publication . Article . Other literature type . 2015

Contrasting anticancer activity of half-sandwich iridium(III) complexes bearing functionally diverse 2-phenylpyridine ligands

Millett, Adam J.; Habtemariam, Abraha; Romero-Canelón, Isolda; Clarkson, Guy J.; Sadler, Peter J.;
Open Access English
  • Published: 01 Mar 2015 Journal: Organometallics, volume 34, issue 11, pages 2,683-2,694 (issn: 0276-7333, eissn: 1520-6041, Copyright policy)
  • Publisher: American Chemical Society
Abstract
We report the synthesis, characterization, and antiproliferative activity of 15 iridium(III) half-sandwich complexes of the type [(η5-Cp*)Ir(2-(R′-phenyl)-R-pyridine)Cl] bearing either an electron-donating (−OH, −CH2OH, −CH3) or electron-withdrawing (−F, −CHO, −NO2) group at various positions on the 2-phenylpyridine (2-PhPy) chelating ligand giving rise to six sets of structural isomers. The X-ray crystal structures of [(η5-Cp*)Ir(2-(2′-fluorophenyl)pyridine)Cl] (1) and [(η5-Cp*)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) exhibit the expected “piano-stool” configuration. DFT calculations showed that substituents caused only localized effects on the electrostatic pote...
Subjects
free text keywords: Q1, QD, Article
Funded by
EC| BIOINCMED
Project
BIOINCMED
Bioinorganic Chemistry for the Design of New Medicines
  • Funder: European Commission (EC)
  • Project Code: 247450
  • Funding stream: FP7 | SP2 | ERC
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Novohradsky V.; Liu Z.; Vojtiskova M.; Sadler P. J.; Brabec V.; Kasparkova J.Metallomics 2014, 6, 682–690.24448555 [PubMed]

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a Adamo C.; Barone V.J. Chem. Phys.1999, 110, 6158–6170.

Frisch M. J.; Trucks G. W.; Schlegel H. B.; Scuseria G. E.; Robb M. A.; C J. R.; Montgomery J. A.Jr.; Vreven T.; Kudin K. N.; B J. C.; Millam J. M.; Iyengar S. S.; Tomasi J.; Barone V.; M B.; Cossi M.; Scalmani G.; Rega N.; Petersson G. A.; N H.; Hada M.; Ehara M.; Toyota K.; Fukuda R.; H J.; Ishida M.; Nakajima T.; Honda Y.; Kitao O.; Nakai H.; K M.; Li X.; Knox J. E.; Hratchian H. P.; Cross J. B.; Bakken V.; A C.; Jaramillo J.; Gomperts R.; Stratmann R. E.; Yazyev O.; A A. J.; Cammi R.; Pomelli C.; Ochterski J. W.; Ayala P. Y.; M K.; Voth G. A.; Salvador P.; Dannenberg J. J.; Zakrzewski V. G.; D S.; Daniels A. D.; Strain M. C.; Farkas O.; M D. K.; Rabuck A. D.; Raghavachari K.; Foresman J. B.; O J. V.; Cui Q.; Baboul A. G.; Clifford S.; Cioslowski J.; S B. B.; Liu G.; Liashenko A.; Piskorz P.; Komaromi I.; M R. L.; Fox D. J.; Keith T.; Al-Laham M. A.; Peng C. Y.; N A.; Challacombe M.; Gill P. M. W.; Johnson B.; C W.; Wong M. W.; Gonzalez C.; Pople J. A.Gaussian 03, Revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.

40 references, page 1 of 3
Similar Outcomes
13 research outcomes, page 1 of 2
13 research outcomes, page 1 of 2
Abstract
We report the synthesis, characterization, and antiproliferative activity of 15 iridium(III) half-sandwich complexes of the type [(η5-Cp*)Ir(2-(R′-phenyl)-R-pyridine)Cl] bearing either an electron-donating (−OH, −CH2OH, −CH3) or electron-withdrawing (−F, −CHO, −NO2) group at various positions on the 2-phenylpyridine (2-PhPy) chelating ligand giving rise to six sets of structural isomers. The X-ray crystal structures of [(η5-Cp*)Ir(2-(2′-fluorophenyl)pyridine)Cl] (1) and [(η5-Cp*)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) exhibit the expected “piano-stool” configuration. DFT calculations showed that substituents caused only localized effects on the electrostatic pote...
Subjects
free text keywords: Q1, QD, Article
Funded by
EC| BIOINCMED
Project
BIOINCMED
Bioinorganic Chemistry for the Design of New Medicines
  • Funder: European Commission (EC)
  • Project Code: 247450
  • Funding stream: FP7 | SP2 | ERC
40 references, page 1 of 3

a Garbutcheon-Singh K. B. G. M. P.; Harper B. W.; Krause-Heuer A. M.; Manohar M.; Orkey N.; Aldrich-Wright J. R.Curr. Top. Med. Chem.2011, 11, 521–542.21189131 [PubMed]

