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Dramatic modification
of fluoroquinolones photoreactivity through self-incorporation of their
cationic forms in SDS micelles. A right approach in the design of biocompatible
drug-carrier devices?
Sortino, Salvatore1
and Condorelli, Giuseppe 1
Dipartimento di Scienze Chimiche1
Abstract-
It is shown that the suitable choice of an appropriate micellar system
leads to a highly selective and efficient self-incorporation of the
cationic forms of the fluoroquinolones (FQs) lomefloxacin (1), enoxacin
and norfloxacin in the micellar cage at physiological pH. Such a compartmentalization
leads to dramatic increase of the FQs photostability along with drastic
changes of the photoreaction pathways with respect to those observed
in aqueous buffer solution (2). These significant effects are rationalized
on the basis of the multifaceted role played by the micellar microenvironment
as a solvent of low micropolarity, as a medium of high microviscosity
and as a reaction environment of confined space. We believe that the
study presented may represent a fruitful aid in the design of biocompatible
drug-carrier devices able to improve the drug photostability and, as
a consequence, to reduce the high phototoxic effects induced by FQs.
This topic is currently under investigation in our laboratory. 1.S.
Sortino, G. De Guidi and S. Giuffrida, Drastic photochemical stabilization
of lomefloxacin through selective and efficient self-incorporation of
its cationic form in anionic sodium dodecyl sulfate (SDS) micelles,
New J. Chem. 25, 2001, 197-199. 2.S. Monti, S. Sortino, E. Fasani and
A. Albini, Multifaceted photoreactivity of 6-fluoro-7-aminoquinolones
from the lowest excited states in aqueous media: a study by nanosecond
and picosecond spectroscopic techniques Chem. Eur. J. In press.
Keywords: fluoroquinolones,
micelles, photostability
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