Synthetic efforts toward the development of Shc SH2 domain-binding peptides

MEDI 121

Won Jun Choi1, Andrew G. Stephen2, Robert J Fisher2, and Terrence R. Burke Jr.1. (1) Laboratory of Medicinal Chemistry, CCR, NCI, NIH, Frederick, MD 21702, (2) Protein Chemistry Laboratory, SAIC-Frederick, Frederick, MD 21702
Shc is a non-catalytic SH2 domain-containing adapter protein that is involved with Ras activation through several growth factor receptor tyrosine kinases. The importance of Shc in the proliferative signal transduction of certain cancers has made antagonists of Shc signaling potentially attractive as therapeutic targets. Accordingly, we have undertaken efforts to develop Shc SH2 domain binding inhibitors. Modeling studies for binding to Shc SH2 domains have indicated that a hexamer phosphotyrosine-containing peptide should be capable of high affinity binding. Based on a lead peptide, we designed and synthesized a variety of analogues that employed fluorescein isothiocyanate (FITC) labeling at either the N or C terminus with variation of spacer length and configuration for joining the FITC group to the peptide. We also examined N-substituted glycine-containing peptides (peptoids) as an approach toward enhancement of binding affinity. A fluorescence anisotropy assay was used for convenient and efficient evaluation of Shc SH2 domain binding affinity. The design, synthesis and evaluation of these analogues will be reported.
 

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