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Journal of Nanomaterials
Volume 2016, Article ID 2682105, 9 pages
http://dx.doi.org/10.1155/2016/2682105
Research Article

Construction of a Nanodiamond–Tamoxifen Complex as a Breast Cancer Drug Delivery Vehicle

1NANOCOSMOS Virtual Lab, Centro de Investigación en Materiales Avanzados, SC, Miguel de Cervantes 120, Complejo Industrial Chihuahua, 31136 Chihuahua, CHIH, Mexico
2Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Chihuahua, CHIH, Mexico

Received 9 June 2016; Revised 24 August 2016; Accepted 21 September 2016

Academic Editor: Guoqing Ning

Copyright © 2016 Linda-Lucila Landeros-Martínez 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. V. C. Jordan, “Tamoxifen: a most unlikely pioneering medicine,” Nature Reviews Drug Discovery, vol. 2, no. 3, pp. 205–213, 2003. View at Publisher · View at Google Scholar · View at Scopus
  2. B. Sahana, K. Santra, S. Basu, and B. Mukherjee, “Development of biodegradable polymer based tamoxifen citrate loaded nanoparticles and effect of some manufacturing process parameters on them: a physicochemical and in-vitro evaluation,” International Journal of Nanomedicine, vol. 5, no. 1, pp. 621–630, 2010. View at Publisher · View at Google Scholar · View at Scopus
  3. V. C. Jordan, “Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer,” British Journal of Pharmacology, vol. 147, supplement 1, pp. S269–S276, 2006. View at Publisher · View at Google Scholar · View at Scopus
  4. H. Brauch and V. C. Jordan, “Targeting of tamoxifen to enhance antitumour action for the treatment and prevention of breast cancer: the ‘personalised’ approach?” European Journal of Cancer, vol. 45, no. 13, pp. 2274–2283, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. “Relevance of breast cancer hormone receptors and other factors to the efficacy of adjuvant tamoxifen: patient-level meta-analysis of randomised trials,” The Lancet, vol. 378, no. 9793, pp. 771–784, 2011. View at Publisher · View at Google Scholar
  6. Y.-P. Lim, C.-L. Lin, Y.-N. Lin, W.-C. Ma, D.-Z. Hung, and C.-H. Kao, “Tamoxifen treatment and the reduced risk of hyperlipidemia in Asian patients with breast cancer: a population-based cohort study,” Clinical Breast Cancer, vol. 15, no. 4, pp. 294–300, 2015. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Rossini, S. Lello, I. Sblendorio et al., “Profile of bazedoxifene/conjugated estrogens for the treatment of estrogen deficiency symptoms and osteoporosis in women at risk of fracture,” Drug Design, Development and Therapy, vol. 7, pp. 601–610, 2013. View at Publisher · View at Google Scholar · View at Scopus
  8. S. Nazir, T. Hussain, A. Ayub, U. Rashid, and A. J. MacRobert, “Nanomaterials in combating cancer: therapeutic applications and developments,” Nanomedicine: Nanotechnology, Biology, and Medicine, vol. 10, no. 1, pp. 19–34, 2014. View at Publisher · View at Google Scholar · View at Scopus
  9. R. Kaur and I. Badea, “Nanodiamonds as novel nanomaterials for biomedical applications: drug delivery and imaging systems,” International Journal of Nanomedicine, vol. 8, pp. 203–220, 2013. View at Publisher · View at Google Scholar · View at Scopus
  10. Y. Zhu, J. Li, W. Li et al., “The biocompatibility of nanodiamonds and their application in drug delivery systems,” Theranostics, vol. 2, no. 3, pp. 302–312, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. A. Mostofizadeh, Y. Li, B. Song, and Y. Huang, “Synthesis, properties, and applications of low-dimensional carbon-related nanomaterials,” Journal of Nanomaterials, vol. 2011, Article ID 685081, 21 pages, 2011. View at Publisher · View at Google Scholar · View at Scopus
