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Oxidative Medicine and Cellular Longevity
Volume 2017, Article ID 9326454, 12 pages
https://doi.org/10.1155/2017/9326454
Review Article

Aspects of Carbon Monoxide in Form of CO-Releasing Molecules Used in Cancer Treatment: More Light on the Way

Cardiff China Medical Research Collaborative (CCMRC), School of Medicine, Cardiff University, Heath Park, Cardiff CF14 4XN, UK

Correspondence should be addressed to Jun Cai; ku.ca.ffidrac@5jiac

Received 1 September 2016; Revised 10 January 2017; Accepted 15 January 2017; Published 13 February 2017

Academic Editor: Swaran J. S. Flora

Copyright © 2017 Malamati Kourti et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. C. Romão and H. L. A. Vieira, “Metal carbonyl prodrugs: CO delivery and beyond,” in Bioorganometallic Chemistry: Applications in Drug Discovery, Biocatalysis, and Imaging, pp. 165–202, Wiley-VCH, 2015. View at Google Scholar
  2. R. Foresti, M. G. Bani-Hani, and R. Motterlini, “Use of carbon monoxide as a therapeutic agent: promises and challenges,” Intensive Care Medicine, vol. 34, no. 4, pp. 649–658, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. F. Gullotta, A. Di Masi, and P. Ascenzi, “Carbon monoxide: an unusual drug,” IUBMB Life, vol. 64, no. 5, pp. 378–386, 2012. View at Publisher · View at Google Scholar · View at Scopus
  4. F. Zobi, “CO and CO-releasing molecules in medicinal chemistry,” Future Medicinal Chemistry, vol. 5, no. 2, pp. 175–188, 2013. View at Publisher · View at Google Scholar · View at Scopus
  5. R. Motterlini, B. E. Mann, and R. Foresti, “Therapeutic applications of carbon monoxide-releasing molecules,” Expert Opinion on Investigational Drugs, vol. 14, no. 11, pp. 1305–1318, 2005. View at Publisher · View at Google Scholar · View at Scopus
  6. S. Hayashi, Y. Omata, H. Sakamoto et al., “Characterization of rat heme oxygenase-3 gene. Implication of processed pseudogenes derived from heme oxygenase-2 gene,” Gene, vol. 336, no. 2, pp. 241–250, 2004. View at Publisher · View at Google Scholar · View at Scopus
  7. R. Motterlini and L. E. Otterbein, “The therapeutic potential of carbon monoxide,” Nature Reviews Drug Discovery, vol. 9, no. 9, pp. 728–743, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. B. Wegiel, D. Gallo, E. Csizmadia et al., “Carbon monoxide expedites metabolic exhaustion to inhibit tumor growth,” Cancer Research, vol. 73, no. 23, pp. 7009–7021, 2013. View at Publisher · View at Google Scholar · View at Scopus
  9. A. R. Marques, L. Kromer, D. J. Gallo et al., “Generation of carbon monoxide releasing molecules (CO-RMs) as drug candidates for the treatment of acute liver injury: targeting of CO-RMs to the liver,” Organometallics, vol. 31, no. 16, pp. 5810–5822, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. C. C. Romão, W. A. Blättler, J. D. Seixas, and G. J. L. Bernardes, “Developing drug molecules for therapy with carbon monoxide,” Chemical Society Reviews, vol. 41, no. 9, pp. 3571–3583, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. L. Lo Iacono, J. Boczkowski, R. Zini et al., “A carbon monoxide-releasing molecule (CORM-3) uncouples mitochondrial respiration and modulates the production of reactive oxygen species,” Free Radical Biology and Medicine, vol. 50, no. 11, pp. 1556–1564, 2011. View at Publisher · View at Google Scholar · View at Scopus
  12. R. Long, I. Salouage, A. Berdeaux, R. Motterlini, and D. Morin, “CORM-3, a water soluble CO-releasing molecule, uncouples mitochondrial respiration via interaction with the phosphate carrier,” Biochimica et Biophysica Acta—Bioenergetics, vol. 1837, no. 1, pp. 201–209, 2014. View at Publisher · View at Google Scholar · View at Scopus
  13. U. Schatzschneider, “Novel lead structures and activation mechanisms for CO-releasing molecules (CORMs),” British Journal of Pharmacology, vol. 172, no. 6, pp. 1638–1650, 2015. View at Publisher · View at Google Scholar · View at Scopus
  14. P. V. Simpson and U. Schatzschneider, “Release of bioactive molecules using metal complexes,” Inorganic Chemical Biology: Principles, Techniques and Applications, pp. 309–339, 2014. View at Publisher · View at Google Scholar · View at Scopus
