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Journal of Chemistry
Volume 2013, Article ID 935646, 9 pages
http://dx.doi.org/10.1155/2013/935646
Research Article

2-[3,5-Bis-(2-fluorobenzylidene)-4-piperidon-1-yl]-N-(4-fluorobenzyl)-acetamide and Its Evaluation as an Anticancer Agent

Department of Pharmaceutical Sciences and Research Imaging Facility, University of Oklahoma Health Science Center, 1110 N. Stonewall Avenue, Oklahoma City, OK 73117, USA

Received 2 May 2013; Accepted 1 July 2013

Academic Editor: Liviu Mitu

Copyright © 2013 Pallavi Lagisetty 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. G. L. Griffiths, “The imaging probe development center and the production of molecular imaging probes,” Current Chemical Genomics, vol. 1, pp. 65–69, 2008. View at Google Scholar
  2. M. G. Pomper, “Can small animal imaging accelerate drug development?” Journal of Cellular Biochemistry, no. 39, pp. 211–220, 2002. View at Google Scholar · View at Scopus
  3. C. A. Altar, “The biomarkers consortium: on the critical path of drug discovery,” Clinical Pharmacology and Therapeutics, vol. 83, no. 2, pp. 361–364, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. C. A. Altar, D. Amakye, D. Bounos et al., “A prototypical process for creating evidentiary standards for biomarkers and diagnostics,” Clinical Pharmacology and Therapeutics, vol. 83, no. 2, pp. 368–371, 2008. View at Publisher · View at Google Scholar · View at Scopus
  5. J. Woodcock and R. Woosley, “The FDA critical path initiative and its influence on new drug development,” Annual Review of Medicine, vol. 59, pp. 1–12, 2008. View at Publisher · View at Google Scholar · View at Scopus
  6. A. Iagaru, S. S. Gambhir, and M. L. Goris, “90Y-ibritumomab therapy in refractory non-Hodgkin's lymphoma: observations from 111In-ibritumomab pretreatment imaging,” Journal of Nuclear Medicine, vol. 49, no. 11, pp. 1809–1812, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. P. Anand, A. B. Kunnumakkara, R. A. Newman, and B. B. Aggarwal, “Bioavailability of curcumin: problems and promises,” Molecular Pharmaceutics, vol. 4, no. 6, pp. 807–818, 2007. View at Publisher · View at Google Scholar · View at Scopus
  8. H. N. Pati, U. Das, J. W. Quail, M. Kawase, H. Sakagami, and J. R. Dimmock, “Cytotoxic 3,5-bis(benzylidene)piperidin-4-ones and N-acyl analogs displaying selective toxicity for malignant cells,” European Journal of Medicinal Chemistry, vol. 43, no. 1, pp. 1–7, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. T. P. Robinson, R. B. Hubbard, T. J. Ehlers, J. L. Arbiser, D. J. Goldsmith, and J. P. Bowen, “Synthesis and biological evaluation of aromatic enones related to curcumin,” Bioorganic and Medicinal Chemistry, vol. 13, no. 12, pp. 4007–4013, 2005. View at Publisher · View at Google Scholar · View at Scopus
  10. A. Sun, M. Shoji, Y. J. Lu, D. C. Liotta, and J. P. Snyder, “Synthesis of EF24-tripeptide chloromethyl ketone: a novel curcumin-related anticancer drug delivery system,” Journal of Medicinal Chemistry, vol. 49, no. 11, pp. 3153–3158, 2006. View at Publisher · View at Google Scholar · View at Scopus
  11. D. Subramaniam, R. May, S. M. Sureban et al., “Diphenyl difluoroketone: a curcumin derivative with potent in vivo anticancer activity,” Cancer Research, vol. 68, no. 6, pp. 1962–1969, 2008. View at Publisher · View at Google Scholar · View at Scopus
  12. K. Selvendiran, L. Tong, S. Vishwanath et al., “EF24 induces G2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by increasing PTEN expression,” Journal of Biological Chemistry, vol. 282, no. 39, pp. 28609–28618, 2007. View at Publisher · View at Google Scholar · View at Scopus
  13. B. K. Adams, E. M. Ferstl, M. C. Davis et al., “Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents,” Bioorganic and Medicinal Chemistry, vol. 12, no. 14, pp. 3871–3883, 2004. View at Publisher · View at Google Scholar · View at Scopus