  12. J. Xiao, X. Duan, Q. Yin, Z. Zhang, H. Yu, and Y. Li, “Nanodiamonds-mediated doxorubicin nuclear delivery to inhibit lung metastasis of breast cancer,” Biomaterials, vol. 34, no. 37, pp. 9648–9656, 2013. View at Publisher · View at Google Scholar · View at Scopus
  13. N. Ribelles, A. Santonja, B. Pajares, C. Llácer, and E. Alba, “The seed and soil hypothesis revisited: current state of knowledge of inherited genes on prognosis in breast cancer,” Cancer Treatment Reviews, vol. 40, no. 2, pp. 293–299, 2014. View at Publisher · View at Google Scholar · View at Scopus
  14. P. Bourassa, T. J. Thomas, J. Bariyanga, and H. A. Tajmir-Riahi, “Breast anticancer drug tamoxifen and its metabolites bind tRNA at multiple sites,” International Journal of Biological Macromolecules, vol. 72, pp. 692–698, 2015. View at Publisher · View at Google Scholar · View at Scopus
  15. A. Laikhtman, A. Lafosse, Y. Le Coat, R. Azria, and A. Hoffman, “Clarification of oxygen bonding on diamond surfaces by low energy electron stimulated desorption and high resolution electron energy loss spectroscopy,” The Journal of Chemical Physics, vol. 119, no. 3, pp. 1794–1799, 2003. View at Publisher · View at Google Scholar · View at Scopus
  16. P.-H. Chung, E. Perevedentseva, J.-S. Tu, C. C. Chang, and C.-L. Cheng, “Spectroscopic study of bio-functionalized nanodiamonds,” Diamond and Related Materials, vol. 15, no. 4–8, pp. 622–625, 2006. View at Publisher · View at Google Scholar · View at Scopus
  17. Q. Guan, W. Chen, and X. Hu, “Development of lovastatin-loaded poly(lactic acid) microspheres for sustained oral delivery: in vitro and ex vivo evaluation,” Drug Design, Development and Therapy, vol. 9, pp. 791–798, 2015. View at Publisher · View at Google Scholar · View at Scopus
  18. D. Gu, G. Feng, G. Kang et al., “Improved biocompatibility of novel biodegradable scaffold composed of poly-L-lactic acid and amorphous calcium phosphate nanoparticles in porcine coronary artery,” Journal of Nanomaterials, vol. 2016, Article ID 2710858, 8 pages, 2016. View at Publisher · View at Google Scholar
  19. M. Obarzanek-Fojt, Y. Elbs-Glatz, E. Lizundia, L. Diener, J.-R. Sarasua, and A. Bruinink, “From implantation to degradation—are poly (L-lactide)/multiwall carbon nanotube composite materials really cytocompatible?” Nanomedicine: Nanotechnology, Biology, and Medicine, vol. 10, no. 5, pp. e1041–e1051, 2014. View at Publisher · View at Google Scholar · View at Scopus
  20. H. Tamber, P. Johansen, H. P. Merkle, and B. Gander, “Formulation aspects of biodegradable polymeric microspheres for antigen delivery,” Advanced Drug Delivery Reviews, vol. 57, no. 3, pp. 357–376, 2005. View at Publisher · View at Google Scholar · View at Scopus
  21. D. Ho, C.-H. K. Wang, and E. K.-H. Chow, “Nanodiamonds: the intersection of nanotechnology, drug development, and personalized medicine,” Science Advances, vol. 1, no. 7, Article ID e1500439, 2015. View at Publisher · View at Google Scholar
  22. R. A. Shimkunas, E. Robinson, R. Lam et al., “Nanodiamond-insulin complexes as pH-dependent protein delivery vehicles,” Biomaterials, vol. 30, no. 29, pp. 5720–5728, 2009. View at Publisher · View at Google Scholar · View at Scopus
  23. Y. Zhu, W. Li, Q. Li et al., “Effects of serum proteins on intracellular uptake and cytotoxicity of carbon nanoparticles,” Carbon, vol. 47, no. 5, pp. 1351–1358, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. Y. Zhu, T. Ran, Y. Li, J. Guo, and W. Li, “Dependence of the cytotoxicity of multi-walled carbon nanotubes on the culture medium,” Nanotechnology, vol. 17, no. 18, pp. 4668–4674, 2006. View at Publisher · View at Google Scholar · View at Scopus
  25. Y. Li, Y. Tong, R. Cao, Z. Tian, B. Yang, and P. Yang, “In vivo enhancement of anticancer therapy using bare or chemotherapeutic drug-bearing nanodiamond particles,” International Journal of Nanomedicine, vol. 9, no. 1, pp. 1065–1082, 2014. View at Publisher · View at Google Scholar · View at Scopus