  15. R. D. Rimmer, A. E. Pierri, and P. C. Ford, “Photochemically activated carbon monoxide release for biological targets. Toward developing air-stable photoCORMs labilized by visible light,” Coordination Chemistry Reviews, vol. 256, no. 15-16, pp. 1509–1519, 2012. View at Publisher · View at Google Scholar · View at Scopus
  16. E. Palao, T. Slanina, L. Muchová, T. Šolomek, L. Vítek, and P. Klán, “Transition-metal-free CO-releasing BODIPY derivatives activatable by visible to NIR light as promising bioactive molecules,” Journal of the American Chemical Society, vol. 138, no. 1, pp. 126–133, 2016. View at Publisher · View at Google Scholar · View at Scopus
  17. B. E. Mann, “Carbon monoxide: an essential signalling molecule,” in Topics in Organometallic Chemistry, vol. 32, pp. 247–285, 2010. View at Google Scholar
  18. A. Loboda, A. Jozkowicz, and J. Dulak, “HO-1/CO system in tumor growth, angiogenesis and metabolism—targeting HO-1 as an anti-tumor therapy,” Vascular Pharmacology, vol. 74, pp. 11–22, 2015. View at Publisher · View at Google Scholar · View at Scopus
  19. S. Ahmad, P. W. Hewett, T. Fujisawa et al., “Carbon monoxide inhibits sprouting angiogenesis and vascular endothelial growth factor receptor-2 phosphorylation,” Thrombosis and Haemostasis, vol. 113, no. 2, pp. 329–337, 2015. View at Publisher · View at Google Scholar · View at Scopus
  20. G. Li Volti, D. Sacerdoti, B. Sangras et al., “Carbon monoxide signaling in promoting angiogenesis in human microvessel endothelial cells,” Antioxidants and Redox Signaling, vol. 7, no. 5-6, pp. 704–710, 2005. View at Publisher · View at Google Scholar · View at Scopus
  21. P. K. Chatterjee, “Physiological activities of carbon monoxide-releasing molecules: Ça ira,” British Journal of Pharmacology, vol. 150, no. 8, pp. 961–962, 2007. View at Publisher · View at Google Scholar · View at Scopus
  22. A. Loboda, A. Jozkowicz, J. Dulak et al., “Carbon monoxide: pro- or anti-angiogenic agent? Comment on Ahmad et al. (Thromb Haemost 2015; 113: 329–337),” Thrombosis and Haemostasis, vol. 114, no. 2, pp. 432–433, 2015. View at Publisher · View at Google Scholar
  23. W.-Y. Lee, Y.-C. Chen, C.-M. Shih et al., “The induction of heme oxygenase-1 suppresses heat shock protein 90 and the proliferation of human breast cancer cells through its byproduct carbon monoxide,” Toxicology and Applied Pharmacology, vol. 274, no. 1, pp. 55–62, 2014. View at Publisher · View at Google Scholar · View at Scopus
  24. S. J. Carrington, I. Chakraborty, and P. K. Mascharak, “Rapid CO release from a Mn(i) carbonyl complex derived from azopyridine upon exposure to visible light and its phototoxicity toward malignant cells,” Chemical Communications, vol. 49, no. 96, pp. 11254–11256, 2013. View at Publisher · View at Google Scholar · View at Scopus
  25. I. Chakraborty, S. J. Carrington, J. Hauser, S. R. J. Oliver, and P. K. Mascharak, “Rapid eradication of human breast cancer cells through trackable light-triggered CO delivery by mesoporous silica nanoparticles packed with a designed photoCORM,” Chemistry of Materials, vol. 27, no. 24, pp. 8387–8397, 2015. View at Publisher · View at Google Scholar · View at Scopus
  26. S. J. Carrington, I. Chakraborty, J. M. L. Bernard, and P. K. Mascharak, “Synthesis and characterization of a ‘turn-on’ photoCORM for trackable co delivery to biological targets,” ACS Medicinal Chemistry Letters, vol. 5, no. 12, pp. 1324–1328, 2014. View at Publisher · View at Google Scholar · View at Scopus
  27. E. Üstün, A. Özgür, K. A. Coşkun, S. Demir, İ. Özdemir, and Y. Tutar, “CO-releasing properties and anticancer activities of manganese complexes with imidazole/benzimidazole ligands,” Journal of Coordination Chemistry, vol. 69, no. 22, pp. 3384–3394, 2016. View at Publisher · View at Google Scholar
  28. C. S. Jackson, S. Schmitt, Q. P. Dou, and J. J. Kodanko, “Synthesis, characterization, and reactivity of the stable iron carbonyl complex [Fe(CO)(N4Py)](ClO4)2: photoactivated carbon monoxide release, growth inhibitory activity, and peptide ligation,” Inorganic Chemistry, vol. 50, no. 12, pp. 5336–5338, 2011. View at Publisher · View at Google Scholar · View at Scopus
