Organometallic Half-Sandwich Iridium Anticancer Complexes

The low-spin 5d6 IrIII organometallic half-sandwich complexes [(η5-Cpx)Ir(XY)Cl]0/+, Cpx = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cpxph), or tetramethyl(biphenyl)cyclopentadienyl (Cpxbiph), XY = 1,10-phenanthroline (4−6), 2,2′-bipyridine (7−9), ethylenediamine (10 and 11), or picolinate (12−14),...

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Published inJournal of medicinal chemistry Vol. 54; no. 8; pp. 3011 - 3026
Main Authors Liu, Zhe, Habtemariam, Abraha, Pizarro, Ana M, Fletcher, Sally A, Kisova, Anna, Vrana, Oldrich, Salassa, Luca, Bruijnincx, Pieter C. A, Clarkson, Guy J, Brabec, Viktor, Sadler, Peter J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.04.2011
Amer Chemical Soc
Subjects
Cell Line, Tumor
Chemistry, Medicinal
Drug Screening Assays, Antitumor
Female
Humans
Iridium - chemistry
Life Sciences & Biomedicine
Models, Molecular
Organometallic Compounds - chemistry
Organometallic Compounds - pharmacology
Pharmacology & Pharmacy
Science & Technology
(ETA-PENTAMETHYLCYCLOPENTADIENYL)IRIDIUM(III) COMPLEXES
RUTHENIUM(II) ARENE COMPLEXES
N-HETEROCYCLIC CARBENE
MOLECULAR CALCULATIONS
CYCLOMETALATED IRIDIUM(III)
DNA-BINDING PROPERTIES
LIGAND SUBSTITUTION-REACTIONS
ANTITUMOR COMPLEXES
PLATINUM COMPLEXES
METAL-COMPLEXES
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Abstract The low-spin 5d6 IrIII organometallic half-sandwich complexes [(η5-Cpx)Ir(XY)Cl]0/+, Cpx = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cpxph), or tetramethyl(biphenyl)cyclopentadienyl (Cpxbiph), XY = 1,10-phenanthroline (4−6), 2,2′-bipyridine (7−9), ethylenediamine (10 and 11), or picolinate (12−14), hydrolyze rapidly. Complexes with N,N-chelating ligands readily form adducts with 9-ethylguanine but not 9-ethyladenine; picolinate complexes bind to both purines. Cytotoxic potency toward A2780 human ovarian cancer cells increases with phenyl substitution on Cp*: Cpxbiph > Cpxph > Cp*; Cpxbiph complexes 6 and 9 have submicromolar activity. Guanine residues are preferential binding sites for 4−6 on plasmid DNA. Hydrophobicity (log P), cell and nucleus accumulation of Ir correlate with cytotoxicity, 6 > 5 > 4; they distribute similarly within cells. The ability to displace DNA intercalator ethidium bromide from DNA correlates with cytotoxicity and viscosity of Ir−DNA adducts. The hydrophobicity and intercalative ability of Cpxph and Cpxbiph make a major contribution to the anticancer potency of their IrIII complexes.
AbstractList The low-spin 5d(6) Ir(III) organometallic half-sandwich complexes [(η(5)-Cp(x))Ir(XY)Cl](0/+), Cp(x) = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cp(xph)), or tetramethyl(biphenyl)cyclopentadienyl (Cp(xbiph)), XY = 1,10-phenanthroline (4-6), 2,2'-bipyridine (7-9), ethylenediamine (10 and 11), or picolinate (12-14), hydrolyze rapidly. Complexes with N,N-chelating ligands readily form adducts with 9-ethylguanine but not 9-ethyladenine; picolinate complexes bind to both purines. Cytotoxic potency toward A2780 human ovarian cancer cells increases with phenyl substitution on Cp*: Cp(xbiph) > Cp(xph) > Cp*; Cp(xbiph) complexes 6 and 9 have submicromolar activity. Guanine residues are preferential binding sites for 4-6 on plasmid DNA. Hydrophobicity (log P), cell and nucleus accumulation of Ir correlate with cytotoxicity, 6 > 5 > 4; they distribute similarly within cells. The ability to displace DNA intercalator ethidium bromide from DNA correlates with cytotoxicity and viscosity of Ir-DNA adducts. The hydrophobicity and intercalative ability of Cp(xph) and Cp(xbiph) make a major contribution to the anticancer potency of their Ir(III) complexes.
The low-spin 5d(6) Ir-III organometallic half-sandwich complexes [(eta(5)-Cp-x)Ir(XY)Cl](0/+), Cp-x = Cp*, tetramethyl(phenyl, cyclopentadienyl (Cp-xph), or tetramethyl(biphenyl)-cyclopertadienyl (Cp-xbiph), XY = 1,10-phenanthroline (4-6), 2,2'-bipyridine (7-9), ethylenediamine (10 and 11), or picolinate (12-14), hydrolyze rapidly. Complexes with N,N-chelating ligands readily form adducts with 9-ethylguanine but not 9-ethyladenine; picolinate complexes bind to both purines. Cytotoxic potency toward A2780 human ovarian cancer cells increases with phenyl substitution on Cp*: Cp-xbiph > Cp-xph > Cp*; Cp-xbiph complexes 6 and 9 have submicromolar activity. Guanine residues are preferential binding sites for 4-6 on plasmid DNA. Hydrophobicity (log P), cell and nucleus accumulation of Ir correlate with cytotoxicity, 6 > 5 > 4, they:distribute similarly within cells. The ability to displace DNA intercalator ethidium bromide from DNA correlates with cytotoxicity and viscosity of Ir DNA adducts. The hydrophobicity and intercalative ability of Cp-xph and Cp-xbiph male a major contribution to the anticancer potency of their Ir-III complexes.
The low-spin 5d(6) Ir(III) organometallic half-sandwich complexes [(η(5)-Cp(x))Ir(XY)Cl](0/+), Cp(x) = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cp(xph)), or tetramethyl(biphenyl)cyclopentadienyl (Cp(xbiph)), XY = 1,10-phenanthroline (4-6), 2,2'-bipyridine (7-9), ethylenediamine (10 and 11), or picolinate (12-14), hydrolyze rapidly. Complexes with N,N-chelating ligands readily form adducts with 9-ethylguanine but not 9-ethyladenine; picolinate complexes bind to both purines. Cytotoxic potency toward A2780 human ovarian cancer cells increases with phenyl substitution on Cp*: Cp(xbiph) > Cp(xph) > Cp*; Cp(xbiph) complexes 6 and 9 have submicromolar activity. Guanine residues are preferential binding sites for 4-6 on plasmid DNA. Hydrophobicity (log P), cell and nucleus accumulation of Ir correlate with cytotoxicity, 6 > 5 > 4; they distribute similarly within cells. The ability to displace DNA intercalator ethidium bromide from DNA correlates with cytotoxicity and viscosity of Ir-DNA adducts. The hydrophobicity and intercalative ability of Cp(xph) and Cp(xbiph) make a major contribution to the anticancer potency of their Ir(III) complexes.The low-spin 5d(6) Ir(III) organometallic half-sandwich complexes [(η(5)-Cp(x))Ir(XY)Cl](0/+), Cp(x) = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cp(xph)), or tetramethyl(biphenyl)cyclopentadienyl (Cp(xbiph)), XY = 1,10-phenanthroline (4-6), 2,2'-bipyridine (7-9), ethylenediamine (10 and 11), or picolinate (12-14), hydrolyze rapidly. Complexes with N,N-chelating ligands readily form adducts with 9-ethylguanine but not 9-ethyladenine; picolinate complexes bind to both purines. Cytotoxic potency toward A2780 human ovarian cancer cells increases with phenyl substitution on Cp*: Cp(xbiph) > Cp(xph) > Cp*; Cp(xbiph) complexes 6 and 9 have submicromolar activity. Guanine residues are preferential binding sites for 4-6 on plasmid DNA. Hydrophobicity (log P), cell and nucleus accumulation of Ir correlate with cytotoxicity, 6 > 5 > 4; they distribute similarly within cells. The ability to displace DNA intercalator ethidium bromide from DNA correlates with cytotoxicity and viscosity of Ir-DNA adducts. The hydrophobicity and intercalative ability of Cp(xph) and Cp(xbiph) make a major contribution to the anticancer potency of their Ir(III) complexes.
