Cytotoxicity evaluation and DNA interaction of Ru<sup>II</sup>-bipy complexes containing coumarin-based ligands

Almeida, Patrícia Saraiva Vilas Boas de; Arruda, Henrique Jefferson de; Sousa, Gleyton; Ribeiro, Felipe Vitório; Azevedo-França, José Aleixo de; Ferreira, Larissa A.; Guedes, Guilherme P.; Silva, Heveline; Kümmerle, Arthur Eugen; Neves, Adriana Freitas

doi:10.1039/d1dt01567b

Cited by 6 publications

(1 citation statement)

References 81 publications

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“…Through the docking results provided by GOLD software, the intermolecular interactions were determined and used as a starting point to measure the affinity of the ligand for the interaction site. The conformation with the best score was analyzed using the Pymol 2.3.2 software, evaluating the distance and connection with the receptor for the outcomes of molecular modeling studies [ 103 ].…”

Section: Methodsmentioning

confidence: 99%

ACW-02 an Acridine Triazolidine Derivative Presents Antileishmanial Activity Mediated by DNA Interaction and Immunomodulation

et al. 2023

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The present study proposed the synthesis of a novel acridine derivative not yet described in the literature, chemical characterization by NMR, MS, and IR, followed by investigations of its antileishmanial potential. In vitro assays were performed to assess its antileishmanial activity against L. amazonensis strains and cytotoxicity against macrophages through MTT assay and annexin V-FITC/PI, and the ability to perform an immunomodulatory action using CBA. To investigate possible molecular targets, its interaction with DNA in vitro and in silico targets were evaluated. As results, the compound showed good antileishmanial activity, with IC50 of 6.57 (amastigotes) and 94.97 (promastigotes) µg mL−1, associated with non-cytotoxicity to macrophages (CC50 > 256.00 µg mL−1). When assessed by flow cytometry, 99.8% of macrophages remained viable. The compound induced an antileishmanial effect in infected macrophages and altered TNF-α, IL-10 and IL-6 expression, suggesting a slight immunomodulatory activity. DNA assay showed an interaction with the minor grooves due to the hyperchromic effect of 47.53% and Kb 1.17 × 106 M−1, and was sustained by docking studies. Molecular dynamics simulations and MM-PBSA calculations propose cysteine protease B as a possible target. Therefore, this study demonstrates that the new compound is a promising molecule and contributes as a model for future works.

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Section: Methodsmentioning

confidence: 99%

ACW-02 an Acridine Triazolidine Derivative Presents Antileishmanial Activity Mediated by DNA Interaction and Immunomodulation

et al. 2023

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Coumarin‐modified ruthenium complexes: Synthesis, characterization, and antiproliferative activity against human cancer cells

Jakopec,

Hamzic,

Bočkor

et al. 2024

Archiv der Pharmazie

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Among ruthenium complexes studied as anticancer metallodrugs, NKP‐1339, NAMI‐A, RM175, and RAPTA‐C have already entered clinical trials due to their potent antitumor activity demonstrated in preclinical studies and reduced toxicity in comparison with platinum drugs. Considering the advantages of ruthenium‐based anticancer drugs and the cytostatic activity of organometallic complexes with triazole‐ and coumarin‐derived ligands, we set out to synthesize Ru(II) complexes of coumarin‐1,2,3,‐triazole hybrids (L) with the general formula [Ru(L)(p‐cymene)(Cl)]ClO4. The molecular structure of the complex [Ru(2a)(p‐cymene)(Cl)]ClO4 (2aRu) was determined by single‐crystal X‐ray diffraction, which confirmed the coordination of the ligand to the central ruthenium(II) cation by bidentate mode of coordination. Coordination with Ru(II) resulted in the enhancement of cytostatic activity in HepG2 hepatocellular carcinoma cells and PANC‐1 pancreatic cancer cells. Coumarin derivative 2a positively regulated the expression and activity of c‐Myc and NPM1 in RKO colon carcinoma cells, while the Ru(II) half‐sandwich complex 2cRu induced downregulation of AKT and ERK signaling in PANC‐1 cells concomitant with reduced intracellular levels of reactive oxygen species. Altogether, our findings indicated that coumarin‐modified half‐sandwich Ru(II) complexes held potential as anticancer agents against gastrointestinal malignancies.

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Coumarin-imidazopyridine hybrids and their first-in-class ZnII metal complexes as potent dual entry and replication inhibitors of Zika viral infection

Jefferson de Arruda,

Almeida Ferreira,

Leonel S. Sousa

et al. 2024

Bioorganic Chemistry

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Cytotoxicity evaluation and DNA interaction of Ru^II-bipy complexes containing coumarin-based ligands

Abstract: Despite the various treatment options for cancer, this disease still has caused increasing number of deaths, demanding more efficient, selective and less harmful drugs. Several class of ruthenium compounds have...

Cited by 6 publications

References 81 publications

ACW-02 an Acridine Triazolidine Derivative Presents Antileishmanial Activity Mediated by DNA Interaction and Immunomodulation

ACW-02 an Acridine Triazolidine Derivative Presents Antileishmanial Activity Mediated by DNA Interaction and Immunomodulation

Coumarin‐modified ruthenium complexes: Synthesis, characterization, and antiproliferative activity against human cancer cells

Coumarin-imidazopyridine hybrids and their first-in-class ZnII metal complexes as potent dual entry and replication inhibitors of Zika viral infection

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Cytotoxicity evaluation and DNA interaction of RuII-bipy complexes containing coumarin-based ligands

Abstract: Despite the various treatment options for cancer, this disease still has caused increasing number of deaths, demanding more efficient, selective and less harmful drugs. Several class of ruthenium compounds have...

Cited by 6 publications

References 81 publications

ACW-02 an Acridine Triazolidine Derivative Presents Antileishmanial Activity Mediated by DNA Interaction and Immunomodulation

ACW-02 an Acridine Triazolidine Derivative Presents Antileishmanial Activity Mediated by DNA Interaction and Immunomodulation

Coumarin‐modified ruthenium complexes: Synthesis, characterization, and antiproliferative activity against human cancer cells

Coumarin-imidazopyridine hybrids and their first-in-class ZnII metal complexes as potent dual entry and replication inhibitors of Zika viral infection

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Cytotoxicity evaluation and DNA interaction of Ru^II-bipy complexes containing coumarin-based ligands