Synthesis, characterization, DNA binding and cytotoxicity of fluoro-dipyrrin based arene ruthenium(II) complexes

Paitandi, Rajendra Prasad; Singh, Roop Shikha; Mukhopadhyay, Sujay; Sharma, Gunjan; Koch, Biplob; Vishnoi, Pratap; Pandey, Daya Shankar

doi:10.1016/j.ica.2016.03.003

Cited by 30 publications

(17 citation statements)

References 56 publications

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“…97 It is well-known that a DNA−intercalator complex stabilizes via van der Waals forces, hydrogen bonding, hydrophobic charge transfer, and electrostatic complementarities. 35,58,76,98,99 The most stable binding conformation of 1 and DNA revealed that it stacks in minor grooves via electrostatic interactions and the complex is adjusted in such a way that a part of the planar dipyrrin core makes the stacking interaction favorable with DNA base pairs and fits inside the DNA strands by van der Waals forces and hydrophobic contacts (Figures 10 and S14). 27,80 The resulting relative binding energies for docked structures of 1 and 2 have been found to be −285.75 and −277.11 eV, respectively, which indicates the better binding capability of 1 relative to 2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…To understand the binding mode of the compounds with DNA, competitive binding studies have been carried out between EB (3,8-diamino-5-ethyl-6-phenylphenanthridine bromide) and 1 and 2 with CT-DNA. , EB is an intercalating weakly fluorescent labeling agent often used for staining nucleic acid and other biomolecules. ,,− , After binding with DNA, its fluorescence intensity increases and displacement of EB (λ ex , 540 nm; λ em , 600 nm) from an EB–DNA complex by other compounds causes quenching of intrinsic fluorescence of the EB–DNA system. This occurs because of an increase in the concentration of free EB in solution and a lowering of the number of binding sites accessible for EB–DNA binding.…”

Section: Resultsmentioning

confidence: 99%

“…To explore the most feasible binding site, interaction mode, and binding affinity, molecular docking studies have been carried out on 1 and 2 using B-DNA (PDB ID: 1BNA). It is well-known that a DNA–intercalator complex stabilizes via van der Waals forces, hydrogen bonding, hydrophobic charge transfer, and electrostatic complementarities. ,,,, …”

Section: Resultsmentioning

confidence: 99%

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Anticancer Activity of Iridium(III) Complexes Based on a Pyrazole-Appended Quinoline-Based BODIPY

et al. 2017

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A pyrazole-appended quinoline-based 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (L1, BODIPY) has been synthesized and used as a ligand for the preparation of iridium(III) complexes [Ir(phpy)(L1)]PF (1; phpy = 2-phenylpyridine) and [(η-CMe)Ir(L1)Cl]PF (2). The ligand L1 and complexes 1 and 2 have been meticulously characterized by elemental analyses and spectral studies (IR, electrospray ionization mass spectrometry, H andC NMR, UV/vis, fluorescence) and their structures explicitly authenticated by single-crystal X-ray analyses. UV/vis, fluorescence, and circular dichroism studies showed that complexes strongly bind with calf-thymus DNA and bovine serum albumin. Molecular docking studies clearly illustrated binding through DNA minor grooves via van der Waals forces and their electrostatic interaction and occurrence in the hydrophobic cavity of protein (subdomain IIA). Cytotoxicity, morphological changes, and apoptosis have been explored by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and Hoechst 33342 staining. IC values for complexes (1, 30 μM; 2, 50 μM) at 24 h toward the human cervical cancer cell line (HeLa) are as good as that of cisplatin (21.6 μM) under analogous conditions, and their ability to kill cancer cells lies in the order 1 > 2. Because of the inherent emissive nature of the BODIPY moiety, these are apt for intracellular visualization at low concentration and may find potential applications in cellular imaging and behave as a theranostic agent.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Anticancer Activity of Iridium(III) Complexes Based on a Pyrazole-Appended Quinoline-Based BODIPY

et al. 2017

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“…Furthermore, dipyrrinato‐iridium and ‐ruthenium complexes show high potential for an application as chemotherapeutic agents. Specifically, ferrocene‐appended (dipyrrinato)(pentamethylcyclopentadienyl)iridium(III) and (dipyrrinato)( p ‐cymene)ruthenium(II) complexes have been reported to exhibit an increased binding affinity to DNA [23c, 26] . Also, dipyrrinato complexes of zinc, ruthenium and gallium show promising potential for PDT [27]…”

