title: Synthesis of rhodamine 6G-based compounds for the ATRP synthesis of fluorescently labeled biocompatible polymers.
abstract: Facile derivatization of rhodamine 6G in the 2' position by direct reaction with secondary amines is reported. If the secondary amine contains a hydroxy group, the hydroxyl-functional intermediate can be readily esterified to give either fluorescent initiators for atom transfer radical polymerization (ATRP) or a fluorescent methacrylic comonomer. In contrast to rhodamine dyes functionalized using primary amines, which are only fluorescent at low pH, these compounds are highly fluorescent at physiological pH. These new compounds were subsequently used to prepare a range of fluorescently labeled biocompatible polymers based on the biomimetic monomer, 2-(methacryloyloxy)ethyl phosphorylcholine (MPC), for biomedical studies.
authors.affiliation: Department of Chemistry, University of Sheffield, Sheffield, Yorkshire, UK. p.madsen@sheffield.ac.uk
authors.forename: Jeppe
authors.initials: J
authors.lastname: Madsen
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Warren
authors.forename: Steven P
authors.initials: SP
authors.lastname: Armes
authors.forename: Andrew L
authors.initials: AL
authors.lastname: Lewis
mesh_terms: D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000378:metabolism; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000378:metabolism; D016503:Drug Delivery Systems / Q000379:methods; D005456:Fluorescent Dyes / Q000737:chemistry*; D008689:Methacrylates / Q000737:chemistry; D057054:Molecular Imaging / Q000379:methods; D010767:Phosphorylcholine / Q000737:chemistry; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis* / Q000378:metabolism; D012235:Rhodamines / Q000737:chemistry* / Q000378:metabolism; D013050:Spectrometry, Fluorescence
chemical_list: D001672:Biocompatible Materials; D005456:Fluorescent Dyes; D008689:Methacrylates; D011108:Polymers; D012235:Rhodamines; C026188:rhodamine 6G; D010767:Phosphorylcholine