title: Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by a combination of aromatic, hydrogen bond and electrostatic interactions.
abstract: Bis-polyaza pyridinophane scorpiands bind nucleotides in aqueous medium with 10-100 micromolar affinity, predominantly by electrostatic interactions between nucleotide phosphates and protonated aliphatic amines and assisted by aromatic stacking interactions. The pyridine-scorpiand receptor showed rare selectivity toward CMP with respect to other nucleotides, whereby two orders of magnitude affinity difference between CMP and UMP was the most appealing. The phenanthroline-scorpiand receptor revealed at pH 5 strong selectivity toward AMP with respect to other NMPs, based on the protonation of adenine heterocyclic N1. The results stress that the efficient recognition of small biomolecules within scorpiand-like receptors relies mostly on the electrostatic and H-bonding interactions despite the competitive interactions in the bulk solvent, thus supporting further optimisation of this versatile artificial moiety.
authors.affiliation: ICMOL, Departamentos de Química Inorgánica y Orgánica, Facultad de Química, Universidad de Valencia, C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain. enrique.garcia-es@ uv.es.
authors.forename: Jorge
authors.initials: J
authors.lastname: González-García
authors.forename: Sanja
authors.initials: S
authors.lastname: Tomić
authors.forename: Alberto
authors.initials: A
authors.lastname: Lopera
authors.forename: Lluís
authors.initials: L
authors.lastname: Guijarro
authors.forename: Ivo
authors.initials: I
authors.lastname: Piantanida
authors.forename: Enrique
authors.initials: E
authors.lastname: García-España
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D047028:Macrocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009711:Nucleotides / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D055672:Static Electricity
chemical_list: D001372:Aza Compounds; D047028:Macrocyclic Compounds; D009711:Nucleotides; D010710:Phosphates