Solid phase synthesis and evaluation of novel amino acid based 3,2-hydroxypyridinone (HOPO) chelators for iron(III)

CHED 442

Aravamudan S. Gopalan, agopalan@nmsu.edu, Hayley A. Brown, hab@nmsu.edu, Rajesh Pandey, Vincent J Huber, and Hollie K. Jacobs, hjacobs@nmsu.edu. Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003-8001
Iron (III) chelators have potential applications in the treatment of patients suffering from iron overload diseases and as possible anti-bacterial and anti-cancer agents. Chelators carrying the 3-hydroxy 2-pyridinone (3,2-HOPO) ligand have been shown to form strong and stable complexes with iron(III) generating much interest in their development as potential drugs. In this paper, we report our results on the solid phase synthesis of several poly HOPO chelators anchored around a single amino acid that serves as the platform. The method is convenient and allows the preparation of target molecules readily with purification necessary only after cleavage from the resin. The data shows that this class of chelators are capable of forming strong water soluble complexes with iron (III), comparable to EDTA. The trends in metal ion binding as a function of ligand structure will permit further optimization of this novel class of chelators to provide therapeutically interesting targets.
 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008