Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

Melanie Schmidlehner; Verena Pichler; Alexander Roller; Michael A. Jakupec; Wolfgang Kandioller; Bernhard K. Keppler

doi:10.1016/j.jorganchem.2014.10.044

Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

Melanie Schmidlehner, Verena Pichler, Alexander Roller, Michael A. Jakupec, Wolfgang Kandioller (Corresponding author), Bernhard K. Keppler

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Abstract Organometallic complexes with (thio)pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio)pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by ¹H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay.

Original language	English
Pages (from-to)	69-76
Number of pages	8
Journal	Journal of Organometallic Chemistry
Volume	782
DOIs	https://doi.org/10.1016/j.jorganchem.2014.10.044
Publication status	Published - 15 Apr 2015

Austrian Fields of Science 2012

104003 Inorganic chemistry
104015 Organic chemistry

Keywords

Organometallic chemistry
Ruthenium
Rhodium
Half-sandwich complexes
Pyrones
Thiopyrones
METAL ANTICANCER COMPLEXES
IN-VITRO
IRON CHELATORS
RUTHENIUM
DRUGS
BINDING
MALTOL
TRICHLORIDE
THIOPYRONE
PRODRUGS

UN SDGs

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

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10.1016/j.jorganchem.2014.10.044

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title = "Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations",

abstract = "Abstract Organometallic complexes with (thio)pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio)pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by 1H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay. ",

keywords = "Organometallic chemistry, Ruthenium, Rhodium, Half-sandwich complexes, Pyrones, Thiopyrones, METAL ANTICANCER COMPLEXES, IN-VITRO, IRON CHELATORS, RUTHENIUM, DRUGS, BINDING, MALTOL, TRICHLORIDE, THIOPYRONE, PRODRUGS",

author = "Melanie Schmidlehner and Verena Pichler and Alexander Roller and Jakupec, {Michael A.} and Wolfgang Kandioller and Keppler, {Bernhard K.}",

year = "2015",

month = apr,

day = "15",

doi = "10.1016/j.jorganchem.2014.10.044",

language = "English",

volume = "782",

pages = "69--76",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier Procedia Computer Science",

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TY - JOUR

T1 - Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

AU - Schmidlehner, Melanie

AU - Pichler, Verena

AU - Roller, Alexander

AU - Jakupec, Michael A.

AU - Kandioller, Wolfgang

AU - Keppler, Bernhard K.

PY - 2015/4/15

Y1 - 2015/4/15

N2 - Abstract Organometallic complexes with (thio)pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio)pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by 1H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay.

AB - Abstract Organometallic complexes with (thio)pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio)pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by 1H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay.

KW - Organometallic chemistry

KW - Ruthenium

KW - Rhodium

KW - Half-sandwich complexes

KW - Pyrones

KW - Thiopyrones

KW - METAL ANTICANCER COMPLEXES

KW - IN-VITRO

KW - IRON CHELATORS

KW - RUTHENIUM

KW - DRUGS

KW - BINDING

KW - MALTOL

KW - TRICHLORIDE

KW - THIOPYRONE

KW - PRODRUGS

UR - http://www.scopus.com/inward/record.url?scp=84925664172&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2014.10.044

DO - 10.1016/j.jorganchem.2014.10.044

M3 - Article

SN - 0022-328X

VL - 782

SP - 69

EP - 76

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

Abstract

Austrian Fields of Science 2012

Keywords

UN SDGs

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