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A Computational Study of Anticancer Activity of Curcumin Derivatives Using in silico Drug Designing and Molecular Docking Tools
Corresponding Author(s) : Asha Asokan Manakadan
Asian Journal of Chemistry,
Vol. 30 No. 6 (2018): Vol 30 Issue 6
Abstract
Cancer is an abnormal growth of cells beyond a defined area. Curcumin, the principal curcuminoid of turmeric (Curcuma longa), have wide therapeutic uses like anti-inflammatory, antitumor activities, etc. The present study aims to propose anticancer activity of 11 curcumin derivatives which include curcubitacin E, demethoxycurcumin, bisdemethoxycurcumin, α-elemene, (-) β-elemene, (-)δ-elemene, (-) γ-elemene, germacrone, curdione, furanodiene, calebin A and aromatic turmerone, against a standard drug, megestrol acetate used for the treatment of endometrial cancer, using computer aided drug designing (CAAD). The computational studies include calculation of bioactivity scores, molecular properties, analysis of primary and secondary structure of protein, toxicity prediction using various online tools including admetSAR, Pass Server, PepDraw, RaptorX, Molinspiration, ChemSketch and SwissPDB. The docking score of 11 ligands and Megestrol acetate was found using ArgusLab 4.0.1. It was interpreted that these molecules could be a great lead for further development of anticancer drug against the disease.
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- T. Kaewmaneekul and G. Lothongkum, Corros. Sci., 66, 67 (2013); https://doi.org/10.1016/j.corsci.2012.09.004.
- W. Xiong, G.T. Qi, X.P. Guo and Z.L. Lu, Corros. Sci., 53, 1298 (2011); https://doi.org/10.1016/j.corsci.2011.01.001.
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- I.L. Muller and J.R. Galvele, Corros. Sci., 17, 191 (1977); https://doi.org/10.1016/0010-938X(77)90044-0.
- J.B. Bessone, R.A. Suarez Baldo and S.M. de Micheli, Corrosion, 37, 533 (1981); https://doi.org/ 10.5006/1.3580802.
- J.B. Bessone, D.O. Flamini, S.B. Saidman, Corros. Sci., 47, 95 (2005); https://doi.org/ 10.1016/j.corsci.2004.05.002.
- A.G. Munoz, S.B. Saidman and J.B. Bessone, J. Electrochem. Soc., 146, 2123 (1999) https://doi.org/10.1149/1.1391902.
- A.G. Munoz and J.B. Bessone, Electrochim. Acta, 43, 1067 (1998); https://doi.org/10.1016/S0013-4686(97)00279-X.
- A.G. Munoz, S.B. Saidman and J.B. Bessone, Corros. Sci., 44, 2171 (2002); https://doi.org/10.1016/S0010-938X(02)00042-2.
- J. He, J. Wen and X. Li, Corros. Sci., 53, 1948 (2011); https://doi.org/10.1016/j.corsci.2011.02.016 1948-1953.
- S.M.A. Shibli, S.R. Archana and P.M. Ashraf, Corros. Sci., 50, 2232 (2008); https://doi.org/10.1016/j.corsci.2008.06.017.
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- S.M.A. Shibli, V.S. Dilimon and A. Mohan, Appl. Electrochem., 37, 1015 (2007); https://doi.org/10.1007/s10800-011-0301-4.
- H.L. Hsu, J.M. Jehng and Y.C. Liu, Mater. Chem. Phys., 113, 166 (2009); https://doi.org/10.1016/j.matchemphys.2008.07.067.
- J.R. Sohn and S.I. Lee, Langmuir, 16, 5024 (2000); https://doi.org/10.1021/la980637k.
- K.G. Fournaris, M.A. Karakassides and D. Petridis, Chem Mater., 11, 2372 (1999); https://doi.org/10.1021/cm981140z.
- I. Isik, U. Yilmazer and G. Bayram, Polymer, 44, 6371 (2003); https://doi.org/10.1016/S0032-3861(03)00634-7.
- C.R. Reddy, G. Nagendrappa and B.S. Jai Prakash, Catal. Commun., 8, 241 (2007); https://doi.org/10.1016/j.catcom.2006.06.023.
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- P.B. Messersmith and E.P. Giannelis, Chem. Mater., 6, 1719 (1994); https://doi.org/10.1021/cm00046a026.
- J.J. Lin, Y.N. Chan and Y.F. Lan, Materials, 3, 2588 (2010); https://doi.org/10.3390/ma3042588.
