Singlet oxygen sensitization by organic molecules is a topic of major interest in the development of both efficient photodynamic therapy (PDT) and aerobic oxidations under complete green chemistry conditions. We report on the design, synthesis, biology, and complete spectroscopic characterization (vis-NIR linear and two-photon absorption spectroscopy, singlet oxygen generation efficiencies for both one-and two-photon excitation, electrochemistry, intrinsic dark toxicity, cellular uptake, and subcellular localization) of three classes of innovative singlet oxygen sensitizers pertaining to the family of symmetric squaraine derivatives originating from pi-excessive heterocycles. The main advantage of pi-extended squaraine photosensitizers over the large number of other known photosensitizers is their exceedingly strong two-photon absorption enabling, together with sizable singlet oxygen sensitization capabilities, for their use at the clinical application relevant wavelength of 806 nm. We finally show encouraging results about the dark toxicity and cellular uptake capabilities of water-soluble squaraine photosensitizers, opening the way for clinical small animal PDT trials.
Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers: Design, synthesis, and characterization / L. Beverina, M. Crippa, LANDENNA MIRKO, R. Ruffo, P. Salice, F. Silvestri, S. Versari, A. Villa, L. Ciaffoni, E. Collini, C. Ferrante, S. Bradamante, C.M. Mari, R. Bozio, G.A. Pagani. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 130:6(2008), pp. 1894-1902.
|Titolo:||Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers: Design, synthesis, and characterization|
|Parole Chiave:||Absorption cross-sections; optical-data storage; photodynamic therapy; unsymmetrical squaraines; fluorescence microscopy; basic principles; dyes; derivatives; generation; chemistry|
|Settore Scientifico Disciplinare:||Settore BIO/14 - Farmacologia|
|Data di pubblicazione:||2008|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1021/ja075933a|
|Appare nelle tipologie:||01 - Articolo su periodico|