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.

Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy-Tetraglucosylcalix[4]arene / M., Torvinen; E., Kalenius; Sansone, Francesco; Casnati, Alessandro; J., Jänis. - In: JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY. - ISSN 1044-0305. - 23:(2012), pp. 359-365. [10.1007/s13361-011-0289-3]

Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy-Tetraglucosylcalix[4]arene

SANSONE, Francesco;CASNATI, Alessandro;
2012-01-01

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.
2012
Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy-Tetraglucosylcalix[4]arene / M., Torvinen; E., Kalenius; Sansone, Francesco; Casnati, Alessandro; J., Jänis. - In: JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY. - ISSN 1044-0305. - 23:(2012), pp. 359-365. [10.1007/s13361-011-0289-3]
File in questo prodotto:
File Dimensione Formato  
Neurotransmitter JASMS.pdf

non disponibili

Tipologia: Documento in Post-print
Licenza: Creative commons
Dimensione 270.87 kB
Formato Adobe PDF
270.87 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2369319
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 14
  • ???jsp.display-item.citation.isi??? 15
social impact