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Diketopyrrolopyrrole Bis‐Phosphonate Conjugate: A New Fluorescent Probe for In Vitro Bone Imaging
Author(s) -
Chiminazzo Andrea,
Borsato Giuseppe,
Favero Alessia,
Fabbro Chiara,
McKenna Charles E.,
Dalle Carbonare Luca Giuseppe,
Valenti Maria Teresa,
Fabris Fabrizio,
Scarso Alessandro
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805436
Subject(s) - conjugate , phosphonate , fluorescence , in vitro , chemistry , materials science , combinatorial chemistry , biochemistry , optics , physics , mathematical analysis , mathematics
The synthesis of a conjugate molecule between an unusual red‐fluorescent diketopyrrolopyrrole (DPP) unit and a bis‐phosphonate (BP) precursor by a click‐chemistry strategy to target bone tissue and monitor the interaction is reported. After thorough investigation, conjugation through a triazole unit between a γ‐azido rather than a β‐azido BP and an alkyne‐functionalized DPP fluorophore group turned out to be the winning strategy. Visualization of the DPP‐BP conjugate on osteoclasts and specific antiresorption activity were successfully demonstrated.