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Vol. 26 No. 9 (2014): Vol 26 Issue 9

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Characterization and Anticancer Potential of Newly Synthesized Propofol Conjugates

https://doi.org/10.14233/ajchem.2014.16778
Amer M. Alanazi
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia
Azmat Ali Khan
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia
Jamal Mustafa
University Polytechnic, Faculty of Engineering, Aligarh Muslim University, Aligarh-202 002, India
Mohammad Khalid Parvez
Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia
Adel S. El-Azab
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia
Ali Saber Abdelhameed
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia

Corresponding Author(s) : Azmat Ali Khan

azmatbiotech@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 9 (2014): Vol 26 Issue 9

Abstract

The present study reports the synthesis, characterization and anticancer potential of novel ester conjugates of stearic acid (SA) and palmitic acid (PA). An ester conjugates were chemically designed by esterification of the terminal COOH group of the fatty acid to C1-OH position of 2,6-diisopropylphenol (propofol). The structure of new ester conjugates viz; propofol stearate and propofol palmitate were characterized by UV, NMR (1H, 13C) and FAB mass spectroscopy. The anticancer efficacy of the conjugates was examined on HepG2, Lovo, HT1080, A549 and MDA-MB-231 cancer cell lines. Treatment with propofol stearate significantly inhibited the growth of MDA-MB-231 cancer cells whereas propofol palmitate exhibited cytotoxicity towards A549 cancer cells. However, both of the conjugates showed significant (p < 0.05) growth inhibition of all types of tested cancer cells in a dose-dependent manner. The preliminary results suggest that novel conjugates possess anticancer properties that reduce the proliferation of cancer cells in vitro.

