Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies
A small family of [Co2(Lpytrz)3]6+ cylinders was synthesised from bis(bidentate) 2-pyridyl-1,2,3-triazole “click” ligands (Lpytrz) through an “assembly-followed-by-oxidation” method. The cylinders were characterised using 1H, 13C, and DOSY NMR, IR, and UV-Vis spectroscopies, along with electrospray...
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MDPI AG
2016-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/11/1548 |
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| author | Roan A. S. Vasdev Dan Preston Synøve Ø. Scottwell Heather J. L. Brooks James D. Crowley Michael P. Schramm |
| author_facet | Roan A. S. Vasdev Dan Preston Synøve Ø. Scottwell Heather J. L. Brooks James D. Crowley Michael P. Schramm |
| author_sort | Roan A. S. Vasdev |
| collection | DOAJ |
| description | A small family of [Co2(Lpytrz)3]6+ cylinders was synthesised from bis(bidentate) 2-pyridyl-1,2,3-triazole “click” ligands (Lpytrz) through an “assembly-followed-by-oxidation” method. The cylinders were characterised using 1H, 13C, and DOSY NMR, IR, and UV-Vis spectroscopies, along with electrospray ionisation mass spectrometry (ESMS). Stability studies were conducted in dimethyl sulfoxide (DMSO) and D2O. In contrast to similar, previously studied, [Fe2(Lpytrz)3]4+ helicates the more kinetically inert [Co2(Lpytrz)3]6+ systems proved stable (over a period of days) when exposed to DMSO and were even more stable in D2O. The triply stranded [Co2(Lpytrz)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 [Co2(Lpytrz)3]6+ cylinders were not active against either strain of bacteria. It is presumed that a high charge of the [Co2(Lpytrz)3]6+ cylinders is preventing them from crossing the bacterial cell membranes, rendering the compounds biologically inactive. |
| first_indexed | 2024-12-11T08:11:18Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T08:11:18Z |
| publishDate | 2016-11-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a594f289fcfc43a6853433a74c43ae1e2022-12-22T01:14:52ZengMDPI AGMolecules1420-30492016-11-012111154810.3390/molecules21111548molecules21111548Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial StudiesRoan A. S. Vasdev0Dan Preston1Synøve Ø. Scottwell2Heather J. L. Brooks3James D. Crowley4Michael P. Schramm5Department of Chemistry, University of Otago, P.O. Box 56, Dunedin 9016, Otago, New ZealandDepartment of Chemistry, University of Otago, P.O. Box 56, Dunedin 9016, Otago, New ZealandDepartment of Chemistry, University of Otago, P.O. Box 56, Dunedin 9016, Otago, New ZealandDepartment of Microbiology and Immunology, University of Otago, P.O. Box 56, 720 Cumberland Street, Dunedin 9054, Otago, New ZealandDepartment of Chemistry, University of Otago, P.O. Box 56, Dunedin 9016, Otago, New ZealandDepartment of Chemistry and Biochemistry, California State University, Long Beach, 1250 Bellflower Boulevard, Long Beach, CA 90840-9507, USAA small family of [Co2(Lpytrz)3]6+ cylinders was synthesised from bis(bidentate) 2-pyridyl-1,2,3-triazole “click” ligands (Lpytrz) through an “assembly-followed-by-oxidation” method. The cylinders were characterised using 1H, 13C, and DOSY NMR, IR, and UV-Vis spectroscopies, along with electrospray ionisation mass spectrometry (ESMS). Stability studies were conducted in dimethyl sulfoxide (DMSO) and D2O. In contrast to similar, previously studied, [Fe2(Lpytrz)3]4+ helicates the more kinetically inert [Co2(Lpytrz)3]6+ systems proved stable (over a period of days) when exposed to DMSO and were even more stable in D2O. The triply stranded [Co2(Lpytrz)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 [Co2(Lpytrz)3]6+ cylinders were not active against either strain of bacteria. It is presumed that a high charge of the [Co2(Lpytrz)3]6+ cylinders is preventing them from crossing the bacterial cell membranes, rendering the compounds biologically inactive.http://www.mdpi.com/1420-3049/21/11/1548cobalt(III)metallosupramolecularcylindersantimicrobial agents |
| spellingShingle | Roan A. S. Vasdev Dan Preston Synøve Ø. Scottwell Heather J. L. Brooks James D. Crowley Michael P. Schramm Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies Molecules cobalt(III) metallosupramolecular cylinders antimicrobial agents |
| title | Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies |
| title_full | Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies |
| title_fullStr | Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies |
| title_full_unstemmed | Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies |
| title_short | Oxidatively Locked [Co2L3]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Stability, and Antimicrobial Studies |
| title_sort | oxidatively locked co2l3 6 cylinders derived from bis bidentate 2 pyridyl 1 2 3 triazole click ligands synthesis stability and antimicrobial studies |
| topic | cobalt(III) metallosupramolecular cylinders antimicrobial agents |
| url | http://www.mdpi.com/1420-3049/21/11/1548 |
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