphthalocyanine to Hemoglobin and Myoglobin. The Protein Journal 2010, 29 (4) , 265-275. https://doi.org/10.1007/s10930-010-9248-2
    59. Diego Esteban-Fernández, Estefanía Moreno-Gordaliza, Benito Cañas, María Antonia Palacios, María Milagros Gómez-Gómez. Analytical methodologies for metallomics studies of antitumor Pt-containing drugs. Metallomics 2010, 2 (1) , 19-38. https://doi.org/10.1039/B911438F
    60. Elham Zeini Jahromi, Jürgen Gailer. Probing bioinorganic chemistry processes in the bloodstream to gain new insights into the origin of human diseases. Dalton Trans. 2010, 39 (2) , 329-336. https://doi.org/10.1039/B912941N
    61. S. Hann, T. Falta, K. Boeck, M. Sulyok, G. Koellensperger. On-line fast column switching SEC × IC separation combined with ICP-MS detection for mapping metallodrug–biomolecule interaction. Journal of Analytical Atomic Spectrometry 2010, 25 (6) , 861. https://doi.org/10.1039/c000427h
    62. S. Zolghadri, A. A. Saboury, A. Golestani, A. Divsalar, S. Rezaei-Zarchi, A. A. Moosavi-Movahedi. Interaction between silver nanoparticle and bovine hemoglobin at different temperatures. Journal of Nanoparticle Research 2009, 11 (7) , 1751-1758. https://doi.org/10.1007/s11051-008-9538-1
    63. Hong-Mei Zhang, Yan-Qing Wang, Ma-Li Jiang. A fluorimetric study of the interaction of C.I. Solvent Red 24 with haemoglobin. Dyes and Pigments 2009, 82 (2) , 156-163. https://doi.org/10.1016/j.dyepig.2008.12.008
    64. Jongchol Jang, Hui Liu, Wei Chen, Guolin Zou. Binding of mitomycin C to blood proteins: A spectroscopic analysis and molecular docking. Journal of Molecular Structure 2009, 928 (1-3) , 72-77. https://doi.org/10.1016/j.molstruc.2009.03.016
    65. Shawn A Manley, Jürgen Gailer. Analysis of the plasma metalloproteome by SEC–ICP-AES: bridging proteomics and metabolomics. Expert Review of Proteomics 2009, 6 (3) , 251-265. https://doi.org/10.1586/epr.09.44
    66. . References. 2009, 643-764. https://doi.org/10.1002/9780470447758.refs
    67. Yan-Qing Wang, Hong-Mei Zhang, Qiu-Hua Zhou, Hai-Lan Xu. A study of the binding of colloidal Fe3O4 with bovine hemoglobin using optical spectroscopy. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2009, 337 (1-3) , 102-108. https://doi.org/10.1016/j.colsurfa.2008.12.003
    68. Hong-Mei Zhang, Yan-Qing Wang, Qiu-Hua Zhou, Guang-Li Wang. Molecular interaction between phosphomolybdate acid and bovine hemoglobin. Journal of Molecular Structure 2009, 921 (1-3) , 156-162. https://doi.org/10.1016/j.molstruc.2008.12.049
    69. Abdulgabar Salama. Drug-induced immune hemolytic anemia. Expert Opinion on Drug Safety 2009, 8 (1) , 73-79. https://doi.org/10.1517/14740330802577351
    70. Ivan Spasojević, Svetislav Jelić, Joanna Zakrzewska, Goran Bačić. Decreased Oxygen Transfer Capacity of Erythrocytes as a Cause of 5-Fluorouracil Related Ischemia. Molecules 2009, 14 (1) , 53-67. https://doi.org/10.3390/molecules14010053
    71. Sei-Jun Han, Tae-Kyu Ahn, Han-Song Choi, Jin-Na Shin, Sujan Piya, Tae-Hyoung Kim. TRAIL-induced cell death and caspase-8 activation are inhibited by cisplatin but not carboplatin. Journal of Gynecologic Oncology 2009, 20 (2) , 113. https://doi.org/10.3802/jgo.2009.20.2.113
