JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 61 No 4 (2016): Journal of the Chilean Chemical Society
Original Research Papers

ANTIPROLIFERATIVE ACTIVITY OF NEW 6-BROMINE DERIVATIVES OF 7-ANILINO-1- ARYLISOQUINOLINEQUINONES

Juana Andrea Ibacache
Facultad de Química y Biología, Universidad de Santiago de Chile
Jaime A. Valderrama
Facultad de Ciencias de la Salud, Universidad Arturo Prat Instituto de Ciencias Exactas y Naturales Universidad Arturo Prat
Verónica Arancibia
Facultad de Química, Pontificia Universidad Católica de Chile
Cristina Theoduloz
Facultad de Ciencias de la Salud, Universidad de Talca
Giulio G. Muccioli
Bioanalysis and Pharmacology of Bioactive Lipids Laboratory, Louvain Drug Research Institute, Université Catholique de Louvain
Julio Benites
Facultad de Ciencias de la Salud, Universidad Arturo Prat Instituto de Ciencias Exactas y Naturales Universidad Arturo Prat
Published May 29, 2017
Keywords
  • Isoquinolinequinones,
  • Half-wave potentials,
  • MTT assay,
  • Antiproliferative activity
How to Cite
Ibacache, J. A., Valderrama, J. A., Arancibia, V., Theoduloz, C., Muccioli, G. G., & Benites, J. (2017). ANTIPROLIFERATIVE ACTIVITY OF NEW 6-BROMINE DERIVATIVES OF 7-ANILINO-1- ARYLISOQUINOLINEQUINONES. Journal of the Chilean Chemical Society, 61(4). Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/108

Abstract

A variety of 6-bromine-containing 7-anilino-1-arylisoquinolinequinones 2a-g were synthesized to evaluate their half-wave potentials and in vitro antiproliferative activity on gastric and leukemia cancer cell lines. The new compounds displayed significant IC50 values in the range: 1.31 to 11.04 μM. The structure activity relationship analysis of the new series suggest that the antiproliferative activity is dependent, in part, on the push-pull electronic effects of the nitrogen and bromine substituents inserted into the redox fragment of the 1-arylisoquinolinequinone scaffold. Linear regression analysis provided satisfactory relationships between the log IC50 and ClogP values for the AGS gastric cancer cell line. 

References

  1. W. Hai-Quian, H. Zhi-Shu, B. Xian-Zhang, S. Yu-Dong, Z. Zhu-Lin, X. Bing-Fen, L. Zong-Chao, G. Lian-Quan, C. Albert. Eur. J. Med. Chem. 40, (2005), 1341–1345.
  2. L. Rossi, G.A. Moore, S. Orrenius, P.J. O’Brien. Arch. Biochem. Biophys. 251, (1986), 25–35.
  3. M.A. Tapper, B.R. Sheedy, D.E Hammermeister, P.K. Schmieder. Toxicol. Sci. 55 (2000), 327–334.
  4. R. Osman, K. Namboodiri, H. Weinstein, J.R. Rabinowitz. J. Am. Chem. Soc. 110, (1988), 1701–1707.
  5. A. Plubrukran, S. Yuenyongsawad, T. Thammasaroj, A. Jitsue. Pharm. Biol. 41, (2003), 439.
  6. T. Sandoval, R.A. Davis, T.S. Bugni, G.P. Concepcion, M.K. Harper, C.M. Ireland. Nat.Prod.Res. 18, (2004), 89.
  7. U.W. Hawas, M. Shaaban, K.A. Shaaban, M. Speitling, A. Maier, G. Kelter, H.H. Fiebig, M. Meiners, E. Helmke, H. Laatsch. J. Nat. Prod. 71, (2009), 2120–2124.
  8. D.J. Milanowski, K.R. Gustafson, J.A. Kelley, J.B. McMahon. J. Nat. Prod. 67, (2004), 70–73.
  9. P. Wipf, B. Joo, T. Nguyenb, J.S. Lazo. Org. Biomol. Chem. 2, (2004), 2173–2174.
  10. M. Brisson, C. Foster, P. Wipf, B. Joo, R.J. Tomk, T. Nguyen, J.S. Lazo. Mol. Pharmacol. 71, (2007), 184–192.
  11. J.A. Valderrama, J.A. Ibacache, V. Arancibia, J. Rodriguez, C. Theoduloz. Bioorg. Med. Chem. 17, (2009), 2894–2901.
  12. V. Delgado, J.A. Ibacache, C. Theoduloz, J.A. Valderrama. Molecules. 17, (2012), 7042–7056.
  13. V. Delgado, J.A. Ibacache, V. Arancibia, C. Theoduloz, J.A. Valderrama. Molecules. 18, (2013), 721–734.
  14. J.S. Lazo, D.C. Aslan, E.C. Southwick, K.A. Cooley, A.P. Ducruet, B. Joo, A. Vogt, P. Wipf. J. Med. Chem. 44, (2001), 4042–4049.
  15. B.J. Mulchin, C.G. Newton, J.W. Baty, C.H. Grasso, W.J. Martin, M.C. Walton, E.M. Dangerfield, C.H. Plunkett, M.V. Berridge, J.L. Harper, J.L. Bioorg. Med. Chem. 18, (2010), 3238–3251.
  16. V.K. Tandom, H.K. Maurya, N.N. Mishra. Eur. J. Med. Chem. 44, (2009), 3130–3137.
  17. J.A. Ibacache, V. Delgado, J. Benites, C. Theoduloz, V. Arancibia, G. Muccioli, J.A. Valderrama. Molecules. 19, (2014), 726-739.
  18. Y. Prieto, M. Muñoz, V. Arancibia, M. Valderrama, F.J. Lahoz, M.L. Martín. Polyhedron. 26, (2007), 5527–5532.
  19. F.C. De Abreu, P.A. de Ferraz, M.O.F. Goulart. J. Braz. Chem. Soc.13, (2002), 19–35.
  20. M. Aguilar-Martinez, G. Cuevas, M. Jimenez-Estrada, I. González, B. Lotina-Hennsen, N. Macias-Ruvalcaba. J. Org. Chem. 64, (1999), 3684– 3694.
  21. M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, M.R. Boy. Cancer Res. 48, (1988), 589–601.
  22. A.A.Van de Loosdrecht, R.H. Beelen, G.J. Ossenkoppele, M.G. Broekhoven, M.M. Langenhuijsen. J. Immunol. Methods. 174, (1994), 311–320.
  23. D.A. Scudiero, R.H. Shoemaker, K.D. Paull, A. Monks, S. Tierney, T.H. Nofziger, M.J. Currens, D. Seniff, M.R. Boyd. Cancer Res.48, (1988), 4827–4833.
  24. E. M. Hodnett, C. Wongwiechintana, W.J. Dunn, P.J. Marra. J. Med. Chem. 26, (1983), 570.
  25. R.P. Verma. Anti-Cancer Agent Med. Chem. 6, (2006), 489.

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP