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 (Korresp. Autor*in), Dan Gibson (Korresp. Autor*in), Wolfgang Weigand (Korresp. Autor*in)

Institut für Anorganische Chemie

Veröffentlichungen: Beitrag in Fachzeitschrift › Artikel › Peer Reviewed

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.

Originalsprache	Englisch
Aufsatznummer	e202200695
Seitenumfang	11
Fachzeitschrift	Chemistry & Biodiversity
Jahrgang	19
Ausgabenummer	10
Frühes Online-Datum	26 Aug. 2022
DOIs	https://doi.org/10.1002/cbdv.202200695
Publikationsstatus	Veröffentlicht - Okt. 2022

ÖFOS 2012

104004 Chemische Biologie
104003 Anorganische Chemie

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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 = "lipoic acid, Pt(IV) prodrugs, multi-action, cyclovoltammetry, ROS, ALPHA-LIPOIC ACID, RAPID COLORIMETRIC ASSAY, BREAST-CANCER CELLS, ANTICANCER AGENTS, REDOX REGULATION, ANTIOXIDANT, PROLIFERATION, OXALIPLATIN, DERIVATIVES, GENERATION",

author = "Xiao Liu and Marie-Christin Barth 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",

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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

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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.

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