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New fluorescent molecules for monitoring drug loading and release in nanoparticles

The aim of this work is to develop a fluorescent molecule for labeling different kinds of nanoparticles, particularly polymeric micelles and vesicles. The fluorophore will be covalently bound to the nanoparticles and it will switch them OFF and ON as a consequence of loading and releasing their content, respectively. To reach this aim a new fluorescent tags are being designed and developed to achieve fluorescence switching upon addition of protons.

Different strategies are currently being studied to link the fluorophore to either micelles or liposomes.

The fluorescent unit has been chosen within the family of 1,8-naphtalic-anhydride compounds and derivatised in order to:
  1. introduce a functional group, normally a protected thiolate, able to initiate the able to initiate the synthesis of amphiphilic block-copolymers (link to project n.7). In this case the self-assembling ability of the polymers was used to prepare imaging nanoparticles (micelles and vesicles) sensitive to pH;

  2. introduce a good leaving group to be easy substituted with thiol reactive compounds (including drugs and peptides).
Figure1
Figure 1: scheme of derivatised fluorescent tag switchable upon protonation. R can be a protected thiolated or a good leaving group for nucleophilic substitution

References
P. da Silva et al. Trends Biotechnology 2001, 19, 29-34
E. Pérez-Inestrosa, U. Pischel. Org. Lett. 2011, 13, 20, 5572-5557
Y.N. Kalia, R.H. Guy. J Control Release 2004, 99, 53-62


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