- R.A. Horch, T.D. Golden, N.A. D’Souza and L. Riester, Chem. Mater., 14, 3531 (2002); https://doi.org/10.1021/cm010812+.
- K.D. Ralston, D. Fabijanic and N. Birbilis, Electrochim. Acta, 56, 1729 (2011); https://doi.org/10.1016/j.electacta.2010.09.023.
- M. Zhao, H. Song, J. Li, G. He and Y. Gui, Comput. Mater. Sci. 102, 78 (2015); https://doi.org/10.1016/j.commatsci.2015.02.020.
- I.B. Singh, M. Singh and S. Das, J. Magn. Alloys, 3, 142 (2015); https://doi.org/10.1016/j.jma.2015.02.004.
- C.B. Breslin, L.P. Friery and W.M. Carroll, Corros. Sci., 36, 85 (1994); https://doi.org/10.1016/0010-938X(94)90111-2.
- C.B. Breslin, L.P. Friery, Corros. Sci., 36, 231 (1994); https://doi.org/10.1016/0010-938X(94)90155-4.
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- J. Ma, J. Wen, W. Zhai and Q. Li, Mater. Charact., 65, 86 (2012); https://doi.org/10.1016/j.matchar.2012.01.003.
- D.R. Salinnas and J.B. Bessone, Electrochim. Acta, 42, 413 (1997); https://doi.org/10.1016/S0013-4686(96)00236-8.
- M. Jingling, W. Jiuba, L. Xudong, Z. Shengli and Y. Yanfu, Rare metals, 28, 187 (2009); https://doi.org/10.1007/s12598-009-0037-z.
- S. Khireche, D. Boughrara, A. Kadri, L. Hamadou and N. Benbrahim, Corros. Sci., 87, 504 (2014); https://doi.org/10.1016/j.corsci.2014.07.018.
- D.O. Flamini and S.B. Saidman, Mater. Chem. Phys., 136, 103 (2012); https://doi.org/10.1016/j.matchemphys.2012.06.036.
- J. Li, K. Wan, Q. Jiang, H. Sun, Y. Li, B. Hou, L. Zhu and M. Liu, Metals, 65, 1 (2016).
- H. Zarrok, A. Zarrouk, R. Salghi, M.E. Touhami, H. Oudda, B. Hammouti, R. Touir, F. Bentiss, S.S. Al-Deyab, Int. J. Electrochem. Sci., 8, 6014 (2013).
- J.Q. Jiang and Z. Zeng, Chemosphere, 53, 53 (2003); https://doi.org/10.1016/S0045-6535(03)00449-1.
References
T. Kaewmaneekul and G. Lothongkum, Corros. Sci., 66, 67 (2013); https://doi.org/10.1016/j.corsci.2012.09.004.
W. Xiong, G.T. Qi, X.P. Guo and Z.L. Lu, Corros. Sci., 53, 1298 (2011); https://doi.org/10.1016/j.corsci.2011.01.001.
I. Gurrappa, I.V.S. Yashwanth, I. Mounika, Proc. Natl. Acad. Sci. India Sect. A: Phys. Sci., 85, 1 (2015); https://doi.org/10.1007/s40010-014-0182-0.
I.L. Muller and J.R. Galvele, Corros. Sci., 17, 191 (1977); https://doi.org/10.1016/0010-938X(77)90044-0.
J.B. Bessone, R.A. Suarez Baldo and S.M. de Micheli, Corrosion, 37, 533 (1981); https://doi.org/ 10.5006/1.3580802.
J.B. Bessone, D.O. Flamini, S.B. Saidman, Corros. Sci., 47, 95 (2005); https://doi.org/ 10.1016/j.corsci.2004.05.002.
A.G. Munoz, S.B. Saidman and J.B. Bessone, J. Electrochem. Soc., 146, 2123 (1999) https://doi.org/10.1149/1.1391902.
A.G. Munoz and J.B. Bessone, Electrochim. Acta, 43, 1067 (1998); https://doi.org/10.1016/S0013-4686(97)00279-X.
A.G. Munoz, S.B. Saidman and J.B. Bessone, Corros. Sci., 44, 2171 (2002); https://doi.org/10.1016/S0010-938X(02)00042-2.
J. He, J. Wen and X. Li, Corros. Sci., 53, 1948 (2011); https://doi.org/10.1016/j.corsci.2011.02.016 1948-1953.
S.M.A. Shibli, S.R. Archana and P.M. Ashraf, Corros. Sci., 50, 2232 (2008); https://doi.org/10.1016/j.corsci.2008.06.017.
