Molecular docking and P-glycoprotein inhibitory activity of Flavonoids

Interdisciplinary Sciences – Computational Life Sciences

Volumn 6, Issue 3, 2014, Pages 167-175

  Daddam, Jayasimha Rayalu ^a   Dowlathabad, Muralidhara Rao ^b   Panthangi, Seshapani ^c   Jasti, Pramodakumari ^c  

^a Global Institute of Biotechnology   (India)

^b SRI KRISHNADEVARAYA UNIVERSITY   (India)

^c SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

docking; flavonoids; homology modelling; molecular dynamics; P glycoprotein

Indexed keywords

FLAVONOID; MULTIDRUG RESISTANCE PROTEIN;

AMINO ACID SEQUENCE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER PROGRAM; HUMAN; MOLECULAR DYNAMICS; MOLECULAR GENETICS; PROTEIN TERTIARY STRUCTURE; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS;

AMINO ACID SEQUENCE; BINDING SITES; FLAVONOIDS; HUMANS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MOLECULAR SEQUENCE DATA; P-GLYCOPROTEIN; PROTEIN STRUCTURE, TERTIARY; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, PROTEIN; SOFTWARE;

EID: 84929511635     PISSN: 19132751     EISSN: 18671462     Source Type: Journal    
DOI: 10.1007/s12539-012-0197-7     Document Type: Article

References (37)

