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