Dissymmetric thiosemicarbazone ligands containing substituted aldehyde arm and their ruthenium(II) carbonyl complexes with PPh3/AsPh3 as ancillary ligands: Synthesis, structural characterization, DNA/BSA interaction and in vitro anticancer activity

Vijayan, Paranthaman; Viswanathamurthi, Periasamy; Silambarasan, Vaidhyanathan; Velmurugan, D.; Velmurugan, K.; Nandhakumar, Raju; Butcher, Ray J.; Selvan, Silambarasan Tamil; Dandapani, Ramamurthy

doi:10.1016/j.jorganchem.2014.06.026

Cited by 38 publications

(22 citation statements)

References 75 publications

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“…In such compounds, the metal ion may play important roles based on its electronic structure, oxidation states, magnetic behaviour and coordination geometry . The cytotoxicity and antitumour activity of such metal complexes are possibly due to their ability to bind to DNA and proteins via intercalative, electrostatic or groove binding . Among metal‐based drugs, ruthenium and vanadium complexes as anticancer agents are of considerable interest.…”

Section: Introductionmentioning

confidence: 99%

Oxovanadium(IV) and ruthenium(II) carbonyl complexes of ONS‐donor ligands derived from dehydroacetic acid and dithiocarbazate: Synthesis, characterization, antioxidant activity, DNA binding and in vitro cytotoxicity

Sarhan

Elsayed

Mashaly

et al. 2018

Applied Organom Chemis

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A series of new complexes of oxovanadium(IV) [VO(L)(B)] and ruthenium(II) [Ru(CO)(PPh3)2(L)] (1.1- 1.3, 2.1–2.3) (H2L = dehydroacetic acid Schiff base of S‐methyldithiocarbazate, H2smdha (1) or S‐benzyldithiocarbazate, H2sbdha (2); B = 2,2′‐bipyridine (bpy) or 1,10‐phenanthroline (phen)) have been synthesized. The structure of these complexes was authenticated using elemental analyses and spectroscopic techniques, and their magnetic properties and electrochemical behaviour were studied. The molecular structures of oxovanadium(IV) complexes [VO(smdha)(bpy)]⋅CH2Cl2 (1.1) and [VO(sbdha)(phen)]⋅2H2O (2.2) were confirmed using single‐crystal X‐ray crystallography. Analytical data showed that the ligands 1 and 2 are chelated to the metal centres in a bi‐negative tridentate fashion through azomethine N, thiol S and deprotonated hydroxyl group. The antioxidant activity of the synthesized compounds was tested against 2,2‐diphenyl‐1‐picrylhydrazyl) radical, which showed that the complexes demonstrate a better scavenging activity than their corresponding ligands. The cupric ion reducing antioxidant capacity method was also employed and the total equivalent antioxidant capacity values were found to be higher for the oxovandium(IV) complexes. DNA binding affinity of the compounds was determined using UV–visible and fluorescence spectra, revealing an intercalation binding mode. Higher cytotoxicity for the complexes compared to their ligands was found against human liver hepatocellular carcinoma (HepG2) and breast adenocarcinoma (MCF7) cell lines using MTT assay.

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Section: Introductionmentioning

confidence: 99%

Oxovanadium(IV) and ruthenium(II) carbonyl complexes of ONS‐donor ligands derived from dehydroacetic acid and dithiocarbazate: Synthesis, characterization, antioxidant activity, DNA binding and in vitro cytotoxicity

Sarhan

Elsayed

Mashaly

et al. 2018

Applied Organom Chemis

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“…Absence of these bands indicates coordination of the thioamidate-S to the ruthenium(II) centre in the complexes. 28,[47][48][49][50] The complexes display the ν C=N stretch in the region 1555-1585 cm −1 which is at a lower frequency than that of the free H 2 L n (∼1600 cm −1 ) indicating coordination of the azomethine nitrogen to the metal centre. 28,[48][49][50] The typical strong band for the terminally coordinated carbonyl group in 1−6 is observed in the range 1918-1956 cm −1 .…”

Section: Spectroscopic Characteristicsmentioning

confidence: 94%

“…28,[47][48][49][50] The complexes display the ν C=N stretch in the region 1555-1585 cm −1 which is at a lower frequency than that of the free H 2 L n (∼1600 cm −1 ) indicating coordination of the azomethine nitrogen to the metal centre. 28,[48][49][50] The typical strong band for the terminally coordinated carbonyl group in 1−6 is observed in the range 1918-1956 cm −1 . 29,32,48,50 Three strong bands displayed by all the complexes at ∼520, ∼695 and ∼745 cm −1 are attributed to the metal coordinated EPh 3 ligands.…”

Section: Spectroscopic Characteristicsmentioning

confidence: 94%

“…28,[48][49][50] The typical strong band for the terminally coordinated carbonyl group in 1−6 is observed in the range 1918-1956 cm −1 . 29,32,48,50 Three strong bands displayed by all the complexes at ∼520, ∼695 and ∼745 cm −1 are attributed to the metal coordinated EPh 3 ligands. 19,20,24,25,29,32 The 1 H-NMR spectra of 1−6 were recorded in CDCl 3 and compared to the spectra of H 2 L n recorded in (CD 3 ) 2 SO.…”