  29. A. E. Pierri, A. Pallaoro, G. Wu, and P. C. Ford, “A luminescent and biocompatible photoCORM,” Journal of the American Chemical Society, vol. 134, no. 44, pp. 18197–18200, 2012. View at Publisher · View at Google Scholar · View at Scopus
  30. J. Niesel, A. Pinto, H. W. Peindy N'Dongo et al., “Photoinduced CO release, cellular uptake and cytotoxicity of a tris(pyrazolyl)methane (tpm) manganese tricarbonyl complex,” Chemical Communications, no. 15, pp. 1798–1800, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. N. E. Brückmann, M. Wahl, G. J. Reiß, M. Kohns, W. Wätjen, and P. C. Kunz, “Polymer conjugates of photoinducible CO-releasing molecules,” European Journal of Inorganic Chemistry, pp. 4571–4577, 2011. View at Google Scholar
  32. S. Hu, X. Cui, W. He et al., “Synthesis, structural characterization and preliminary biological studies of several heterocyclic transition metal carbonyl complexes,” Zeitschrift fur Anorganische und Allgemeine Chemie, vol. 641, no. 14, pp. 2452–2459, 2015. View at Publisher · View at Google Scholar · View at Scopus
  33. Y. Gong, T. Zhang, H. Liu et al., “Synthesis, toxicities and cell proliferation inhibition of CO-releasing molecules containing cobalt,” Transition Metal Chemistry, vol. 40, no. 4, pp. 413–426, 2015. View at Publisher · View at Google Scholar · View at Scopus
  34. L. Vítek, H. Gbelcová, L. Muchová et al., “Antiproliferative effects of carbon monoxide on pancreatic cancer,” Digestive and Liver Disease, vol. 46, no. 4, pp. 369–375, 2014. View at Publisher · View at Google Scholar · View at Scopus
  35. C. I. Schwer, P. Stoll, S. Rospert et al., “Carbon monoxide releasing molecule-2 CORM-2 represses global protein synthesis by inhibition of eukaryotic elongation factor eEF2,” International Journal of Biochemistry and Cell Biology, vol. 45, no. 2, pp. 201–212, 2013. View at Publisher · View at Google Scholar · View at Scopus
  36. M. Allanson and V. E. Reeve, “Carbon monoxide signalling reduces photocarcinogenesis in the hairless mouse,” Cancer Immunology, Immunotherapy, vol. 56, no. 11, pp. 1807–1815, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. A. Loureiro, G. J. L. Bernardes, U. Shimanovich et al., “Folic acid-tagged protein nanoemulsions loaded with CORM-2 enhance the survival of mice bearing subcutaneous A20 lymphoma tumors,” Nanomedicine: Nanotechnology, Biology, and Medicine, vol. 11, no. 5, pp. 1077–1083, 2015. View at Publisher · View at Google Scholar · View at Scopus
  38. D. Schlawe, A. Majdalani, J. Velcicky et al., “Iron-containing nucleoside analogues with pronounced apoptosis-inducing activity,” Angewandte Chemie—International Edition, vol. 43, no. 13, pp. 1731–1734, 2004. View at Publisher · View at Google Scholar · View at Scopus
  39. P. Peng, C. Wang, Z. Shi et al., “Visible-light activatable organic CO-releasing molecules (PhotoCORMs) that simultaneously generate fluorophores,” Organic and Biomolecular Chemistry, vol. 11, no. 39, pp. 6671–6674, 2013. View at Publisher · View at Google Scholar · View at Scopus
  40. J. Boczkowski, J. J. Poderoso, and R. Motterlini, “CO-metal interaction: vital signaling from a lethal gas,” Trends in Biochemical Sciences, vol. 31, no. 11, pp. 614–621, 2006. View at Publisher · View at Google Scholar · View at Scopus
  41. N. Takano, T. Yamamoto, T. Adachi, and M. Suematsu, “Assessing a shift of glucose biotransformation by LC-MS/MS-based metabolome analysis in carbon monoxide-exposed cells,” in Oxygen Transport to Tissue XXXI, vol. 662 of Advances in Experimental Medicine and Biology, pp. 101–107, Springer, Berlin, Germany, 2010. View at Publisher · View at Google Scholar
  42. H. Soni, G. Pandya, P. Patel, A. Acharya, M. Jain, and A. A. Mehta, “Beneficial effects of carbon monoxide-releasing molecule-2 (CORM-2) on acute doxorubicin cardiotoxicity in mice: role of oxidative stress and apoptosis,” Toxicology and Applied Pharmacology, vol. 253, no. 1, pp. 70–80, 2011. View at Publisher · View at Google Scholar · View at Scopus
