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Evidence-Based Complementary and Alternative Medicine
Volume 2016 (2016), Article ID 4138263, 9 pages
http://dx.doi.org/10.1155/2016/4138263
Research Article

The Effect of Geometrical Isomerism of 3,5-Dicaffeoylquinic Acid on Its Binding Affinity to HIV-Integrase Enzyme: A Molecular Docking Study

1Department of Biochemistry, University of Johannesburg, P.O. Box 524, Auckland Park, Johannesburg 2006, South Africa
2Council for Scientific and Industrial Research (CSIR), Biosciences, Natural Products and Agroprocessing Group, Pretoria 0001, South Africa
3Department of Chemistry, Faculty of Agriculture, Science and Technology, School of Mathematical and Physical Science, North-West University, Mafikeng Campus, Private Bag X2046, Mmabatho 2735, South Africa
4Material Science Innovation and Modelling (MaSIM) Research Focus Area, Faculty of Agriculture, Science and Technology, North-West University, Mafikeng Campus, Private Bag X2046, Mmabatho 2735, South Africa
5Department of Microbiological, Biochemical and Food Biotechnology, University of the Free State, Bloemfontein, South Africa

Received 3 June 2016; Accepted 18 September 2016

Academic Editor: Juntra Karbwang

Copyright © 2016 Mpho M. Makola 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. M. Hill, G. Tachedjian, and J. Mak, “The packaging and maturation of the HIV-1 pol proteins,” Current HIV Research, vol. 3, no. 1, pp. 73–85, 2005. View at Publisher · View at Google Scholar · View at Scopus
  2. K. Kassahun, I. McIntosh, D. Cui et al., “Metabolism and disposition in humans of raltegravir (MK-0518), an anti-AIDS drug targeting the human immunodeficiency virus 1 integrase enzyme,” Drug Metabolism and Disposition, vol. 35, no. 9, pp. 1657–1663, 2007. View at Publisher · View at Google Scholar · View at Scopus
  3. D. J. McColl and X. Chen, “Strand transfer inhibitors of HIV-1 integrase: bringing IN a new era of antiretroviral therapy,” Antiviral Research, vol. 85, no. 1, pp. 101–118, 2010. View at Publisher · View at Google Scholar · View at Scopus
  4. A. Engelman and P. Cherepanov, “Retroviral integrase structure and DNA recombination mechanism,” Microbiology Spectrum, vol. 2, no. 6, pp. 1–22, 2014. View at Publisher · View at Google Scholar · View at Scopus
  5. R. Craigie, “HIV integrase, a brief overview from chemistry to therapeutics,” The Journal of Biological Chemistry, vol. 276, no. 26, pp. 23213–23216, 2001. View at Publisher · View at Google Scholar · View at Scopus
  6. T. M. Jenkins, D. Esposito, A. Engelman, and R. Craigie, “Critical contacts between HIV-1 integrase and viral DNA identified by structure-based analysis and photo-crosslinking,” The EMBO Journal, vol. 16, no. 22, pp. 6849–6859, 1997. View at Publisher · View at Google Scholar · View at Scopus
  7. K. Zhu, M. L. Cordeiro, J. Atienza, W. Edward Robinson Jr., and S. A. Chow, “Irreversible inhibition of human immunodeficiency virus type 1 integrase by dicaffeoylquinic acids,” Journal of Virology, vol. 73, no. 4, pp. 3309–3316, 1999. View at Google Scholar · View at Scopus
  8. H. Tamura, T. Akioka, K. Ueno et al., “Anti-human immunodeficiency virus activity of 3,4,5-tricaffeoylquinic acid in cultured cells of lettuce leaves,” Molecular Nutrition and Food Research, vol. 50, no. 4-5, pp. 396–400, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. H. M. Heyman, F. Senejoux, I. Seibert, T. Klimkait, V. J. Maharaj, and J. J. M. Meyer, “Identification of anti-HIV active dicaffeoylquinic- and tricaffeoylquinic acids in Helichrysum populifolium by NMR-based metabolomic guided fractionation,” Fitoterapia, vol. 103, pp. 155–164, 2015. View at Publisher · View at Google Scholar · View at Scopus
  10. T. Satake, K. Kamiya, Y. An, T. Oishi, and J. Yamamoto, “The anti-thrombotic active constituents from Centella asiatica,” Biological and Pharmaceutical Bulletin, vol. 30, no. 5, pp. 935–940, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. A. Prasad, M. Singh, N. P. Yadav, A. K. Mathur, and A. Mathur, “Molecular, chemical and biological stability of plants derived from artificial seeds of Centella asiatica (L.) Urban-an industrially important medicinal herb,” Industrial Crops and Products, vol. 60, pp. 205–211, 2014. View at Publisher · View at Google Scholar · View at Scopus
