TY - JOUR
T1 - Modulation of the solubility properties of arene ruthenium complexes bearing stannyl ligands as potential anti-cancer agents
AU - Berg, Clara
AU - Chari, Suviti
AU - Jurgaityte, Kaste
AU - Laurora, Alice
AU - Naldony, Mateusz
AU - Pope, Frances
AU - Romano, Dario
AU - Medupe, Thato
AU - Prince, Sharon
AU - Ngubane, Siyabonga
AU - Baumgartner, Judith
AU - Blom, Burgert
N1 - Funding Information:
The authors wish to thank the Maastricht Science Programme (MSP) and Maastricht University for financial support of this research. The University of Cape Town acknowledges financial support from the National Research Foundation (NRF), Cancer Association of South Africa (CANSA) and the South African Medical Research Council (SAMRC). We would like to thank Dr. Jade Peres and Mrs. Alexis Neumann-Mufweba who kindly assisted with the cell culture and cytotoxicity assays described in this study.
Funding Information:
The authors wish to thank the Maastricht Science Programme (MSP) and Maastricht University for financial support of this research. The University of Cape Town acknowledges financial support from the National Research Foundation ( NRF ), Cancer Association of South Africa ( CANSA ) and the South African Medical Research Council ( SAMRC ). We would like to thank Dr. Jade Peres and Mrs. Alexis Neumann-Mufweba who kindly assisted with the cell culture and cytotoxicity assays described in this study.
Publisher Copyright:
© 2019
PY - 2019/8/1
Y1 - 2019/8/1
N2 - Cleavage of the known ruthenium dimer [RuCl2(η6-C6H5OCH2CH2OH)]2(1), bearing a hydrophilic substituent on the η6 coordinated aromatic ring, with the phosphine ligands: triphenyl phosphine, triphenyl phosphite, trimethyl phosphite, and 1,3,5-triaza-7-phosphaadamantane (PTA) afforded the known complexes [RuCl2(η6-C6H5OCH2CH2OH)(PPh3)] (2a), [RuCl2(η6-C6H5OCH2CH2OH){P(OPh)3}] (2b), [RuCl2(η6-C6H5OCH2CH2OH){P(OMe3)}] (2c), and [RuCl2 (η6-C6H5OCH2CH2OH)(PTA)] (4). The reaction of the known complex 2a with SnCl2afforded, by facile insertion of the SnCl2moiety into the Ru-Cl bond, the novel complex [RuCl(η6-C6H5OCH2CH2OH)(PPh3)(SnCl3)] (3a). Similarly, the reaction of complex 2b with SnCl2afforded the novel complex [RuCl(η6-C6H5OCH2CH2OH){P(OPh)3}(SnCl3)] (3b). Complexes 3a and 3b were fully characterized by spectroscopy (Infrared (IR) -spectroscopy, 1H, 31P and 119Sn Nuclear Magnetic Resonance (NMR) spectroscopy, UV-Vis spectroscopy and high resolution ESI-MS) and their thermal behaviour elucidated by Thermogravimetric Analysis (TGA). Density Functional Theory (DFT) calculations (Level of theory B3LYP, basis set for H, C, P, O, N and Cl is 6-31+G(d,p) and for Ru and Sn is DGDZVP) for complex 3a, 3b and 4 were also carried out, in particular to elucidate the bonding situation between Ru and Sn in complexes. The hitherto unprecedented anti-cancer activity of the complexes 2a – 2c as well as the novel stannyl complexes 3a and 3b were evaluated against MCF-7 (oestrogen receptor positive) human breast adenocarcinoma cell lines. All complexes show activity active against MCF-7 cell lines, indicating potential application as an anti-tumor agent.
AB - Cleavage of the known ruthenium dimer [RuCl2(η6-C6H5OCH2CH2OH)]2(1), bearing a hydrophilic substituent on the η6 coordinated aromatic ring, with the phosphine ligands: triphenyl phosphine, triphenyl phosphite, trimethyl phosphite, and 1,3,5-triaza-7-phosphaadamantane (PTA) afforded the known complexes [RuCl2(η6-C6H5OCH2CH2OH)(PPh3)] (2a), [RuCl2(η6-C6H5OCH2CH2OH){P(OPh)3}] (2b), [RuCl2(η6-C6H5OCH2CH2OH){P(OMe3)}] (2c), and [RuCl2 (η6-C6H5OCH2CH2OH)(PTA)] (4). The reaction of the known complex 2a with SnCl2afforded, by facile insertion of the SnCl2moiety into the Ru-Cl bond, the novel complex [RuCl(η6-C6H5OCH2CH2OH)(PPh3)(SnCl3)] (3a). Similarly, the reaction of complex 2b with SnCl2afforded the novel complex [RuCl(η6-C6H5OCH2CH2OH){P(OPh)3}(SnCl3)] (3b). Complexes 3a and 3b were fully characterized by spectroscopy (Infrared (IR) -spectroscopy, 1H, 31P and 119Sn Nuclear Magnetic Resonance (NMR) spectroscopy, UV-Vis spectroscopy and high resolution ESI-MS) and their thermal behaviour elucidated by Thermogravimetric Analysis (TGA). Density Functional Theory (DFT) calculations (Level of theory B3LYP, basis set for H, C, P, O, N and Cl is 6-31+G(d,p) and for Ru and Sn is DGDZVP) for complex 3a, 3b and 4 were also carried out, in particular to elucidate the bonding situation between Ru and Sn in complexes. The hitherto unprecedented anti-cancer activity of the complexes 2a – 2c as well as the novel stannyl complexes 3a and 3b were evaluated against MCF-7 (oestrogen receptor positive) human breast adenocarcinoma cell lines. All complexes show activity active against MCF-7 cell lines, indicating potential application as an anti-tumor agent.
KW - Ruthenium
KW - Solubility
KW - Stannyl ligands
KW - Arene
KW - Anti-cancer
KW - MCF-7 human breast adenocarcinoma cells
KW - CYTOTOXICITY
KW - CISPLATIN
U2 - 10.1016/j.jorganchem.2019.04.002
DO - 10.1016/j.jorganchem.2019.04.002
M3 - Article
SN - 0022-328X
VL - 891
SP - 12
EP - 19
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
ER -