Table of Contents Author Guidelines Submit a Manuscript
Table of Contents Alerts

To receive news and publication updates for International Journal of Medicinal Chemistry, enter your email address in the box below.

International Journal of Medicinal Chemistry
Volume 2014, Article ID 658016, 15 pages
http://dx.doi.org/10.1155/2014/658016
Research Article

Target Based Designing of Anthracenone Derivatives as Tubulin Polymerization Inhibiting Agents: 3D QSAR and Docking Approach

Abdul Samad,1 Moawiah M. Naffaa,2 Mohammed Afroz Bakht,1 Manav Malhotra,3 and Majid A. Ganaie4

1Department of Pharmaceutical Chemistry, College of Pharmacy, Salman bin Abdul Aziz University, P.O. Box 173, Al-kharj 11942, Saudi Arabia
2Faculty of Pharmacy, University of Sydney, NSW 2006, Australia
3Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Ferozepur Road, Moga 142 001, India
4Department of Pharmacology, College of Pharmacy, Salman bin Abdul Aziz University, P.O. Box 173, Al-kharj 11942, Saudi Arabia

Received 31 August 2013; Revised 17 February 2014; Accepted 25 February 2014; Published 17 April 2014

Academic Editor: Arie Zask

Copyright © 2014 Abdul Samad 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. B. A. Teicher and P. A. Andrews, Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials and Approvaled, Humana Press, Totowa, NJ, USA, 2nd edition, 2004.
  2. C. Theisen, “Statistical projections, modeling techniques help researchers measure progress, effectiveness,” Journal of the National Cancer Institute, vol. 95, no. 13, pp. 937–938, 2003. View at Google Scholar · View at Scopus
  3. http://www.who.int/mediacentre/factsheets/fs297/en/.
  4. R. Kaplow, “Innovations in antineoplastic therapy,” Nursing Clinics of North America, vol. 40, no. 1, pp. 77–94, 2005. View at Publisher · View at Google Scholar · View at Scopus
  5. M. A. Cabrera, I. González, C. Fernández, C. Navarro, and M. Bermejo, “A topological substructural approach for the prediction of P-glycoprotein substrates,” Journal of Pharmaceutical Sciences, vol. 95, no. 3, pp. 589–606, 2006. View at Publisher · View at Google Scholar · View at Scopus
  6. M. P. González, C. Terán, M. Teijeira, and A. M. Helguera, “Quantitative structure activity relationships as useful tools for the design of new adenosine receptor ligands. 1. Agonist,” Current Medicinal Chemistry, vol. 13, no. 19, pp. 2253–2266, 2006. View at Publisher · View at Google Scholar · View at Scopus
  7. W. H. Van, Chemometric Methods in Molecular Design, Wiley-VCH, New York, NY, USA, 1995.
  8. P. Willett, “Computational tools for the analysis of molecular diversity,” Perspectives in Drug Discovery and Design, vol. 7-8, pp. 1–11, 1997. View at Google Scholar · View at Scopus
  9. S. A. Best, K. M. Merz Jr., and C. H. Reynolds, “Free energy perturbation study of octanol/water partition coefficients: comparison with continuum GB/SA calculations,” Journal of Physical Chemistry B, vol. 103, no. 4, pp. 714–726, 1999. View at Google Scholar · View at Scopus
  10. K.-C. Chou, C.-T. Zhang, and G. M. Maggiora, “Solitary wave dynamics as a mechanism for explaining the internal motion during microtubule growth,” Biopolymers, vol. 34, no. 1, pp. 143–153, 1994. View at Google Scholar · View at Scopus
  11. M. E. Pichichero and C. J. Avers, “The evolution of cellular movement in eukaryotes: the role of microfilaments and microtubules,” Sub-Cellular Biochemistry, vol. 2, no. 1, pp. 97–105, 1973. View at Google Scholar · View at Scopus
  12. J. S. Hyams and H. Stebbings, “The mechanism of microtubule associated cytoplasmic transport. Isolation and preliminary characterisation of a microtubule transport system,” Cell and Tissue Research, vol. 196, no. 1, pp. 103–116, 1979. View at Google Scholar · View at Scopus