  12. H. C. Kwon, C. M. Jung, C. G. Shin et al., “A new caffeoyl quinic acid from Aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase,” Chemical and Pharmaceutical Bulletin, vol. 48, no. 11, pp. 1796–1798, 2000. View at Publisher · View at Google Scholar · View at Scopus
  13. Z. Hu, D. Chen, L. Dong, and W. M. Southerland, “Prediction of the interaction of HIV-1 integrase and its dicaffeoylquinic acid inhibitor through molecular modeling approach,” Ethnicity and Disease, vol. 20, no. 1, pp. S145–S149, 2010. View at Google Scholar · View at Scopus
  14. M. M. Makola, P. A. Steenkamp, I. A. Dubery, M. M. Kabanda, and N. E. Madala, “Preferential alkali metal adduct formation by cis geometrical isomers of dicaffeoylquinic acids allows for efficient discrimination from their trans isomers during ultra‐high‐performance liquid chromatography/quadrupole time‐of‐flight mass spectrometry,” Rapid Communications in Mass Spectrometry, vol. 30, no. 8, pp. 1011–1018, 2016. View at Publisher · View at Google Scholar
  15. E. F. Healy, J. Sanders, P. J. King, and W. E. Robinson Jr., “A docking study of l-chicoric acid with HIV-1 integrase,” Journal of Molecular Graphics and Modelling, vol. 27, no. 5, pp. 584–589, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. M. N. Clifford, J. Kirkpatrick, N. Kuhnert, H. Roozendaal, and P. R. Salgado, “LC–MSn analysis of the cis isomers of chlorogenic acids,” Food Chemistry, vol. 106, no. 1, pp. 379–385, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. H. Karaköse, R. Jaiswal, S. Deshpande, and N. Kuhnert, “Investigation of the photochemical changes of chlorogenic acids induced by ultraviolet light in model systems and in agricultural practice with Stevia rebaudiana cultivation as an example,” Journal of Agricultural and Food Chemistry, vol. 63, no. 13, pp. 3338–3347, 2015. View at Publisher · View at Google Scholar · View at Scopus
  18. J. Mc Conathy and M. J. Owens, “Stereochemistry in drug action,” The Primary Care Companion to the Journal of Clinical Psychiatry, vol. 5, no. 2, pp. 70–73, 2003. View at Publisher · View at Google Scholar
  19. A. G. Tzakos, N. Naqvi, K. Comporozos et al., “The molecular basis for the selection of captopril cis and trans conformations by angiotensin I converting enzyme,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 19, pp. 5084–5087, 2006. View at Publisher · View at Google Scholar · View at Scopus
  20. F. Jamali, R. Mehvar, and F. M. Pasutto, “Enantioselective aspects of drug action and disposition: therapeutuc pitfalls,” Journal of Pharmaceutical Sciences, vol. 78, no. 9, pp. 695–715, 1989. View at Publisher · View at Google Scholar · View at Scopus
  21. N. J. Farrer, J. A. Woods, L. Salassa et al., “A potent trans-diimine platinum anticancer complex photoactivated by visible light,” Angewandte Chemie—International Edition, vol. 49, no. 47, pp. 8905–8908, 2010. View at Publisher · View at Google Scholar · View at Scopus
  22. M. Fréneau, P. de Sainte Claire, N. Hoffmann et al., “Phototransformation of tetrazoline oxime ethers: photoisomerization vs. photodegradation,” RSC Advances, vol. 6, no. 7, pp. 5512–5522, 2016. View at Publisher · View at Google Scholar · View at Scopus
  23. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 09, Revision C.01, Gaussian, Inc, Wallingford, Conn, USA, 2009.
  24. E. Krieger and G. Vriend, “YASARA view—molecular graphics for all devices—from smartphones to workstations,” Bioinformatics, vol. 30, no. 20, pp. 2981–2982, 2014. View at Publisher · View at Google Scholar · View at Scopus
  25. O. Trott and A. J. Olson, “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 Google Scholar
  26. M. L. Vueba, M. E. Pina, F. Veiga, J. J. Sousa, and L. A. E. B. De Carvalho, “Conformational study of ketoprofen by combined DFT calculations and Raman spectroscopy,” International Journal of Pharmaceutics, vol. 307, no. 1, pp. 56–65, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. S. A. DePriest, D. Mayer, C. B. Naylor, and G. R. Marshall, “3D-QSAR of angiotensin-converting enzyme and thermolysin inhibitors: a comparison of CoMFA models based on deduced and experimentally determined active site geometries,” Journal of the American Chemical Society, vol. 115, no. 13, pp. 5372–5384, 1993. View at Publisher · View at Google Scholar · View at Scopus
  28. N. Nunthaboot, S. Pianwanit, V. Parasuk, S. Kokpol, and P. Wolschann, “Theoretical study on the HIV-1 integrase inhibitor 1-(5-chloroindol-3-yl)-3-hydroxy-3-(2H-tetrazol-5-yl)-propenone (5CITEP),” Journal of Molecular Structure, vol. 844-845, pp. 208–214, 2007. View at Publisher · View at Google Scholar · View at Scopus
  29. C. L. Padgett, A. P. Hanek, H. A. Lester, D. A. Dougherty, and S. C. R. Lummis, “Unnatural amino acid mutagenesis of the GABAA receptor binding site residues reveals a novel cation-π interaction between GABA and β2Tyr97,” The Journal of Neuroscience, vol. 27, no. 4, pp. 886–892, 2007. View at Publisher · View at Google Scholar · View at Scopus
  30. D. A. Dougherty, “The cation−π interaction,” Accounts of Chemical Research, vol. 46, no. 4, pp. 885–893, 2013. View at Publisher · View at Google Scholar · View at Scopus
  31. D. Esposito and R. Craigie, “HIV integrase structure and function,” Advances in Virus Research, vol. 52, pp. 319–333, 1999. View at Publisher · View at Google Scholar · View at Scopus
  32. Á. Peña, J. Yosa, Y. Cuesta-Astroz, O. Acevedo, L. Lareo, and F. García-Vallejo, “Influence of Mg2+ ions on the interaction between 3,5-dicaffeoylquinic acid and HTLV-I integrase,” Universitas Scientiarum, vol. 17, no. 1, pp. 5–15, 2012. View at Publisher · View at Google Scholar · View at Scopus
  33. X.-W. Jiang, J.-P. Bai, Q. Zhang et al., “Caffeoylquinic acid derivatives from the roots of Arctium lappa L. (burdock) and their structure-activity relationships (SARs) of free radical scavenging activities,” Phytochemistry Letters, vol. 15, pp. 159–163, 2016. View at Publisher · View at Google Scholar · View at Scopus
  34. Y.-L. Chen, S.-T. Huang, F.-M. Sun et al., “Transformation of cinnamic acid from trans- to cis-form raises a notable bactericidal and synergistic activity against multiple-drug resistant Mycobacterium tuberculosis,” European Journal of Pharmaceutical Sciences, vol. 43, no. 3, pp. 188–194, 2011. View at Publisher · View at Google Scholar · View at Scopus
  35. W. Liu, X. Han, Y. Xiao et al., “Synthesis, photostability and bioactivity of 2,3-cyclopropanated abscisic acid,” Phytochemistry, vol. 96, pp. 72–80, 2013. View at Publisher · View at Google Scholar · View at Scopus
  36. R. Guimarães, L. Barros, M. Dueñas et al., “Infusion and decoction of wild German chamomile: bioactivity and characterization of organic acids and phenolic compounds,” Food Chemistry, vol. 136, no. 2, pp. 947–954, 2013. View at Publisher · View at Google Scholar · View at Scopus
  37. M. I. Dias, L. Barros, M. Dueñas et al., “Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction,” Food Chemistry, vol. 141, no. 4, pp. 4152–4160, 2013. View at Publisher · View at Google Scholar · View at Scopus
  38. T. Ramabulana, R. D. Mavunda, P. A. Steenkamp, L. A. Piater, I. A. Dubery, and N. E. Madala, “Perturbation of pharmacologically relevant polyphenolic compounds in Moringa oleifera against photo-oxidative damages imposed by gamma radiation,” Journal of Photochemistry and Photobiology B: Biology, vol. 156, pp. 79–86, 2016. View at Publisher · View at Google Scholar · View at Scopus
  39. M. I. Mhlongo, L. A. Piater, P. A. Steenkamp, N. E. Madala, and I. A. Dubery, “Metabolomic fingerprinting of primed tobacco cells provide the first evidence for the biological origin of cis-chlorogenic acid,” Biotechnology Letters, vol. 37, no. 1, pp. 205–209, 2015. View at Publisher · View at Google Scholar · View at Scopus