Arene-ruthenium(II) complexes with tetracyclic oxime derivatives: synthesis, structure and antiproliferative activity against human breast cancer cells

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Arene-ruthenium(II) complexes with tetracyclic oxime derivatives: synthesis, structure and antiproliferative activity against human breast cancer cells. / Matveevskaya, Vladislava V.; Pavlov, Dmitry I.; Samsonenko, Denis G. et al.

In: Inorganica Chimica Acta, Vol. 535, 120879, 24.05.2022.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{bfc2512946214abe84fc5d3d8e3efd54,

title = "Arene-ruthenium(II) complexes with tetracyclic oxime derivatives: synthesis, structure and antiproliferative activity against human breast cancer cells",

abstract = "Six new arene-ruthenium(II) complexes containing two different η6-arene ligands – benzene and hexamethylbenzene, with indenoquinoxalinone oxime analogues (11H-indeno[1,2-b]quinoxalin-11-one oxime, 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one oxime and 6–(hydroxyimino)indolo[2,1-b]quinazolin-12(6H)-one oxime (tryptanthrin-6-oxime)) as N,N{\textquoteright}- chelating ligands are reported. The complexes were characterized by elemental analysis, IR, UV–VIS, 1H and 13C NMR spectroscopy and by single-crystal X-ray structure analysis. Complexes adopt a half-sandwich «piano-stool» geometry with oxime ligands in anionic form, the ruthenium(II) center coordinates one arene, one N,N-bidentate oximate and one chloride ligand. The computational analysis of non-covalent intermolecular interactions revealed weak attraction between the oxime oxygen atoms and the nearest hydrogen atoms of the oxime and the arene ligands. The cytotoxic activity of the complexes was evaluated against human breast cancer cell line MCF-7 and cisplatin-resistant human breast cancer cell line MCF-7CR as well as non-cancerous human breast epithelial cell line MCF10A. The cytotoxicity tests show micromolar IC50 values and tryptanthrin-6-oxime hexamethylbenzene-ruthenium(II) complex was found to exhibit the best antiproliferative activity among the studied compounds against the MCF-7 and MCF-7CR cell lines (IC50 9.0 ± 4.4 and 8.9 ± 1.5 µM, respectively).",

keywords = "Arene-ruthenium complexes, Cytotoxicity, Indenoquinoxaline, Nitrogen ligands, Oxime ligands, Tryptanthrin",

author = "Matveevskaya, {Vladislava V.} and Pavlov, {Dmitry I.} and Samsonenko, {Denis G.} and Laura Bonfili and Massimiliano Cuccioloni and Enrico Benassi and Riccardo Pettinari and Potapov, {Andrei S.}",

note = "Funding Information: This research was funded by the Ministry of Science and Higher Education of the Russian Federation, project number 121031700321-3. The Siberian Branch of the Russian Academy of Sciences (SB RAS) Siberian Supercomputer Center is gratefully acknowledged for providing supercomputer facilities. The authors thank Dr. T.S. Sukhikh and Dr. A.S. Sukhikh for providing the data collected in XRD Facility of NIIC SB RAS. Publisher Copyright: {\textcopyright} 2022 Elsevier B.V.",

year = "2022",

month = may,

day = "24",

doi = "10.1016/j.ica.2022.120879",

language = "English",

volume = "535",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Arene-ruthenium(II) complexes with tetracyclic oxime derivatives: synthesis, structure and antiproliferative activity against human breast cancer cells

AU - Matveevskaya, Vladislava V.

AU - Pavlov, Dmitry I.

AU - Samsonenko, Denis G.

AU - Bonfili, Laura

AU - Cuccioloni, Massimiliano

AU - Benassi, Enrico

AU - Pettinari, Riccardo

AU - Potapov, Andrei S.