    72. Yan-Qing Wang, Hong-Mei Zhang, Rong-Hua Wang. Investigation of the interaction between colloidal TiO2 and bovine hemoglobin using spectral methods. Colloids and Surfaces B: Biointerfaces 2008, 65 (2) , 190-196. https://doi.org/10.1016/j.colsurfb.2008.04.001
    73. Hongmei Zhang, Yanqing Wang, Zhenghao Fei, Lin Wu, Qiuhua Zhou. Characterization of the interaction between Fe(III)-2,9,16,23-tetracarboxyphthalocyanine and blood proteins. Dyes and Pigments 2008, 78 (3) , 239-247. https://doi.org/10.1016/j.dyepig.2007.12.011
    74. Bente Gammelgaard, Helle Rüsz Hansen, Stefan Stürup, Charlotte Møller. The use of inductively coupled plasma mass spectrometry as a detector in drug metabolism studies. Expert Opinion on Drug Metabolism & Toxicology 2008, 4 (9) , 1187-1207. https://doi.org/10.1517/17425255.4.9.1187
    75. Yan-Qing Wang, Hong-Mei Zhang, Gen-Cheng Zhang, Qiu-Hua Zhou, Zheng-Hao Fei, Zong-Tang Liu, Zhen-Xing Li. Fluorescence spectroscopic investigation of the interaction between benzidine and bovine hemoglobin. Journal of Molecular Structure 2008, 886 (1-3) , 77-84. https://doi.org/10.1016/j.molstruc.2007.10.039
    76. Chiara Gabbiani, Angela Casini, Guido Mastrobuoni, Noam Kirshenbaum, Ofra Moshel, Giuseppe Pieraccini, Gloriano Moneti, Luigi Messori, Dan Gibson. Peculiar mechanistic and structural features of the carboplatin–cytochrome c system revealed by ESI-MS analysis. JBIC Journal of Biological Inorganic Chemistry 2008, 13 (5) , 755-764. https://doi.org/10.1007/s00775-008-0361-z
    77. Tibebe Lemma, Rupasri Mandal, Xing‐Fang Li, Janusz Pawliszyn. Investigation of interaction between human hemoglobin A 0 and platinum anticancer drugs by capillary isoelectric focusing with whole column imaging detection. Journal of Separation Science 2008, 31 (10) , 1803-1809. https://doi.org/10.1002/jssc.200700418
    78. Angela Casini, Annalisa Guerri, Chiara Gabbiani, Luigi Messori. Biophysical characterisation of adducts formed between anticancer metallodrugs and selected proteins: New insights from X-ray diffraction and mass spectrometry studies. Journal of Inorganic Biochemistry 2008, 102 (5-6) , 995-1006. https://doi.org/10.1016/j.jinorgbio.2007.12.022
    79. Elke E.M. Brouwers, Matthijs Tibben, H. Rosing, Jan H.M. Schellens, Jos H. Beijnen. The application of inductively coupled plasma mass spectrometry in clinical pharmacological oncology research. Mass Spectrometry Reviews 2008, 27 (2) , 67-100. https://doi.org/10.1002/mas.20159
    80. F. Thomas, E. Chatelut. Les dérivés du platine. Oncologie 2007, 9 (11) , 741-745. https://doi.org/10.1007/s10269-007-0700-7
    81. Yan-Qing Wang, Hong-Mei Zhang, Gen-Cheng Zhang, Shuang-Xia Liu, Qiu-Hua Zhou, Zheng-Hao Fei, Zong-Tang Liu. Studies of the interaction between paraquat and bovine hemoglobin. International Journal of Biological Macromolecules 2007, 41 (3) , 243-250. https://doi.org/10.1016/j.ijbiomac.2007.02.011