  43. Y. Tayem, T. R. Johnson, B. E. Mann, C. J. Green, and R. Motterlini, “Protection against cisplatin-induced nephrotoxicity by a carbon monoxide-releasing molecule,” American Journal of Physiology—Renal Physiology, vol. 290, no. 4, pp. F789–F794, 2006. View at Publisher · View at Google Scholar · View at Scopus
  44. L. Tong, K. N. Yu, L. Bao, W. Wu, H. Wang, and W. Han, “Low concentration of exogenous carbon monoxide protects mammalian cells against proliferation induced by radiation-induced bystander effect,” Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, vol. 759, pp. 9–15, 2014. View at Publisher · View at Google Scholar · View at Scopus
  45. Y. K. Choi, E. D. Por, Y.-G. Kwon, and Y.-M. Kim, “Regulation of ROS production and vascular function by carbon monoxide,” Oxidative Medicine and Cellular Longevity, vol. 2012, Article ID 794237, 17 pages, 2012. View at Publisher · View at Google Scholar · View at Scopus
  46. Y. K. Choi, C.-K. Kim, H. Lee et al., “Carbon monoxide promotes VEGF expression by increasing HIF-1α protein level via two distinct mechanisms, translational activation and stabilization of HIF-1α protein,” The Journal of Biological Chemistry, vol. 285, no. 42, pp. 32116–32125, 2010. View at Publisher · View at Google Scholar · View at Scopus
  47. S. Fayad-Kobeissi, J. Ratovonantenaina, H. Dabiré et al., “Vascular and angiogenic activities of CORM-401, an oxidant-sensitive CO-releasing molecule,” Biochemical Pharmacology, vol. 102, pp. 64–77, 2016. View at Publisher · View at Google Scholar · View at Scopus
  48. J. Fang, H. Qin, H. Nakamura, K. Tsukigawa, T. Shin, and H. Maeda, “Carbon monoxide, generated by heme oxygenase-1, mediates the enhanced permeability and retention effect in solid tumors,” Cancer Science, vol. 103, no. 3, pp. 535–541, 2012. View at Publisher · View at Google Scholar · View at Scopus
  49. F. K. Johnson and R. A. Johnson, “Carbon monoxide promotes endothelium-dependent constriction of isolated gracilis muscle arterioles,” American Journal of Physiology—Regulatory Integrative and Comparative Physiology, vol. 285, no. 3, pp. R536–R541, 2003. View at Publisher · View at Google Scholar · View at Scopus
  50. A. Jözkowicz, I. Huk, A. Nigisch et al., “Heme oxygenase and angiogenic activity of endothelial cells: stimulation by carbon monoxide and inhibition by tin protoporphyrin-IX,” Antioxidants and Redox Signaling, vol. 5, no. 2, pp. 155–162, 2003. View at Publisher · View at Google Scholar · View at Scopus
  51. J. Dulak, J. Deshane, A. Jozkowicz, and A. Agarwal, “Heme oxygenase-1 and carbon monoxide in vascular pathobiology: focus on angiogenesis,” Circulation, vol. 117, no. 2, pp. 231–241, 2008. View at Publisher · View at Google Scholar · View at Scopus
  52. M. Ferrando, G. Gueron, B. Elguero et al., “Heme oxygenase 1 (HO-1) challenges the angiogenic switch in prostate cancer,” Angiogenesis, vol. 14, no. 4, pp. 467–479, 2011. View at Publisher · View at Google Scholar · View at Scopus
  53. K. Skrzypek, M. Tertil, S. Golda et al., “Interplay between heme oxygenase-1 and miR-378 affects non-small cell lung carcinoma growth, vascularization, and metastasis,” Antioxidants and Redox Signaling, vol. 19, no. 7, pp. 644–660, 2013. View at Publisher · View at Google Scholar · View at Scopus
  54. C.-W. Lin, S.-C. Shen, W.-C. Hou, L.-Y. Yang, and Y.-C. Chen, “Heme oxygenase-1 inhibits breast cancer invasion via suppressing the expression of matrix metalloproteinase-9,” Molecular Cancer Therapeutics, vol. 7, no. 5, pp. 1195–1206, 2008. View at Publisher · View at Google Scholar · View at Scopus
  55. X. Ji, K. Damera, Y. Zheng, B. Yu, L. E. Otterbein, and B. Wang, “Toward carbon monoxide-based therapeutics: critical drug delivery and developability issues,” Journal of Pharmaceutical Sciences, vol. 105, no. 2, pp. 406–415, 2016. View at Publisher · View at Google Scholar · View at Scopus
  56. S. García-Gallego and G. J. L. Bernardes, “Carbon-monoxide-releasing molecules for the delivery of therapeutic co in vivo,” Angewandte Chemie—International Edition, vol. 53, no. 37, pp. 9712–9721, 2014. View at Publisher · View at Google Scholar · View at Scopus