A molecularly imprinted receptor for separation of testosterone and epitestosterone, based on a steroidal cross-linker.
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.
Drug Control Centre, King's College London, London SE1 9NH, United Kingdom.
Ivana
I
Gavrilović
Karen
K
Mitchell
Alan D
AD
Brailsford
David A
DA
Cowan
Andrew T
AT
Kicman
Richard J
RJ
Ansell
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003432:Cross-Linking Reagents / Q000737:chemistry; D004845:Epitestosterone / Q000302:isolation & purification*; D008722:Methods; D054802:Molecular Imprinting / Q000379:methods*; D011108:Polymers; D013256:Steroids; D013739:Testosterone / Q000302:isolation & purification*
D003432:Cross-Linking Reagents; D011108:Polymers; D013256:Steroids; D013739:Testosterone; D004845:Epitestosterone