    82. Rossella Sasanelli, Angelina Boccarelli, Domenico Giordano, Mariarita Laforgia, Fabio Arnesano, Giovanni Natile, Cosimo Cardellicchio, Maria A. M. Capozzi, Mauro Coluccia. Platinum Complexes Can Inhibit Matrix Metalloproteinase Activity:  Platinum−Diethyl[(methylsulfinyl)methyl]phosphonate Complexes as Inhibitors of Matrix Metalloproteinases 2, 3, 9, and 12. Journal of Medicinal Chemistry 2007, 50 (15) , 3434-3441. https://doi.org/10.1021/jm061435l
    83. Stefan K. Weidt, C. Logan Mackay, Pat R. R. Langridge-Smith, Peter J. Sadler. Platination of superoxide dismutase with cisplatin: tracking the ammonia ligands using Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). Chemical Communications 2007, 99 (17) , 1719. https://doi.org/10.1039/b701903c
    84. Rupasri Mandal, Michael B. Sawyer, Xing‐Fang Li. Mass spectrometry study of hemoglobin‐oxaliplatin complexes in colorectal cancer patients and potential association with chemotherapeutic responses. Rapid Communications in Mass Spectrometry 2006, 20 (17) , 2533-2538. https://doi.org/10.1002/rcm.2622
    85. Angela Casini, Chiara Gabbiani, Guido Mastrobuoni, Luigi Messori, Gloriano Moneti, Giuseppe Pieraccini. Exploring Metallodrug–Protein Interactions by ESI Mass Spectrometry: The Reaction of Anticancer Platinum Drugs with Horse Heart Cytochrome c. ChemMedChem 2006, 1 (4) , 413-417. https://doi.org/10.1002/cmdc.200500079
    86. Vito Calderone, Angela Casini, Stefano Mangani, Luigi Messori, Pier Luigi Orioli. Structural Investigation of Cisplatin–Protein Interactions: Selective Platination of His19 in a Cuprozinc Superoxide Dismutase. Angewandte Chemie International Edition 2006, 45 (8) , 1267-1269. https://doi.org/10.1002/anie.200502599
    87. Vito Calderone, Angela Casini, Stefano Mangani, Luigi Messori, Pier Luigi Orioli. Structural Investigation of Cisplatin–Protein Interactions: Selective Platination of His19 in a Cuprozinc Superoxide Dismutase. Angewandte Chemie 2006, 118 (8) , 1289-1291. https://doi.org/10.1002/ange.200502599
    88. Jun Peng, Rupasri Mandal, Michael Sawyer, Xing-Fang Li. Characterization of Intact Hemoglobin and Oxaliplatin Interaction by Nanoelectrospray Ionization Tandem Mass Spectrometry. Clinical Chemistry 2005, 51 (12) , 2274-2281. https://doi.org/10.1373/clinchem.2005.051847
    89. Gaosheng Yang, Ren Miao, Chen Jin, Yuhua Mei, Huiwei Tang, Jin Hong, Zijian Guo, Longgen Zhu. Determination of binding sites in carboplatin‐bound cytochrome c using electrospray ionization mass spectrometry and tandem mass spectrometry. Journal of Mass Spectrometry 2005, 40 (8) , 1005-1016. https://doi.org/10.1002/jms.875
    90. Yuan‐Yuan Zhao, Rupasri Mandal, Xing‐Fang Li. Intact human holo‐transferrin interaction with oxaliplatin. Rapid Communications in Mass Spectrometry 2005, 19 (14) , 1956-1962. https://doi.org/10.1002/rcm.2010
    91. A. Delgado-Cañedo, J.A.B. Chies, N.B. Nardi. Induction of fetal haemoglobin expression in erythroid cells – A model based on iron availability signalling. Medical Hypotheses 2005, 65 (5) , 932-936. https://doi.org/10.1016/j.mehy.2005.02.046
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