1. Aller, S.G., Yu, J., Ward, A., Weng, Y., Chittaboina, S., Zhuo, R., Harrell, P.M., Trinh, Y.T., Zhang. Q., Urbatsch, I.L., Chang, G. 2009. Structure of Pglycoprotein reveals a molecular basis for poly-specific drug binding. Science 323, 1718–1722.
2. Altschul, S.F., Gish, W., Miller, W., Myers, E.W. and Lipman, D.J. 1990. A basic local alignment search tool. J. Mol. Biol. 215, 403–410.
3. Altschul, S.F. and Gish, W. 1997. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acid Research 25, 3389–3402.
4. Ambudkar, S.V., Kimchi-Sarfaty, C., Sauna, Z.E., and Gottesman, M.M. 2003. P-glycoprotein: from genomics to mechanism. Oncogene 22, 7468–7485.
5. Carpena, X., Soriano, M., Klotz, M.G., Duckworth, H.W., Donald, L.J., Melik, A.W., Fita, I., Loewen, P.C. 2003. Structure of the Clade 1 Cyp51A&B, CatF of Pseudomonas syringae, at 1.8 Å resolution. Proteins: Structure, Function, and Genetics 50, 423–436.
6. Castro A.F., Altenberg G.A. 1997. Inhibition of drug transport by genistein in multidrug-resistant cells expressing P-glycoprotein. Biochem Pharmacol 53, 89–93.
7. Critchfield J.W., Welsh C.J., Phang J.M., Yeh G.C. 1994. Modulation of adriamycin accumulation and efflux by flavonoids in HCT-15 colon cells, Activation of P-glycoprotein as a putative mechanism. Biochem Pharmacol 48, 1437–45.
8. Doige, C.A. and Ames, G.F. 1993. ATP-dependent transport systems in bacteria and humans: relevance to cystic fibrosis and multidrug resistance. Annu. Rev. Microbiol 47, 291–319.
9. Eytan, G.D. 2005. Mechanism of multidrug resistance in relation to passive membrane permeation. Biomed Pharmacother 59, 90–97.
10. Grubmuller, H., Heller, H., Windemuth, A., Schulten, K. 1991. Generalized Verlet Algorithm for Efficient Molecular Dynamics Simulations with Long-range Interactions. Molecular Simulation 6, 121–142.
11. Higgins, C.F. 1992. ABC transporters: from microorganisms to man. Annu. Rev. Cell. Biol. 8, 67–113.
12. Jean-Paul Becker, Gregoire Depret, Francoise Van Bambeke, Paul M Tulkens., Martine Prevost 2009. Molecular models of human P-glycoprotein in two different catalytic states. BMC Struct Biol. 9, 3.
13. Jones, P.M., George, A.M. 2004. The ABC transporter structure and mechanism: perspectives on recent research. Cell Mol Life Sci 61, 682–699
14. Jorgensen, W.L., Chandresekhar, J., Madura, J.D., Impey. R.W., Klein, M.L. 1983. Comparison of simple potential functions for simulating liquid water. J. Chem. Phys. 79, 926–935.
15. Kalabis, G.M., Kostaki, A., Andrews, M.H., Petropoulos, S., Gibb, W., Matthews, S.G. 2005. Multidrug resistance phosphoglycoprotein (ABCB1) in the mouse placenta: Fetal protection. Biol Reprod 73, 591–597.
16. Kale, L., Skeel, R., Bhandarkar, M., Brunner, R., Gursoy, A., Krawetz, N., Phillips, J., Shinozaki, A., Varadarajan, K., Schulten, K. 1999. NAMD2: Greater scalability for parallel molecular dynamics. J Comput Phys 151, 283.
17. Laskowski, R.A., MacArthur, M.W., Moss., D.S., Thornton, J.M. 1993. PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Cryst 26, 283–291.
18. Lee, J., Urbatsch, I.L., Senior, A.E., Wilkens, S. 2008. Nucleotide-induced Structural Changes in Pglycoprotein Observed by Electron Microscopy. J Biol Chem. 283, 5769–5779.
19. Loo, T.W., Bartlett, M.C., Clarke, D.M. 2003. Simultaneous binding of two different drugs in the binding pocket of the human multidrug resistance P-glycoprotein. J Biol Chem 278, 39706–39710.
20. Loo, T.W., Bartlett, M.C., Clarke, D.M. 2003. Substrate-induced conformational, changes in the transmembrane segments of human P-glycoprotein — Direct evidence for the substrate induced fit mechanism for drug binding. J Biol Chem 278, 13603–13606.
21. Lugo, M.R., Sharom, F.J. 2005. Interaction of LDS-751 and rhodamine 123 with Pglycoprotein: evidence for simultaneous binding of both drugs. Biochemistry 44, 14020–14029.
22. Middleton, E.J., Kandaswami, C., and Theoharides, T.C. 2000. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease and cancer. Pharmacol Rev. 52, 673–751.
23. Mitsunaga, Y., Takanaga, H., Matsuo, H. 2000. Effect of bioflavonoids on vincristine transport across bloodbrain barrier. Eur J Pharmacol 395, 193–201.
24. Morris, M.E., and Zhang, S. 2006. Flavonoid-drug interactions: effects of flavonoids on ABC transporters, Life Sci. 78, 2116–2130.
25. Narayana, K.R., Reddy, M.S., Chaluvadi, M.R., and Krishna, D.R. 2001. Bioflavonoids classification, pharmacological, biochemical effects and therapeutic potential. Ind. J Pharmacol. 33, 2–16.
26. Needleman, S.B., and Wunsch, C.D. 1970. A general method applicable to the search for similarities in the amino acid sequence of two proteins. J. Mol. Biol. 48, 443–453.
27. Ohtani, H., Ikegawa, T., Honda, Y., Kohyama, N., Morimoto, S., Shoyama, Y., Juichi, M., Naito, M., Tsuruo, T., Sawada, Y. Effects of various methoxyflavones on vincristine uptake and multidrug resistance to vincristine in P-gp-overexpressing K562/ADM cells. Pharm Res 2007, 24, 1936–1943.
28. Phang, J.M., Poore, C.M., Lopaczynska, J., Yeh, G.C. 1993. Flavonol-stimulated efflux of 7, 12-dime thylbenz(a) anthracene in multidrug-resistant breast cancer cells. Cancer Res 53, 5977–81.
29. Rosenberg, M.F., Kamis, A.B., Callaghan, R., Higgins, C.F., Ford, R.C. 2003. Three-dimensional structures of the mammalian multidrug resistance P-glycoprotein demonstrate major conformational changes in the transmembrane domains upon nucleotide binding. J Biol Chem 278, 8294–8299.
30. Rosenberg, M.F., Callaghan, R., Modok, S., Higgins, C.F., Ford, R.C. 2005. Three-dimensional structure of P-glycoprotein — The transmembrane regions adopt an asymmetric configuration in the nucleotide-bound state. J Biol Chem 280, 2857–2862.
31. Sali, A., Blundell, T.L. 1993. Comparative protein modelling by satisfaction of spatial restraints. J. Mol. Biol. 234, 779–815.
32. Schrickx, J.A., Fink-Gremmels, J. 2008. Implications of ABC transporters on the disposition of typical veterinary medicinal products. Eur J Pharmacol 585, 510–519.
33. Schumacher, M.A., Miller, M.C., Brennan, R.G. 2004. Structural mechanism of the simultaneous binding of two drugs to a multidrug-binding protein. EMBO J 23, 2923–2930.
34. Shikic, B.I. 1993. Modulation of multidrug resistance; at the threshold. J. Clin. Oncol 11, 1629–1635.
35. Soo Yeon Chung, Min Kyung Sung, Na Hyung Kim, Jung Ok Jang, Eun Jung Go, and Hwa Jeong Lee 2005. Inhibition of P-Glycoprotein by Natural Products in Human Breast Cancer Cells, Arch Pharm Res 28, 823–828.
36. Takano, K., Tabata, Y., Kitao, Y., Murakami, R., Suzuki, H., Yamada, M., Iinuma, M., Yoneda, Y., Ogawa, S., Hori, O. 2007. Methoxy?avones protect cells against endoplasmic reticulum stress and neurotoxin. Am J Physiol Cell Physiol, 292, C353–361.
37. Zhang, D., Fan, D. 2007. Multidrug resistance in gastric cancer: recent research advances and ongoing therapeutic challenges. Expert Rev Anticancer Ther 7, 1369–1378.