title: A Theranostic Agent Combining a Two-Photon-Absorbing Photosensitizer for Photodynamic Therapy and a Gadolinium(III) Complex for MRI Detection.
abstract: The convergent synthesis and characterization of a potential theranostic agent, [DPP-ZnP-GdDOTA](-), which combines a diketopyrrolopyrrole-porphyrin component DPP-ZnP as a two-photon photosensitizer for photodynamic therapy (PDT) with a gadolinium(III) DOTA complex as a magnetic resonance imaging probe, is presented. [DPP-ZnP-GdDOTA](-) has a remarkably high longitudinal water proton relaxivity (19.94 mm(-1)  s(-1) at 20 MHz and 25 °C) for a monohydrated molecular system of this size. The Nuclear Magnetic Relaxation Dispersion (NMRD) profile is characteristic of slow rotation, related to the extended and rigid aromatic units integrated in the molecule and to self-aggregation occurring in aqueous solution. The two-photon properties were examined and large two-photon absorption cross-sections around 1000 GM were determined between 910 and 940 nm in DCM with 1 % pyridine and in DMSO. Furthermore, the new conjugate was able to generate singlet oxygen, with quantum yield of 0.42 and 0.68 in DCM with 1 % pyridine and DMSO, respectively. Cellular studies were also performed. The [DPP-ZnP-GdDOTA](-) conjugate demonstrated low dark toxicity and was able to induce high one-photon and moderate two-photon phototoxicity on cancer cells.
authors.affiliation: Laboratoire de Synthèse des Assemblages Moléculaires Multifonctionnels, Institut de Chimie de Strasbourg, CNRS/UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, 67000, Strasbourg, France.
authors.forename: Julie
authors.initials: J
authors.lastname: Schmitt
authors.affiliation: Laboratoire de Synthèse des Assemblages Moléculaires Multifonctionnels, Institut de Chimie de Strasbourg, CNRS/UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, 67000, Strasbourg, France. v.heitz@unistra.fr.
authors.forename: Valérie
authors.initials: V
authors.lastname: Heitz
authors.affiliation: Laboratoire de Synthèse des Assemblages Moléculaires Multifonctionnels, Institut de Chimie de Strasbourg, CNRS/UMR 7177, Université de Strasbourg, 4, rue Blaise Pascal, 67000, Strasbourg, France.
authors.forename: Angélique
authors.initials: A
authors.lastname: Sour
authors.affiliation: CAMB, UMR 7199, UdS/CNRS, Faculté de Pharmacie, Université de Strasbourg, 74 route du Rhin, 67401, Illkirch, France. frederic.bolze@unistra.fr.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Bolze
authors.affiliation: Institute of Genetics and Molecular and Cellular Biology, 1, rue Laurent Fries, 67404, Illkirch, France.
authors.forename: Pascal
authors.initials: P
authors.lastname: Kessler
authors.affiliation: Istituto ISOF-CNR, Via P. Gobetti 101, 40129, Bologna, Italy.
authors.forename: Lucia
authors.initials: L
authors.lastname: Flamigni
authors.affiliation: Istituto ISOF-CNR, Via P. Gobetti 101, 40129, Bologna, Italy. barbara.ventura@isof.cnr.it.
authors.forename: Barbara
authors.initials: B
authors.lastname: Ventura
authors.affiliation: Centre de Biophysique Moléculaire UPR4301, CNRS, Université d'Orléans, rue Charles Sadron, 45071, Orléans, France.
authors.forename: Célia S
authors.initials: CS
authors.lastname: Bonnet
authors.affiliation: Centre de Biophysique Moléculaire UPR4301, CNRS, Université d'Orléans, rue Charles Sadron, 45071, Orléans, France. eva.jakabtoth@cnrs-orleans.fr.
authors.forename: Éva
authors.initials: É
authors.lastname: Tóth
mesh_terms: D056831:Coordination Complexes / Q000032:analysis / Q000737:chemistry*; D005682:Gadolinium / Q000737:chemistry*; D006801:Humans; D008279:Magnetic Resonance Imaging / Q000379:methods; D010778:Photochemotherapy / Q000379:methods*; D017785:Photons; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000494:pharmacology*; D011166:Porphyrins / Q000737:chemistry / Q000494:pharmacology*; D026082:Singlet Oxygen / Q000737:chemistry*; D000068936:Theranostic Nanomedicine / Q000379:methods
chemical_list: D056831:Coordination Complexes; D017319:Photosensitizing Agents; D011166:Porphyrins; D026082:Singlet Oxygen; D005682:Gadolinium
keywords: diketopyrrolopyrrole; gadolinium; magnetic resonance imaging; porphyrins; theranostic; two-photon absorption