Gold(i)–BODIPY–imidazole bimetallic complexes as new potential anti-inflammatory and anticancer trackable agents

Abstract

Two new gold(i)-BODIPY-imidazole based trackable therapeutic bimetallic complexes have been synthesized and fully characterized. They display strong antiproliferative properties on several types of cancers including colon, breast, and prostate and one of them presents a significant anti-inflammatory effect. Additionally, the two compounds could be visualised in vitro by confocal microscopy in the submicromolar range.

Gold(I)–Coumarin–Caffeine‐Based Complexes as New Potential Anti‐Inflammatory and Anticancer Trackable Agents

“…Another explanation could be that the proximity of the coumarin to the imidazole ring may cause a photoinduced electron‐transfer phenomenon, but ligand 1 displays an interesting quantum yield. Otherwise, it is worth noting that, as observed in previous studies, coordination to the gold(I) ion does not quench the fluorescence, but even increases the quantum yields of 1 and 2 by a factor of two.…”

“…The formation of the complexes can be easily monitored by 31 PNMR spectroscopy.M oreover,i nt he 1 HNMR spectrum,i ti si nterestingt on ote that the imidazole CÀH proton shifts from d % 7.6 to 8.9 ppm, which is close to the Scheme1.Strategyd eveloped herein to combine results from two of our previous studies. [12,13] Scheme2.Syntheses of gold(I) complexes 4-8. ChemMedChem 2018ChemMedChem , 13,2408ChemMedChem -2414 www.chemmedchem.org chemicals hift observed for the caffeinium derivative.…”

“…In the last few years, Trávníček and co‐workers designed several adenine‐based gold complexes that displayed anticancer and anti‐inflammatory properties . Recently, we have drawn our inspiration from their work and combined it with our expertise in the design of trackable metal‐based therapeutics (a kind of optical theranostics) to synthesise a fluorescent gold(I)–homo‐bimetallic complex A , which gave very promising results …”

“…[7][8][9][10] Recently,w eh ave drawn our inspirationf rom their work and combined it with our expertise in the design of trackable metal-basedt herapeutics (a kind of opticalt heranostics [11] )t os ynthesise af luorescent gold(I)homo-bimetallic complex A,w hich gave very promising results. [12] Otherwise, we have developed numerous gold(I)-N-heterocycle carbene based anticancer agents. [13][14][15][16][17] Amongt he structures investigated, we noticed that replacing imidazoliumo r benzimidazolium scaffolds by ac affeinium derivative could increased ramatically the biological suitability of corresponding complex B (decrease of toxicityo nh ealthy tissues; Scheme1).…”

Metal-based BODIPY derivatives as multimodal tools for life sciences

“…Moreover, upon incubation at 4 o C, uptake of BODI-Au-2 appeared to be reduced in both cell lines, suggesting the possible involvement of active transporters in its uptake mechanism [54]. In the same vein, following Trávníček's work -he reported on the antitumor and anti-inflammatory effect of some imidazole-gold complexes - [55][56][57][58], two homobimetallic gold(I) complexes using a BODIPY scaffold have been synthesized [59]. It was reported that BODI-Au-5 displays both strong antiproliferative and anti-inflammatory properties, along with a high in vitro brightness (tracking at submicromolar scale).…”