Gold(I) Complexes Derived from Alkynyloxy-Substituted Anthraquinones: Syntheses, Luminescence, Preliminary Cytotoxicity, and Cell Imaging Studies

A series of mono- and dimetallic Au­(I) triphenylphosphine complexes derived from 1,2-, 1,4-, and 1,8-dialkynyloxyanthraquinone have been prepared. The photophysical and cytotoxic behavior of the ligands and complexes have been explored, with all of the complexes showing both appreciable cytotoxicity against the MCF-7 carcinoma cell line and useful room-temperature anthraquinone-based visible luminescence, which allowed their successful application as fluorophores in cell imaging microscopy. The implications of the photophysical and toxicological properties for the design and investigation of gold-based anticancer agents are discussed

Gold(I) Complexes Derived from Alkynyloxy-Substituted Anthraquinones: Syntheses, Luminescence, Preliminary Cytotoxicity, and Cell Imaging Studies

A series of mono- and dimetallic Au­(I) triphenylphosphine complexes derived from 1,2-, 1,4-, and 1,8-dialkynyloxyanthraquinone have been prepared. The photophysical and cytotoxic behavior of the ligands and complexes have been explored, with all of the complexes showing both appreciable cytotoxicity against the MCF-7 carcinoma cell line and useful room-temperature anthraquinone-based visible luminescence, which allowed their successful application as fluorophores in cell imaging microscopy. The implications of the photophysical and toxicological properties for the design and investigation of gold-based anticancer agents are discussed

Alkynyl-naphthalimide Fluorophores: Gold Coordination Chemistry and Cellular Imaging Applications

A range of fluorescent alkynyl-naphthalimide fluorophores has been synthesized and their photophysical properties examined. The fluorescent ligands are based upon a 4-substituted 1,8-naphthalimide core and incorporate structural variations (at the 4-position) to tune the amphiphilic character: chloro (<b>L1</b>), 4-[2-(2-aminoethoxy)­ethanol] (<b>L2</b>), 4-[2-(2-methoxyethoxy)­ethylamino] (<b>L3</b>), piperidine (<b>L4</b>), morpholine (<b>L5</b>), 4-methylpiperidine (<b>L6</b>), and 4-piperidone ethylene ketal (<b>L7</b>) variants. The amino-substituted species (<b>L2</b>–<b>L7</b>) are fluorescent in the visible region at around 517–535 nm through a naphthalimide-localized intramolecular charge transfer (ICT), with appreciable Stokes’ shifts of ca. 6500 cm^–1 and lifetimes up to 10.4 ns. Corresponding two-coordinate Au­(I) complexes [Au­(L)­(PPh₃)] were isolated, with X-ray structural studies revealing the expected coordination mode via the alkyne donor. The Au­(I) complexes retain the visible fluorescence associated with the coordinated alkynyl-naphthalimide ligand. The ligands and complexes were investigated for their cytotoxicity across a range of cell lines (LOVO, MCF-7, A549, PC3, HEK) and their potential as cell imaging agents for HEK (human embryonic kidney) cells and Spironucleus vortens using confocal fluorescence microscopy. The images reveal that these fluorophores are highly compatible with fluorescence microscopy and show some clear intracellular localization patterns that are dependent upon the specific nature of the naphthalimide substituent