Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.4.1051

Facile Docking and Scoring Studies of Carborane Ligands with Estrogen Receptor  

Ok, Kiwon (College of Pharmacy, Korea University)
Jung, Yong Woo (College of Pharmacy, Korea University)
Jee, Jun-Goo (College of Pharmacy, Kyungpook National University)
Byun, Youngjoo (College of Pharmacy, Korea University)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.4, 2013 , pp. 1051-1054 More about this Journal
Abstract
Closo-carborane has been considered as an efficient boron-carrier for boron neutron capture therapy (BNCT) and an attractive surrogate of lipophilic phenyl or cyclohexyl ring in drug design. Despite a great number of carborane-containing ligands have been synthesized and evaluated, molecular modeling studies of carborane ligands with macromolecules have been rarely reported. We herein describe a facile docking and scoring-function strategy of 16 carborane ligands with an estrogen receptor by using the commercial Gaussian, Chem3D Pro and Discovery Studio (DS) computational programs. Docked poses of the carborane ligands in silico exhibited similar binding modes to that of the crystal ligand in the active site of estrogen receptor. Score analysis of the best docked pose for each ligand indicated that the Ligscore1 and the Dockscore have a moderate correlation with in vitro biological activity. This is the first report on the scoring-correlation studies of carborane ligands with macromolecules. The integrated Gaussian-DS approach has a potential application for virtual screening, De novo design, and optimization of carborane ligands in medicinal chemistry.
Keywords
Carborane; In silico docking; Scoring functions; Estrogen receptor; Drug design;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Ohta, K.; Ogawa, T.; Suzuki, T.; Ohta, S.; Endo, Y. Bioorg. Med. Chem. 2009, 17, 7958.   DOI   ScienceOn
2 Ogawa, T.; Ohta, K.; Yoshimi, T.; Yamazaki, H.; Suzuki, T.; Ohta, S.; Endo, Y. Bioorg. Med. Chem. Lett. 2006, 16, 3943.   DOI   ScienceOn
3 Endo, Y.; Yoshimi, T.; Miyaura, C. Pure Appl. Chem. 2003, 75, 1197.   DOI   ScienceOn
4 Endo, Y.; Iijima, T.; Yamakoshi, Y.; Fukasawa, H.; Miyaura, C.; Inada, M.; Kubo, A.; Itai, A. Chem. Biol. 2001, 8, 341.   DOI   ScienceOn
5 Fujii, S.; Ohta, K.; Goto, T.; Oda, A.; Masuno, H.; Endo, Y.; Kagechika, H. Med. Chem. Comm. 2012, 3, 680.   DOI
6 Goto, T.; Ohta, K.; Fujii, S.; Ohta, S.; Endo, Y. J. Med. Chem. 2010, 53, 4917.   DOI   ScienceOn
7 Ohta, K.; Goto, T.; Fijii, S.; Suzuki, T.; Ohta, S.; Endo, Y. Bioorg. Med. Chem. 2008, 16, 8022.   DOI   ScienceOn
8 Ohta, K.; Goto, T.; Fujii, S.; Kawahata, M.; Oda, A.; Ohta, S.; Yamaguchi, K.; Hirono, S.; Endo, Y. Bioorg. Med. Chem. 2011, 19, 3540.   DOI   ScienceOn
9 Calvaresi, M.; Zerbetto, F. J. Chem. Inf. Model. 2011, 51, 1882.   DOI   ScienceOn
10 Tiwari, R.; Mahasenan, K.; Pavlovicz, R.; Li, C. L.; Tjarks, W. J. Chem. Inf. Model 2009, 49, 1581.   DOI   ScienceOn
11 Montes, M.; Miteva, M. A.; Villoutreix, B. O. Proteins 2007, 68, 712.   DOI   ScienceOn
12 Warren, G. L.; Andrews, C. W.; Capelli, A. M.; Clarke, B.; LaLonde, J.; Lambert, M. H.; Lindvall, M.; Nevins, N.; Semus, S. F.; Senger, S.; Tedesco, G.; Wall, I. D.; Woolven, J. M.; Peishoff, C. E.; Head, M. S. J. Med. Chem. 2006, 49, 5912.   DOI   ScienceOn
13 Reynolds, R. C.; Campbell, S. R.; Fairchild, R. G.; Kisliuk, R. L.; Micca, P. L.; Queener, S. F.; Riordan, J. M.; Sedwick, W. D.; Waud, W. R.; Leung, A. K. W.; Dixon, R. W.; Suling, W. J.; Borhani, D. W. J. Med. Chem. 2007, 50, 3283.   DOI   ScienceOn
14 Cigler, P.; Kozisek, M.; Rezacova, P.; Brynda, J.; Otwinowski, Z.; Pokorna, J.; Plesek, J.; Gruner, B.; Doleckova-Maresova, L.; Masa, M.; Sedlacek, J.; Bodem, J.; Krausslich, H. G.; Kral, V.; Konvalinka, J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 15394.   DOI   ScienceOn
15 Fujii, S.; Masuno, H.; Taoda, Y.; Kano, A.; Wongmayura, A.; Nakabayashi, M.; Ito, N.; Shimizu, M.; Kawachi, E.; Hirano, T.; Endo, Y.; Tanatani, A.; Kagechika, H. J. Am. Chem. Soc. 2011, 133, 20933.   DOI   ScienceOn
16 Brzozowski, A. M.; Pike, A. C. W.; Dauter, Z.; Hubbard, R. E.; Bonn, T.; Engstrom, O.; Ohman, L.; Greene, G. L.; Gustafsson, J. A.; Carlquist, M. Nature 1997, 389, 753.   DOI   ScienceOn
17 Issa, F.; Kassiou, M.; Rendina, L. M. Chem. Rev. 2011, 111, 5701.   DOI   ScienceOn
18 Scholz, M.; Hey-Hawkins, E. Chem. Rev. 2011, 111, 7035.   DOI   ScienceOn
19 Soloway, A. H.; Tjarks, W.; Barnum, B. A.; Rong, F. G.; Barth, R. F.; Codogni, I. M.; Wilson, J. G. Chem. Rev. 1998, 98, 1515.   DOI   ScienceOn
20 Hawthorne, M. F. Angew. Chem. Int. Edit. 1993, 32, 950.   DOI   ScienceOn