a Tripathy S. K.; De U.; Dehury N.; Pal S.; Kim H. S.; Patra S.Dalton Trans.2014, 43, 14546–14549.25160655 [PubMed]

a Novohradsky V.; Zerzankova L.; Stepankova J.; Kisova A.; Kostrhunova H.; Liu Z.; Sadler P. J.; Kasparkova J.; Brabec V.Metallomics 2014, 6, 1491–1501.24828756 [PubMed]

a Liu Z.; Habtemariam A.; Pizarro A. M.; Fletcher S. A.; Kisova A.; Vrana O.; Salassa L.; Bruijnincx P. C. A.; Clarkson G. J.; Brabec V.; Sadler P. J.J. Med. Chem.2011, 54, 3011–3026.21443199 [PubMed]

Liu Z.; Salassa L.; Habtemariam A.; Pizarro A. M.; Clarkson G. J.; Sadler P. J.Inorg. Chem.2011, 50, 5777–5783.21618978 [PubMed]

Wirth S.; Rohbogner C.; Cieslak M.; Kazmierczak-Baranska J.; Donevski S.; Nawrot B.; Lorenz I.-P.J. Biol. Inorg. Chem.2010, 15, 429–440.20091072 [PubMed]

Almodares Z.; Lucas S. J.; Crossley B. D.; Basri A. M.; Pask C. M.; Hebden A. J.; Phillips R. M.; McGowan P. C.Inorg. Chem.2014, 53, 727–736.24397747 [PubMed]

a Liu Z.; Deeth R. J.; Butler J. S.; Habtemariam A.; Newton M. E.; Sadler P. J.Angew. Chem., Int. Ed.2013, 52, 4194–4197.

Romero-Canelón I.; Sadler P. J.Inorg. Chem.2013, 52, 12276–12291.23879584 [PubMed]

Liu Z.; Romero-Canelón I.; Qamar B.; Hearn J. M.; Habtemariam A.; Barry N. P. E.; Pizarro A. M.; Clarkson G. J.; Sadler P. J.Angew. Chem., Int. Ed.2014, 53, 3941–3946.

a Ruiz J.; Rodriguez V.; Cutillas N.; Samper K. G.; Capdevila M.; Palacios O.; Espinosa A.Dalton Trans.2012, 41, 12847–12856.22983366 [PubMed]

Novohradsky V.; Liu Z.; Vojtiskova M.; Sadler P. J.; Brabec V.; Kasparkova J.Metallomics 2014, 6, 682–690.24448555 [PubMed]

Steunenberg P.; Ruggi A.; van den Berg N. S.; Buckle T.; Kuil J.; van Leeuwen F. W. B.; Velders A. H.Inorg. Chem.2012, 51, 2105–2114.22303934 [PubMed]

a Adamo C.; Barone V.J. Chem. Phys.1999, 110, 6158–6170.

Frisch M. J.; Trucks G. W.; Schlegel H. B.; Scuseria G. E.; Robb M. A.; C J. R.; Montgomery J. A.Jr.; Vreven T.; Kudin K. N.; B J. C.; Millam J. M.; Iyengar S. S.; Tomasi J.; Barone V.; M B.; Cossi M.; Scalmani G.; Rega N.; Petersson G. A.; N H.; Hada M.; Ehara M.; Toyota K.; Fukuda R.; H J.; Ishida M.; Nakajima T.; Honda Y.; Kitao O.; Nakai H.; K M.; Li X.; Knox J. E.; Hratchian H. P.; Cross J. B.; Bakken V.; A C.; Jaramillo J.; Gomperts R.; Stratmann R. E.; Yazyev O.; A A. J.; Cammi R.; Pomelli C.; Ochterski J. W.; Ayala P. Y.; M K.; Voth G. A.; Salvador P.; Dannenberg J. J.; Zakrzewski V. G.; D S.; Daniels A. D.; Strain M. C.; Farkas O.; M D. K.; Rabuck A. D.; Raghavachari K.; Foresman J. B.; O J. V.; Cui Q.; Baboul A. G.; Clifford S.; Cioslowski J.; S B. B.; Liu G.; Liashenko A.; Piskorz P.; Komaromi I.; M R. L.; Fox D. J.; Keith T.; Al-Laham M. A.; Peng C. Y.; N A.; Challacombe M.; Gill P. M. W.; Johnson B.; C W.; Wong M. W.; Gonzalez C.; Pople J. A.Gaussian 03, Revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.

40 references, page 1 of 3
Similar Outcomes
13 research outcomes, page 1 of 2
13 research outcomes, page 1 of 2
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publication . Article . Other literature type . 2015

Contrasting anticancer activity of half-sandwich iridium(III) complexes bearing functionally diverse 2-phenylpyridine ligands

Millett, Adam J.; Habtemariam, Abraha; Romero-Canelón, Isolda; Clarkson, Guy J.; Sadler, Peter J.;