Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. X-ray Structures of the Complexes [Ni3(abb)3(H2O)3(μ-ttc)](ClO4)3·3H2O·EtOH (1) and [(tbbH2)(ttcH2)2(ttcH3)(H2O)] (2)
Ni1-N1B | 2.041(3) | Ni2-N5 | 2.030(3) | Ni3-N1F | 2.044(3) |
Ni1-N1 | 2.047(3) | Ni2-N1C | 2.056(4) | Ni3-N3 | 2.043(3) |
Ni1-N1A | 2.057(3) | Ni2-N1D | 2.062(4) | Ni3-N1E | 2.057(3) |
Ni1-O1 | 2.102(3) | Ni2-N22 | 2.101(4) | Ni3-O3 | 2.100(3) |
Ni1-N11 | 2.121(3) | Ni2-O2 | 2.109(3) | Ni3-N33 | 2.107(3) |
N1B-Ni1-N1 | 101.50(14) | N5-Ni2-N1C | 99.59(14) | N1F-Ni3-N3 | 100.24(13) |
N1B-Ni1-N1A | 159.97(15) | N5-Ni2-N1D | 98.94(13) | N1F-Ni3-N1E | 160.83(14) |
N1-Ni1-N1A | 97.76(13) | N1C-Ni2-N1D | 161.06(14) | N3-Ni3-N1E | 97.92(13) |
N1B-Ni1-O1 | 92.65(13) | N5-Ni2-N22 | 170.79(14) | N1F-Ni3-O3 | 90.79(14) |
N1-Ni1-O1 | 97.07(12) | N1C-Ni2-N22 | 80.76(15) | N3-Ni3-O3 | 98.86(13) |
N1A-Ni1-O1 | 90.41(13) | N1D-Ni2-N22 | 80.33(14) | N1E-Ni3-O3 | 92.42(14) |
N1B-Ni1-N11 | 80.27(14) | N5-Ni2-O2 | 96.53(12) | N1F-Ni3-N33 | 79.92(14) |
N1-Ni1-N11 | 165.69(14) | N1C-Ni2-O2 | 90.31(13) | N3-Ni3-N33 | 163.52(14) |
N1A-Ni1-N11 | 79.71(14) | N1D-Ni2-O2 | 91.45(13) | N1E-Ni3-N33 | 80.92(14) |
O1-Ni1-N11 | 97.03(13) | N22-Ni2-O2 | 92.67(14) | O3-Ni3-N33 | 97.62(13) |
N1B-Ni1-S6 | 89.81(10) | N5-Ni2-S4 | 67.54(9) | N1F-Ni3-S2 | 88.42(11) |
N1-Ni1-S6 | 67.36(9) | N1C-Ni2-S4 | 89.22(10) | N3-Ni3-S2 | 67.60(9) |
N1A-Ni1-S6 | 92.54(10) | N1D-Ni2-S4 | 94.26(10) | N1E-Ni3-S2 | 92.90(10) |
O1-Ni1-S6 | 164.40(9) | N22-Ni2-S4 | 103.30(11) | O3-Ni3-S2 | 166.03(10) |
N11-Ni1-S6 | 98.56(10) | O2-Ni2-S4 | 163.73(9) | N33-Ni3-S2 | 95.98(10) |
S1-C1A | 1.810(4) | S1C-C1C | 1.666(4) | C8A-C3A-N1A | 106.9(3) |
S1-C1B | 1.828(4) | S2C-C2C | 1.635(4) | N2A-C8A-C3A | 105.9(3) |
C1A-C2A | 1.490(5) | S3C-C3C | 1.648(4) | C2B-C1B-S1 | 111.4(3) |
N1A-C2A | 1.332(5) | S1D-C1D | 1.656(4) | C2B-N1B-C3B | 109.4(3) |
N1A-C3A | 1.405(5) | S2D-C2D | 1.647(4) | C2B-N2B-C8B | 109.8(3) |
N2A-C2A | 1.335(5) | S3D-C3D | 1.681(4) | N2B-C2B-N1B | 109.0(3) |
N2A-C8A | 1.389(5) | S1E-C1E | 1.675(4) | N1B-C3B-C8B | 105.9(3) |
C3A-C8A | 1.404(5) | S2E-C2E | 1.692(4) | N1C-C1C-N3C | 115.0(3) |
C1B-C2B | 1.485(5) | S3E-C3E | 1.645(4) | N2C-C2C-N1C | 113.5(3) |
N1B-C2B | 1.331(5) | C1A-S1-C1B | 101.20(18) | N2C-C3C-N3C | 114.1(3) |
N1B-C3B | 1.397(5) | C2A-C1A-S1 | 115.2(3) | N1D-C2D-N2D | 113.5(3) |
