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Reference type: Journal
Authors: Sanglar C, Jansen T, Silaghi MC, Mernier J, Mignon P, Chermette H
Article Title: Study of Prepolymerization Complex Formation in the Synthesis of Steroid-Based Molecularly Imprinted Polymers.
Publication date: 2012
Journal: Analytical Chemistry
Volume: 84
Issue: (10)
Page numbers: 4481-4488.
DOI: 10.1021/ac3003159

Abstract: The preparation of steroid-based molecularly imprinted polymers (MIPs) based upon noncovalent interaction is particularly suited for selective capture of steroid hormones in biological and environmental samples. The success of this method lies in the optimization of the interaction between steroids (template) and methacrylic acid (functional monomer) in the prepolymerization mixture. NMR techniques coupled with DFT calculations were used to evaluate the capacity of the methacrylic acid to bind a steroid for future applications. The androstane derivative steroids considered in the present study have two functional groups at C3 and C17, which may interact with the methacrylic acid. These can be hydroxyl or ketone groups. Experimental results show that the steroids can be divided in three groups corresponding to the ketone type at C3, the H-bond strength increasing with the number of double bonds. DFT calculations are in very good agreement with experimental results, showing increasing binding energy from no bonds, a single bond, and two double bond steroids. For steroids holding a hydroxyl group the binding energy obtained in the solvent model is comparable to the binding energy of single bond ketone steroids.
Template and target information: adrostane steroids, androsterone, ADT, dihydroandosterone, DHA, dihydrotestosterone, DHT, testosterone, TEST, 17α-methyltestosterone, MTEST, androstenedione, ANDRO, boldenone, BOLD, methandienone, METH


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