Section: Introductionmentioning

confidence: 99%

Dipyrrinato‐Iridium(III) Complexes for Application in Photodynamic Therapy and Antimicrobial Photodynamic Inactivation

Hohlfeld

Gitter

Kingsbury

et al. 2021

Chemistry A European J

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The generation of bio‐targetable photosensitizers is of utmost importance to the emerging field of photodynamic therapy and antimicrobial (photo‐)therapy. A synthetic strategy is presented in which chelating dipyrrin moieties are used to enhance the known photoactivity of iridium(III) metal complexes. Formed complexes can thus be functionalized in a facile manner with a range of targeting groups at their chemically active reaction sites. Dipyrrins with N‐ and O‐substituents afforded (dipy)iridium(III) complexes via complexation with the respective Cp*‐iridium(III) and ppy‐iridium(III) precursors (dipy=dipyrrinato, Cp*=pentamethyl‐η5‐cyclopentadienyl, ppy=2‐phenylpyridyl). Similarly, electron‐deficient [IrIII(dipy)(ppy)2] complexes could be used for post‐functionalization, forming alkenyl, alkynyl and glyco‐appended iridium(III) complexes. The phototoxic activity of these complexes has been assessed in cellular and bacterial assays with and without light; the [IrIII(Cl)(Cp*)(dipy)] complexes and the glyco‐substituted iridium(III) complexes showing particular promise as photomedicine candidates. Representative crystal structures of the complexes are also presented.

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“…In the field of synthetic chemistry of transition metals, ruthenium is well developed and has attracted much attention as a building block for innovative new metalloid pharmaceuticals due to its low general toxicity, which contrasts with the pharmacological properties of platinum drugs. This low toxicity has been ascribed to selective uptake of ruthenium compounds by cancer cells mediated via the transferrin cycle and to mechanisms such as activation through reduction …”

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confidence: 99%

Synthesis, spectroscopic characterization, thermal behaviour, in vitro antimicrobial and anticancer activities of novel ruthenium tricarbonyl complexes containing monodentate V‐shaped Schiff bases

Ramadan

Elsheemy

Hassan

et al. 2017

Applied Organom Chemis

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The interaction of Ru3(CO)12 with a novel family of monodentate V‐shaped Schiff base ligands (L1–4; L1: (E)‐1‐(4‐((4‐bromobenzylidene)amino)phenyl)ethanone, L2: (E)‐1‐(3‐(4‐(dimethylamino)benzylideneamino)phenyl)ethanone, L3: (E)‐1‐(4‐(4‐(dimethylamino)benzylideneamino)phenyl)ethanone, L4: (E)‐1‐(3‐(3,4‐dimethoxybenzylideneamino)phenyl)ethanone) in air under atmospheric pressure afforded the novel complexes [Ru(CO)3(L1–4)2]. The parent ligands and their complexes were characterized using elemental analyses and spectroscopic techniques. In addition, the structure of the representative ligand L1 was determined using single‐crystal X‐ray analysis. The stereochemistry and theoretical optimization of the three‐dimensional geometry of the ligands and their complexes were justified. In vitro antimicrobial screening against bacterial stains Escherichia coli and Staphylococcus aureus and fungus Candida albicans was conducted. Cytotoxicity of the compounds as anti‐tumour agents was evaluated against liver carcinoma (HepG2), breast carcinoma (MCF7) and colon carcinoma (HCT‐116) cell lines relative to cisplatin and doxorubicin. The complexes showed variable in vitro cytotoxic activities against the three studied cell lines, with IC50 values less than those of cis‐platin, and thus appear to be building blocks for promising anti‐tumour agents.

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Synthesis, characterization, DNA binding and cytotoxicity of fluoro-dipyrrin based arene ruthenium(II) complexes

Cited by 30 publications

References 56 publications

Anticancer Activity of Iridium(III) Complexes Based on a Pyrazole-Appended Quinoline-Based BODIPY

Anticancer Activity of Iridium(III) Complexes Based on a Pyrazole-Appended Quinoline-Based BODIPY

Dipyrrinato‐Iridium(III) Complexes for Application in Photodynamic Therapy and Antimicrobial Photodynamic Inactivation

Synthesis, spectroscopic characterization, thermal behaviour, in vitro antimicrobial and anticancer activities of novel ruthenium tricarbonyl complexes containing monodentate V‐shaped Schiff bases

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