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Controlled click-assembly of well-defined hetero-bifunctional cubic silsesquioxanes and their application in targeted bioimaging

AuthorsPérez-Ojeda, M. Eugenia ; Trastoy, Beatriz ; Rol, Alvaro; Chiara, María D.; Garcia-Moreno, I. ; Chiara, José Luis
Issue Date2013
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 19: 6630- 6640 (2013)
AbstractA general procedure for the assembly of hetero-bifunctional cubic silsesquioxanes with diverse functionality and a perfectly controlled distribution of functional groups on the inorganic framework has been developed. The method is based on a two-step sequence of mono- and hepta-functionalization through the ligand-accelerated copper(I)-catalyzed azide-alkyne cycloaddition of a readily available octaazido cubic silsesquioxane. The stoichiometry of the reactants and the law of binomial distribution essentially determine the selectivity of the key monofunctionalization reaction when a copper catalyst with strong donor ligands is used. The methodology has been applied to the preparation of a set of bifunctional nano-building-blocks with orthogonal reactivity for the controlled assembly of precisely defined hybrid nanomaterials and a fluorescent multivalent probe for application in targeted cell-imaging. The inorganic cage provides an improved photostability to the covalently attached dye as well as a convenient framework for the 3D multivalent display of the pendant epitopes. Thus, fluorescent bioprobes based on well-defined cubic silsesquioxanes offer interesting advantages over more conventional fully organic analogues and ill-defined hybrid nanoparticles and promise to become powerful tools for the study of cell biology and for biomedical applications. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Identifiersdoi: 10.1002/chem.201300339
issn: 0947-6539
e-issn: 1521-3765
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