Abstract
By superposition of the molecules of opiate receptor ligands of various structural classes, three regions responsible for the nonselective ligand affinity were distinguished in the opiate pharmacophore. Spatial arrangement features, electronic properties, the capability of H-bonding and hydrophobic and electrostatic interactions of these regions were determined. The set of geometric parameters found can be used as a criterion for estimation of the opiate activity in simulation of new types of ligands.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. S. Horn and J. R. Rodgers, J. Pharm. Pharmacol., 1977, 29, 257.
L. I. Wei, J.-I. Hao, Y. Tang, Y. Chen, and Zh. Qiu, Acta Pharmacogica Sinica, 2005, 26, 334.
L. Dosen-Micovic, J. Serb. Soc., 2004, 69, 843.
A. Lavecchia, G. Greco, E. Novellino, F. Vittorio, and G. Ronsisvalle, J. Med. Chem., 2000, 43, 2124.
G. H. Loew, Modern Drug Discovery, 1999, 2, 24.
N. E. Kuz’mina, E. S. Osipova, V. S. Kuz’min, and V. B. Sitnikov, Izv. Akad. Nauk. Ser. Khim., 2006, 1462 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1516].
K. Befort, L. Tabbara, and S. Bausch, Mol. Pharm., 1996, 49, 216.
J. G. Li, C. Chen, and J. Yin, Life Sci., 1998, 65, 175.
A. Mansour, L. P. Taylor, and J. L. Fine, J. Neurochem., 1997, 68, 344.
V. M. Kolb and S. Scheiner, J. Pharm. Sci., 1984, 73, 719.
N. E. Kuz’mina, E. S. Osipova, V. S. Kuz’min, and V. B. Sitnikov, Khim.-Farm. Zh., 2005, 39, 24 [Pharm. Chem. J., 2005, 39 (Engl. Transl.)].
J. B. Thomas, R. Atkinson, N. Namdev, R. Rothman, K. M. Gistard, S. E. Fix, S. W. Mascarella, J. B. Burgess, N. A. Vinson, H. Xu, C. M. Dersch, B. E. Cantrell, D. M. Zimmerman, and F. I. Carrol, J. Med. Chem., 2002, 45, 3524.
A. Lavecchia, G. Greco, E. Novellino, F. Vittorio, and G. Ronsisvalle, J. Med. Chem., 2000, 43, 2124.
G. R. Lenz, S. M. Evans, and D. E. Walters, Opiates, Academic Press Inc., New York, 1986, p. 560.
Chemical Reactivity and Reaction Paths, Ed. G. Klopman, J. Wiley and Sons, 1974, 383.
M. Karelson and V. S. Lobanov, Chem. Rev., 1996, 96, 1027.
P. S. Phortogese, J. Med. Chem., 1992, 35, 1927.
Accelrys Software Inc., Material Studio, Release 3.2, San Diego, 2003.
N. L. Allinger, J. Am. Chem. Soc., 1977, 99, 8127.
J. P. Stewart, J. Computer-Aided Molecular Design, 1990, 4, 1.
K. B. Lipkowitz and D. B. Boyd, Reviews in Computational Chemistry, VCH Publishers, New York, 1990, p. 165.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1469–1475, September, 2006.
Rights and permissions
About this article
Cite this article
Kuz’mina, N.E., Osipova, E.S., Kuz’min, V.S. et al. A general model of the opiate pharmacophore 1. Regions of the opiate pharmacophore responsible for nonselective affinity for the opiate receptor. Russ Chem Bull 55, 1523–1529 (2006). https://doi.org/10.1007/s11172-006-0450-5
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0450-5