  26. A. S. Barnard, “Shape-dependent confinement of the nanodiamond band gap,” Crystal Growth & Design, vol. 9, no. 11, pp. 4860–4863, 2009. View at Publisher · View at Google Scholar · View at Scopus
  27. J.-Y. Raty and G. Galli, “First principle study of nanodiamond optical and electronic properties,” Computer Physics Communications, vol. 169, no. 1–3, pp. 14–19, 2005. View at Publisher · View at Google Scholar · View at Scopus
  28. H. B. Man, H. Kim, H.-J. Kim et al., “Synthesis of nanodiamond-daunorubicin conjugates to overcome multidrug chemoresistance in leukemia,” Nanomedicine: Nanotechnology, Biology, and Medicine, vol. 10, no. 2, pp. 359–369, 2014. View at Publisher · View at Google Scholar · View at Scopus
  29. P. Hohenberg and W. Kohn, “Inhomogeneous electron gas,” Physical Review, vol. 136, no. 3B, pp. B864–B871, 1964. View at Publisher · View at Google Scholar · View at Scopus
  30. W. Kohn and L. J. Sham, “Self-consistent equations including exchange and correlation effects,” Physical Review, vol. 140, no. 4, pp. A1133–A1138, 1965. View at Google Scholar
  31. M. J. T. Frisch, G. W. Schlegel, H. B. Scuseria et al., Gaussian 09, Gaussian, Inc., Wallingford, Conn, USA, 2009.
  32. Y. Zhao and D. G. Truhlar, “Density functionals with broad applicability in chemistry,” Accounts of Chemical Research, vol. 41, no. 2, pp. 157–167, 2008. View at Publisher · View at Google Scholar · View at Scopus
  33. Y. Zhao and D. G. Truhlar, “The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals,” Theoretical Chemistry Accounts, vol. 120, no. 1–3, pp. 215–241, 2008. View at Publisher · View at Google Scholar · View at Scopus
  34. V. A. Rassolov, M. A. Ratner, J. A. Pople, P. C. Redfern, and L. A. Curtiss, “6-31G basis set for third-row atoms,” Journal of Computational Chemistry, vol. 22, no. 9, pp. 976–984, 2001. View at Google Scholar
  35. J. Tomasi and M. Persico, “Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent,” Chemical Reviews, vol. 94, no. 7, pp. 2027–2094, 1994. View at Publisher · View at Google Scholar · View at Scopus
  36. J. J. P. Stewart, “Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements,” Journal of Molecular Modeling, vol. 13, no. 12, pp. 1173–1213, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. B. Temelso, K. A. Alser, A. Gauthier, A. K. Palmer, and G. C. Shields, “Structural analysis of α-fetoprotein (AFP)-like peptides with anti-breast-cancer properties,” The Journal of Physical Chemistry B, vol. 118, no. 17, pp. 4514–4526, 2014. View at Publisher · View at Google Scholar · View at Scopus
  38. M. Eto, K. Yamaguchi, I. Shinohara, F. Ito, Y. Yoshitake, and K. Harano, “Role of edge-to-face interaction between aromatic rings in clathrate formation of 1-benzoyl-2-hydroxyindoline derivatives with benzene. X-ray crystal and PM6 analyses of the interaction,” Tetrahedron, vol. 67, no. 38, pp. 7400–7405, 2011. View at Publisher · View at Google Scholar · View at Scopus
  39. S. Benghodbane and D. Khatmi, “A theoretical study on the inclusion complexation of doxycycline with Crysmeb,” Comptes Rendus Chimie, vol. 15, no. 5, pp. 371–377, 2012. View at Publisher · View at Google Scholar · View at Scopus
  40. R. G. Pearson, “Absolute electronegativity and hardness correlated with molecular orbital theory,” Proceedings of the National Academy of Sciences, vol. 83, no. 22, pp. 8440–8441, 1986. View at Publisher · View at Google Scholar
  41. R. G. Parr, L. V. Szentpály, and S. Liu, “Electrophilicity index,” Journal of the American Chemical Society, vol. 121, no. 9, pp. 1922–1924, 1999. View at Publisher · View at Google Scholar · View at Scopus
