Steroids 2011-04-01

A molecularly imprinted receptor for separation of testosterone and epitestosterone, based on a steroidal cross-linker.

Ivana Gavrilović, Karen Mitchell, Alan D Brailsford, David A Cowan, Andrew T Kicman, Richard J Ansell

Index: Steroids 76(5) , 478-83, (2011)

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Abstract

A series of molecularly imprinted polymers have been prepared and investigated as stationary phases in high performance liquid chromatography for the separation of testosterone and epitestosterone using non-polar mobile phases. The polymers were imprinted using 5α-dihydrotestosterone as template, and all retain testosterone more strongly than its 17α-OH epimer. The best polymer was prepared using trifluoromethylacrylic acid as functional monomer (interacting with the template via hydrogen bonds), divinylbenzene as 'inert' cross-linker, and chloroform as porogen. It also included a steroid-based cross-linker, which may interact with the template via van der Waals interactions to lend additional 'shape selectivity'. A 250×4.6mm column packed with this polymer gave baseline resolution of testosterone and epitestosterone (15 μg each) in under 20 min. Preparation of the steroid based cross-linker included the selective reduction of 5α-dihydrotestosterone (17β-hydroxy-5α-androstan-3-one) to the 3α,17β-diol using K-selectride.Copyright © 2011 Elsevier Inc. All rights reserved.