  13. O. Valiron, N. Caudron, and D. Job, “Microtubule dynamics,” Cellular and Molecular Life Sciences, vol. 58, no. 14, pp. 2069–2084, 2001. View at Google Scholar · View at Scopus
  14. S. Sengupta and S. A. Thomas, “Drug target interaction of tubulin-binding drugs in cancer therapy,” Expert Review of Anticancer Therapy, vol. 6, no. 10, pp. 1433–1447, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. R. O. Carlson, “New tubulin targeting agents currently in clinical development,” Expert Opinion on Investigational Drugs, vol. 17, no. 5, pp. 707–722, 2008. View at Publisher · View at Google Scholar · View at Scopus
  16. B. R. Hearn, S. J. Shaw, and D. C. Myles, “Microtubule targeting agents,” Medicinal Chemistry & Computer, vol. 7, pp. 81–110, 2007. View at Google Scholar
  17. M. A. Jordan, “Mechanism of action of antitumor drugs that interact with microtubules and tubulin,” Current Medicinal Chemistry, Anti-Cancer Agents, vol. 2, no. 1, pp. 1–17, 2002. View at Google Scholar · View at Scopus
  18. Q. Li and H. L. Sham, “Discovery and development of antimitotic agents that inhibit tubulin polymerisation for the treatment of cancer,” Expert Opinion on Therapeutic Patents, vol. 12, no. 11, pp. 1663–1702, 2002. View at Publisher · View at Google Scholar · View at Scopus
  19. N. Mahindroo, J.-P. Liou, J.-Y. Chang, and H.-P. Hsieh, “Antitubulin agents for the treatment of cancer—a medicinal chemistry update,” Expert Opinion on Therapeutic Patents, vol. 16, no. 5, pp. 647–691, 2006. View at Publisher · View at Google Scholar · View at Scopus
  20. G. R. Pettit, S. B. Singh, E. Hamel, C. M. Lin, D. S. Alberts, and D. Garcia-Kendall, “Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4,” Experientia, vol. 45, no. 2, pp. 209–211, 1989. View at Google Scholar · View at Scopus
  21. S. Goodin, M. P. Kane, and E. H. Rubin, “Epothilones: mechanism of action and biologic activity,” Journal of Clinical Oncology, vol. 22, no. 10, pp. 2015–2025, 2004. View at Publisher · View at Google Scholar · View at Scopus
  22. K. Yoshimatsu, A. Yamaguchi, H. Yoshino, N. Koyanagi, and K. Kitoh, “Mechanism of action of E7010, an orally active sulfonamide antitumor agent: inhibition of mitosis by binding to the colchicine site of tubulin,” Cancer Research, vol. 57, no. 15, pp. 3208–3213, 1997. View at Google Scholar · View at Scopus
  23. S. Arora, X. I. Wang, S. M. Keenan et al., “Novel microtubule polymerization inhibitor with potent antiproliferative and antitumor activity,” Cancer Research, vol. 69, no. 5, pp. 1910–1915, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. H. C. Nickel, P. Schmidt, K. J. Böhm et al., “Synthesis, antiprolife ativeactivity and inhibition of tubulinpolymerization by 1,5-and 1,8-disubstituted 10H-anthracen-9-onesbearinga 10-benzylidene or 10-(2-oxo-2-phenylethylidene) moiety,” European Journal of Medicinal Chemistry, vol. 45, no. 8, pp. 3420–3438, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. H. Prinz, P. Schmidt, K. J. Böhm et al., “10-(2-oxo-2-Phenylethylidene)-10H-anthracen-9-ones as highly active antimicrotubule agents: synthesis, antiproliferative activity, and inhibition of tubulin polymerization,” Journal of Medicinal Chemistry, vol. 52, no. 5, pp. 1284–1294, 2009. View at Publisher · View at Google Scholar · View at Scopus
  26. H. S. Huang, J. F. Chiou, H. F. Chiu, R. F. Chen, and Y. L. Lai, “Synthesis and cytotoxicity of 9-alkoxy-1,5-dichloroanthracene derivatives in murine and human cultured tumor cells,” Archiv der Pharmazie, vol. 335, pp. 33–38, 2002. View at Google Scholar
