Exploiting the higher alkynophilicity of Au-species: development of a highly selective fluorescent probe for gold ions

Abstract

A new approach, involving the anchoring-unanchoring of a fluorophore, has been developed for the detection of Au-species. The fluorescent probe was found to be highly selective for sensing gold species in the presence of several other metal ions. A successful application to bioimaging has also been demonstrated with A549 lung cancer cells.

Fluorescent imaging of Au3+ in living cells with two new high selective Au3+ probes

“…Gold ion shows an excellent appropriation and biocompatibility for its application in medication. Gold-based drugs are valuable for the treatment of a wide variety of diseases including rheumatic arthritis, asthma, tuberculosis, malaria, cancer, HIV, and brain lesions (Adhikari et al, 2015;Patil et al, 2012;Yuan et al, 2011;Jeong, et al, 2012).…”

“…It is a challenge to develop rapidly responsive fluorescent probes which can function in water for bio-applications (Jandl et al, 1957;Luckey et al, 1975;Seo et al, 2012;Wang, et al, 2012). A few well-designed fluorescent probes for gold ions in organic solvents or aqueous-organic media have been reported, and some probes have been employed successfully to detect gold ions in cells (Dong et al, 2010;Egorova et al, 2010;Jou et al, 2009;Patil et al, 2012;Wang et al, 2011).…”

Bioorthogonal release of anticancer drugs via gold-triggered 2-alkynylbenzamide cyclization

“…Originally conceived as a means for glycosylation, [44][45][46] later adaptations developed Au(I)/Au(III) sensing probes that functioned by releasing alcohol-containing uorophores. 47,48 Unfortunately, one major shortcoming of this reaction is the susceptibility of esters to hydrolysis. 49 A search of available literature revealed no successful attempts had been made to replace the ester with an amide, likely due to its added chemical stability.…”

A BODIPY/pyridine conjugate for reversible fluorescence detection of gold(iii) ions

“…[1][2][3][4][5] Besides their peerless catalytic activities, gold ions present interesting biological properties. Several gold ion selective molecular sensors utilizing various fluorophore units-including rhodamine, [17][18][19][20][21] BODIPY, [22][23][24][25] fluorescein, 26,27 naphthalimide, 28,29 and coumarin 30 dyes-have been developed over the last years. [6][7][8] In contrast to their beneficial roles in disease treatment, the intake of gold ions can also cause toxicity to the living organisms because of the possibility to interact with biomolecules such as enzymes and DNA.…”