Antimicrobial activity of an iron triple helicate

Richards, Adair D.; Rodger, Alison; Hannon, Michael J.; Bolhuis, Albert

doi:10.1016/j.ijantimicag.2008.10.031

Cited by 64 publications

(44 citation statements)

References 13 publications

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“…In recent years we have investigated the antimicrobial activity of compounds containing iron, ruthenium, copper and palladium [16,[21][22][23][24]. All of these compounds have been reported to bind DNA, either through groove binding or intercalation.…”

Section: Introductionmentioning

confidence: 99%

“…All of these compounds have been reported to bind DNA, either through groove binding or intercalation. Several compounds showed good antimicrobial activity on both Gramnegative and Gram-positive bacteria, albeit that the latter are generally more sensitive to metal complexes [16,[21][22][23][24]. These complexes have only been tested on planktonic cells, and we therefore sought to investigate the activity of a panel of copper(II) complexes against biofilms, and focussed this specifically on a clinical isolate of meticillin-resistant Staphylococcus aureus (MRSA) that is capable of forming stable 5 biofilms.…”

Section: Introductionmentioning

confidence: 99%

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The antimicrobial and antibiofilm activities of copper(II) complexes

Beeton

Aldrich‐Wright

Bolhuis

2014

Journal of Inorganic Biochemistry

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Gram-positive and Gram-negative bacteria, albeit that activity was generally higher for the former. The antibiofilm activity was then determined against a clinical isolate of meticillin-resistant Staphylococcus aureus (MRSA). Strikingly, the copper complexes tested showed significant activity against biofilms, and were better in the removal of biofilms than vancomycin, an antibiotic that is currently used in the treatment of MRSA infections.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The antimicrobial and antibiofilm activities of copper(II) complexes

Beeton

Aldrich‐Wright

Bolhuis

2014

Journal of Inorganic Biochemistry

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“…The ligands (L1 [26], L2 [26], and L3 [44]) were constructed in good yields using previously reported methods. The new ligand L4 was synthesised with a 72% yield using an analogous procedure and characterised via 1 H-NMR, 13 C-NMR, and infrared spectroscopies and high-resolution electrospray mass spectrometry (HR-ESMS) (Scheme 1, Supplementary Materials, Figures S1 and S2).…”

Section: Cylinder Design and Synthesismentioning

confidence: 99%

“…Unfortunately, these experiments also indicated that the cobalt(III) cylinders are not active antimicrobial agents, and no inhibition of bacterial growth was observed over a range of concentrations, from 1024 µg·mL −1 to 1 µg·mL −1 . Given the stability of the [Co 2 (L pytrz ) 3 ](OTf) 6 cylinders in aqueous and pseudo-biological conditions and the activity of other triply stranded helicates [13,18], related dinuclear ruthenium(II) compounds [53,57], and cobalt(III) complexes [41,42], the observed lack of activity was initially surprising. However, a series of elegant papers from Keene and co-workers have shown that the charge of the metal complex is an important factor for obtaining active antimicrobial complexes.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…The latter displayed the ability to induce conformational changes in the DNA decamer [d(GACGGCCGTC) 2 ] [5]. Hannon also showed that this triply stranded helicate non-covalently binds at the centre of three-way (Y-shaped) DNA [6][7][8][9] and RNA [10] 4+ helicates have been found to display micromolar cytotoxicity against a range of cancer cell lines [11,12] 4+ helicate has been shown to display modest antibacterial activity against Bacillus subtilis (minimum inhibitory concentration (MIC) = 32 µg·mL −1 ) and Escherichia coli (MIC = 64 µg·mL −1 ) [13].…”

Section: Introductionmentioning

confidence: 99%

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Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies

et al. 2016

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Abstract:A small family of [Co 2 (L pytrz ) 3 ] 6+ cylinders was synthesised from bis(bidentate) 2-pyridyl-1,2,3-triazole "click" ligands (L pytrz ) through an "assembly-followed-by-oxidation" method. The cylinders were characterised using 1 H, 13 C, and DOSY NMR, IR, and UV-Vis spectroscopies, along with electrospray ionisation mass spectrometry (ESMS). Stability studies were conducted in dimethyl sulfoxide (DMSO) and D 2 O. In contrast to similar, previously studied, [Fe 2 (L pytrz ) 3 ] 4+ helicates the more kinetically inert [Co 2 (L pytrz ) 3 ] 6+ systems proved stable (over a period of days) when exposed to DMSO and were even more stable in D 2 O. The triply stranded [Co 2 (L pytrz ) 3 ] 6+ systems and the corresponding "free" ligands were tested for antimicrobial activity in vitro against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) microorganisms. Agar-based disk diffusion and Mueller-Hinton broth micro-dilution assays showed that the [Co 2 (L pytrz ) 3 ] 6+ cylinders were not active against either strain of bacteria. It is presumed that a high charge of the [Co 2 (L pytrz ) 3 ] 6+ cylinders is preventing them from crossing the bacterial cell membranes, rendering the compounds biologically inactive.

