Increasing the cytotoxicity of Ru(<scp>ii</scp>) polypyridyl complexes by tuning the electron-donating ability of 1,10-phenanthroline ligands

Lu, Yang; Hou, Zhiying; Li, Mengshan; Wang, Ning; Wang, Jinhui; Ni, Feng; Zhao, Yufen; Zhang, Bin; Xi, Ning

doi:10.1039/d2dt02332f

Cited by 5 publications

(2 citation statements)

References 71 publications

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“…Found: C, 46.16; H, 3.10; N, 9.33%. MS (MALDI-TOF) m / z : [M] + calcd for C 29 H 23 ClN 5 O 2 Ru, 610.06; found, 610.13 (as shown in Figures S7–S9 ) [ 27 ].…”

Section: Methodsmentioning

confidence: 99%

“…Gasser’s group claimed that the Ru(II) polypyridyl core with the electron-donating group preferred negatively charged semiquinonate ligands and benefitted the cytotoxicity of Ru(II) complexes toward multiple targets [ 26 ]. Very recently, we have also demonstrated that tuning the electron-donating ability of 1,10-phenanthroline by amino substituents could enhance the interaction with certain protein residues and DNA to increase cytotoxicity [ 27 ]. However, in stark contrast to the description above, the electron-withdrawing group also contributed significantly to the promotion of antitumor activity.…”

Section: Introductionmentioning

confidence: 99%

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Investigation of the Relationship between Electronic Structures and Bioactivities of Polypyridyl Ru(II) Complexes

Hou

Zhang

et al. 2023

Molecules

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Ruthenium (Ru)-based organometallic drugs have gained attention as chemotherapeutic and bioimaging agents due to their fewer side effects and excellent physical optical properties. Tuning the electronic structures of Ru complexes has been proven to increase the cytotoxicity of cancer cells and the luminescent efficiency of the analytical probes. However, the relationship between electronic structures and bioactivities is still unclear due to the potential enhancement of both electron donor and acceptor properties. Thus, we investigated the relationship between the electronic structures of Ru(II) complexes and cytotoxicity by optimizing the electron-withdrawing (complex 1), electron-neutral (complex 2), and electron-donating (complex 3) ligands through DFT calculations, bioactivities tests, and docking studies. Our results indicated that it was not sufficient to consider only either the effect of electron-withdrawing or electron-donating effects on biological activities instead of the total electronic effects. Furthermore, these complexes with electron-donating substituents (complex 3) featured unique “off-on” luminescent emission phenomena caused by the various “HOMO-LUMO” distributions when they interacted with DNA, while complex with electron-withdrawing substituent showed an “always-on” signature. These findings offer valuable insight into the development of bifunctional chemotherapeutic agents along with bioimaging ability.

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“…Found: C, 46.16; H, 3.10; N, 9.33%. MS (MALDI-TOF) m / z : [M] + calcd for C 29 H 23 ClN 5 O 2 Ru, 610.06; found, 610.13 (as shown in Figures S7–S9 ) [ 27 ].…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Investigation of the Relationship between Electronic Structures and Bioactivities of Polypyridyl Ru(II) Complexes

Hou

Zhang

et al. 2023

Molecules

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Synthesis, Characterization, and Biological Activity of New 4‘‐Functionalized Bis‐Terpyridine Ruthenium(II) Complexes: Anti‐Inflammatory Activity Advances

Elnagar,

Abou‐El‐Sherbini,

Samir

et al. 2024

ChemMedChem

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Ruthenium complexes incorporating 2,2':6',2''‐terpyridine ligands have emerged as promising candidates due to their versatile biological activities including DNA‐binding, anti‐inflammatory, antimicrobial, and anticancer properties. In this study, three novel 4'‐functionalized bis(terpyridine) ruthenium (II) complexes were synthesized. These complexes feature one ligand as 4‐(2,2':6',2''‐terpyridine‐4'‐yl) benzoic acid and the second ligand as either 4'‐(2‐thienyl)‐2,2':6',2''‐terpyridine, 4'‐(3,4‐dimethoxyphenyl)‐2,2':6',2''‐terpyridine, or 4'‐(4‐dimethylaminophenyl)‐2,2':6',2''‐terpyridine. Besides the chemical characterization by 1H and 13C NMR, mass spectrometry, and absorption and emission spectroscopy, the complexes were tested for their biological activity as anti‐inflammatory, anticancer, and antimicrobial agents. Moreover, the toxicity of the Ru(II) complexes was assessed and benchmarked against diclofenac potassium and ibuprofen using a haemolysis assay. Biological evaluations demonstrate that these ruthenium complexes exhibit promising therapeutic potential with reduced haemolytic activity compared to standard drugs. They demonstrate substantial anti‐inflammatory effects through inhibition of albumin denaturation along with moderate cytotoxicity against cancer cell lines and broad‐spectrum antimicrobial activity. These findings highlight the multifaceted biomedical applications of 4'‐functionalized bis(terpyridine) ruthenium (II) complexes, suggesting their potential for further development as effective and safe therapeutic agents.

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Insights into the antineoplastic activity and mechanisms of action of coumarin-coordinated 8-hydroxyquinoline ruthenium(II/III) compounds

Du,

Yang,

Ruan

et al. 2024

Journal of Inorganic Biochemistry

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Increasing the cytotoxicity of Ru(ii) polypyridyl complexes by tuning the electron-donating ability of 1,10-phenanthroline ligands

Abstract: Ruthenium (Ru)-based chemotherapeutic agents are a choice to replace traditional platinum-containing metallodrugs due to the fewer side effects. It has been proved that the mechanism for Ru complex drugs is...

Cited by 5 publications

References 71 publications

Investigation of the Relationship between Electronic Structures and Bioactivities of Polypyridyl Ru(II) Complexes

Investigation of the Relationship between Electronic Structures and Bioactivities of Polypyridyl Ru(II) Complexes

Synthesis, Characterization, and Biological Activity of New 4‘‐Functionalized Bis‐Terpyridine Ruthenium(II) Complexes: Anti‐Inflammatory Activity Advances

Insights into the antineoplastic activity and mechanisms of action of coumarin-coordinated 8-hydroxyquinoline ruthenium(II/III) compounds

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