Synthesis of 4′-substituted-2,2′;6′,2″-terpyridine Ru(II) complexes electrochemical, fluorescence quenching and antibacterial studies

Ezhilarasu, Tamilarasu; Sathiyaseelan, Anbazhagan; Kalaichelvan, P. T.; Balasubramanian, S.

doi:10.1016/j.molstruc.2016.12.102

Cited by 23 publications

(16 citation statements)

References 57 publications

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“…Recently, the coordination chemistry of 2,2′:6′,2″‐terpyridines has been of particular interest due to their various applications such as catalysts, in nanoscience, as antibacterial agents and in supramolecular chemistry . As far as Sn–N complexes are concerned, the reported examples consist mostly of species possessing bidentate N‐donor ligands.…”

Section: Introductionmentioning

confidence: 99%

Structure–reactivity studies of chloro and isothiocyanato diorganotin (IV) complexes based on multidentate N‐donor ligands: Synthesis, spectral characterization and crystal structures

Momeni

Sefidabi

Khademi

et al. 2018

Applied Organom Chemis

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The reaction of [SnMe2Cl2] with the bidentate ligand 4,7‐phenanthroline (4,7‐phen) resulted in the formation of [SnMe2Cl2 (4,7‐phen)]n (1a) which is probably a polymeric chain in solution. On the other hand, the reaction of [SnEt2Cl2] with 4,7‐phen afforded the complex [Sn2Et4Cl4 (κ1‐N‐4,7‐phen)2(μ‐κ2‐N,N‐4,7‐phen)] (1b) which dissociates in dimethylsulfoxide solution. The reaction of [SnR2Cl2] (R = Me, Et) with 2,2′‐biquinoline (biq) yielded the complexes [SnMe2Cl2 (κ2‐N,N‐biq)] (2a) and [SnEt2Cl2 (κ1‐N‐biq)2] (2b) in the solid state. Moreover, the reaction of [SnR2Cl2] (R = Me, Et) with the tridentate ligand 4′‐(2‐furyl)‐2,2′:6′,2″‐terpyridine (ftpy) resulted in the formation of ionic penta‐ and hexa‐coordinated tin complexes [SnMe2Cl (ftpy)][SnMe2Cl3] (3a) and [SnEt2Cl (ftpy)]Cl (3b). The reaction of [SnMe2 (NCS)2] with ftpy afforded the hepta‐coordinated complex [SnMe2 (NCS)2(ftpy)] (4a). The products were fully characterized using elemental analysis, and infrared, UV–visible, multinuclear (1H, 13C, 119Sn) NMR, DEPT‐135°, HH‐COSY and HSQC NMR spectroscopies. The crystal structure of complex 3a reveals that it contains the simultaneous presence of penta‐ and hexa‐coordinated tin (IV) atoms. Notably, the crystal structure of complex 4a shows that tin (IV) is hepta‐coordinated in a pentagonal bipyramidal geometry SnC2N5 by three nitrogen atoms of ftpy, two nitrogen atoms of NCS− and two Me groups with trans‐[SnMe2] configuration. These data indicate the influence of halide or pseudo‐halide group on the coordination number and geometry of tin. Hirshfeld surface analysis and two‐dimensional fingerprint plots were calculated for 3a and 4a which show the π–π interaction between molecules in the solid is relatively weak.

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Section: Introductionmentioning

confidence: 99%

Structure–reactivity studies of chloro and isothiocyanato diorganotin (IV) complexes based on multidentate N‐donor ligands: Synthesis, spectral characterization and crystal structures

Momeni

Sefidabi

Khademi

et al. 2018

Applied Organom Chemis

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“…Complexes 1 and 3 show moderate activity against all the bacteria and complex 3 shows maximum activity against K. pneumonia at 50 µg mL -1 , complex 2 shows minimum activity against all the bacteria while complex 4 shows maximum activity against E. coli and S. aureus at 50 µg mL -1 and it shows moderate activity against other bacteria. All the complexes showed significant antibacterial activities against all the tested bacteria [41]. These results suggested that the cytotoxicity depends upon the nature of bidentate and tridentate ligand coordinated to the metal center [42].…”

Section: H Nmr Spectramentioning

confidence: 84%

Studies on DNA Interactions and Biological Activities of Lanthanum(III) Complexes with 4-Quinoline Terpyridine and 1,10-Phenanthroline

et al. 2019

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A series of lanthanum(III) complexes [La(4-qtpy)2(NO3)2](NO3) (1), [La(4-qtpy)3(NO3)](NO3)2 (2), [La(4-qtpy)(phen)(NO3)2](NO3) (3) and [La(4-qtpy)(phen)2(NO3)2](NO3) (4) (4-qtpy = 4′-[(4-quinoline)-2,2′;6′,2′′-terpyridine]) were synthesized and characterized. The cyclic voltammetric studies revealed that the complexes 1 and 3 are redox active. UV-visible absorption spectral studies and viscosity measurements revealed that complexes bind to DNA through intercalation. Complexes 1 and 3 have shown the highest binding propensity (Kb = 4.241 + 0.2 × 106 for 1 and 1.492 + 0.2 × 106 for 3). The results of chemical nuclease studies revealed that the complexes 3 and 4 have shown maximum chemical nuclease activity in the presence of H2O2 and the mechanism involves hydroxyl radicals. The antibacterial activities of the complexes 1 to 4 were tested against Gram positive and Gram negative bacteria in which complex 3 shows comparable results with the standard antibiotic tetracycline. The cytotoxic activities of 4-qtpy and complex 4 were done by MTT assay against HeLa cell lines.