N1 - Funding Information: This research was funded by the Ministry of Science and Higher Education of the Russian Federation, project number 121031700321-3. The Siberian Branch of the Russian Academy of Sciences (SB RAS) Siberian Supercomputer Center is gratefully acknowledged for providing supercomputer facilities. The authors thank Dr. T.S. Sukhikh and Dr. A.S. Sukhikh for providing the data collected in XRD Facility of NIIC SB RAS. Publisher Copyright: © 2022 Elsevier B.V.

PY - 2022/5/24

Y1 - 2022/5/24

N2 - Six new arene-ruthenium(II) complexes containing two different η6-arene ligands – benzene and hexamethylbenzene, with indenoquinoxalinone oxime analogues (11H-indeno[1,2-b]quinoxalin-11-one oxime, 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one oxime and 6–(hydroxyimino)indolo[2,1-b]quinazolin-12(6H)-one oxime (tryptanthrin-6-oxime)) as N,N’- chelating ligands are reported. The complexes were characterized by elemental analysis, IR, UV–VIS, 1H and 13C NMR spectroscopy and by single-crystal X-ray structure analysis. Complexes adopt a half-sandwich «piano-stool» geometry with oxime ligands in anionic form, the ruthenium(II) center coordinates one arene, one N,N-bidentate oximate and one chloride ligand. The computational analysis of non-covalent intermolecular interactions revealed weak attraction between the oxime oxygen atoms and the nearest hydrogen atoms of the oxime and the arene ligands. The cytotoxic activity of the complexes was evaluated against human breast cancer cell line MCF-7 and cisplatin-resistant human breast cancer cell line MCF-7CR as well as non-cancerous human breast epithelial cell line MCF10A. The cytotoxicity tests show micromolar IC50 values and tryptanthrin-6-oxime hexamethylbenzene-ruthenium(II) complex was found to exhibit the best antiproliferative activity among the studied compounds against the MCF-7 and MCF-7CR cell lines (IC50 9.0 ± 4.4 and 8.9 ± 1.5 µM, respectively).

AB - Six new arene-ruthenium(II) complexes containing two different η6-arene ligands – benzene and hexamethylbenzene, with indenoquinoxalinone oxime analogues (11H-indeno[1,2-b]quinoxalin-11-one oxime, 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one oxime and 6–(hydroxyimino)indolo[2,1-b]quinazolin-12(6H)-one oxime (tryptanthrin-6-oxime)) as N,N’- chelating ligands are reported. The complexes were characterized by elemental analysis, IR, UV–VIS, 1H and 13C NMR spectroscopy and by single-crystal X-ray structure analysis. Complexes adopt a half-sandwich «piano-stool» geometry with oxime ligands in anionic form, the ruthenium(II) center coordinates one arene, one N,N-bidentate oximate and one chloride ligand. The computational analysis of non-covalent intermolecular interactions revealed weak attraction between the oxime oxygen atoms and the nearest hydrogen atoms of the oxime and the arene ligands. The cytotoxic activity of the complexes was evaluated against human breast cancer cell line MCF-7 and cisplatin-resistant human breast cancer cell line MCF-7CR as well as non-cancerous human breast epithelial cell line MCF10A. The cytotoxicity tests show micromolar IC50 values and tryptanthrin-6-oxime hexamethylbenzene-ruthenium(II) complex was found to exhibit the best antiproliferative activity among the studied compounds against the MCF-7 and MCF-7CR cell lines (IC50 9.0 ± 4.4 and 8.9 ± 1.5 µM, respectively).

KW - Arene-ruthenium complexes

KW - Cytotoxicity

KW - Indenoquinoxaline

KW - Nitrogen ligands

KW - Oxime ligands

KW - Tryptanthrin

UR - http://www.scopus.com/inward/record.url?scp=85125136122&partnerID=8YFLogxK

U2 - 10.1016/j.ica.2022.120879

DO - 10.1016/j.ica.2022.120879

M3 - Article

AN - SCOPUS:85125136122

VL - 535

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

SN - 0020-1693

M1 - 120879

ER -

ID: 35589138