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New bodipy dyads for two-photons fluorescence imaging in cells

Collado-Martín, Daniel

Published
2016-09-01
Repository
riuma.uma.es
Language
en

Abstract

Fluorescent probes are essential tools for studying biological systems. The last decade has witnessed particular interest in the development of two-photon excitable probes, due to their advantageous features in tissue imaging compared to the corresponding one-photon probes [1]. Recently, we have designed and synthetized an aminonaphthalimide–BODIPY derivative as energy transfer cassettes and were found to show very fast and efficient BODIPY fluorescence sensitization [2]. This was observed upon one- and two-photon excitation, which extends the application range of the investigated bichromophoric dyads in terms of accessible excitation wavelengths. In order to increase the two-photon absorption of the system aminonaphthalimide fluorophore was replace with a Prodan analog (BODIPY dyad 1), which presents found a variety of applications as probes and labels in biology [3]. The two-photon absorption cross-section  of the dyads is significantly incremented by the presence of the 6-acetyl-2-naphthylamine donor group. The emission maximum of a BODIPY fluorophore can significantly be red-shifted in comparison to their precursors by conjugation with aromatic aldehydes. [4] We use a synthetic strategy to obtain BODIPY dyad 2 that incorporates an imidazole ring. This molecule can be used in biological media as a near-neutral pH indicator based on one- and two-photon excitable BODIPY acceptor.

Full text

NEW BODIPY DYADS FOR TWO-PHOTONS FLUORESCENCE IMAGING IN CELLS D. Collado,1,2 Y. Vida,1,2 F. Nájera,1,2 E. Pérez-Inestrosa,1,2 A. Domínguez,3 V. F. Pais,3 U. Pischel3 1 Department of Organic Chemistry, Universidad de Málaga, Spain 2 Andalusian Centre for Nanomedicine and Biotechnology-BIONAND, Parque Tecnológico de Andalucía, 29590 Málaga, Spain 3 CIQSO - Center for Research in Sustainable Chemistry and Department of Chemical Engineering, Physical Chemistry, and Organic Chemistry, Universidad de Huelva, Spain E-mail: [email protected] Fluorescent probes are essential tools for studying biological systems. The last decade has witnessed particular interest in the development of two-photon excitable probes, due to their advantageous features in tissue imaging compared to the corresponding one-photon probes [1]. Recently, we have designed and synthetized an aminonaphthalimide–BODIPY derivative as energy transfer cassettes and were found to show very fast and efficient BODIPY fluorescence sensitization [2]. This was observed upon oneand two-photon excitation, which extends the application range of the investigated bichromophoric dyads in terms of accessible excitation wavelengths. In order to increase the two-photon absorption of the system aminonaphthalimide fluorophore was replace with a Prodan analog (BODIPY dyad 1), which presents found a variety of applications as probes and labels in biology [3]. The two-photon absorption cross-section  of the dyads is significantly incremented by the presence of the 6-acetyl-2-naphthylamine donor group. The emission maximum of a BODIPY fluorophore can significantly be red-shifted in comparison to their precursors by conjugation with aromatic aldehydes. [4] We use a synthetic strategy to obtain BODIPY dyad 2 that incorporates an imidazole ring. This molecule can be used in biological media as a near-neutral pH indicator based on oneand two-photon excitable BODIPY acceptor. [1] Kim, D.; Ryua, H. G.; Ahn , K. H. Org. Biomol. Chem., 2014,12, 4550-4566. [2] Collado, D.; Remón, P.; Vida, Y.; Nájera, F.; Sen, P.; Pischel, U.; Perez-Inestrosa, E. Chem. Asian J. 2014, 9, 797-804. [3] Kucherak, O. A.; Didier, P.; Mely, Y.; Klymchenko, A. S. J. Phys. Chem. Lett. 2010, 1, 616– 620. [4] Boens, N.; Qin, W.; Baruah, M.; De Borggraeve, W. M.; Filarowski, A.; Smisdon, N.; Ameloot, M.; Crovetto, L.; Talavera, E. M.; Alvarez-Pez, J. M. Chem. Eur. J. 2011, 17, 10924-10934.