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“…[ 45,46 ] It was reported that the observation of this band for 4′‐substituted‐2,2′;6′,2″‐tpy Ru (II) complexes is characteristic for an octahedral geometry corresponding to 1 T 1(g) ← 1 A 1(g) transition. [ 47 ] The corresponding molar extinction coefficients of complexes 9 , 10 , and 11 are 1.30 × 10 4 , 2.1 × 10 4 , and 1.50 × 10 4 M −1 cm −1 , respectively. These high absorptivity values result from the wide π‐conjugation due to the presence of the thiophene or the 4‐methoxy phenyl moieties on the terpyridyl ligand.…”

Section: Resultsmentioning

confidence: 99%

“…These findings were in agreement with those obtained with the Ru (II) tpy complexes [Ru(4′‐(4‐benzyloxybenzaldehyde)‐2,2′:6′,2″‐terpyridine) 2 ](PF 6 ) 2 , [Ru(4′‐(4‐benzyloxy‐3‐methoxybenzaldehyde)‐2,2′:6′,2″‐terpyridine)) 2 ](PF 6 ) 2 and [Ru(4′‐(4‐benzyloxy‐3‐ethoxybenzaldehyde)‐2,2′:6′,2″‐terpyridine) 2 ](PF 6 ) 2 ) for the Gram‐negative and Gram‐positive bacteria. [ 47 ]…”

Section: Resultsmentioning

confidence: 99%

“…[Ru(4 0 -(4-benzyloxy-3-ethoxybenzaldehyde)-2,2 0 :6 0 ,2 00 -terpyridine) 2 ](PF 6 ) 2 ) for the Gram-negative and Gram-positive bacteria. [47] 4 | CONCLUSIONS 4 0 -Substituted-2,2 0 :6 0 ,2 00 -tpy ligands and their Ru (II) complexes have been synthesized and characterized. The absorption spectra of the synthesized spectra show the main MLCT peak at about 500 nm with relatively high extinction coefficients due to the presence of thiophene or the 4-methoxy phenyl moieties on the 4 0substituted-2,2 0 :6 0 ,2 00 -tpy ligands.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

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Synthesis, characterization, and evaluation of biological activities of new 4′‐substituted ruthenium (II) terpyridine complexes: Prospective anti‐inflammatory properties

Elnagar

Samir

Shaker

et al. 2020

Applied Organom Chemis

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The synthesis and characterization of Ru (II) terpyridine complexes derived from 4′ functionalized 2,2′:6′,2″‐terpyridine (tpy) ligands are reported. The heteroleptic complexes comprise the synthesized ligands 4′‐(2‐thienyl)‐ 2,2′:6′,2″‐terpyridine) or (4′‐(3,4‐dimethoxyphenyl)‐2,2′:6′,2″‐terpyridine and (dimethyl 5‐(pyrimidin‐5‐yl)isophthalate). The new complexes [Ru(4′‐(2‐thienyl)‐2,2′:6′,2″‐terpyridine)(5‐(pyrimidin‐5‐yl)‐isophthalic acid)Cl2] (9), [Ru(4′‐(3,4‐dimethoxyphenyl)‐2,2′:6′,2″‐terpyridine)(5‐(pyrimidin‐5‐yl)‐isophthalic acid)Cl2] (10), and [Ru(4′‐(2‐thienyl)‐2,2′:6′,2″‐terpyridine)(5‐(pyrimidin‐5‐yl)‐isophthalic acid)(NCS)2] (11) were characterized by 1H‐ and 13C‐NMR spectroscopy, C, H, N, and S elemental analysis, UPLC‐ESI‐MS, TGA, FT‐IR, and UV‐Vis spectroscopy. The biological activities of the synthesized ligands and their Ru (II) complexes as anti‐inflammatory, antimicrobial, and anticancer agents were evaluated. Furthermore, the toxicity of the synthesized compounds was studied and compared with the standard drugs, namely, diclofenac potassium and ibuprofen, using hemolysis assay. The results indicated that the ligands and the complex 9 possess superior anti‐inflammatory activities inhibiting albumin denaturation (89.88–100%) compared with the standard drugs (51.5–88.37%) at a concentration of 500 μg g−1. These activities were related to the presence of the chelating N‐atoms in the ligands and the exchangeable chloro‐ groups in the complex. Moreover, the chloro‐ and thiophene groups in complex 9 produce a higher anticancer activity compared with its isothiocyanate derivative in the complex 11 and the 3,4‐dimethoxyphenyl moiety in complex 10. Considering the toxicity results, the synthesized ligands are nontoxic or far less toxic compared with the standard drugs and the metal complexes. Therefore, these newly synthesized compounds are promising anti‐inflammatory agents in addition to their moderate unique broad antimicrobial activity.

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Synthesis of 4′-substituted-2,2′;6′,2″-terpyridine Ru(II) complexes electrochemical, fluorescence quenching and antibacterial studies

Cited by 23 publications

References 57 publications

Structure–reactivity studies of chloro and isothiocyanato diorganotin (IV) complexes based on multidentate N‐donor ligands: Synthesis, spectral characterization and crystal structures

Structure–reactivity studies of chloro and isothiocyanato diorganotin (IV) complexes based on multidentate N‐donor ligands: Synthesis, spectral characterization and crystal structures

Studies on DNA Interactions and Biological Activities of Lanthanum(III) Complexes with 4-Quinoline Terpyridine and 1,10-Phenanthroline

Synthesis, characterization, and evaluation of biological activities of new 4′‐substituted ruthenium (II) terpyridine complexes: Prospective anti‐inflammatory properties

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