Modulation of the solubility properties of arene ruthenium complexes bearing stannyl ligands as potential anti-cancer agents

Clara Berg, Suviti Chari, Kaste Jurgaityte, Alice Laurora, Mateusz Naldony, Frances Pope, Dario Romano, Thato Medupe, Sharon Prince, Siyabonga Ngubane, Judith Baumgartner, Burgert Blom

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Cleavage of the known ruthenium dimer [RuCl 26 -C 6 H 5 OCH 2 CH 2 OH)] 2 (1), bearing a hydrophilic substituent on the η 6 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 [RuCl 26 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )] (2a), [RuCl 26 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }] (2b), [RuCl 26 -C 6 H 5 OCH 2 CH 2 OH){P(OMe 3 )}] (2c), and [RuCl 26 -C 6 H 5 OCH 2 CH 2 OH)(PTA)] (4). The reaction of the known complex 2a with SnCl 2 afforded, by facile insertion of the SnCl 2 moiety into the Ru[sbnd]Cl bond, the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )(SnCl 3 )] (3a). Similarly, the reaction of complex 2b with SnCl 2 afforded the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }(SnCl 3 )] (3b). Complexes 3a and 3b were fully characterized by spectroscopy (Infrared (IR) -spectroscopy, 1 H, 31 P and 119 Sn 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.

Original languageEnglish
Pages (from-to)12-19
Number of pages8
JournalJournal of organometallic chemistry
Volume891
Early online date2019
DOIs
Publication statusPublished - 1 Aug 2019

Fingerprint

phosphine
Bearings (structural)
Ruthenium
Solubility
ruthenium
Spectrum Analysis
trimethyl phosphite
solubility
cancer
Ligands
Cells
Modulation
Spectroscopy
methylidyne
modulation
ligands
Dimers
Nuclear magnetic resonance spectroscopy
Density functional theory
Thermogravimetric analysis

Keywords

  • Anti-cancer
  • Arene
  • MCF-7 human breast adenocarcinoma cells
  • Ruthenium
  • Solubility
  • Stannyl ligands

ASJC Scopus subject areas

  • Materials Chemistry
  • Biochemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Modulation of the solubility properties of arene ruthenium complexes bearing stannyl ligands as potential anti-cancer agents. / Berg, Clara; Chari, Suviti; Jurgaityte, Kaste; Laurora, Alice; Naldony, Mateusz; Pope, Frances; Romano, Dario; Medupe, Thato; Prince, Sharon; Ngubane, Siyabonga; Baumgartner, Judith; Blom, Burgert.

In: Journal of organometallic chemistry, Vol. 891, 01.08.2019, p. 12-19.

Research output: Contribution to journalArticleResearchpeer-review

Berg, C, Chari, S, Jurgaityte, K, Laurora, A, Naldony, M, Pope, F, Romano, D, Medupe, T, Prince, S, Ngubane, S, Baumgartner, J & Blom, B 2019, 'Modulation of the solubility properties of arene ruthenium complexes bearing stannyl ligands as potential anti-cancer agents' Journal of organometallic chemistry, vol. 891, pp. 12-19. https://doi.org/10.1016/j.jorganchem.2019.04.002
Berg, Clara ; Chari, Suviti ; Jurgaityte, Kaste ; Laurora, Alice ; Naldony, Mateusz ; Pope, Frances ; Romano, Dario ; Medupe, Thato ; Prince, Sharon ; Ngubane, Siyabonga ; Baumgartner, Judith ; Blom, Burgert. / Modulation of the solubility properties of arene ruthenium complexes bearing stannyl ligands as potential anti-cancer agents. In: Journal of organometallic chemistry. 2019 ; Vol. 891. pp. 12-19.
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abstract = "Cleavage of the known ruthenium dimer [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)] 2 (1), bearing a hydrophilic substituent on the η 6 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 [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )] (2a), [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }] (2b), [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OMe 3 )}] (2c), and [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)(PTA)] (4). The reaction of the known complex 2a with SnCl 2 afforded, by facile insertion of the SnCl 2 moiety into the Ru[sbnd]Cl bond, the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )(SnCl 3 )] (3a). Similarly, the reaction of complex 2b with SnCl 2 afforded the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }(SnCl 3 )] (3b). Complexes 3a and 3b were fully characterized by spectroscopy (Infrared (IR) -spectroscopy, 1 H, 31 P and 119 Sn 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.",
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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

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N2 - Cleavage of the known ruthenium dimer [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)] 2 (1), bearing a hydrophilic substituent on the η 6 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 [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )] (2a), [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }] (2b), [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OMe 3 )}] (2c), and [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)(PTA)] (4). The reaction of the known complex 2a with SnCl 2 afforded, by facile insertion of the SnCl 2 moiety into the Ru[sbnd]Cl bond, the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )(SnCl 3 )] (3a). Similarly, the reaction of complex 2b with SnCl 2 afforded the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }(SnCl 3 )] (3b). Complexes 3a and 3b were fully characterized by spectroscopy (Infrared (IR) -spectroscopy, 1 H, 31 P and 119 Sn 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 [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)] 2 (1), bearing a hydrophilic substituent on the η 6 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 [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )] (2a), [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }] (2b), [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OMe 3 )}] (2c), and [RuCl 2 (η 6 -C 6 H 5 OCH 2 CH 2 OH)(PTA)] (4). The reaction of the known complex 2a with SnCl 2 afforded, by facile insertion of the SnCl 2 moiety into the Ru[sbnd]Cl bond, the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH)(PPh 3 )(SnCl 3 )] (3a). Similarly, the reaction of complex 2b with SnCl 2 afforded the novel complex [RuCl(η 6 -C 6 H 5 OCH 2 CH 2 OH){P(OPh) 3 }(SnCl 3 )] (3b). Complexes 3a and 3b were fully characterized by spectroscopy (Infrared (IR) -spectroscopy, 1 H, 31 P and 119 Sn 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 - Anti-cancer

KW - Arene

KW - MCF-7 human breast adenocarcinoma cells

KW - Ruthenium

KW - Solubility

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