Latent Naphthalimide Bearing Water-Soluble Nanoprobes with Catechol-Fe(III) Cores for in Vivo Fluorescence Imaging of Intracellular Thiols.

Here, a novel latent naphthalimide bearing water-soluble nanoprobes with catechol-Fe(III) cores (Fe@LNNPs) was designed, synthesized, and evaluated for in vivo fluorescence imaging of intracellular thiols, as various diseases are associated with overexpression of cellular biothiols. The Fe@LNNPs are mainly composed of three components. The inner part constitutes pyrocatechol groups, which can coordinate with Fe(III) to form a cross-linked core for improving the stability in the complex biological environment. The naphthalimide group is linked by disulfide with the core to quench the probe fluorescence. The outer part is designed to be a hydrophilic glycol corona for prolonging blood circulation. Also, a biotin group can be easily introduced into the nanoprobe for actively targeting the HepG2 cells. The fluorescence spectra reveals that the Fe@LNNPs can be reduced explicitly by glutathione to trigger the fluorescence emission. Confocal microscopic imagings and animal experiments manifest that the Fe@LNNPs, especially with biotin groups, have much better fluorescence signal imaging compared to the reported small-molecule probe 1' both in vitro and in vivo (up to 24 h). The Fe@LNNPs thus feature great advantages such as specificity, stability, biocompatibility, and long retention time for thiol-recognition imaging and hold potential applications in clinical cancer diagnosis.