Acidic hydrolysis of N-ethoxybenzylimidazoles: Potential applications as pH-sensitive linkers for drug delivery

ORGN 103

Seong Deok Kong, Alice Luong, and Jerry Yang, jerryyang@ucsd.edu. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Dr, MC 0358, La Jolla, CA 92093-0358
This talk will describe the development of a new class of N-linked imidazoles as potential pH-sensitive, cleavable linkers for use in cancer drug delivery systems. We will discuss kinetic studies on the rates of cleavage of N-ethoxybenzylimidazoles that exhibit accelerated hydrolysis in mild aqueous acidic solutions compared to in solutions at normal, physiological pH. We demonstrate methods to tune the rates of hydrolysis of N-ethoxybenzylimidazoles under mild acidic conditions with half-lives ranging from minutes to months. We will also present some initial studies towards the development of N-ethoxybenzylimidazoles as linkers to conjugate cytotoxic agents to drug delivery vessels for potential cancer therapy applications.
 

Materials, Devices, and Switches
1:00 PM-5:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

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