Summer Undergraduate Research Symposium
Wednesday, 11 August 2004

Plenary Lecture
101 Brown Laboratory (Auditorium)
11:30 AM - 12:45 PM
CHIRAL DRUGS: THE DIFFICULTY OF DEALING WITH THESE JEKYLL-HYDE  TWINS IN THE PHARMACEUTICAL INDUSTRY



Dr. Isiah Warner
HHMI Professor

Vice Chancellor, Office of Strategic Initiatives
Boyd Professor and Philip W. West Professor of Analytical and Environmental Chemistry
Louisiana State University, Baton Rouge, Louisiana

Abstract

Many active pharmaceutical drugs are chiral and are marketed as racemic mixtures, i.e. as an equal mole ratio of their individual enantiomers.  The problem is that one enantiomeric form of a chiral drug may be medicinally beneficial while the other enantiomeric form may be completely useless or even toxic.  An example of the latter is the drug, thalidomide, which was administered to pregnant women in the 1960's.  One of the enantiomeric forms was found to be medicinally beneficial while the other was found to be teratogenic.  The result was babies born with severe limb deformities.  Since this time, the FDA has required detailed studies of chiral drugs.  However, a major limitation in the analyses of chiral drugs is that their chemical properties are identical in an achiral environment and thus separation methods for these compounds are extremely difficult.   Over the past several years, we have developed chiral polymeric surfactants as mobile phase additives for use as chiral separation media in capillary electrophoresis.  The advantages of these polymeric surfactants over conventional micelles include 1) increased stability,  2) zero critical micelle concentration,  3) no deleterious monomer interactions, and 4) demonstrated selectivity in micellar capillary electrophoresis(MCE).  We have recently shown that polymeric surfactants are broadly applicable to a variety of analyses, including enantiomeric separations.  Our studies have shown that these polymers are more suitable than conventional micelles in MCE.  In this talk, I will focus on the medicinal problems of chiral drugs and the use of  polymeric surfactants as chiral separation reagents in MCE.  The advantages of these reagents in comparison to regular micelles and cyclodextrins will also be discussed, particularly with regard to the wide variety of applications that are possible.  A comparison of the use of polymeric surfactants for separations will also be made directly to separations by use of conventional (unpolymerized) micelles.  The advantages of combining CE with polymeric surfactants to achieve improved analytical measurements will be discussed.
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Created 22 July 2004 and last modified 9 August 2004 by Hal White, [halwhite at udel.edu]
Copyright 2004 Harold B. White, Department of Chemistry and Biochemistry, University of Delaware