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

TY - JOUR

T1 - A molecularly imprinted receptor for separation of testosterone and epitestosterone, based on a steroidal cross-linker

AU - Gavrilovic, Ivana

AU - Mitchell, Karen

AU - Brailsford, Alan

AU - Cowan, David A.

AU - Kicman, Andrew T.

AU - Ansell, Richard J.

N1 - Copyright © 2011 Elsevier Inc. All rights reserved.

PY - 2011/4

Y1 - 2011/4

N2 - 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.

AB - 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.

KW - Testosterone

KW - Cross-Linking Reagents

KW - Epitestosterone

KW - Methods

KW - Polymers

KW - Steroids

KW - Molecular Imprinting

KW - Chromatography, High Pressure Liquid

U2 - 10.1016/j.steroids.2011.01.004

DO - 10.1016/j.steroids.2011.01.004

M3 - Article

C2 - 21255594

VL - 76

SP - 478

EP - 483

JO - Steroids

JF - Steroids

IS - 5

ER -