Ruthenium(II) bipyridine complexes with pendant anthracenyl and naphthyl moieties: A strategy for a ROS generator with DNA binding selectivity

Abreu, Felipe D.; Diógenes, Izaura C.N.; Lopes, Luiz Gonzaga de França; Sousa, Eduardo Henrique Silva; Carvalho, Idalina M.M. de

doi:10.1016/j.ica.2015.09.034

Cited by 20 publications

(25 citation statements)

References 44 publications

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“…Syntheses. 4′-Methyl-2,2′-bipyridine-4-carboxylic acid (mbpy-OH), 13 4′-methyl-N-(anthracen-2-yl)-2,2′-bipyridine-4-carboxyamide (mbpy-anth), and 4′-methyl-N-(naphthalen-2-yl)-2,2′-bipyridine-4carboxyamide (mbpy-naph), 14 and dipyrido[3,2a:2,3-c]phenazine (dppz) 9 were prepared following the procedure described in the literature.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Aryl-Substituted Ruthenium(II) Complexes: A Strategy for Enhanced Photocleavage and Efficient DNA Binding

et al. 2017

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Ruthenium polypyridine complexes have shown promise as agents for photodynamic therapy (PDT) and tools for molecular biology (chromophore-assisted light inactivation). To accomplish these tasks, it is important to have at least target selectivity and great reactive oxygen species (ROS) photogeneration: two properties that are not easily found in the same molecule. To prepare such new agents, we synthesized two new ruthenium complexes that combine an efficient DNA binding moiety (dppz ligand) together with naphthyl-modified (1) and anthracenyl-modified (2) bipyridine as a strong ROS generator bound to a ruthenium complex. The compounds were fully characterized and their photophysical and photochemical properties investigated. Compound 2 showed one of the highest quantum yields for singlet oxygen production ever reported (Φ= 0.96), along with very high DNA binding (log K = 6.78). Such photochemical behavior could be ascribed to the lower triplet state involving the anthracenyl-modified bipyridine, which is associated with easier oxygen quenching. In addition, the compounds exhibited moderate selectivity toward G-quadruplex DNA and binding to the minor groove of DNA, most likely driven by the pendant ligands. Interestingly, they also showed DNA photocleavage activity even upon exposure to a yellow light-emitting diode (LED). Regarding their biological activity, the compounds exhibited an exciting antibacterial action, particularly against Gram-positive bacteria, which was enhanced upon blue LED irradiation. Altogether, these results showed that our strategy succeeded in producing light-triggered DNA binding agents with pharmacological and biotechnological potential.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Aryl-Substituted Ruthenium(II) Complexes: A Strategy for Enhanced Photocleavage and Efficient DNA Binding

et al. 2017

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“…We hypothesize that the photoexcitation of [Ru(bpy) 3 ] 2+ in the presence of O 2 generates ROS to induce lipid membrane oxidation in the photoreactors, which then subsequently initiates release of antibacterial Ag + and [Ru(bpy) 3 ] 2+ into the medium. Three types of ROS are likely to be generated from [Ru(bpy) 3 ] 2+ in H 2 O in the presence of O 2 : singlet oxygen ( 1 O 2 ), superoxide anion (O 2 – ), and/or hydroxyl radicals ( • OH). ,− To test our hypothesis and to determine the specific types of ROS that participate in the inactivation of bacteria, we quantified LRVs for illuminated photoreactors in the presence of different ROS scavengers [sodium azide (scavenger for 1 O 2 ), MnTBAP (scavenger for O 2 – ), and mannitol (scavenger for • OH)], as demonstrated previously . As shown in Figure C, both 1 O 2 (dashed brown line) and O 2 – (dashed green line) scavengers significantly reduce the levels of inactivation of the bactericides.…”

Section: Resultsmentioning

confidence: 99%

Hybrid Plasmonic Photoreactors as Visible Light-Mediated Bactericides

Naowarojna

Liu

et al. 2019

ACS Appl. Mater. Interfaces

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Photocatalytic compounds and complexes, such as tris(bipyridine)ruthenium(II), [Ru(bpy)3]2+, have shown promise as light-mediated bactericides. However, transition metal-based complexes require relatively high concentrations (ppm level) to achieve reliable antibacterial effects. There is consequently a need for new approaches that provide improved efficacy and control of the antibacterial function of these complexes. In this work, we demonstrate strong, visible light-dependent bacterial inactivation with a nanocomposite design that incorporates [Ru(bpy)3]2+ as photocatalyst and a Ag nanoparticle (NP) core as light-concentrating nanoantenna into a plasmonic hybrid photoreactor. The hybrid photoreactor platform is facilitated by a self-assembled lipid membrane that encapsulates the Ag NP and binds the photocatalyst. The lipid membrane renders the nanocomposite biocompatible in the absence of resonant illumination. Upon illumination, the plasmon-enhanced photoexcitation of the metal-toligand-charge-transfer band of [Ru(bpy)3]2+ prepares the reactive excited state of the complex that oxidizes the nanocomposite membrane and increases its permeability. The photooxidation induces the release of [Ru(bpy)3]2+, Ag+, and peroxidized lipids into the ambient medium, where they interact synergistically to inactivate bacteria. We measured seven orders of magnitude decrease in Gram-positive Arthrobacter sp. and four orders of magnitude decrease in Gramnegative Escherichia coli (E. coli) colony forming units (CFUs) with the photoreactor bactericides after 1-hour of visible light illumination. In both cases the photoreactor exceeds the bactericidal standard of a log reduction value (LRV) of 3, and surpasses the antibacterial effect of free Ag NPs or [Ru(bpy)3]2+ by more than four orders of magnitude. We also implement the inactivation of a bacterial thin film in a proof-of-concept study.

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“…Indeed, a large variety of components were inserted by this synthetic way into trisbipyridine ruthenium complexes such as sugars, aliphatic chains, aromatic rings,, or cage molecules , . One, two,, , and six, , functionalizations are the most common numbers of functionalization reported in the literature. Few examples of four and three inserted groups have also been described , , , …”

Section: Introductionmentioning

confidence: 99%

Multivalent Azide‐Functionalized Polypyridyl Ruthenium Complexes and Their DNA Conjugates through Click Chemistry

et al. 2017

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Ruthenium(II) bipyridine complexes with pendant anthracenyl and naphthyl moieties: A strategy for a ROS generator with DNA binding selectivity

Cited by 20 publications

References 44 publications

Aryl-Substituted Ruthenium(II) Complexes: A Strategy for Enhanced Photocleavage and Efficient DNA Binding

Aryl-Substituted Ruthenium(II) Complexes: A Strategy for Enhanced Photocleavage and Efficient DNA Binding

Hybrid Plasmonic Photoreactors as Visible Light-Mediated Bactericides

Multivalent Azide‐Functionalized Polypyridyl Ruthenium Complexes and Their DNA Conjugates through Click Chemistry

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