Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations

Janos P. Meszaros; Heiko Geisler; Jelena M. Poljarevic; Alexander Roller; Maria S. Legina; Michaela Hejl; Michael A. Jakupec; Bernhard K. Keppler; Wolfgang Kandioller; Eva A. Enyedy

doi:10.1016/j.jorganchem.2019.121070

Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations

Janos P. Meszaros, Heiko Geisler, Jelena M. Poljarevic, Alexander Roller, Maria S. Legina, Michaela Hejl, Michael A. Jakupec, Bernhard K. Keppler, Wolfgang Kandioller, Eva A. Enyedy (Corresponding author)

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Abstract

Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values. (C) 2019 Elsevier B.V. All rights reserved.

Original language	English
Article number	121070
Number of pages	10
Journal	Journal of Organometallic Chemistry
Volume	907
DOIs	https://doi.org/10.1016/j.jorganchem.2019.121070
Publication status	Published - 1 Feb 2020
Event	9th International Symposium on Bioorganometallic Chemistry (ISBOMC) - York, United Kingdom Duration: 28 Jul 2019 → 1 Aug 2019

Austrian Fields of Science 2012

104003 Inorganic chemistry
104015 Organic chemistry

Keywords

Solution stability
X-ray crystal structures
Cytotoxicity
Natural ligands
Half-sandwich complexes
RUTHENIUM(II)-ARENE COMPLEXES
BIOLOGICAL EVALUATION
ANTICANCER
DERIVATIVES
1,4-NAPHTHOQUINONE
CANCER
AGENTS
CONSTANTS
DRUGS

UN SDGs

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

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10.1016/j.jorganchem.2019.121070

Cite this

Meszaros, J. P., Geisler, H., Poljarevic, J. M., Roller, A., Legina, M. S., Hejl, M., Jakupec, M. A., Keppler, B. K., Kandioller, W., & Enyedy, E. A. (2020). Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations. Journal of Organometallic Chemistry, 907, Article 121070. https://doi.org/10.1016/j.jorganchem.2019.121070

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abstract = "Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values. (C) 2019 Elsevier B.V. All rights reserved.",

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author = "Meszaros, {Janos P.} and Heiko Geisler and Poljarevic, {Jelena M.} and Alexander Roller and Legina, {Maria S.} and Michaela Hejl and Jakupec, {Michael A.} and Keppler, {Bernhard K.} and Wolfgang Kandioller and Enyedy, {Eva A.}",

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doi = "10.1016/j.jorganchem.2019.121070",

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AU - Meszaros, Janos P.

AU - Geisler, Heiko

AU - Poljarevic, Jelena M.

AU - Roller, Alexander

AU - Legina, Maria S.

AU - Hejl, Michaela

AU - Jakupec, Michael A.

AU - Keppler, Bernhard K.

AU - Kandioller, Wolfgang

AU - Enyedy, Eva A.

PY - 2020/2/1

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N2 - Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values. (C) 2019 Elsevier B.V. All rights reserved.

AB - Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values. (C) 2019 Elsevier B.V. All rights reserved.

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KW - X-ray crystal structures

KW - Cytotoxicity

KW - Natural ligands

KW - Half-sandwich complexes

KW - RUTHENIUM(II)-ARENE COMPLEXES

KW - BIOLOGICAL EVALUATION

KW - ANTICANCER

KW - DERIVATIVES

KW - 1,4-NAPHTHOQUINONE

KW - CANCER

KW - AGENTS

KW - CONSTANTS

KW - DRUGS

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U2 - 10.1016/j.jorganchem.2019.121070

DO - 10.1016/j.jorganchem.2019.121070

M3 - Article

SN - 0022-328X

VL - 907

JO - Journal of Organometallic Chemistry

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M1 - 121070

T2 - 9th International Symposium on Bioorganometallic Chemistry (ISBOMC)

Y2 - 28 July 2019 through 1 August 2019

ER -

Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations

Abstract

Austrian Fields of Science 2012

Keywords

UN SDGs

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