  27. H.-S. Huang, J.-F. Chiou, H.-F. Chiu et al., “Synthesis of symmetrical 1,5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation,” Chemical and Pharmaceutical Bulletin, vol. 50, no. 11, pp. 1491–1494, 2002. View at Publisher · View at Google Scholar · View at Scopus
  28. H.-S. Huang, H.-F. Chiu, W.-C. Lu, and C.-L. Yuan, “Synthesis and antitumor activity of 1,8-diaminoanthraquinone derivatives,” Chemical and Pharmaceutical Bulletin, vol. 53, no. 9, pp. 1136–1139, 2005. View at Publisher · View at Google Scholar · View at Scopus
  29. E. M. Perchellet, Y. Wang, K. Lou et al., “Novel substituted 1,4-anthracenediones with antitumor activity directly induce permeability transition in isolated mitochondria,” International Journal of Oncology, vol. 31, no. 5, pp. 1231–1241, 2007. View at Google Scholar · View at Scopus
  30. G. Zagotto, C. Sissi, L. Lucatello et al., “Aminoacyl-anthraquinone conjugates as telomerase inhibitors: synthesis, biophysical and biological evaluation,” Journal of Medicinal Chemistry, vol. 51, no. 18, pp. 5566–5574, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. N. Metropolis, A. W. Rosenbluth, M. N. Rosenbluth, A. H. Teller, and E. Teller, “Equation of state calculations by fast computing machines,” The Journal of Chemical Physics, vol. 21, no. 6, pp. 1087–1092, 1953. View at Google Scholar · View at Scopus
  32. R. D. Cramer III, D. E. Patterson, and J. D. Bunce, “Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins,” Journal of the American Chemical Society, vol. 110, no. 18, pp. 5959–5967, 1988. View at Google Scholar · View at Scopus
  33. K. K. Jha, A. Samad, Y. Kumar et al., “3D QSAR studies of 1,3,4-oxadiazole derivatives as antimycobacterial agents,” Iranian Journal of Pharmaceutical Research, vol. 8, no. 3, pp. 163–167, 2009. View at Google Scholar · View at Scopus
  34. G. Mustata, A. V. Follis, D. I. Hammoudeh et al., “Discovery of novel Myc-Max heterodimer disruptors with a three-dimensional pharmacophore model,” Journal of Medicinal Chemistry, vol. 52, no. 5, pp. 1247–1250, 2009. View at Publisher · View at Google Scholar
  35. G. Mustata, A. V. Follis, D. I. Hammoudeh et al., “Discovery of novel myc-max heterodimer disruptors with a three-dimensional pharmacophore model,” Journal of Medicinal Chemistry, vol. 52, no. 5, pp. 1247–1250, 2009. View at Publisher · View at Google Scholar · View at Scopus
  36. C.-H. Yun, T. J. Boggon, Y. Li et al., “Structures of lung cancer-derived EGFR mutants and inhibitor complexes: mechanism of activation and insights into differential inhibitor sensitivity,” Cancer Cell, vol. 11, no. 3, pp. 217–227, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. O. Trott and A. J. Olson, “Software news and update AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading,” Journal of Computational Chemistry, vol. 31, no. 2, pp. 455–461, 2010. View at Publisher · View at Google Scholar · View at Scopus
  38. The Pymol Molecular Graphics system, version 1. 3, Schrodinger, LLC.
  39. J. Gasteiger and M. Marsili, “Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges,” Tetrahedron, vol. 36, no. 22, pp. 3219–3228, 1980. View at Google Scholar · View at Scopus
  40. P. J. Goodford, “A computational procedure for determining energetically favorable binding sites on biologically important macromolecules,” Journal of Medicinal Chemistry, vol. 28, no. 7, pp. 849–857, 1985. View at Google Scholar · View at Scopus
  41. F. J. Solis and R. J. B. Wets, “Minimization by random search techniques,” Mathematics of Operations Research, vol. 6, no. 1, pp. 19–30, 1981. View at Google Scholar · View at Scopus