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Synthesis, Characterisation and Antimicrobial Studies of some 2,6‐bis(1,2,3‐Triazol‐4‐yl)Pyridine Ruthenium(II) “Click” Complexes

et al. 2019

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A family of homo-and hetero-leptic ruthenium(II) bis-tridentate complexes generated from 2,6-bis(1-R-1,2,3triazol-4-yl)pyridine "click" ligands (R-tripy) with either aliphatic or aromatic substituents were synthesized (35-97%).The family of compounds were tested for antimicrobial activity in vitro against both Staphylococcus aureus (S. aureus, ATCC 25923) and Escherichia coli (E. coli, ATCC 25922) bacteria. The antibacterial activity showed dependence on the alkyl chain length of the [Ru(R-tripy) 2 ] 2 + (Cl À ) 2 complexes, with the best activity occurring for the three complexes featuring either hexyl or heptyl substituents on the ligands. The minimum inhibitory concentrations (MICs) for the most active mononuclear complex [Ru(hexyltripy)(heptyltripy)] 2 + (Cl À ) 2 were 2 μg/mL and 8 μg/mL respectively against S. aureus and E. coli. The three most active complexes were screened against other pathogenic bacteria, including two strains of Methicillin resistant S. aureus (MRSA). The compounds showed good activity against the Gram positive strains (MIC = 4-8 μg/mL) but were less effective against Gram negative bacteria (MIC = 8-16 μg/mL). Cytotoxicity experiments with eukaryotic cells lines (cancer and skin) suggested that the R-tripy ligands and complexes were reasonably cytotoxic (IC 50 = 2-25 μM) and displayed little to no selectivity for bacteria over eukaryotic cells lines.[a] Q. /phen ligands and have been used to develop metal complexes for a range of applications. [19] Two of the complexes ([Ru(hexpytri) 3 ] 2 + and [Ru(octpytri) 3 ] 2 + (where hexpytri = 2-(1hexyl-1H-1,2,3-triazol-4-yl)pyridine and octpytri = 2-(1-octyl-1H-1,2,3-triazol-4-yl)pyridine) showed good antimicrobial activity against Gram positive S. aureus and MRSA (MICs = 1-8 μg/mL) but little to no activity against Gram negative bacteria (MIC = 16-> 128 μg/mL). The mer and fac isomers of the complexes showed no difference in activity. Propidium iodide assays and transmission electron microscopy (TEM) indicated that the main mode of action for these ruthenium(II) R-pytri complexes was cytoplasmic membrane disruption.Building on that work, herein we report the synthesis of a structurally related family of ruthenium(II) "click" complexes generated from tridentate 2,6-bis(1-R-1H-1,2,3-triazol-4-yl) pyridine (R-tripy) ligands (Scheme 1). The new bis-tridentate ruthenium(II) complexes, [Ru(R-tripy) 2 ] 2 + (Cl À ) 2 , retain most of the structural features of the previously studied [Ru(R-pytri) 3 ] 2 + (X À ) 2 complexes but they do not form isomers (either enantiomers or diastereomers). The new "click" complexes were tested for antimicrobial activity in vitro against both S. aureus and Escherichia coli (E. coli) bacteria. Additionally, the cytotoxicity of the most active complexes was examined against three human cell lines. Results and DiscussionSynthesis of Tridentate 2,6-bis(1-R-1,2,3-triazol-4-yl)pyridine (R-tripy) Ligands . TEM images a) untreated S. aureus b) S. aureus incubated with 4 μg/mL of [Ru(hexyltripy)(heptyltripy)] 2 + , c) and d) S...

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Antimicrobial activity of an iron triple helicate

Cited by 64 publications

References 13 publications

The antimicrobial and antibiofilm activities of copper(II) complexes

The antimicrobial and antibiofilm activities of copper(II) complexes

Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies

Synthesis, Characterisation and Antimicrobial Studies of some 2,6‐bis(1,2,3‐Triazol‐4‐yl)Pyridine Ruthenium(II) “Click” Complexes

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