Section: Spectroscopic Characteristicsmentioning

confidence: 99%

“…The downfield shift suggests deshielding of the azomethine proton due to its coordination to the metal centre. 50,51 The methyl protons in each of H 2 L 2 , 2 and 5 resonate as a doublet at δ ∼ 3.10 ppm (J = 5−7 Hz). The remaining protons of (L n ) 2− and PPh 3 /AsPh 3 ligands in 1−6 appear as multiplets in the region δ 6.9−8.5 ppm.…”

Section: Spectroscopic Characteristicsmentioning

confidence: 99%

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Cyclometallated ruthenium(II) carbonyl complexes with 1-pyrenaldehyde 4-R-3-thiosemicarbazones: Regioselective ruthenation of the 1-pyrenyl group

Prabhu

Pal

2015

J Chem Sci

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A facile method for the synthesis of a series of cyclometallated ruthenium(II) carbonyl complexes with 1-pyrenaldehyde 4-R-3-thiosemicarbazones (H 2 L n where the two H's represent the dissociable thioamide and pyrenyl protons; R = H, Me and Ph) has been described. The characterization of the complexes having the general molecular formula trans-[Ru(L n )(CO)(EPh 3 ) 2 ] (where E = P or As) were accomplished by elemental (CHN) analysis, magnetic susceptibility and spectroscopic (ESI-MS, IR, UV-Vis, emission and 1 H-NMR) measurements. Electronic spectra of the complexes display multiple strong absorptions in the range 440-224 nm due to intraligand transitions. All the complexes exhibit emission bands that are characteristic of ligand centred emissive states. X-ray diffraction studies with representative complexes reveal a pincer-like 5,5-membered fused chelate rings forming CNS coordination mode of the thiosemicarbazonate ligand (L n ) 2− via regioselective activation of 1-pyrenyl ortho C-H and formation of a distorted octahedral C 2 NSE 2 coordination sphere around the ruthenium(II) centre.

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Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

Vijayan

Viswanathamurthi

Sugumar

et al. 2016

Applied Organom Chemis

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N,N-[(diethylamino)(thiocarbonyl)]-substituted benzamidine ligands have been synthesized from the reaction of N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride with functionalized amines such as 2-aminophenol and 2-picolylamine. The reaction of N,N-[(diethylamino)(thiocarbonyl)]-2-hydroxyphenylbenzamidine (H 2 L 1 ) with ruthenium(II) precursor [RuHCl(CO)(PPh 3 ) 3 ] afforded complex 1 of the type [Ru(L 1 )(CO)(PPh 3 ) 2 ] in which the ligand coordinated in tridentate ONS mode. The reaction of H 2 L 1 with copper precursor [Cu(CH 3 COO)(PPh 3 ) 2 ] induced C═N bond cleavage of the ligand and afforded complex 3 of the type [Cu(1,1-DT) (Cl)(PPh 3 ) 2 ] (1,1-DT = 1,1-diethylthiourea) in which the ligand coordinated in a monodentate fashion. The ligand N,N-[(diethylamino)(thiocarbonyl)]-2picolylbenzamidine (HL 2 ) reacted with ruthenium(II) and copper(I) precursors to form complex 2 of the type [Ru(1,1-DT)(Cl 2 )(CO)(PPh 3 ) 2 ] and complex 3, respectively, in which the ligand underwent C═N cleavage and coordinated in a monodentate fashion via C═S group. In complexes 1 and 2, the two triphenylphosphine co-ligands coordinated in trans position whereas, in complex 3, the two triphenylphosphine co-ligands coordinated in cis position. All the compounds were characterized using infrared, UV-visible, ( 1 H, 13 C, 31 P) NMR, ESI-MS and elemental analyses. The molecular structures of ligand H 2 L 1 and complexes 1-3 were determined using X-ray crystallography, which confirmed the coordination mode of the ligands with metals. The crystal structure of complexes 1 and 2 revealed a distorted octahedral geometry around the ruthenium ion and the structure of complex 3 indicated a tetrahedral geometry around the copper ion. With the X-ray structures, density functional theory computations were carried out to determine the electronic structure of the compounds. The interactions of complexes 1-3 with calf thymus DNA and bovine serum albumin protein were investigated using UV-visible and fluorescence spectroscopic and viscometric methods. Catecholase-and phosphatase-like activities promoted by complexes 1-3 under physiological conditions have been studied. In vitro anticancer activities have been demonstrated by MTT assay, acridine orange/ethidium bromide and diamidino-2-phenylindole staining against various cancerous cell lines.

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Dissymmetric thiosemicarbazone ligands containing substituted aldehyde arm and their ruthenium(II) carbonyl complexes with PPh3/AsPh3 as ancillary ligands: Synthesis, structural characterization, DNA/BSA interaction and in vitro anticancer activity

Cited by 38 publications

References 75 publications

Oxovanadium(IV) and ruthenium(II) carbonyl complexes of ONS‐donor ligands derived from dehydroacetic acid and dithiocarbazate: Synthesis, characterization, antioxidant activity, DNA binding and in vitro cytotoxicity

Oxovanadium(IV) and ruthenium(II) carbonyl complexes of ONS‐donor ligands derived from dehydroacetic acid and dithiocarbazate: Synthesis, characterization, antioxidant activity, DNA binding and in vitro cytotoxicity

Cyclometallated ruthenium(II) carbonyl complexes with 1-pyrenaldehyde 4-R-3-thiosemicarbazones: Regioselective ruthenation of the 1-pyrenyl group

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

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