pKa tuning in quadrupolar-type two-photon ratiometric fluorescent membrane probes

Jonathan Daniel (1) , Cristiano Mastrodonato (1) , Aude Sourdon (2, 3) , Guillaume Clermont (1) , Jean-Marie Vabre (2) , Bertrand Goudeau (1) , Hannah Voldoire (1) , Stéphane Arbault (1) , Olivier Mongin (3, 2) , Mireille Blanchard-Desce (1, 2)

1 ISM - Institut des Sciences Moléculaires
2 CPM - Chimie et Photonique Moléculaires
3 ISCR - Institut des Sciences Chimiques de Rennes

Two bolaamphiphilic quadrupoles built from a fluorene core conjugated with azine endgroups were designed and successfully used to stain GUV membranes. Their quadrupolar character induces both a shift of the pKa values close to the physiological pH and large two-photon absorption responses (i.e. over 1000 GM for acidic forms). As such they hold promise as ratiometric two-photon pH probes for monitoring slight variations of pH near cell membranes using two-photon excitation in the NIR region

Domaines: Chimie

Jonathan Daniel, Cristiano Mastrodonato, Aude Sourdon, Guillaume Clermont, Jean-Marie Vabre, et al.. pKa tuning in quadrupolar-type two-photon ratiometric fluorescent membrane probes. Chemical Communications, 2015, 51 (83), pp.15245--15248. ⟨10.1039/C5CC04573H⟩. ⟨hal-01231149⟩