Keywords

Saturated fatty acids Propofol Cytotoxicity Cancer cell lines
M. Alanazi, A., Ali Khan, A., Mustafa, J., Khalid Parvez, M., S. El-Azab, A., & Saber Abdelhameed, A. (2014). Characterization and Anticancer Potential of Newly Synthesized Propofol Conjugates. Asian Journal of Chemistry, 26(9), 2773–2780. https://doi.org/10.14233/ajchem.2014.16778
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References
  1. C.R. Miller and H.L. McLeod, J. Support. Oncol., 5, 9 (2007).
  2. S.E. James, H. Burden, R. Burgess, Y. Xie, T. Yang, S.M. Massa, F.M. Longo and Q. Lu, Neurotoxicol., 29, 605 (2008); doi:10.1016/j.neuro.2008.04.008.
  3. M. Takahashi, Carcinogenesis, 18, 1337 (1997); doi:10.1093/carcin/18.7.1337.
  4. M.O. Bradley, C.S. Swindell, F.H. Anthony, P.A. Witman, P. Devanesan, N.L. Webb, S.D. Baker, A.C. Wolff and R.C. Donehower, J. Control. Rel., 74, 233 (2001); doi:10.1016/S0168-3659(01)00321-2.
  5. M. Zerouga, W. Stillwell and L.J. Jenski, Anticancer Drugs, 13, 301 (2002); doi:10.1097/00001813-200203000-00012.
  6. M.P. Moyer, W.E. Hardman and I. Canceron, U.S. Patent 102907 (2002).
  7. J.A. Manendez, S. Ropero, R. Lupu and R. Colomer, Oncol. Rep., 11, 1241 (2004).
  8. A.A. Khan, M. Jabeen, A.A. Khan and M. Owais, Nanomedicine, 8, 1281 (2013); doi:10.2217/nnm.12.166.
  9. K.J. Tronstad, K. Berge, R.K. Berge and Ø. Bruserud, Expert Opin. Ther. Targets, 7, 663 (2003); doi:10.1517/14728222.7.5.663.
  10. R.A. Siddiqui, M. Zerouga, M. Wu, A. Castillo, K. Harvey, G.P. Zaloga and W. Stillwell, Breast Cancer Res., 7, 645 (2005); doi:10.1186/bcr1036.
  11. K.A. Harvey, Z. Xu, P. Whitley, V. Jo Davisson and R.A. Siddiqui, Bioorg. Med. Chem., 18, 1866 (2010); doi:10.1016/j.bmc.2010.01.045.
  12. A.A. Khan, M. Alam, S. Tufail, J. Mustafa and M. Owais, Eur. J. Med. Chem., 46, 4878 (2011); doi:10.1016/j.ejmech.2011.07.044.
  13. A.A. Khan, A. Husain, M. Jabeen, J. Mustafa and M. Owais, Lipids, 47, 973 (2012); doi:10.1007/s11745-012-3707-9.
  14. S. Klein and R.R. Wolfe, Am. J. Physiol., 262, 631 (1992)..
  15. D.A. Fraser, J. Thoen and A.C. Rustan, Rheumatology, 38, 948 (1999); doi:10.1093/rheumatology/38.10.948.
  16. N.S. Wickramasinghe, H. Jo, J.M. McDonald and R.W. Hardy, Am. J. Pathol., 148, 987 (1996).
  17. R.W. Hardy, N.S. Wickramasinghe, S.C. Ke and A. Wells, Adv. Exp. Med. Biol., 422, 57 (1997); doi:10.1007/978-1-4757-2670-1_5.
  18. L.M. Evans, S.L. Cowey, G.P. Siegal and R.W. Hardy, Nutr. Cancer, 61, 746 (2009); doi:10.1080/01635580902825597.
  19. N.A. Habib, C.B. Wood, K. Apostolov, W. Barker, M.J. Hershman, M. Aslam, D. Heinemann, B. Fermor, R.C.N. Williamson and W.E. Jenkins, Br. J. Cancer, 56, 455 (1987); doi:10.1038/bjc.1987.223.
  20. L.M. Evans, E.C. Toline, R.A. Desmond, G.P. Siegal, A.I. Hashim and R.W. Hardy, Clin. Exp. Metastasis, 26, 415 (2009); doi:10.1007/s10585-009-9239-x.
  21. M. Saadatian-Elahi, T. Norat, J. Goudable and E. Riboli, Int. J. Cancer, 111, 584 (2004); doi:10.1002/ijc.20284.
  22. A.A. Khan, A.M. Alanazi, M. Jabeen, A. Chauhan and A.S. Abdelhameed, Anticancer Res., 33, 2517 (2013).
  23. H. Harada, U. Yamashito, H. Kurilara and F. Fukushi, Anticancer Res., 22, 2587 (2002).
  24. S. Karna, W.B. Lim, J.S. Kim, S.W. Kim, H. Zheng, M.S. Cho, H.K. Oh, O.S. Kim and H.R. Choi, Food and Nutri. Sci., 3, 1220 (2012); doi:10.4236/fns.2012.39160.
  25. T. Mammoto, M. Mukai, A. Mammoto, Y. Yamanaka, Y. Hayashi, T. Mashimo, Y. Kishi and H. Nakamura, Cancer Lett., 184, 165 (2002); doi:10.1016/S0304-3835(02)00210-0.
  26. H. Covington, Crit. Care Nurse, 18, 34 (1998).
  27. M. Tsuchiya, A. Asada, K. Arita, T. Utsumi, T. Yoshida, E.F. Sato, K. Utsumi and M. Inoue, Acta Anaesthesiol. Scand., 46, 1068 (2002).
  28. Y. Miao, Y. Zhang, H. Wan, L. Chen and F. Wang, Biomed. Pharmacother., 64, 583 (2010); doi:10.1016/j.biopha.2010.03.006.
  29. J.D. Altenburg, K.A. Harvey, S. McCray, Z. Xu and R.A. Siddiqui, Biochem. Biophys. Res. Commun., 411, 427 (2011); doi:10.1016/j.bbrc.2011.06.172.
  30. American Cancer Society, Cancer Facts and Figures, Atlanta, American Cancer Society (2006).
  31. D.J. Hunter, D. Spiegelman, H.O. Adami, L. Beeson, P.A. van den Brandt, A.R. Folsom, G.E. Fraser, R.A. Goldbohm, S. Graham, G.R. Howe, L.H. Kushi, J.R. Marshall, A. McDermott, A.B. Miller, F.E. Speizer, A. Wolk, S.-S. Yaun and W. Willett, N. Engl. J. Med., 334, 356 (1996); doi:10.1056/NEJM199602083340603.
  32. L. Van Horn, Circulation, 95, 2701 (1997); doi:10.1161/01.CIR.95.12.2701.
  33. Proceedings of the Workshop on Individual Fatty Acids and Cancer, Am. J. Clin. Nutr., 66, 1505S (1997).
  34. D.P. Rose and J.M. Connolly, Cancer Res., 50, 7139 (1990).
  35. C.W. Welsch, Cancer Res., 52, 2040s (1992).
  36. M.M. Lee and S.S. Lin, Annu. Rev. Nutr., 20, 221 (2000); doi:10.1146/annurev.nutr.20.1.221.
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