Abstract
Metal salen/salophen complexes have been used as fluorescent probes for cell imaging with various metal centers. Herein we synthesized cryptand-type aluminum salophen complexes LAl3 and the corresponding mononuclear compound LAl. X-ray crystal diffraction verifies the cryptand-type structure of LAl3 with C3h symmetry. Both LAl3 and LAl show moderate green fluorescence with quantum yields of 0.17 and 0.05, respectively. The hydrophilic and cationic nature of these aluminum salophen complexes renders them enhanced cellular uptake. Both complexes are internalized into cells by energy-dependent pathways and they distribute in lysosomal organelles.
Highlights
Metal salen/salophen complexes have been widely studied in catalysis [1,2,3,4] and supramolecular chemistry [5,6,7], and in recent years they have attracted a great deal of attention for their biological applications as fluorescent probes and prodrugs [8,9,10,11,12,13,14,15,16]
Mononuclear salophen ligand and Al salophen complexes were synthesized according to the reported methods methods [35,36,37,38,39,40]
1.0), indicating are to much more hydrophilic, which might be due to the cationic nature of the Al salophen complexes
Summary
Metal salen/salophen complexes have been widely studied in catalysis [1,2,3,4] and supramolecular chemistry [5,6,7], and in recent years they have attracted a great deal of attention for their biological applications as fluorescent probes and prodrugs [8,9,10,11,12,13,14,15,16]. To minimize the effect of the intermolecular Zn···O interactions, several approaches have been reported, such as adding an axial ligand, introducing positive charges in the ligand, and increasing the number of sterically hindered substituents [31] This includes a series of trinuclear Zn salophen complexes with cryptand-type structures, which could reduce the intermolecular Zn···O interactions [32]. To enhance the cellular uptake, we envisioned to use the main group element Al (3+) cation for (1) form the cation complexes; (2) closed shell structure similar to Zn2+ ; and (3) Lewis acid reactivity. These features render Al salen/salophen complexes better cell imaging probes than Zn complexes [33,34].
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