authors |
Quintal, S; da Silva, MJP; Martins, SRM; Sales, R; Felix, V; Drew, MGB; Meireles, M; Mourato, AC; Nunes, CD; Saraiva, MS; Machuqueiro, M; Calhorda, MJ |
nationality |
International |
journal |
DALTON TRANSACTIONS |
keywords |
DICARBONYL COMPLEXES; DYNAMIC-BEHAVIOR; DIIMINE; CATALYSTS; DNA; POLYMERIZATION; CYTOTOXICITY; MONONUCLEAR; EQUILIBRIA; REACTIVITY |
abstract |
New complexes [Mo(eta(3)-C3H5)X(CO)(2)(4-Y-BIAN)] (4-Y-BIAN = bis(4-Y-phenyl)-acenaphthenequinonediimine), with X = Br and Y = H, Me, OMe, COOH and X = Cl, Y = OMe, as well as the cation with X = NCMe and Y = OMe were synthesized, expanding the scope of this family. Two single crystal X-ray structures (X = Br, Y = Me, OMe) display a less symmetric arrangement (axial isomer), where one N donor atom is trans to the allyl group and the second to one CO. DFT studies showed similar energies for the two possible isomers of the complexes, with a very small preference for the observed axial isomer. The HOMO of the complexes is localized in the metal and the HOMO-1 of the oxidized species has a contribution from the BIAN ligand, while the LUMO is fully localized in BIAN. Electrochemical studies showed one process corresponding to the oxidation of Mo(ii) to Mo(iii) for complexes with X = Br, Y = H, Me, and two oxidation reactions for those with X = Br, Y = Cl, OMe, while the COOH derivative exhibited no oxidation wave. The antitumor effect of the complexes with X = Br was tested in cancer lines, and the H and OMe complexes were particularly active, with EC50 values below 8 mu M in HeLa cell lines. The DNA binding constants determined by titration experiments were comparable with those of doxorubicin and ethidium bromide, suggesting a mechanism of action based on intercalation in DNA. |
publisher |
ROYAL SOC CHEMISTRY |
issn |
1477-9226 |
isbn |
1477-9234 |
year published |
2019 |
volume |
48 |
issue |
23 |
beginning page |
8449 |
ending page |
8463 |
digital object identifier (doi) |
10.1039/c9dt00469f |
web of science category |
Chemistry, Inorganic & Nuclear |
subject category |
Chemistry |
unique article identifier |
WOS:000472537600047
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ciceco authors
impact metrics
journal analysis (jcr 2019):
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journal impact factor |
4.174 |
5 year journal impact factor |
3.812 |
category normalized journal impact factor percentile |
90 |
dimensions (citation analysis):
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altmetrics (social interaction):
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