Self-assembly of manganese(I) and rhenium(I) based semi-rigid ester functionalized M 2 L 2 -type metallacyclophanes: Synthesis, characterization and cytotoxicity evaluation

Kumar, Chowan Ashok; Divya, D.; Nagarajaprakash, R.; Veena, V.; Vidhyapriya, Pitchavel; Sakthivel, Natarajan; Manimaran, Bala.

doi:10.1016/j.jorganchem.2017.06.003

Cited by 31 publications

(7 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The cytotoxicity of the complexes was analyzed using MTT assay. [ 66 ] Lung and cervical cancer cells and HEK 293 cells were suspended in DMEM supplemented with 10% FBS at a density of 20,000 cells per well in 96‐well plate and incubated overnight. Colon cancer cells were suspended in RPMI supplemented with 10% FBS and plated as mentioned above.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies

Thomas

Vidhyapriya²,

Sivan

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

Two different series of manganese(I) tricarbonyl complexes containing phosphine‐based (1–5) and 4′‐substituted 2,2′:6′,2″‐terpyridine‐based ligands (6–10) have been synthesized in order to study their CO‐releasing ability and to investigate their anticancer activity. All the synthesized complexes (1–10) have been fully characterized using standard spectroscopic and analytical techniques. Further 5, 7, and 9 have also been characterized by single‐crystal X‐ray diffraction studies. Although both the sets of ligands are π‐acceptors, they tend to change the Mn—CO bond strength upon complexation, thus affecting the CO release. Photoactivation of 1–5 and 6–10 has been achieved using 365 nm UV irradiation and low intensity visible light, respectively. The MnCO bond strength has been examined using the density functional theory (DFT) and time‐dependent DFT (TD‐DFT) calculations. In order to find the therapeutic viability of the visible light activated complexes, their cytotoxicity has been investigated both in the dark and under irradiation. The MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl tetrazolium bromide) assay reveals the potential application of some of the synthesized complexes especially towards the lung cancer cells in the dark condition.

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies

Thomas

Vidhyapriya²,

Sivan

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…IR spectra of compounds 1–8 displayed strong bands in the range of ν 2029–1897 cm –1 for terminal carbonyl ligands of an octahedrally coordinated fac -Re(CO) 3 core. 10 The amide C=O stretching frequency of bpce/bpcpm appeared as a weak band at around ν 1605–1681 cm –1 . 1 H and 13 C NMR spectra of compounds 1–8 showed appropriate signals for the bridging ligands, and the spectral data are given in the experimental section.…”

Section: Results and Discussionmentioning

confidence: 99%

“…IR spectra of compounds 1–8 displayed strong bands in the range of ν 2029–1897 cm –1 for terminal carbonyl ligands of an octahedrally coordinated fac -Re(CO) 3 core . The amide CO stretching frequency of bpce/bpcpm appeared as a weak band at around ν 1605–1681 cm –1 .…”

Section: Results and Discussionmentioning

confidence: 99%

Amide-Functionalized Chalcogen-Bridged Flexible Tetranuclear Rhenacycles: Synthesis, Characterization, Solvent Effect on the Structure, and Guest Binding

et al. 2018

Self Cite

View full text Add to dashboard Cite

The synthesis of flexible rhenium(I)-based amide-functionalized chalcogen-bridged tetranuclear metallacycles of general formula [{(CO) 3 Re(μ-ER) 2 Re(CO) 3 } 2 (μ-L) 2 ] ( 1–8 ) was achieved by treating rhenium carbonyl with dialkyl/diaryl chalcogenide (RE–ER; E = S and Se) in the presence of ditopic flexible or semiflexible pyridyl ligand with amide functionality (L = N , N ′-bis(4-pyridylcarboxamide)-1,2-ethane (bpce) and N , N ′-bis(4-(4-pyridylcarboxamide)phenyl)methane (bpcpm)). Compounds 1–8 were formed by multicomponent self-assembly under one-pot reaction conditions via oxidative addition of dialkyl/diaryl chalcogenide to rhenium carbonyl with pyridyl ligands. The resultant metallacyclophanes were characterized using elemental analyses, infrared, ultraviolet–visible, and NMR spectroscopic techniques. Metallacyclophanes 1–3 and 7 were structurally characterized by single-crystal X-ray diffraction methods. The solvent-induced structural change of flexible tetranuclear metallacyclophane 2 was demonstrated by crystallizing 2 in dichloroethane and dimethylformamide. Molecular recognition capabilities of 2 and 7 were studied with few aromatic compounds containing ethereal linkages.

show abstract

“…168 Two novel binuclear semi-rigid ester Mn(I)-based carbonyl complexes, 9 and 10 (Figure 3), were prepared and proved to release CO via illumination at 365 nm. 169 The reduced Mb solution of 10 remained stable for 12 h, however, by exposure to the light source, 10 released 1.8 equivalents of CO. Upon illumination, 9 showed cytotoxicity against lung (IC50 = 15.7 ± 0.98 µM) and colon (IC50 = 28.7 ± 0.16 µM) cancer cells only, while 10 showed cytotoxicity against cervical, lung, and colon cancer cell lines with IC50 values of 15.4 ± 0.67, 15.8 ± 1.75 and 14.5 ± 0.97 µM, respectively.…”

Section: Manganese(i) Cormsmentioning

confidence: 98%

“…Although this has yet to be confirmed, the anticancer effect of 98 could be a result of apoptosis triggered by the CO release. 171…”

Section: Perspective Dalton Transactionsmentioning

confidence: 99%

Metal-based carbon monoxide releasing molecules with promising cytotoxic properties

Mansour,

Khaled,

Ferraro

et al. 2024

Dalton Trans.

View full text Add to dashboard Cite

show abstract

Self-assembly of manganese(I) and rhenium(I) based semi-rigid ester functionalized M 2 L 2 -type metallacyclophanes: Synthesis, characterization and cytotoxicity evaluation

Cited by 31 publications

References 57 publications

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies

Amide-Functionalized Chalcogen-Bridged Flexible Tetranuclear Rhenacycles: Synthesis, Characterization, Solvent Effect on the Structure, and Guest Binding

Metal-based carbon monoxide releasing molecules with promising cytotoxic properties

Contact Info

Product

Resources

About

Self-assembly of manganese(I) and rhenium(I) based semi-rigid ester functionalized M 2 L 2 -type metallacyclophanes: Synthesis, characterization and cytotoxicity evaluation

Cited by 31 publications

References 57 publications

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)3(L–L)Br] complexes: Experimental and density functional theory studies

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)3(L–L)Br] complexes: Experimental and density functional theory studies

Amide-Functionalized Chalcogen-Bridged Flexible Tetranuclear Rhenacycles: Synthesis, Characterization, Solvent Effect on the Structure, and Guest Binding

Metal-based carbon monoxide releasing molecules with promising cytotoxic properties

Contact Info

Product

Resources

About

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies