Mono-carboxylated diaminedichloridoplatinum(IV) complexes - selective synthesis, characterization, and cytotoxicity

Verena Pichler; Seied Mojtaba Valiahdi; Michael Jakupec; Vladimir Arion; Mathea Sophia Galanski; Bernhard Keppler

doi:10.1039/c1dt10301f

Mono-carboxylated diaminedichloridoplatinum(IV) complexes - selective synthesis, characterization, and cytotoxicity

Verena Pichler, Seied Mojtaba Valiahdi, Michael Jakupec, Vladimir Arion, Mathea Sophia Galanski (Corresponding author), Bernhard Keppler

Department of Inorganic Chemistry

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

(OC-6-43)-Dichlorido(N,N-dimethyl-ethane-1,2-diamine)dihydroxidoplatinum(IV) could selectively be mono-carboxylated with succinic anhydride based on the steric hindrance caused by the two methyl groups of the equatorial ligand. Subsequent esterification of the uncoordinated carboxylic acid with alcohols of different lengths (methanol, butanol, hexanol and octanol) afforded the corresponding esters. The synthesized complexes were characterized in detail by elemental analysis, ESI-MS, multinuclear ((1)H, (13)C, (15)N and (195)Pt) NMR spectroscopy and in two cases by X-ray crystallography. Cytotoxicity of novel platinum(IV) compounds was investigated in four human cancer cell lines (CH1, A549, SW480 and SK-OV-3). Remarkably, the most lipophilic complexes showed IC(50) values down to the low micromolar or even nanomolar range.

Original language	English
Pages (from-to)	8187-8192
Number of pages	6
Journal	Dalton Transactions
Volume	40
Issue number	32
DOIs	https://doi.org/10.1039/c1dt10301f
Publication status	Published - 2011

Austrian Fields of Science 2012

104003 Inorganic chemistry

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10.1039/c1dt10301f

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title = "Mono-carboxylated diaminedichloridoplatinum(IV) complexes - selective synthesis, characterization, and cytotoxicity",

abstract = "(OC-6-43)-Dichlorido(N,N-dimethyl-ethane-1,2-diamine)dihydroxidoplatinum(IV) could selectively be mono-carboxylated with succinic anhydride based on the steric hindrance caused by the two methyl groups of the equatorial ligand. Subsequent esterification of the uncoordinated carboxylic acid with alcohols of different lengths (methanol, butanol, hexanol and octanol) afforded the corresponding esters. The synthesized complexes were characterized in detail by elemental analysis, ESI-MS, multinuclear ((1)H, (13)C, (15)N and (195)Pt) NMR spectroscopy and in two cases by X-ray crystallography. Cytotoxicity of novel platinum(IV) compounds was investigated in four human cancer cell lines (CH1, A549, SW480 and SK-OV-3). Remarkably, the most lipophilic complexes showed IC(50) values down to the low micromolar or even nanomolar range.",

author = "Verena Pichler and Valiahdi, {Seied Mojtaba} and Michael Jakupec and Vladimir Arion and Galanski, {Mathea Sophia} and Bernhard Keppler",

year = "2011",

doi = "10.1039/c1dt10301f",

language = "English",

volume = "40",

pages = "8187--8192",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "ROYAL SOC CHEMISTRY",

number = "32",

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TY - JOUR

T1 - Mono-carboxylated diaminedichloridoplatinum(IV) complexes - selective synthesis, characterization, and cytotoxicity

AU - Pichler, Verena

AU - Valiahdi, Seied Mojtaba

AU - Jakupec, Michael

AU - Arion, Vladimir

AU - Galanski, Mathea Sophia

AU - Keppler, Bernhard

PY - 2011

Y1 - 2011

N2 - (OC-6-43)-Dichlorido(N,N-dimethyl-ethane-1,2-diamine)dihydroxidoplatinum(IV) could selectively be mono-carboxylated with succinic anhydride based on the steric hindrance caused by the two methyl groups of the equatorial ligand. Subsequent esterification of the uncoordinated carboxylic acid with alcohols of different lengths (methanol, butanol, hexanol and octanol) afforded the corresponding esters. The synthesized complexes were characterized in detail by elemental analysis, ESI-MS, multinuclear ((1)H, (13)C, (15)N and (195)Pt) NMR spectroscopy and in two cases by X-ray crystallography. Cytotoxicity of novel platinum(IV) compounds was investigated in four human cancer cell lines (CH1, A549, SW480 and SK-OV-3). Remarkably, the most lipophilic complexes showed IC(50) values down to the low micromolar or even nanomolar range.

AB - (OC-6-43)-Dichlorido(N,N-dimethyl-ethane-1,2-diamine)dihydroxidoplatinum(IV) could selectively be mono-carboxylated with succinic anhydride based on the steric hindrance caused by the two methyl groups of the equatorial ligand. Subsequent esterification of the uncoordinated carboxylic acid with alcohols of different lengths (methanol, butanol, hexanol and octanol) afforded the corresponding esters. The synthesized complexes were characterized in detail by elemental analysis, ESI-MS, multinuclear ((1)H, (13)C, (15)N and (195)Pt) NMR spectroscopy and in two cases by X-ray crystallography. Cytotoxicity of novel platinum(IV) compounds was investigated in four human cancer cell lines (CH1, A549, SW480 and SK-OV-3). Remarkably, the most lipophilic complexes showed IC(50) values down to the low micromolar or even nanomolar range.

U2 - 10.1039/c1dt10301f

DO - 10.1039/c1dt10301f

M3 - Article

SN - 1477-9226

VL - 40

SP - 8187

EP - 8192

JO - Dalton Transactions

JF - Dalton Transactions

IS - 32

ER -

Mono-carboxylated diaminedichloridoplatinum(IV) complexes - selective synthesis, characterization, and cytotoxicity

Abstract

Austrian Fields of Science 2012

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