The low-spin 5d6 IrIII organometallic half-sandwich complexes [(η5-Cpx)Ir(XY)Cl]0/+, Cpx = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cpxph), or tetramethyl(biphenyl)cyclopentadienyl (Cpxbiph), XY = 1,10-phenanthroline (4−6), 2,2′-bipyridine (7−9), ethylenediamine (10 and 11), or picolinate (12−14), hydrolyze rapidly. Complexes with N,N-chelating ligands readily form adducts with 9-ethylguanine but not 9-ethyladenine; picolinate complexes bind to both purines. Cytotoxic potency toward A2780 human ovarian cancer cells increases with phenyl substitution on Cp*: Cpxbiph > Cpxph > Cp*; Cpxbiph complexes 6 and 9 have submicromolar activity. Guanine residues are preferential binding sites for 4−6 on plasmid DNA. Hydrophobicity (log P), cell and nucleus accumulation of Ir correlate with cytotoxicity, 6 > 5 > 4; they distribute similarly within cells. The ability to displace DNA intercalator ethidium bromide from DNA correlates with cytotoxicity and viscosity of Ir−DNA adducts. The hydrophobicity and intercalative ability of Cpxph and Cpxbiph make a major contribution to the anticancer potency of their IrIII complexes.
Author Liu, Zhe
Kisova, Anna
Habtemariam, Abraha
Fletcher, Sally A
Brabec, Viktor
Pizarro, Ana M
Clarkson, Guy J
Sadler, Peter J
Vrana, Oldrich
Salassa, Luca
Bruijnincx, Pieter C. A
AuthorAffiliation Academy of Sciences of the Czech Republic
University of Warwick
AuthorAffiliation_xml – name: University of Warwick
– name: Academy of Sciences of the Czech Republic
Author_xml – sequence: 1
  givenname: Zhe
  surname: Liu
  fullname: Liu, Zhe
– sequence: 2
  givenname: Abraha
  surname: Habtemariam
  fullname: Habtemariam, Abraha
– sequence: 3
  givenname: Ana M
  surname: Pizarro
  fullname: Pizarro, Ana M
– sequence: 4
  givenname: Sally A
  surname: Fletcher
  fullname: Fletcher, Sally A
– sequence: 5
  givenname: Anna
  surname: Kisova
  fullname: Kisova, Anna
– sequence: 6
  givenname: Oldrich
  surname: Vrana
  fullname: Vrana, Oldrich
– sequence: 7
  givenname: Luca
  surname: Salassa
  fullname: Salassa, Luca
– sequence: 8
  givenname: Pieter C. A
  surname: Bruijnincx
  fullname: Bruijnincx, Pieter C. A
– sequence: 9
  givenname: Guy J
  surname: Clarkson
  fullname: Clarkson, Guy J
– sequence: 10
  givenname: Viktor
  surname: Brabec
  fullname: Brabec, Viktor
– sequence: 11
  givenname: Peter J
  surname: Sadler
  fullname: Sadler, Peter J
  email: p.j.sadler@warwick.ac.uk
BackLink https://www.ncbi.nlm.nih.gov/pubmed/21443199$$D View this record in MEDLINE/PubMed
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RUTHENIUM(II) ARENE COMPLEXES
N-HETEROCYCLIC CARBENE
MOLECULAR CALCULATIONS
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SSID ssj0003123
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Snippet The low-spin 5d6 IrIII organometallic half-sandwich complexes [(η5-Cpx)Ir(XY)Cl]0/+, Cpx = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cpxph), or...
The low-spin 5d(6) Ir-III organometallic half-sandwich complexes [(eta(5)-Cp-x)Ir(XY)Cl](0/+), Cp-x = Cp*, tetramethyl(phenyl, cyclopentadienyl (Cp-xph), or...
The low-spin 5d(6) Ir(III) organometallic half-sandwich complexes [(η(5)-Cp(x))Ir(XY)Cl](0/+), Cp(x) = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cp(xph)), or...
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SubjectTerms Cell Line, Tumor
Chemistry, Medicinal
Drug Screening Assays, Antitumor
Female
Humans
Iridium - chemistry
Life Sciences & Biomedicine
Models, Molecular
Organometallic Compounds - chemistry
Organometallic Compounds - pharmacology
Pharmacology & Pharmacy
Science & Technology
Title Organometallic Half-Sandwich Iridium Anticancer Complexes
URI http://dx.doi.org/10.1021/jm2000932
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