S.M.A. Shibli and K.K. Binoj, J. Appl. Electrochem., 39, 159 (2009); https://doi.org/10.1007/s10800-008-9659-3.
S.M.A. Shibli, V.S. Dilimon and A. Mohan, Appl. Electrochem., 37, 1015 (2007); https://doi.org/10.1007/s10800-011-0301-4.
H.L. Hsu, J.M. Jehng and Y.C. Liu, Mater. Chem. Phys., 113, 166 (2009); https://doi.org/10.1016/j.matchemphys.2008.07.067.
J.R. Sohn and S.I. Lee, Langmuir, 16, 5024 (2000); https://doi.org/10.1021/la980637k.
K.G. Fournaris, M.A. Karakassides and D. Petridis, Chem Mater., 11, 2372 (1999); https://doi.org/10.1021/cm981140z.
I. Isik, U. Yilmazer and G. Bayram, Polymer, 44, 6371 (2003); https://doi.org/10.1016/S0032-3861(03)00634-7.
C.R. Reddy, G. Nagendrappa and B.S. Jai Prakash, Catal. Commun., 8, 241 (2007); https://doi.org/10.1016/j.catcom.2006.06.023.
A. Dhakshinamoorthy and K. Pitchumani, Tetrahedran Lett., 49, 1818 (2008); https://doi.org/10.1016/j.tetlet.2008.01.061.
P.B. Messersmith and E.P. Giannelis, Chem. Mater., 6, 1719 (1994); https://doi.org/10.1021/cm00046a026.
J.J. Lin, Y.N. Chan and Y.F. Lan, Materials, 3, 2588 (2010); https://doi.org/10.3390/ma3042588.
R.A. Horch, T.D. Golden, N.A. D’Souza and L. Riester, Chem. Mater., 14, 3531 (2002); https://doi.org/10.1021/cm010812+.
K.D. Ralston, D. Fabijanic and N. Birbilis, Electrochim. Acta, 56, 1729 (2011); https://doi.org/10.1016/j.electacta.2010.09.023.
M. Zhao, H. Song, J. Li, G. He and Y. Gui, Comput. Mater. Sci. 102, 78 (2015); https://doi.org/10.1016/j.commatsci.2015.02.020.
I.B. Singh, M. Singh and S. Das, J. Magn. Alloys, 3, 142 (2015); https://doi.org/10.1016/j.jma.2015.02.004.
C.B. Breslin, L.P. Friery and W.M. Carroll, Corros. Sci., 36, 85 (1994); https://doi.org/10.1016/0010-938X(94)90111-2.
C.B. Breslin, L.P. Friery, Corros. Sci., 36, 231 (1994); https://doi.org/10.1016/0010-938X(94)90155-4.
H.A. El-Shayeb, F.M. Abdel-Wahab and S.J. Zeinel-Abedin, Appl. Electrochem., 29, 473 (1999); https://doi.org/10.1023/A:1003425306696.
J. Ma and J. Wen, J. Alloy. Compd., 496, 110 (2010); https://doi.org/10.1016/j.jallcom.2010.02.174.
J. Ma, J. Wen, W. Zhai and Q. Li, Mater. Charact., 65, 86 (2012); https://doi.org/10.1016/j.matchar.2012.01.003.
D.R. Salinnas and J.B. Bessone, Electrochim. Acta, 42, 413 (1997); https://doi.org/10.1016/S0013-4686(96)00236-8.
M. Jingling, W. Jiuba, L. Xudong, Z. Shengli and Y. Yanfu, Rare metals, 28, 187 (2009); https://doi.org/10.1007/s12598-009-0037-z.
S. Khireche, D. Boughrara, A. Kadri, L. Hamadou and N. Benbrahim, Corros. Sci., 87, 504 (2014); https://doi.org/10.1016/j.corsci.2014.07.018.
D.O. Flamini and S.B. Saidman, Mater. Chem. Phys., 136, 103 (2012); https://doi.org/10.1016/j.matchemphys.2012.06.036.
J. Li, K. Wan, Q. Jiang, H. Sun, Y. Li, B. Hou, L. Zhu and M. Liu, Metals, 65, 1 (2016).
H. Zarrok, A. Zarrouk, R. Salghi, M.E. Touhami, H. Oudda, B. Hammouti, R. Touir, F. Bentiss, S.S. Al-Deyab, Int. J. Electrochem. Sci., 8, 6014 (2013).
J.Q. Jiang and Z. Zeng, Chemosphere, 53, 53 (2003); https://doi.org/10.1016/S0045-6535(03)00449-1.