  42. Y. W. Robert and G. Parr, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, NY, USA, 1989.
  43. M. V. Putz, N. Russo, and E. Sicilia, “Atomic radii scale and related size properties from density functional electronegativity formulation,” The Journal of Physical Chemistry A, vol. 107, no. 28, pp. 5461–5465, 2003. View at Publisher · View at Google Scholar · View at Scopus
  44. R. G. Parr, R. A. Donnelly, M. Levy, and W. E. Palke, “Electronegativity: the density functional viewpoint,” The Journal of Chemical Physics, vol. 68, no. 8, pp. 3801–3807, 1978. View at Google Scholar · View at Scopus
  45. W. Yang and R. G. Parr, “Hardness, softness, and the fukui function in the electronic theory of metals and catalysis,” Proceedings of the National Academy of Sciences of the United States of America, vol. 82, no. 20, pp. 6723–6726, 1985. View at Publisher · View at Google Scholar · View at Scopus
  46. J. Moens, P. Geerlings, and G. Roos, “A conceptual DFT approach for the evaluation and interpretation of redox potentials,” Chemistry-A European Journal, vol. 13, no. 29, pp. 8174–8184, 2007. View at Publisher · View at Google Scholar · View at Scopus
  47. F. De Vleeschouwer, V. Van Speybroeck, M. Waroquier, P. Geerlings, and F. De Proft, “Electrophilicity and nucleophilicity index for radicals,” Organic Letters, vol. 9, no. 14, pp. 2721–2724, 2007. View at Publisher · View at Google Scholar · View at Scopus
  48. S. Krishnamurty and S. Pal, “Intermolecular reactivity trends using the concept of group softness,” The Journal of Physical Chemistry A, vol. 104, no. 32, pp. 7639–7645, 2000. View at Publisher · View at Google Scholar · View at Scopus
  49. P. Bultinck, H. De Winter, W. Langenaeker, and J. P. Tollenare, Computational Medicinal Chemistry for Drug Discovery, CRC Press, 2003.
  50. L. L. Martinez, E. Orrantia Borunda, and N. Flores-Holguin, “DFT chemical reactivity analysis of biological molecules in the presence of silver ion,” Organic Chemistry: Current Research, vol. 4, article 153, 2015. View at Publisher · View at Google Scholar
  51. W. Yang and W. J. Mortier, “The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines,” Journal of the American Chemical Society, vol. 108, no. 19, pp. 5708–5711, 1986. View at Publisher · View at Google Scholar · View at Scopus
