Oxoplatin-Based Pt(IV) Lipoate Complexes and Their Biological Activity

Xiao Liu; Marie Christin Barth; Klaudia Cseh; Christian R. Kowol; Michael A. Jakupec; Bernhard K. Keppler; Dan Gibson; Wolfgang Weigand

doi:10.1002/cbdv.202200695

Oxoplatin-Based Pt(IV) Lipoate Complexes and Their Biological Activity

Xiao Liu, Marie Christin Barth, Klaudia Cseh, Christian R. Kowol, Michael A. Jakupec, Bernhard K. Keppler^*, Dan Gibson^*, Wolfgang Weigand^*

^*Corresponding author for this work

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

α-Lipoic acid, known for its anti-inflammatory and antioxidant activity, represents a promising ligand for Pt(IV) prodrugs. Three new Pt(IV) lipoate complexes were synthesized and characterized by NMR spectroscopy (¹H, ¹³C, ¹⁹⁵Pt), mass spectrometry and elemental analysis. Due to the low solubility of the complex containing two axial lipoate ligands, further experiments to examine the biological activity were performed with two Pt(IV) complexes containing just one axial lipoate ligand. Both complexes exhibit anticancer activity and produce reactive oxygen species (ROS) in the cell lines tested. Especially, the monosubstituted complex can be reduced by ascorbic acid and forms adducts with 9-methylguanine (9MeG), which is favorable for the formation of DNA-crosslinks in the cells.

Original language	English
Article number	e202200695
Journal	Chemistry and Biodiversity
Volume	19
Issue number	10
DOIs	https://doi.org/10.1002/cbdv.202200695
State	Published - Oct 2022

Bibliographical note

Publisher Copyright:
© 2022 The Authors. Chemistry & Biodiversity published by Wiley-VHCA AG, Zurich, Switzerland.

Keywords

cyclovoltammetry
lipoic acid
multi-action
Pt(IV) prodrugs
ROS

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

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10.1002/cbdv.202200695

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title = "Oxoplatin-Based Pt(IV) Lipoate Complexes and Their Biological Activity",

abstract = "α-Lipoic acid, known for its anti-inflammatory and antioxidant activity, represents a promising ligand for Pt(IV) prodrugs. Three new Pt(IV) lipoate complexes were synthesized and characterized by NMR spectroscopy (1H, 13C, 195Pt), mass spectrometry and elemental analysis. Due to the low solubility of the complex containing two axial lipoate ligands, further experiments to examine the biological activity were performed with two Pt(IV) complexes containing just one axial lipoate ligand. Both complexes exhibit anticancer activity and produce reactive oxygen species (ROS) in the cell lines tested. Especially, the monosubstituted complex can be reduced by ascorbic acid and forms adducts with 9-methylguanine (9MeG), which is favorable for the formation of DNA-crosslinks in the cells.",

keywords = "cyclovoltammetry, lipoic acid, multi-action, Pt(IV) prodrugs, ROS",

author = "Xiao Liu and Barth, {Marie Christin} and Klaudia Cseh and Kowol, {Christian R.} and Jakupec, {Michael A.} and Keppler, {Bernhard K.} and Dan Gibson and Wolfgang Weigand",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors. Chemistry & Biodiversity published by Wiley-VHCA AG, Zurich, Switzerland.",

year = "2022",

month = oct,

doi = "10.1002/cbdv.202200695",

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AU - Liu, Xiao

AU - Barth, Marie Christin

AU - Cseh, Klaudia

AU - Kowol, Christian R.

AU - Jakupec, Michael A.

AU - Keppler, Bernhard K.

AU - Gibson, Dan

AU - Weigand, Wolfgang

PY - 2022/10

Y1 - 2022/10

N2 - α-Lipoic acid, known for its anti-inflammatory and antioxidant activity, represents a promising ligand for Pt(IV) prodrugs. Three new Pt(IV) lipoate complexes were synthesized and characterized by NMR spectroscopy (1H, 13C, 195Pt), mass spectrometry and elemental analysis. Due to the low solubility of the complex containing two axial lipoate ligands, further experiments to examine the biological activity were performed with two Pt(IV) complexes containing just one axial lipoate ligand. Both complexes exhibit anticancer activity and produce reactive oxygen species (ROS) in the cell lines tested. Especially, the monosubstituted complex can be reduced by ascorbic acid and forms adducts with 9-methylguanine (9MeG), which is favorable for the formation of DNA-crosslinks in the cells.

AB - α-Lipoic acid, known for its anti-inflammatory and antioxidant activity, represents a promising ligand for Pt(IV) prodrugs. Three new Pt(IV) lipoate complexes were synthesized and characterized by NMR spectroscopy (1H, 13C, 195Pt), mass spectrometry and elemental analysis. Due to the low solubility of the complex containing two axial lipoate ligands, further experiments to examine the biological activity were performed with two Pt(IV) complexes containing just one axial lipoate ligand. Both complexes exhibit anticancer activity and produce reactive oxygen species (ROS) in the cell lines tested. Especially, the monosubstituted complex can be reduced by ascorbic acid and forms adducts with 9-methylguanine (9MeG), which is favorable for the formation of DNA-crosslinks in the cells.

KW - cyclovoltammetry

KW - lipoic acid

KW - multi-action

KW - Pt(IV) prodrugs

KW - ROS

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ER -

Oxoplatin-Based Pt(IV) Lipoate Complexes and Their Biological Activity

Abstract

Bibliographical note

Keywords

UN SDGs

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