Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2017, Article ID 3687182, 8 pages
https://doi.org/10.1155/2017/3687182
Research Article

Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones

1School of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, Vietnam
2Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
3Institute of Biotechnology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
4Hanoi University of Pharmacy (HUP), 13-15 Le Thanh Tong, Hanoi, Vietnam
5Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29A, 18059 Rostock, Germany

Correspondence should be addressed to Tran Khac Vu; nv.ude.tsuh@cahknart.uv

Received 8 June 2017; Revised 19 August 2017; Accepted 13 September 2017; Published 17 October 2017

Academic Editor: Mire Zloh

Copyright © 2017 Vu Van Vu 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. N. Howlader, A. M. Noone, M. Krapcho et al., SEER Cancer Statistics Review, 1975–2012, National Cancer Institute, Bethesda, MD, USA, Based on November 2014 SEER data submission, posted to the SEER web site, April 2015 http://seer.cancer.gov/csr/1975_2012/.
  2. I. K. Mellinghoff and C. L. Sawyers, “The emergence of resistance to targeted cancer therapeutics,” Pharmacogenomics, vol. 3, no. 5, pp. 603–623, 2002. View at Publisher · View at Google Scholar · View at Scopus
  3. M. E. Wall and M. C. Wani, “Camptothecin and taxol: discovery to clinic—thirteenth Bruce F. Cain Memorial Award Lecture,” Cancer Research, vol. 55, no. 4, pp. 753–760, 1995. View at Google Scholar · View at Scopus
  4. C. L. Oliver, J. A. Bauer, K. G. Wolter et al., “In vitro effects of the BH3 mimetic, (-)-gossypol, on head and neck squamous cell carcinoma cells,” Clinical Cancer Research, vol. 10, no. 22, pp. 7757–7763, 2004. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Zhang, H. Liu, Z. Tian, B. N. Griffith, M. Ji, and Q. Q. Li, “Gossypol induces apoptosis in human PC-3 prostate cancer cells by modulating caspase-dependent and caspase-independent cell death pathways,” Life Sciences, vol. 80, no. 8, pp. 767–774, 2007. View at Publisher · View at Google Scholar · View at Scopus
  6. R. M. Mohammad, S. Wang, S. Banerjee, X. Wu, J. Chen, and F. H. Sarkar, “Nonpeptidic small-molecule inhibitor of Bcl-2 and Bcl-XL, (−)-gossypol, enhances biological effect of genistein against BxPC-3 human pancreatic cancer cell line,” Pancreas, vol. 31, no. 4, pp. 317–324, 2005. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Zhang, H. Liu, R. Guo et al., “Molecular mechanism of gossypol-induced cell growth inhibition and cell death of HT-29 human colon carcinoma cells,” Biochemical Pharmacology, vol. 66, no. 1, pp. 93–103, 2003. View at Publisher · View at Google Scholar · View at Scopus
  8. D. W. Hahn, C. Rusticus, A. Probst, R. Homm, and A. N. Johnson, “Antifertility and endocrine activities of gossypol in rodents,” Contraception, vol. 24, no. 1, pp. 97–105, 1981. View at Publisher · View at Google Scholar · View at Scopus
  9. J. Yang, G. Chen, L. L. Li et al., “Synthesis and anti-H5N1 activity of chiral gossypol derivatives and its analogs implicated by a viral entry blocking mechanism,” Bioorganic & Medicinal Chemistry Letters, vol. 23, no. 9, pp. 2619–2623, 2013. View at Publisher · View at Google Scholar · View at Scopus
  10. J. Yang, F. Zhang, J. Li et al., “Synthesis and antiviral activities of novel gossypol derivatives,” Bioorganic & Medicinal Chemistry Letters, vol. 22, no. 3, pp. 1415–1420, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. R. J. Radloff, L. M. Deck, R. E. Royer, and D. L. Vander Jagt, “Antiviral activities of gossypol and its derivatives against herpes simplex virus type II,” Pharmacological Research Communications, vol. 18, no. 11, pp. 1063–1073, 1986. View at Publisher · View at Google Scholar · View at Scopus