  52. G. Thomas, Fundamentals of Medicinal Chemistry, Wiley-Blackwell, 2003.
  53. V. N. Mochalin, O. Shenderova, D. Ho, and Y. Gogotsi, “The properties and applications of nanodiamonds,” Nature Nanotechnology, vol. 7, no. 1, pp. 11–23, 2012. View at Publisher · View at Google Scholar · View at Scopus
  54. S. Stehlik, M. Varga, M. Ledinsky et al., “Size and purity control of HPHT nanodiamonds down to 1 nm,” The Journal of Physical Chemistry C, vol. 119, no. 49, pp. 27708–27720, 2015. View at Publisher · View at Google Scholar · View at Scopus
  55. O. A. Shenderova and D. M. Gruen, “Preface,” in Ultananocrystalline Diamond, pp. 15–18, William Andrew Publishing, Oxford, UK, 2nd edition, 2012. View at Google Scholar
  56. V. Pichot, K. Bonnot, N. Piazzon, M. Schaefer, M. Comet, and D. Spitzer, “Deposition of detonation nanodiamonds by Langmuir–Blodgett technique,” Diamond and Related Materials, vol. 19, no. 5-6, pp. 479–483, 2010. View at Publisher · View at Google Scholar · View at Scopus
  57. M. Comet, V. Pichot, B. Siegert, F. Britz, and D. Spitzer, “Detonation nanodiamonds for doping kevlar,” Journal of Nanoscience and Nanotechnology, vol. 10, no. 7, pp. 4286–4292, 2010. View at Publisher · View at Google Scholar · View at Scopus
  58. D. Garlotta, “A literature review of poly(lactic acid),” Journal of Polymers and the Environment, vol. 9, no. 2, pp. 63–84, 2001. View at Publisher · View at Google Scholar · View at Scopus
  59. J. Stachowicz, E. Krajewska-Kułak, C. Łukaszuk, and A. Niewiadomy, “Relationship between antifungal activity against Candida albicans and electron parameters of selected N-heterocyclic thioamides,” Indian Journal of Pharmaceutical Sciences, vol. 76, no. 4, pp. 287–298, 2014. View at Google Scholar · View at Scopus
  60. R. G. Pearson, Chemical Hardness: Applications from Molecules to Solids, Wiley-VCH, Weinheim, Germany, 1st edition, 1997.
  61. R. G. Pearson, “Recent advances in the concept of hard and soft acids and bases,” Journal of Chemical Education, vol. 64, no. 7, pp. 561–567, 1987. View at Publisher · View at Google Scholar · View at Scopus
  62. P. B. Kelter, M. D. Mosher, and A. Scott, Chemistry: The Practical Science, Volume 10, Edited by B. H. M. Company, 2009.
  63. R. Galindo-Murillo, A. Olmedo-Romero, E. Cruz-Flores, P. M. Petrar, S. Kunsagi-Mate, and J. Barroso-Flores, “Calix[n]arene-based drug carriers: A DFT study of their electronic interactions with a chemotherapeutic agent used against leukemia,” Computational and Theoretical Chemistry, vol. 1035, pp. 84–91, 2014. View at Publisher · View at Google Scholar · View at Scopus
  64. M. H. Helal, S. A. El-Awdan, M. A. Salem et al., “Synthesis, biological evaluation and molecular modeling of novel series of pyridine derivatives as anticancer, anti-inflammatory and analgesic agents,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 135, pp. 764–773, 2015. View at Publisher · View at Google Scholar · View at Scopus
  65. J. B. Forseman and Æ. Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd edition, 1996.
  66. E. Frieden, “Non-covalent interactions: key to biological flexibility and specificity,” Journal of Chemical Education, vol. 52, no. 12, p. 754, 1975. View at Publisher · View at Google Scholar
  67. K. Wendler, J. Thar, S. Zahn, and B. Kirchner, “Estimating the hydrogen bond energy,” Journal of Physical Chemistry A, vol. 114, no. 35, pp. 9529–9536, 2010. View at Publisher · View at Google Scholar · View at Scopus
  68. R. D. Gautam and T. Steiner, The Weak Hydrogen Bond: In Structural Chemistry and Biology, Oxford University Press, New York, NY, USA, 2001.
  69. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University. Press, Oxford, UK, 1991.
  70. T. Steiner, “The hydrogen bond in the solid state,” Angewandte Chemie-International Edition, vol. 41, no. 1, pp. 48–76, 2002. View at Google Scholar · View at Scopus
  71. C. A. Lipinski, F. Lombardo, B. W. Dominy, and P. J. Feeney, “Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings,” Advanced Drug Delivery Reviews, vol. 46, no. 1–3, pp. 3–26, 2001. View at Publisher · View at Google Scholar · View at Scopus