Novel organotin antibacterial and anticancer drugs

Gleeson, Brendan; Claffey, James; Ertler, Daniel; Hogan, Megan; Müller‐Bunz, Helge; Paradisi, Francesca; Wallis, Denise; Tacke, Matthias

doi:10.1016/j.poly.2008.09.009

Cited by 67 publications

(41 citation statements)

References 26 publications

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“…The metal salt (silver acetate) used to prepare the complexes and the solvent (DMSO) used to prepare the stock solutions played no role in growth inhibition on the same bacteria as previously reported. [19,36] Thus, on the basis of the above observation it can be stated that (i) the NHC-silver complexes 4a-c and 8a-c are more active against both Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli than the free NHC-precursors 3a-c and 7a-c. (ii) It was concluded that, as the NHC-precursors and NHC-silver complexes concentration increases, the antimicrobial activity becomes higher; and (iii) it was also observed that, compared with the NHC-precursors the NHC-silver complexes exhibited an approximately 6-fold increase in magnitude of antibacterial activity (see , which is due to the synergistic effect of the increased lipophilicity of the complexes. Chelation decreases the polarity of the metal ion, which further leads to the enhanced lipophilicity of the complex.…”

Section: Biological Evaluationmentioning

confidence: 92%

Synthesis, cytotoxicity and antibacterial studies of symmetrically and non‐symmetrically benzyl‐ or p‐cyanobenzyl‐substituted N‐Heterocyclic carbene–silver complexes

Patil¹,

Deally²,

Gleeson³

et al. 2010

Applied Organom Chemis

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From the reaction of 1H-imidazole (1a), 4,5-dichloro-1H-imidazole (1b) and 1H-benzimidazole (1c) with p-cyanobenzyl (8b) and (1-methyl-3-benzylbenzimidazole-2-ylidene) silver(I) acetate (8c) respectively. The four NHC-precursors 3a-c, 7c and four NHC-silver complexes 4a-c and 8c were characterized by single crystal X-ray diffraction. The preliminary antibacterial activity of all the compounds was studied against Gram-negative bacteria Escherichia coli, and Gram-positive bacteria Staphylococcus aureus using the qualitative Kirby-Bauer disc-diffusion method. All NHC-silver complexes exhibited medium to high antibacterial activity with areas of clearance ranging from 4 to 12 mm at the highest amount used, while the NHC-precursors showed significantly lower activity. In addition, all NHC-silver complexes underwent preliminary cytotoxicity tests on the human renal-cancer cell line Caki-1 and showed medium to high cytotoxicity with IC 50 values ranging from 53 (±8) to 3.2 (±0.6) µM.

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Section: Biological Evaluationmentioning

confidence: 92%

Synthesis, cytotoxicity and antibacterial studies of symmetrically and non‐symmetrically benzyl‐ or p‐cyanobenzyl‐substituted N‐Heterocyclic carbene–silver complexes

Patil¹,

Deally²,

Gleeson³

et al. 2010

Applied Organom Chemis

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“…The solvent used to prepare the stock solutions (DMSO) played no role in growth inhibition on the same bacteria as previously reported. [24] Thus, on the basis of the above observation it can be stated that (i) the complexes 4c and 7c are less active against the both Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli than the free precursors 3c and 6c. This is probably due to the poor solubility of the complexes 4c and 7c in DMSO.…”

Section: Biological Evaluationmentioning

confidence: 93%

Synthesis, Cytotoxicity and Antibacterial Studies of p‐Methoxybenzyl‐Substituted and Benzyl‐Substituted N‐Heterocyclic Carbene–Silver Complexes

