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Synthesis and Characterization of Novel Ruthenium(III) Complexes with Histamine.

Kljun J, Petricek S, Zigon D, Hudej R, Miklavcic D, Turel I - Bioinorg Chem Appl (2010)

Bottom Line: Novel ruthenium(III) complexes with histamine [RuCl(4)(dmso-S)(histamineH)] .H( (2) )O (1a) and [RuCl(4)(dmso-S)(histamineH)] (1b) have been prepared and characterized by X-ray structure analysis.Their crystal structures are similar and show a protonated amino group on the side chain of the ligand which is not very common for a simple heterocyclic derivative such as histamine.

View Article: PubMed Central - PubMed

Affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia.

ABSTRACT
Novel ruthenium(III) complexes with histamine [RuCl(4)(dmso-S)(histamineH)] . H( (2) )O (1a) and [RuCl(4)(dmso-S)(histamineH)] (1b) have been prepared and characterized by X-ray structure analysis. Their crystal structures are similar and show a protonated amino group on the side chain of the ligand which is not very common for a simple heterocyclic derivative such as histamine. Biological assays to test the cytotoxicity of the compound 1b combined with electroporation were performed to determine its potential for future medical applications in cancer treatment.

No MeSH data available.


The hydrogen bonds in the crystal structure of compound 1b. The ammonioethyl groups of the lower two asymmetric units are omitted for clarity.
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fig2: The hydrogen bonds in the crystal structure of compound 1b. The ammonioethyl groups of the lower two asymmetric units are omitted for clarity.

Mentions: The crystal structure of compounds 1a and 1b does not differ significantly from the other NAMI-type compounds. Compounds 1a and 1b have a distorted octahedral geometry with four in-plane chloride anions surrounding the Ru(III) ion in addition to a sulfur atom from an S-bonded dimethylsulfoxide molecule and a nitrogen atom from the histamine molecule in axial positions. The main difference to most of the NAMI-type compounds which are anionic complexes is the protonated amino group on the side chain of the histamine moiety (hence histamineH is used in the formula) that gives compounds 1a and 1b a neutral charge. This structural feature is however more common in NAMI-type compounds with a purine derivative as the nitrogen ligand [21]. The hydrogen atoms on the amino group (H3A, H3B and H3C) form hydrogen bonds with the four chloride atoms and the dmso oxygen. The Cl2 chloride atom forms an additional hydrogen bond with the hydrogen on the imidazole moiety (H2) which results in a slightly longer Ru-Cl2 distance (see Tables 2 and 3 and Figures 1 and 2). Compound 1a exhibits an additional hydrogen bond between the water molecule and one of the chloride anions. It was not possible to locate the positions of two hydrogen atoms bonded to oxygen in a water molecule of the complex 1a by difference Fourier maps.


Synthesis and Characterization of Novel Ruthenium(III) Complexes with Histamine.

Kljun J, Petricek S, Zigon D, Hudej R, Miklavcic D, Turel I - Bioinorg Chem Appl (2010)

The hydrogen bonds in the crystal structure of compound 1b. The ammonioethyl groups of the lower two asymmetric units are omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2901621&req=5

fig2: The hydrogen bonds in the crystal structure of compound 1b. The ammonioethyl groups of the lower two asymmetric units are omitted for clarity.
Mentions: The crystal structure of compounds 1a and 1b does not differ significantly from the other NAMI-type compounds. Compounds 1a and 1b have a distorted octahedral geometry with four in-plane chloride anions surrounding the Ru(III) ion in addition to a sulfur atom from an S-bonded dimethylsulfoxide molecule and a nitrogen atom from the histamine molecule in axial positions. The main difference to most of the NAMI-type compounds which are anionic complexes is the protonated amino group on the side chain of the histamine moiety (hence histamineH is used in the formula) that gives compounds 1a and 1b a neutral charge. This structural feature is however more common in NAMI-type compounds with a purine derivative as the nitrogen ligand [21]. The hydrogen atoms on the amino group (H3A, H3B and H3C) form hydrogen bonds with the four chloride atoms and the dmso oxygen. The Cl2 chloride atom forms an additional hydrogen bond with the hydrogen on the imidazole moiety (H2) which results in a slightly longer Ru-Cl2 distance (see Tables 2 and 3 and Figures 1 and 2). Compound 1a exhibits an additional hydrogen bond between the water molecule and one of the chloride anions. It was not possible to locate the positions of two hydrogen atoms bonded to oxygen in a water molecule of the complex 1a by difference Fourier maps.

Bottom Line: Novel ruthenium(III) complexes with histamine [RuCl(4)(dmso-S)(histamineH)] .H( (2) )O (1a) and [RuCl(4)(dmso-S)(histamineH)] (1b) have been prepared and characterized by X-ray structure analysis.Their crystal structures are similar and show a protonated amino group on the side chain of the ligand which is not very common for a simple heterocyclic derivative such as histamine.

View Article: PubMed Central - PubMed

Affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia.

ABSTRACT
Novel ruthenium(III) complexes with histamine [RuCl(4)(dmso-S)(histamineH)] . H( (2) )O (1a) and [RuCl(4)(dmso-S)(histamineH)] (1b) have been prepared and characterized by X-ray structure analysis. Their crystal structures are similar and show a protonated amino group on the side chain of the ligand which is not very common for a simple heterocyclic derivative such as histamine. Biological assays to test the cytotoxicity of the compound 1b combined with electroporation were performed to determine its potential for future medical applications in cancer treatment.

No MeSH data available.