[Fe2L3]4+ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3- triazole "click" ligands

Synthesis, structures and exploration of biological activity

Sreedhar K. Vellas, James E M Lewis, Madhu Shankar, Alia Sagatova, Joel D A Tyndall, Brian C. Monk, Christopher M. Fitchett, Lyall R. Hanton, James D. Crowley

Research output: Contribution to journalArticleResearchpeer-review

47 Citations (Scopus)

Abstract

A series of metallosupramolecular [Fe2L3](BF 4)4 "click" cylinders have been synthesized in excellent yields (90%-95%) from [Fe(H2O6](BFe 4)2 and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, 1H-, 13C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these "click" complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the "click" complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe 2L3](BF4)4 "click" cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the "click" complexes in DMSO and biological media. 

Original languageEnglish
Pages (from-to)6383-6407
Number of pages25
JournalMolecules
Volume18
Issue number6
DOIs
Publication statusPublished - Jun 2013
Externally publishedYes

Keywords

  • Biological activity
  • CuAAC
  • Iron(II)
  • Metallosupramolecular cylinders

Cite this

Vellas, Sreedhar K. ; Lewis, James E M ; Shankar, Madhu ; Sagatova, Alia ; Tyndall, Joel D A ; Monk, Brian C. ; Fitchett, Christopher M. ; Hanton, Lyall R. ; Crowley, James D. / [Fe2L3]4+ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3- triazole "click" ligands : Synthesis, structures and exploration of biological activity. In: Molecules. 2013 ; Vol. 18, No. 6. pp. 6383-6407.
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abstract = "A series of metallosupramolecular [Fe2L3](BF 4)4 {"}click{"} cylinders have been synthesized in excellent yields (90{\%}-95{\%}) from [Fe(H2O6](BFe 4)2 and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, 1H-, 13C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these {"}click{"} complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the {"}click{"} complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe 2L3](BF4)4 {"}click{"} cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the {"}click{"} complexes in DMSO and biological media. ",
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author = "Vellas, {Sreedhar K.} and Lewis, {James E M} and Madhu Shankar and Alia Sagatova and Tyndall, {Joel D A} and Monk, {Brian C.} and Fitchett, {Christopher M.} and Hanton, {Lyall R.} and Crowley, {James D.}",
year = "2013",
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Vellas, SK, Lewis, JEM, Shankar, M, Sagatova, A, Tyndall, JDA, Monk, BC, Fitchett, CM, Hanton, LR & Crowley, JD 2013, '[Fe2L3]4+ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3- triazole "click" ligands: Synthesis, structures and exploration of biological activity', Molecules, vol. 18, no. 6, pp. 6383-6407. https://doi.org/10.3390/molecules18066383

[Fe2L3]4+ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3- triazole "click" ligands : Synthesis, structures and exploration of biological activity. / Vellas, Sreedhar K.; Lewis, James E M; Shankar, Madhu; Sagatova, Alia; Tyndall, Joel D A; Monk, Brian C.; Fitchett, Christopher M.; Hanton, Lyall R.; Crowley, James D.

In: Molecules, Vol. 18, No. 6, 06.2013, p. 6383-6407.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - [Fe2L3]4+ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3- triazole "click" ligands

T2 - Synthesis, structures and exploration of biological activity

AU - Vellas, Sreedhar K.

AU - Lewis, James E M

AU - Shankar, Madhu

AU - Sagatova, Alia

AU - Tyndall, Joel D A

AU - Monk, Brian C.

AU - Fitchett, Christopher M.

AU - Hanton, Lyall R.

AU - Crowley, James D.

PY - 2013/6

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N2 - A series of metallosupramolecular [Fe2L3](BF 4)4 "click" cylinders have been synthesized in excellent yields (90%-95%) from [Fe(H2O6](BFe 4)2 and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, 1H-, 13C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these "click" complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the "click" complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe 2L3](BF4)4 "click" cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the "click" complexes in DMSO and biological media. 

AB - A series of metallosupramolecular [Fe2L3](BF 4)4 "click" cylinders have been synthesized in excellent yields (90%-95%) from [Fe(H2O6](BFe 4)2 and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, 1H-, 13C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these "click" complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the "click" complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe 2L3](BF4)4 "click" cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the "click" complexes in DMSO and biological media. 

KW - Biological activity

KW - CuAAC

KW - Iron(II)

KW - Metallosupramolecular cylinders

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U2 - 10.3390/molecules18066383

DO - 10.3390/molecules18066383

M3 - Article

VL - 18

SP - 6383

EP - 6407

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 6

ER -