Influence of the π-coordinated arene on the anticancer activity of ruthenium(II) carbohydrate organometallic complexes

Muhammad Hanif; Samuel Matthias Meier; Alexey A. Nazarov; Julie Risse; Anton Legin; Angela Casini; Michael Jakupec; Bernhard Keppler; Christian G. Hartinger

doi:10.3389/fchem.2013.00027

Influence of the π-coordinated arene on the anticancer activity of ruthenium(II) carbohydrate organometallic complexes

Muhammad Hanif, Samuel Matthias Meier, Alexey A. Nazarov, Julie Risse, Anton Legin, Angela Casini, Michael Jakupec, Bernhard Keppler, Christian G. Hartinger

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

The synthesis and in vitro cytotoxicity of a series of RuII(arene) complexes with carbohydrate-derived phosphite ligands and various arene co-ligands is described. The arene ligand has a strong influence on the in vitro anticancer activity of this series of compounds, which correlates fairly well with cellular accumulation. The most lipophilic compound bearing a biphenyl moiety and a cyclohexylidene-protected carbohydrate is the most cytotoxic with unprecedented IC50 values for the compound class in three human cancer cell lines. This compound shows reactivity to the DNA model nucleobase 9-ethylguanine, but does not alter the secondary structure of plasmid DNA, indicating that other biological targets are responsible for its cytotoxic effect.

Original language	English
Article number	27
Journal	Frontiers in Chemistry
Volume	1
DOIs	https://doi.org/10.3389/fchem.2013.00027
Publication status	Published - 31 Oct 2013

Austrian Fields of Science 2012

104003 Inorganic chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3389/fchem.2013.00027Licence: CC BY 3.0

http://phaidra.univie.ac.at/o:502503Licence: CC BY 3.0

Cite this

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title = "Influence of the π-coordinated arene on the anticancer activity of ruthenium(II) carbohydrate organometallic complexes",

abstract = "The synthesis and in vitro cytotoxicity of a series of RuII(arene) complexes with carbohydrate-derived phosphite ligands and various arene co-ligands is described. The arene ligand has a strong influence on the in vitro anticancer activity of this series of compounds, which correlates fairly well with cellular accumulation. The most lipophilic compound bearing a biphenyl moiety and a cyclohexylidene-protected carbohydrate is the most cytotoxic with unprecedented IC50 values for the compound class in three human cancer cell lines. This compound shows reactivity to the DNA model nucleobase 9-ethylguanine, but does not alter the secondary structure of plasmid DNA, indicating that other biological targets are responsible for its cytotoxic effect.",

author = "Muhammad Hanif and Meier, {Samuel Matthias} and Nazarov, {Alexey A.} and Julie Risse and Anton Legin and Angela Casini and Michael Jakupec and Bernhard Keppler and Hartinger, {Christian G.}",

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T1 - Influence of the π-coordinated arene on the anticancer activity of ruthenium(II) carbohydrate organometallic complexes

AU - Hanif, Muhammad

AU - Meier, Samuel Matthias

AU - Nazarov, Alexey A.

AU - Risse, Julie

AU - Legin, Anton

AU - Casini, Angela

AU - Jakupec, Michael

AU - Keppler, Bernhard

AU - Hartinger, Christian G.

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N2 - The synthesis and in vitro cytotoxicity of a series of RuII(arene) complexes with carbohydrate-derived phosphite ligands and various arene co-ligands is described. The arene ligand has a strong influence on the in vitro anticancer activity of this series of compounds, which correlates fairly well with cellular accumulation. The most lipophilic compound bearing a biphenyl moiety and a cyclohexylidene-protected carbohydrate is the most cytotoxic with unprecedented IC50 values for the compound class in three human cancer cell lines. This compound shows reactivity to the DNA model nucleobase 9-ethylguanine, but does not alter the secondary structure of plasmid DNA, indicating that other biological targets are responsible for its cytotoxic effect.

AB - The synthesis and in vitro cytotoxicity of a series of RuII(arene) complexes with carbohydrate-derived phosphite ligands and various arene co-ligands is described. The arene ligand has a strong influence on the in vitro anticancer activity of this series of compounds, which correlates fairly well with cellular accumulation. The most lipophilic compound bearing a biphenyl moiety and a cyclohexylidene-protected carbohydrate is the most cytotoxic with unprecedented IC50 values for the compound class in three human cancer cell lines. This compound shows reactivity to the DNA model nucleobase 9-ethylguanine, but does not alter the secondary structure of plasmid DNA, indicating that other biological targets are responsible for its cytotoxic effect.

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DO - 10.3389/fchem.2013.00027

M3 - Article

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JO - Frontiers in Chemistry

JF - Frontiers in Chemistry

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