Computer-aided rational molecular design of a new non-peptide chitinase inhibitor

COMP 217

Hiroaki Gouda, godah@pharm.kitasato-u.ac.jp, Yusuke Sakoh, and Shuichi Hirono. School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan
Since family 18 chitinases are essential enzymes for fungi and insects, they are potential targets for the design of antifungals and pesticides. Recently, a novel cyclic pentapeptide chitinase inhibitor, argadin, has been isolated. The crystal structure of argadin binding to a family 18 chitinase from Serratia marcescens [ChiB] has been also reported. In this study, we design a new non-peptide chitinase inhibitor using a molecular modeling method on the basis of the interaction mode of argadin with ChiB. First, the peptide backbone of argadin is replaced by a 14-membered macrolide that possesses more drug-like properties. Then, the functional groups corresponding to the side chains of argadin are introduced to the 14-membered macrolide. The docking and free energy calculations suggest that the designed molecule could bind to ChiB in the fashion similar to argadin-ChiB interaction mode and have a binding affinity comparable to that of argadin.
 

Poster Session
6:00 PM-8:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Computers in Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006