title: Myelography iodinated contrast media. I. Unraveling the atropisomerism properties in solution.
abstract: The present work reports a thorough conformational analysis of iodinated contrast media: iomeprol, iopamidol (the world's most utilized contrast agent), and iopromide. Its main aim is the understanding of the complex structural features of these atropisomeric molecules, characterized by the presence of many conformers with hindered rotations, and of the role of atropisomerism in the physicochemical properties of their aqueous solutions. The problem was tackled by using an extensive analysis of (13)C NMR data on the solutions of whole molecules and of simple precursors in addition to FT-IR investigation and molecular simulations. This analysis demonstrated that out of the many possible atropisomers, only a few are significantly populated, and their relative population is provided. The conformational analysis also indicated that the presence of a sterically hindered amidic bond, allowing a significant population of cis forms (E in iopromide and exo in iomeprol), may be the basis for an increased thermodynamic solubility of concentrated solutions of iomeprol.
authors.affiliation: †Laboratory of Physical and Macromolecular Chemistry, Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via Giorgieri 1, 34127 Trieste, Italy.
authors.forename: Luca
authors.initials: L
authors.lastname: Fontanive
authors.affiliation: ‡Bracco Imaging SpA-CRB Trieste, AREA Science Park, SS 14, Km 163,5, 34012 Basovizza (Trieste), Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: D'Amelio
authors.affiliation: †Laboratory of Physical and Macromolecular Chemistry, Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via Giorgieri 1, 34127 Trieste, Italy.|§Elettra Sincrotrone Trieste, Area Science Park, I-34149 Trieste, Italy.
authors.forename: Attilio
authors.initials: A
authors.lastname: Cesàro
authors.affiliation: ∥Department of Life Sciences, University of Trieste, Via Giorgieri 1, 34127 Trieste, Italy.
authors.forename: Amelia
authors.initials: A
authors.lastname: Gamini
authors.affiliation: †Laboratory of Physical and Macromolecular Chemistry, Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via Giorgieri 1, 34127 Trieste, Italy.|⊥Department of Food Science, Cornell University, Ithaca, New York 14853, United States.
authors.forename: Letizia
authors.initials: L
authors.lastname: Tavagnacco
authors.affiliation: #Department of Chemistry, Biology, and Biotechnologies, University of Perugia, Via Elce di Sotto 8, I-06123 Perugia, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Paolantoni
authors.affiliation: ⊥Department of Food Science, Cornell University, Ithaca, New York 14853, United States.
authors.forename: John W
authors.initials: JW
authors.lastname: Brady
authors.affiliation: ◆Centro Ricerche Bracco, Bracco Imaging SpA, Via Ribes 5, 10010 Colleretto Giacosa (TO), Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Maiocchi
authors.affiliation: ◆Centro Ricerche Bracco, Bracco Imaging SpA, Via Ribes 5, 10010 Colleretto Giacosa (TO), Italy.
authors.forename: Fulvio
authors.initials: F
authors.lastname: Uggeri
mesh_terms: D003287:Contrast Media / Q000737:chemistry*; D007472:Iohexol / Q000031:analogs & derivatives / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009192:Myelography / Q000379:methods*; D012996:Solutions / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D003287:Contrast Media; D012996:Solutions; D007472:Iohexol; C038192:iopromide
keywords: IR; MM; NMR; atropisomerism; conformational analysis; iodinated contrast media