et al. 2010

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p‐Methoxybenzyl‐substituted and benzyl‐substituted N‐heterocyclic carbene (NHC) [(3a–c) and (6a–c)] precursors were synthesised from the reaction of 1H‐imidazole (1a), 4,5‐dichloro‐1H‐imidazole (1b), and 1H‐benzimidazole (1c) with p‐methoxybenzyl bromide (2) and benzyl bromide (5). These NHC precursors were then treated with silver(I) acetate to yield the NHC–silver complexes [1,3‐bis(4‐methoxybenzyl)imidazol‐2‐ylidene]silver(I) acetate (4a), [4,5‐dichloro‐1,3‐bis(4‐methoxybenzyl)imidazol‐2‐ylidene]silver(I) acetate (4b), [1,3‐bis(4‐methoxybenzyl)benzimidazol‐2‐ylidene]silver(I) acetate (4c), (1,3‐dibenzylimidazol‐2‐ylidene)silver(I) acetate (7a), (1,3‐dibenzyl‐4,5‐dichloroimidazol‐2‐ylidene)silver(I) acetate (7b), and (1,3‐dibenzylbenzimidazol‐2‐ylidene)silver(I) acetate (7c), respectively. The NHC precursor 3c, four NHC–silver complexes 4c and 7a–c were characterised by single‐crystal X‐ray diffraction method. The preliminary antibacterial activity of all the compounds was studied against Gram‐negative bacteria Escherichia coli, and Gram‐positive bacteria Staphylococcus aureus using the Kirby–Bauer disk‐diffusion method. Almost all the NHC–silver complexes have shown high antibacterial activity compared to the NHC precursors. In addition, the NHC–silver complexes had their cytotoxicity investigated through MTT‐based preliminary in vitro testing on the Caki‐1 cell lines in order to determine their IC50 values. NHC–silver complexes 4a–c and 7a–c were found to have IC50 values of 7.3 (+/–6), 12.7(+/–3), 25.2 (+/–5), 2.5 (+/–3), 10.8 (+/–4) and 12.5 (+/–4) μM respectively on the Caki‐1 cell line.

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“…The results of the antibacterial activities of NHC precursors and their corresponding NHC -AgOAc complexes are given in Tables 3 and 4, respectively. The metal salt (AgOAc) used to prepare the complexes and the solvent (DMSO) played no role in growth inhibition on the same bacteria as previously reported [39] [45].…”

mentioning

confidence: 86%

Synthesis, Cytotoxicity and Antibacterial Studies of Novel Symmetrically and Nonsymmetrically 4‐(Methoxycarbonyl)benzyl‐Substituted N‐Heterocyclic Carbene–Silver Acetate Complexes

Patil

Dietrich

Deally

et al. 2010

Helvetica Chimica Acta

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From the reaction of 1H-imidazole (1a), 4,5-dichloro-1H-imidazole (1b), 1H-benzimidazole (1c), 1-methyl-1H-imidazole (1d), and 1-methyl-1H-benzimidazole (1f) with methyl 4-(bromomethyl)benzoate (2), symmetrically and nonsymmetrically 4-(methoxycarbonyl)benzyl-substituted N-heterocyclic carbene (NHC) precursors, 3a -3f, were synthesized. These NHC precursors were then reacted with silver(I) acetate (AgOAc) to yield the NHC -silver acetate complexes (acetato-kO){1,3-bis[4-(methoxy-, and (acetato-kO){1-[4-(methoxycarbonyl)benzyl]-3-methyl-2,3-dihydro-1H-benzimidazol-2-yl}silver (4f), respectively. The three NHC -AgOAc complexes 4a, 4c, and 4d were characterized by single-crystal X-ray diffraction. All compounds studied in this work were preliminarily screened for their antimicrobial activities in vitro against Gram-positive bacteria Staphylococcus aureus, and Gram-negative bacteria Escherichia coli using the qualitative disk-diffusion method. All NHC -AgOAc complexes exhibited weak-to-medium antibacterial activity with areas of clearance ranging from 4 to 7 mm at the highest amount used, while the NHC precursors showed significantly lower activity. In addition, NHC -AgOAc complexes 4a and 4b, and 4d -4f exhibited in preliminary cytotoxicity tests on the human renal-cancer cell line Caki-1 medium-to-high cytotoxicities with IC 50 values ranging from 3.3 AE 0.4 to 68.3 AE 1 mm.

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Novel organotin antibacterial and anticancer drugs

Cited by 67 publications

References 26 publications

Synthesis, cytotoxicity and antibacterial studies of symmetrically and non‐symmetrically benzyl‐ or p‐cyanobenzyl‐substituted N‐Heterocyclic carbene–silver complexes

Synthesis, cytotoxicity and antibacterial studies of symmetrically and non‐symmetrically benzyl‐ or p‐cyanobenzyl‐substituted N‐Heterocyclic carbene–silver complexes

Synthesis, Cytotoxicity and Antibacterial Studies of p‐Methoxybenzyl‐Substituted and Benzyl‐Substituted N‐Heterocyclic Carbene–Silver Complexes

Synthesis, Cytotoxicity and Antibacterial Studies of Novel Symmetrically and Nonsymmetrically 4‐(Methoxycarbonyl)benzyl‐Substituted N‐Heterocyclic Carbene–Silver Acetate Complexes

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