  12. G. Tegos, F. R. Stermitz, O. Lomovskaya, and K. Lewis, “Multidrug pump inhibitors uncover remarkable activity of plant antimicrobials,” Antimicrobial Agents and Chemotherapy, vol. 46, no. 10, pp. 3133–3141, 2002. View at Publisher · View at Google Scholar · View at Scopus
  13. X. S. Liang, A. J. Rogers, C. L. Webber et al., “Developing gossypol derivatives with enhanced antitumor activity,” Investigational New Drugs, vol. 13, no. 3, pp. 181–186, 1995. View at Publisher · View at Google Scholar · View at Scopus
  14. R. E. Royer, R. G. Mills, L. M. Deck, G. J. Mertz, and D. L. Vander Jagt, “Inhibition of human immunodeficiency virus type I replication by derivatives of gossypol,” Pharmacological Research, vol. 24, no. 4, pp. 407–412, 1991. View at Publisher · View at Google Scholar · View at Scopus
  15. L. Tai-Shun, R. F. Schinazi, J. Zhu et al., “Anti-HIV-1 activity and cellular pharmacology of various analogs of gossypol,” Biochemical Pharmacology, vol. 46, no. 2, pp. 251–255, 1993. View at Publisher · View at Google Scholar · View at Scopus
  16. Y. Lu, S. Wu, Y. Yue et al., “Gossypol with hydrophobic linear esters exhibits enhanced antitumor activity as an inhibitor of antiapoptotic proteins,” ACS Medicinal Chemistry Letters, vol. 7, no. 12, pp. 1185–1190, 2016. View at Publisher · View at Google Scholar · View at Scopus
  17. L. Li, Z. Li, K. Wang et al., “Design, synthesis, and biological activities of aromatic gossypol schiff base derivatives,” Journal of Agricultural and Food Chemistry, vol. 62, no. 46, pp. 11080–11088, 2014. View at Publisher · View at Google Scholar · View at Scopus
  18. Z. Yonghua, C. Xu, L. Yingchao, C. Xueli, and H. Xiaofeng, “Synthesis and biological evaluation of a novel apogossypolone derivative,” Letters in Drug Design & Discovery, vol. 14, pp. 96–101, 2017. View at Google Scholar
  19. Y. Lu, J. Li, C. Dong, J. Huang, H. Zhou, and W. Wang, “Recent advances in gossypol derivatives and analogs: a chemistry and biology view,” Future Medicinal Chemistry, vol. 9, no. 11, pp. 1243–1275, 2017. View at Publisher · View at Google Scholar
  20. J. Qiu, L. R. Levin, J. Buck, and M. M. Reidenberg, “Different pathways of cell killing by gossypol enantiomers,” Experimental Biology and Medicine, vol. 227, no. 6, pp. 398–401, 2002. View at Publisher · View at Google Scholar · View at Scopus
  21. G. Tang, C.-Y. Yang, Z. Nikolovska-Coleska et al., “Pyrogallol-based molecules as potent inhibitors of the antiapoptotic Bcl-2 proteins,” Journal of Medicinal Chemistry, vol. 50, no. 8, pp. 1723–1726, 2007. View at Publisher · View at Google Scholar · View at Scopus
  22. G. Wang, Z. Nikolovska-Coleska, C. Yang et al., “Structure-based design of potent small-molecule inhibitors of anti-apoptotic Bcl-2 proteins,” Journal of Medicinal Chemistry, vol. 49, no. 21, pp. 6139–6142, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. H.-X. Jiang, X.-X. Cao, H. Huang, and B. Jiang, “An expedient route for the practical preparation of optically active (-)-gossypol,” Tetrahedron: Asymmetry, vol. 18, no. 20, pp. 2437–2441, 2007. View at Publisher · View at Google Scholar · View at Scopus
  24. P. Przybylski, K. Pyta, J. Stefańska et al., “Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant - gossypol,” European Journal of Medicinal Chemistry, vol. 44, no. 11, pp. 4393–4403, 2009. View at Publisher · View at Google Scholar · View at Scopus
  25. K. Likhitwitayawuid, C. K. Angerhofer, G. A. Cordell, J. M. Pezzuto, and N. Ruangrungsi, “Cytotoxic and antimalarial bisbenzylisoquinoline alkaloids from Stephania erecta,” Journal of Natural Products, vol. 56, no. 1, pp. 30–38, 1993. View at Publisher · View at Google Scholar · View at Scopus
  26. C. Kurekci, S. L. Bishop-Hurley, P. E. Vercoe, Z. Durmic, R. A. M. Al Jassim, and C. S. McSweeney, “Screening of Australian plants for antimicrobial activity against Campylobacter jejuni,” Phytotherapy Research, vol. 26, no. 2, pp. 186–190, 2012. View at Publisher · View at Google Scholar · View at Scopus