N2B-C2B | 1.324(5) | C2A-N1A-C3A | 107.7(3) | N2E-C3E-N3E | 113.4(3) |
N2B-C8B | 1.392(5) | C2A-N2A-C8A | 109.1(3) | ||
C3B-C8B | 1.397(5) | N1A-C2A-N2A | 110.4(3) |
2.3. Biological Activity
Compounds | IC50 (μg/mL) Measurement after 24 h | |||||
---|---|---|---|---|---|---|
S. aureus | E. coli | S. cerevisiae | S. agalactiae | C. striatum | S. marcescens | |
Ligand abb | 5.6 | 19 | 21.4 | 22.4 | 30.8 | 26.7 |
Ligand tbb | 485.2 | 182.3 | 204.7 | 126.1 | 112.5 | 122.6 |
Ligand ttcNa3 | 625 | 636.8 | 86.4 | 119.5 | 115.8 | 123.9 |
Complex 1 | 4.8 | 23.7 | 15.4 | 21.4 | 24.3 | 27.2 |
Complex 2 | 562.3 | 257.6 | 64.3 | 102.1 | 119.5 | 61.5 |
Complex 3 | 1036.7 | 12.6 | 18.2 | 113.4 | 124.9 | 110.4 |
3. Experimental Section
3.1. General Information
3.2. Preparation of the Compounds
3.2.1. 1-(1H-Benzimidazol-2-yl)-N-(1H-benzimidazol-2-ylmethyl)methanamine (abb)
3.2.2. 2-(1H-Benzimidazol-2-ylmethylsulfanylmethyl)-1H-benzimidazole (tbb)
3.2.3. [Ni3(abb)3(H2O)3(μ-ttc)](ClO4)3·3H2O·EtOH (1)
3.2.4. [(tbbH2)(ttcH2)2(ttcH3)(H2O)] (2)
3.2.5. [Ni3(pmdien)3(μ-ttc)](ClO4)3 (3)
3.3. X-ray Crystallography
3.4. Biological Activity Testing
3.4.1. Cultivation of Commercially Supplied Bacteria and Yeasts
3.4.2. Preparation of Hospital Samples and Their Cultivation
Cohort of Patients with Bacterial Infections
Collection of Wound Swabs from Patients with Bacterial Infections
Cultivation of Clinical Specimens
3.4.3. Determination of Growth Curves
3.4.4. Statistical Analyses
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Kopel, P.; Wawrzak, D.; Langer, V.; Cihalova, K.; Chudobova, D.; Vesely, R.; Adam, V.; Kizek, R. Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes. Molecules 2015, 20, 10360-10376. https://doi.org/10.3390/molecules200610360
Kopel P, Wawrzak D, Langer V, Cihalova K, Chudobova D, Vesely R, Adam V, Kizek R. Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes. Molecules. 2015; 20(6):10360-10376. https://doi.org/10.3390/molecules200610360
Chicago/Turabian StyleKopel, Pavel, Dorota Wawrzak, Vratislav Langer, Kristyna Cihalova, Dagmar Chudobova, Radek Vesely, Vojtech Adam, and Rene Kizek. 2015. "Biological Activity and Molecular Structures of Bis(benzimidazole) and Trithiocyanurate Complexes" Molecules 20, no. 6: 10360-10376. https://doi.org/10.3390/molecules200610360