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F. Gasparrini - Molecular and enantioselective recognition by receptors and proteins studied in the gas phase<br />
With regard to the studies of biorecognition events<br />
monitored by mass spectrometry, we investigated<br />
the nature of the non-covalent interactions<br />
between amphetamine enantiomers and some chiral<br />
resorc[4]arene receptors in the gas phase, under<br />
conditions mimicking the extensive desolvation<br />
complementary to the uptake of amphetamine<br />
inside its biological receptor. Since the mechanisms<br />
of action of amphetamine proceed through initial<br />
interaction with the N-terminal amino acids of<br />
human dopamine transporter (or their phosphorylated<br />
forms), we decided to focus our attention on<br />
chiral macrocyclic hosts, containing either flexible<br />
amino acidic or rigid bis(diamido)-bridged pendants.<br />
The kinetic and dynamic study performed<br />
represents a starting point for a deeper comprehension<br />
of the different affinities of D- and L-amphetamine<br />
towards chiral hosts, their selective binding to<br />
the monoamine transporters and their sensitivity to<br />
inorganic ions.<br />
86<br />
Selected publications<br />
Botta B, D’Acquarica I, Delle Monache G, Subissati<br />
D, Uccello-Barretta G, Mastrini M, Nazzi S,<br />
Speranza M. Synthesis and host-guest studies of chiral<br />
N-linked peptidoresorc[4]arenes. J Org Chem.<br />
2007, 72:9283-90.<br />
Gasparrini F, Ciogli A, D’Acquarica I, Misiti D,<br />
Badaloni E, Giorgi F, Vigevani A. Synthesis and<br />
characterization of novel internal surface reversedphase<br />
silica supports for high-performance liquid<br />
chromatography. J Chromatogr A 2007, 1176:79-88.<br />
Botta B, Tafi A, Caporuscio F, Botta M, Nevola L,<br />
D’Acquarica I, Fraschetti C, Speranza M. Modelling<br />
amphetamine/receptor interactions: a gas-phase<br />
study of the complexes formed between amphetamine<br />
and some chiral amido[4]resorcinarenes. Chem<br />
Eur J. 2008, 14:3585-95.