  14. A. L. Kasinski, Y. Du, S. L. Thomas et al., “Inhibition of IκB kinase-nuclear factor-κB signaling pathway by 3,5-bis(2-flurobenzylidene)piperidin-4-one (EF24), a novel monoketone analog of curcumin?” Molecular Pharmacology, vol. 74, no. 3, pp. 654–661, 2008. View at Publisher · View at Google Scholar · View at Scopus
  15. H. Agashe, K. Sahoo, P. Lagisetty, and V. Awasthi, “Cyclodextrin-mediated entrapment of curcuminoid 4-[3,5-bis(2-chlorobenzylidene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] or CLEFMA in liposomes for treatment of xenograft lung tumor in rats,” Colloids and Surfaces B, vol. 84, no. 2, pp. 329–337, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. P. Lagisetty, D. R. Powell, and V. Awasthi, “Synthesis and structural determination of 3,5-bis(2-fluorobenzylidene)-4-piperidone analogs of curcumin,” Journal of Molecular Structure, vol. 936, no. 1–3, pp. 23–28, 2009. View at Publisher · View at Google Scholar · View at Scopus
  17. U. Landegren, “Measurement of cell numbers by means of the endogenous enzyme hexosaminidase. Applications to detection of lymphokines and cell surface antigens,” Journal of Immunological Methods, vol. 67, no. 2, pp. 379–388, 1984. View at Publisher · View at Google Scholar · View at Scopus
  18. D. W. Frank, “Physiological data of laboratory animals,” in Handbook of Laboratory Animal Science, E. C. Melby Jr., Ed., vol. 3, pp. 23–64, CRC Press, Boca Raton, Fla, USA, 1976. View at Google Scholar
  19. C. Petty, Research Techniques in the Rats, Charles C. Thomas, Springfield, Ill, USA, 1982.
  20. U. Das, S. Das, B. Bandy, J. P. Stables, and J. R. Dimmock, “N-Aroyl-3,5-bis(benzylidene)-4-piperidones: a novel class of antimycobacterial agents,” Bioorganic and Medicinal Chemistry, vol. 16, no. 7, pp. 3602–3607, 2008. View at Publisher · View at Google Scholar · View at Scopus
  21. E. K. Ryu, Y. S. Choe, K.-H. Lee, Y. Choi, and B.-T. Kim, “Curcumin and dehydrozingerone derivatives: synthesis, radiolabeling, and evaluation for β-amyloid plaque imaging,” Journal of Medicinal Chemistry, vol. 49, no. 20, pp. 6111–6119, 2006. View at Publisher · View at Google Scholar · View at Scopus
  22. P. Lagisetty, P. Vilekar, K. Sahoo, S. Anant, and V. Awasthi, “CLEFMA—an anti-proliferative curcuminoid from structure-activity relationship studies on 3,5-bis(benzylidene)-4-piperidones,” Bioorganic and Medicinal Chemistry, vol. 18, no. 16, pp. 6109–6120, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. J. Ravindran, S. Prasad, and B. B. Aggarwal, “Curcumin and cancer cells: how many ways can curry kill tumor cells selectively?” AAPS Journal, vol. 11, no. 3, pp. 495–510, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. P. J. O'Dwyer, F. LaCreta, S. Nash et al., “Phase I study of thiotepa in combination with the glutathione transferase inhibitor ethacrynic acid,” Cancer Research, vol. 51, no. 22, pp. 6059–6065, 1991. View at Google Scholar · View at Scopus
  25. R. Costi, R. Di Santo, M. Artico et al., “2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone: novel potent HIV-1 integrase inhibitors that prevent HIV-1 multiplication in cell-based assays,” Bioorganic and Medicinal Chemistry, vol. 12, no. 1, pp. 199–215, 2004. View at Publisher · View at Google Scholar · View at Scopus
  26. 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
  27. H. Agashe, P. Lagisetty, K. Sahoo, D. Bourne, B. Grady, and V. Awasthi, “Liposome-encapsulated EF24-HPβCD inclusion complex: a preformulation study and biodistribution in a rat model,” Journal of Nanoparticle Research, vol. 13, no. 6, pp. 2609–2623, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. V. J. Stella and Q. He, “Cyclodextrins,” Toxicologic Pathology, vol. 36, pp. 30–42, 2008. View at Google Scholar
  29. V. J. Stella, V. M. Rao, E. A. Zannou, and V. Zia, “Mechanisms of drug release from cyclodextrin complexes,” Advanced Drug Delivery Reviews, vol. 36, no. 1, pp. 3–16, 1999. View at Publisher · View at Google Scholar · View at Scopus