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Intermolecular Interactions in o-Tolidinium Dichloride Dihydrate: X-ray Structural and Quantum Mechanical Study

100%

Kruszynski R.

Polish Journal of Chemistry

2009

tom Vol. 83, nr 4

615-623

The title compound, C14H22Cl2N2O2, (I), was determined by X-ray crystallography, and the intermolecular interactions energy was calculated in terms of Natural Bond Orbital analysis. The (I) is composed from 3,3'-dimethyl-(1,1'-biphenyl)-4,4'-diammonium cation two chloride anions and two water molecules. The mid point of the linking aromatic rings C—C bond is located on two fold rotation axis, and thus asymmetric unit is occupied by half of cation, one anion and one water molecule. All the interatomic distances and angles in (I) are normal. The almost planar aromatic rings are inclined at 38.82(4) graduate. In the structure exists intermolecular N—HźźźO, N—HźźźCl, O—HźźźCl hydrogen bonds with bonding energy ranging from 4 to 26 kcal/mol. All hydrogen bonds of (I) in terms of first level graphs create D motifs. No face-to-face stacking interactions are observed.

New benzimidazole derivatives with potential cytotoxic activity - study of their stability by RP-HPLC

38%

Blaszczak-Swiatkiewicz K. , Mirowski M. , Kaplinska K. , Kruszynski R. , Trzesowska-Kruszynska A. , Mikiciuk-Olasik E.

Acta Biochimica Polonica

2012

tom 59

nr 2

Obtained benzimidazole derivatives, our next synthesized heterocyclic compounds, belong to a new group of chemical bondings with potential anticancer properties (Błaszczak-Świątkiewicz & Mikiciuk-Olasik, 2006, J Liguid Chrom Rel Tech 29: 2367-2385; Błaszczak-Świątkiewicz & Mikiciuk-Olasik, 2008, Wiad Chem 62: 11-12, in Polish; Błaszczak-Świątkiewicz & Mikiciuk-Olasik, 2011, J Liguid Chrom Rel Tech 34: 1901-1912). We used HPLC analysis to determine stability of these compounds in 0.2% DMSO (dimethyl sulfoxide). Optimisation of the chromatographic system and validation of the established analytical method were performed. Reversed phases (RP-18) and a 1:1 mixture of acetate buffer (pH 4.5) and acetonitrile as a mobile phase were used for all the analysed compounds at a flow rate 1.0 mL/min. The eluted compounds were monitored using a UV detector, the wavelength was specific for compounds 6 and 9 and compounds 7 and 10. The retention time was specific for all four compounds. The used method was found to have linearity in the concentration range of (0.1 mg/mL-0.1 μg/mL) with a correlation coefficient not less than r2=0.9995. Statistical validation of the method proved it to be a simple, highly precise and accurate way to determine the stability of benzimidazole derivatives in 0.2% DMSO. The recoveries of all four compounds examined were in the range 99.24-100.00%. The developed HPLC analysis revealed that the compounds studied remain homogeneous in 0.2% DMSO for up to 96 h and that the analysed N-oxide benzimidazole derivatives do not disintegrate into their analogues - benzimidazole derivatives. Compounds 8, 6 and 9 exhibit the best cytotoxic properties under normoxic conditions when tested against cells of human malignant melanoma WM 115.