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. 2016 Jan 28;21(2):87.
doi: 10.3390/molecules21020087.

Antibacterial Activity and Cytotoxicity of Silver(I) Complexes of Pyridine and (Benz)Imidazole Derivatives. X-ray Crystal Structure of [Ag(2,6-di(CH2OH)py)2]NO3

Urszula Kalinowska-Lis  1 , Aleksandra Felczak  2 , Lilianna Chęcińska  3 , Ilona Szabłowska-Gadomska  4 , Emila Patyna  5 , Maciej Małecki  6 , Katarzyna Lisowska  7 , Justyn Ochocki  8
Affiliations

Antibacterial Activity and Cytotoxicity of Silver(I) Complexes of Pyridine and (Benz)Imidazole Derivatives. X-ray Crystal Structure of [Ag(2,6-di(CH2OH)py)2]NO3

Urszula Kalinowska-Lis et al. Molecules. .

Abstract

Selected aspects of the biological activity of a series of six nitrate silver(I) complexes with pyridine and (benz)imidazole derivatives were investigated. The present study evaluated the antibacterial activities of the complexes against three Gram-negative strains: Pseudomonas aeruginosa ATCC 15442, Escherichia coli ATCC 25922 and Proteus hauseri ATCC 13315. The results were compared with those of silver nitrate, a silver sulfadiazine drug and appropriate ligands. The most significant antibacterial properties were exerted by silver(I) complexes containing benzimidazole derivatives. The cytotoxic activity of the complexes was examined against B16 (murine melanoma) and 10T1/2 (murine fibroblasts) cells. All of the tested silver(I) compounds were not toxic to fibroblast cells in concentration inhibited cancer cell (B16) viability by 50%, which ranged between 2.44-28.65 µM. The molecular and crystal structure of silver(I) complex of 2,6-di(hydroxymethyl)pyridine was determined by single-crystal X-ray diffraction analysis. The most important features of the crystal packing and intermolecular non-covalent interactions in the Ag(I) complex were quantified via Hirshfeld surface analysis.

Keywords: 10T1/2 fibroblasts; B16 melanoma cells; Hirshfeld surface; antibacterial activity; cytotoxicity; silver(I) complexes.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The molecular structure of the title Ag(I) complex (MERCURY [36] representation), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Only the major component (A) of disordered oxygen atoms in the anion molecule (NO3−) is shown (minor components B are omitted for clarity).
Figure 2
Figure 2
A scheme of the different-type interactions observed in crystal structure of 3 (a) and a formation of the centrosymmetric dimer (b). Bond distances to Ag1: Ag1–N1 = 2.187(1) Å, Ag1–N1 = 2.198(1) Å, Ag1–O4 = 2.612(1) Å. Intermolecular short contacts to Ag1 (drawn as orange dotted lines): Ag1–O7Ai = 2.87(1) Å and Ag1–O3iii = 2.960(1) Å; bond angles: N1–Ag1–N2 = 171.66(4)°, N2–Ag1–O4 = 71.06(4)°. Blue dotted lines indicate intermolecular interactions (for details see Table 3). H-atoms have been omitted for clarity (except of those involved in H-bonds in Figure 2a). Symmetry codes: (i) −x, y – 1/2, −z; (ii) x + 1, y, z; (iii) −x, 1 − y, −z; (iv) −x, y + ½, −z + 1/2; (v) x − 1, y, z.
Figure 3
Figure 3
Hirshfeld surface of Ag(I) complex-cation molecule with the geometrical function dnorm mapped onto it (a colour scale from red to blue: −0.75 Å–1.2 Å) and corresponding finger plots indicating all types of contacts and these reduced to contact types as following Ag···O/O···Ag, O···H/H···O, C···H/H···C [the distances from a surface point to the nearest interior/exterior atoms (di/e) are given in Å].
Figure 4
Figure 4
Antibacterial activity of the complexes 1–6, given as MIC (minimum inhibitory concentration) values in µmol/L−1. MIC values of the free ligands, i.e., 4-pmOpe, 2-bimOpe, 2,6-di(CH2OH)py, 4-CH2OHpy, 2-CH2OHbim, are >500 mg/L−1. AgSD: silver sulfadiazine. The all experiments were performed in triplicate (SD = 0). * Complex 6 [13].
Figure 5
Figure 5
Response of B16 cell lines to silver complexes 1–6, AgNO3, AgSD (silver sulfadiazine) and cis-DDP (cisplatin). Values presented are IC50 (µM) ± SD for three independent experiments.
Figure 6
Figure 6
Percentage of survival 10T1/2 cells treated with complexes 1–6, AgNO3 and AgSD, in concentrations that correspond with IC50 values for B16 cells. Statistical analyses were done using GraphPad Prism 6 and one-way ANOVA with Bonferroni’s multiple comparisons test. p < 0.05 was considered as statistically significant one. Data were showed as mean with SD of three independent experiments. **** p < 0.0001.
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