title: Noncovalent complexation of monoamine neurotransmitters and related ammonium ions by tetramethoxy tetraglucosylcalix[4]arene.
abstract: The noncovalent complexation of monoamine neurotransmitters and related ammonium and quaternary ammonium ions by a conformationally flexible tetramethoxy glucosylcalix[4]arene was studied by electrospray ionization Fourier transform ion cyclotron resonance (ESI-FTICR) mass spectrometry. The glucosylcalixarene exhibited highest binding affinity towards serotonin, norepinephrine, epinephrine, and dopamine. Structural properties of the guests, such as the number, location, and type of hydrogen bonding groups, length of the alkyl spacer between the ammonium head-group and the aromatic ring structure, and the degree of nitrogen substitution affected the complexation. Competition experiments and guest-exchange reactions indicated that the hydroxyl groups of guests participate in intermolecular hydrogen bonding with the glucocalixarene.
authors: Department of Chemistry, University of Eastern Finland, P.O. Box 111, 80101 Joensuu, Finland.
authors: Mika
authors: M
authors: Torvinen
authors: Elina
authors: E
authors: Kalenius
authors: Francesco
authors: F
authors: Sansone
authors: Alessandro
authors: A
authors: Casnati
authors: Janne
authors: J
authors: Jänis
mesh_terms: D015306:Biogenic Monoamines / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D041961:Deuterium Exchange Measurement / Q000379:methods; D006001:Glycoconjugates / Q000737:chemistry; D013058:Mass Spectrometry / Q000379:methods; D018377:Neurotransmitter Agents / Q000737:chemistry*
chemical_list: D015306:Biogenic Monoamines; D006001:Glycoconjugates; D018377:Neurotransmitter Agents; D047250:Calixarenes