Structure-based design of reversible peptides inhibitors of Factor VII-a

MEDI 74

Cristina C. Clement, cclement_us@yahoo.com, Chemistry Department, Lehman College, City University of New York (CUNY), 250 Bedford Park BLVD West, Bronx, New York City, NY 10468, Lisa Gingold, ms_lisag@msn.com, Department of Chemistry, Lehman College, CUNY, 250 Bedford Park BLVD, West Bronx, New Yorrk City, NY 10468, and Manfred Philipp, Chemistry Department, Lehman College, City University of New York, 250 Bedford Park BLVD West, Bronx, New York City, NY 10468.
We used the structure-based design approach to generate in silico libraries of peptides with potential inhibitory activity against Factor VII-a. The 1qfk.pdb was used as template in docking experiments which were performed using the software “SCULPT” from MDL. We first generated a set of peptides with different chain length and different sequence space and assessed the free energy of interaction between the protein target and the ligands using the MMFF94 (force-field) built-in the software SCULPT. Both the van der Waals and the electrostatic interactions were used to generate the free energy of interaction between Factor VII-a and the peptides ligands during rigid docking experiments. The peptide Gly-Ser-Ala-D-Phe-Phe-Arg-CONH2 was discovered as a lead compound in the original series of peptides and was synthesized using F-moc solid phase peptide chemistry approach. In vitro kinetics of Factor VII-a inhibition showed that this reversible peptide inhibitor has an IC-50 of 20 uM. Ki (inhibitory constant) was estimated to be 2 nM and is the first peptide reported in the field to be a powerful inhibitor of Factor VII-a, supporting the structure-based design as a reliable approach to generate new lead compounds and also to optimize the leads by using powerful docking experiments and reliable scoring functions.
 

Poster Session
7:00 PM-9:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Medicinal Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007