title: Development of PDT/PET Theranostics: Synthesis and Biological Evaluation of an (18)F-Radiolabeled Water-Soluble Porphyrin.
abstract: Synthesis of the first water-soluble porphyrin radiolabeled with fluorine-18 is described: a new molecular theranostic agent which integrates the therapeutic selectivity of photodynamic therapy (PDT) with the imaging efficacy of positron emission tomography (PET). Generation of the theranostic was carried out through the conjugation of a cationic water-soluble porphyrin bearing an azide functionality to a fluorine-18 radiolabeled prosthetic bearing an alkyne functionality through click conjugation, with excellent yields obtained in both cold and hot synthesis. Biological evaluation of the synthesized structures shows the first example of an (18)F-radiolabeled porphyrin retaining photocytotoxicity following radiolabeling and demonstrable conjugate uptake and potential application as a radiotracer in vivo. The promising results gained from biological evaluation demonstrate the potential of this structure as a clinically relevant theranostic agent, offering exciting possibilities for the simultaneous imaging and photodynamic treatment of tumors.
authors.affiliation: Department of Chemistry, University of Hull , Cottingham Road, Hull, Yorkshire HU6 7RX, U.K.
authors.forename: Guy M
authors.initials: GM
authors.lastname: Entract
authors.affiliation: Department of Chemistry, University of Hull , Cottingham Road, Hull, Yorkshire HU6 7RX, U.K.|Positron Emission Tomography Research Centre, University of Hull , Cottingham Road, Hull, Yorkshire, HU6 7RX, U.K.
authors.forename: Francesca
authors.initials: F
authors.lastname: Bryden
authors.affiliation: Department of Chemistry, University of Hull , Cottingham Road, Hull, Yorkshire HU6 7RX, U.K.|Positron Emission Tomography Research Centre, University of Hull , Cottingham Road, Hull, Yorkshire, HU6 7RX, U.K.
authors.forename: Juozas
authors.initials: J
authors.lastname: Domarkas
authors.affiliation: Department of Chemistry, University of Hull , Cottingham Road, Hull, Yorkshire HU6 7RX, U.K.
authors.forename: Huguette
authors.initials: H
authors.lastname: Savoie
authors.affiliation: Institute of Cancer Research , 123 Old Brompton Road, London, SW7 3RP, U.K.
authors.forename: Louis
authors.initials: L
authors.lastname: Allott
authors.affiliation: Department of Chemistry, University of Hull , Cottingham Road, Hull, Yorkshire HU6 7RX, U.K.|Positron Emission Tomography Research Centre, University of Hull , Cottingham Road, Hull, Yorkshire, HU6 7RX, U.K.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Archibald
authors.affiliation: Positron Emission Tomography Research Centre, University of Hull , Cottingham Road, Hull, Yorkshire, HU6 7RX, U.K.|School of Biological, Biomedical and Environmental Sciences, University of Hull , Cottingham Road, Hull, Yorkshire, HU6 7RX, U.K.
authors.forename: Chris
authors.initials: C
authors.lastname: Cawthorne
authors.affiliation: Department of Chemistry, University of Hull , Cottingham Road, Hull, Yorkshire HU6 7RX, U.K.
authors.forename: Ross W
authors.initials: RW
authors.lastname: Boyle
mesh_terms: D005462:Fluorine Radioisotopes / Q000737:chemistry*; D010778:Photochemotherapy / Q000379:methods; D011166:Porphyrins / Q000737:chemistry*; D049268:Positron-Emission Tomography / Q000379:methods; D019275:Radiopharmaceuticals / Q000737:chemistry*; D000068936:Theranostic Nanomedicine / Q000379:methods; D014867:Water / Q000737:chemistry*
chemical_list: D005462:Fluorine Radioisotopes; D011166:Porphyrins; D019275:Radiopharmaceuticals; D014867:Water
keywords: PET imaging; fluorine-18; photodynamic therapy; porphyrins; theranostics