title: Synthesis of molecularly imprinted polymers for amino acid derivates by using different functional monomers.
abstract: Fmoc-3-nitrotyrosine (Fmoc-3-NT) molecularly imprinted polymers (MIPs) were synthesized to understand the influence of several functional monomers on the efficiency of the molecular imprinting process. Acidic, neutral and basic functional monomers, such as acrylic acid (AA), methacrylic acid (MAA), methacrylamide (MAM), 2-vinylpyridine (2-VP), 4-vinylpyridine (4-VP), have been used to synthesize five different polymers. In this study, the MIPs were tested in batch experiments by UV-visible spectroscopy in order to evaluate their binding properties. The MIP prepared with 2-VP exhibited the highest binding affinity for Fmoc-3NT, for which Scatchard analysis the highest association constant (2.49 × 10(4) M(-1)) was obtained. Furthermore, titration experiments of Fmoc-3NT into acetonitrile solutions of 2-VP revealed a stronger bond to the template, such that a total interaction is observed. Non-imprinted polymers as control were prepared and showed no binding affinities for Fmoc-3NT. The results are indicative of the importance of ionic bonds formed between the -OH residues of the template molecule and the pyridinyl groups of the polymer matrix. In conclusion, 2-VP assists to create a cavity which allows better access to the analytes.
authors.affiliation: Dipartimento di Ingegneria dell'Innovazione, Università del Salento, via per Arnesano Km 1, 73100 Lecce, Italy; E-Mails: lucia.mergola@unisalento.it (L.M); roberta.delsole@unisalento.it (R.D.S.).
authors.forename: Sonia
authors.initials: S
authors.lastname: Scorrano
authors.forename: Lucia
authors.initials: L
authors.lastname: Mergola
authors.forename: Roberta
authors.initials: R
authors.lastname: Del Sole
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Vasapollo
mesh_terms: D000178:Acrylamides / Q000737:chemistry; D000179:Acrylates / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D007700:Kinetics; D008689:Methacrylates / Q000737:chemistry; D054802:Molecular Imprinting; D011108:Polymers / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D014443:Tyrosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000178:Acrylamides; D000179:Acrylates; D000596:Amino Acids; D008689:Methacrylates; D011108:Polymers; D011725:Pyridines; C008384:methacrylic acid; C002744:3-nitrotyrosine; D014443:Tyrosine; C030953:2-vinylpyridine; C029351:4-vinylpyridine; C036658:acrylic acid; C045985:methacrylamide