Mixed ligand ruthenium arene complexes containing N-ferrocenyl amino acids: Biomolecular interactions and cytotoxicity against MCF7 cell line

Pulipaka, Ramadevi; Singh, Rajinder; Jana, Sarmita; Devkar, Ranjitsinh; Chakraborty, Debkumar

doi:10.1016/j.jorganchem.2017.01.020

Cited by 26 publications

(15 citation statements)

References 57 publications

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“…The silver salt is an effective Cl‐abstractor, promoting the binding of the amino acidate moiety to ruthenium . Interestingly, [Ru(η 6 ‐cymene)(κ 2 N,O ‐aa)Cl] complexes with the amino acidate group N‐substituted with a ferrocenyl pendant displayed moderate cytotoxicity against breast cancer MCF7 cell line . In addition, an older report claimed the possible in vivo activity exerted by [Ru(η 6 ‐C 6 H 6 )(κ 2 N,O ‐ l ‐prolinato)Cl] against P388 leukaemia cells …”

Section: Introductionmentioning

confidence: 99%

Ruthenium Arene Complexes with α‐Aminoacidato Ligands: New Insights into Transfer Hydrogenation Reactions and Cytotoxic Behaviour

et al. 2018

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The Ru II arene complexes [Ru(η 6 -p-cymene)-(κ 2 N,O-aa)Cl] (aa = L-glutaminato, 1; L-homoserinato, 2; L-tyrosinato, 3; L-serinato, 4; L-prolinato, 5; trans-4-hydroxyl-L-prolinato, 6; L-threoninato, 7; glycinato, 8) were synthesized in high yields by the reactions of [Ru(η 6 -p-cymene)Cl 2 ] 2 with aa/MOH (M = Na, K). The salt [Ru(η 6 -p-cymene)(κ 2 N,O-L-serinato)(PPh 3 )]-[CF 3 SO 3 ], 9[CF 3 SO 3 ], was prepared in 68 % yield from 4 and AgSO 3 CF 3 /PPh 3 . All the products were fully characterized by analytical and spectroscopic methods, moreover the X-ray structures of 1 and 2 were elucidated by X-ray diffraction. Compounds 1-7 and 9[CF 3 SO 3 ] were studied as catalytic precursors for the transfer hydrogenation reaction (THR) of acetophenone, using 2-propanol or sodium formate (in water) as hydrogen [a]

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Section: Introductionmentioning

confidence: 99%

Ruthenium Arene Complexes with α‐Aminoacidato Ligands: New Insights into Transfer Hydrogenation Reactions and Cytotoxic Behaviour

et al. 2018

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“…A series of ferrocenyl‐ N ‐heterocyclic gold(I) carbene complexes were reported to be remarkably cytotoxic to MCF‐7 cells yielding IC 50 values in the range 0.11‐0.71 μM (72 h incubation) while being much less toxic to non‐malignant CCD18‐Co colorectal myofibroblasts (IC 50 : 2.8‐15.0 μM) . Mixed‐ligand ruthenium arene complexes containing N ‐ferrocenyl amino acids were found to exhibit cytotoxic activity against MCF‐7 cells with IC 50 values in the range 73.1‐86.6 μM which are much higher than the present complexes . In another study, ferrocenyl pyridine arene ruthenium complexes were found to exhibit moderate toxicity to A2780 and A2780cisR (cisplatin‐resistant) human ovarian carcinoma cell lines giving IC 50 values in the range 14.8‐57.0 μM which are much higher than the present complexes and the standard control cisplatin .…”

Section: Resultsmentioning

confidence: 99%

“…Ruthenium–arene and ruthenium–cyclopentadienyl half‐sandwich complexes are presently being clinically evaluated as organometallic antitumor/antimetastatic agents . There are reports on mixed‐ligand ruthenium arene complexes containing N ‐ferrocenyl amino acids and ferrocenyl pyridine arene ruthenium complexes showing cytotoxicity against MCF‐7, A2780 and A2780cisR (cisplatin resistant cell line) …”

