title: Smart coumarin-tagged imprinted polymers for the rapid detection of tamoxifen.
abstract: A signalling molecularly imprinted polymer was synthesised for easy detection of tamoxifen and its metabolites. 6-Vinylcoumarin-4-carboxylic acid (VCC) was synthesised from 4-bromophenol to give a fluorescent monomer, designed to switch off upon binding of tamoxifen. Clomiphene, a chlorinated analogue, was used as the template for the imprinting, and its ability to quench the coumarin fluorescence when used in a 1:1 ratio was demonstrated. Tamoxifen and 4-hydroxytamoxifen were also shown to quench coumarin fluorescence. Imprinted and non-imprinted polymers were synthesised using VCC, methacrylic acid as a backbone monomer and ethylene glycol dimethacrylate as cross-linker, and were ground and sieved to particle sizes ranging between 45 and 25 μm. Rebinding experiments demonstrate that the imprinted polymer shows very strong affinity for both clomiphene and tamoxifen, while the non-imprinted polymer shows negligible rebinding. The fluorescence of the imprinted polymer is quenched by clomiphene, tamoxifen and 4-hydroxytamoxifen. The switch off in fluorescence of the imprinted polymer under these conditions could also be detected under a UV lamp with the naked eye, making this matrix suitable for applications when coupled with a sample preparation system.
authors: Department of Chemistry, SBCS, Queen Mary University of London, Mile End Road, London, E1 4NS, UK.
authors: Judith V
authors: JV
authors: Ray
authors: Department of Chemistry, SBCS, Queen Mary University of London, Mile End Road, London, E1 4NS, UK.
authors: Fosca
authors: F
authors: Mirata
authors: POLYINTELL, Pharma Parc II, Voie de l'Innovation, Chaussée du Vexin, 27100, Val-de-Reuil, France.
authors: Celine
authors: C
authors: Pérollier
authors: POLYINTELL, Pharma Parc II, Voie de l'Innovation, Chaussée du Vexin, 27100, Val-de-Reuil, France.
authors: Michel
authors: M
authors: Arotcarena
authors: POLYINTELL, Pharma Parc II, Voie de l'Innovation, Chaussée du Vexin, 27100, Val-de-Reuil, France.
authors: Sami
authors: S
authors: Bayoudh
authors: Department of Chemistry, SBCS, Queen Mary University of London, Mile End Road, London, E1 4NS, UK. m.resmini@qmul.ac.uk.
authors: Marina
authors: M
authors: Resmini
mesh_terms: D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D054802:Molecular Imprinting / Q000379:methods*; D011108:Polymers / Q000737:chemistry*; D020845:Selective Estrogen Receptor Modulators / Q000032:analysis*; D013050:Spectrometry, Fluorescence / Q000379:methods; D013629:Tamoxifen / Q000032:analysis*; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C540394:6-vinylcoumarin-4-carboxylic acid; D003374:Coumarins; D005456:Fluorescent Dyes; D011108:Polymers; D020845:Selective Estrogen Receptor Modulators; D014753:Vinyl Compounds; D013629:Tamoxifen
keywords: 6-Vinylcoumarin-4-carboxylic acid; Clomiphene; Molecularly imprinted polymer; Tamoxifen