Section: Introductionmentioning

confidence: 99%

Ferrocene conjugated copper(II) complexes of terpyridine and traditional Chinese medicine (TCM) anticancer ligands showing selective toxicity towards cancer cells

Deka¹,

Bhattacharyya

Mukherjee

et al. 2018

Applied Organom Chemis

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Six novel mixed-ligand copper(II) complexes, namely, [Cu(R-tpy)(L)]NO 3 (1-6), where R-tpy is 4′-phenyl-2,2′:6′,2′′-terpyridine (Ph-tpy; 1-3) and 4′-ferrocenyl-2,2′:6′,2′′-terpyridine (Fc-tpy; 4-6), L is the bidentate O,O donor monoanion of plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone; plum in 1, 4), chrysin (5,7-dihydroxyflavone; chry in 2, 5) and curcumin (bis(4-hydroxy-3methoxyphenyl)-1,6-diene-3,5-dione; curc in 3, 6) have been synthesized and characterized and their in vitro cytotoxicity against cancer cells is evaluated.The energy optimized structures and the frontier orbitals of the complexes have been obtained from the DFT calculations. Complexes 4-6 with a conjugated ferrocenyl moiety and TCM anticancer ligands, namely, plum (in 4), chry (in 5) and curc (in 6) showed potent cytotoxicity giving respective IC 50 values of 1.2 μM, 0.62 μM and 0.21 μM in HeLa and 2.0 μM and 1.0 μM and 0.34 μM in MCF-7 cancer cells while being much less toxic to MCF-10A normal cells (IC 50 : 8.3-17.1 μM). In contrast, complexes 1-3 with a conjugated phenyl moiety were appreciably less toxic to HeLa cells with respective IC 50 values of 10.4 μM, 8.1 μM and 5.5 μM when compared with their ferrocenyl analogues 4-6. Mechanistic studies using Hoechst staining and Annexin-V-FITC assays on cancer cells revealed an apoptotic pathway of cell death induced by the complexes. Fluorescence imaging study showed that complex 6 having curcumin as ligand localized primarily in the mitochondria of HeLa cells. Thus, we demonstrate in this study that ferrocene conjugation to copper(II) complexes of TCM anticancer ligands significantly increases the selectivity and cytotoxicity of the resulting complexes towards cancer cells over normal cells.

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“…It was postulated that the inclusion of a lipophilic side chain increased cellular uptake. The complexes showed strong interactions with DNA and facilitated cell death through apoptosis …”

Section: Rutheniummentioning

confidence: 99%

Heterometallic Multinuclear Complexes as Anti‐Cancer Agents‐An Overview of Recent Developments

2019

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This review provides a critical assessment of the advances made in the development of heterometallic multinuclear complexes as potential chemotherapeutic agents, with the aim of providing a starting point for future investigators. The combination of the classical transition metals (Pt, Ru and Au) with other metal moieties has the potential to result in complexes with improved pharmacokinetic and pharmacodynamic properties. This enables selective targeting of the bio- [a] 3434 Figure 2. The Pt II -Ru III complexes, IT127 and AH-197, [35] and the macrocyclic rectangles investigated by Chi and colleagues. [36] The IC 50 (μM) values reported are shown below the chemical structures.

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Mixed ligand ruthenium arene complexes containing N-ferrocenyl amino acids: Biomolecular interactions and cytotoxicity against MCF7 cell line

Cited by 26 publications

References 57 publications

Ruthenium Arene Complexes with α‐Aminoacidato Ligands: New Insights into Transfer Hydrogenation Reactions and Cytotoxic Behaviour

Ruthenium Arene Complexes with α‐Aminoacidato Ligands: New Insights into Transfer Hydrogenation Reactions and Cytotoxic Behaviour

Ferrocene conjugated copper(II) complexes of terpyridine and traditional Chinese medicine (TCM) anticancer ligands showing selective toxicity towards cancer cells

Heterometallic Multinuclear Complexes as Anti‐Cancer Agents‐An Overview of Recent Developments

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