The importance of heterolepticity in improving the antibacterial activity of bismuth(III) thiolates

Ahmad Luqman, Victoria L Blair, Rajini Brammananth, Paul K Crellin, Ross L Coppel, Philip C Andrews

Research output: Contribution to journalArticleResearchpeer-review

7 Citations (Scopus)

Abstract

Five mixed thiolatobismuth(III) complexes [BiPh(5-MMTD)2{4-MMT(H)}] (1), [Bi(1-MMTZ)2{(PYM)(PYM(H))2}] (2), [Bi(MBT)2(5-MMTD)] (3), [Bi(4-BrMTD)3{2-MMI(H)}] (4) and [Bi(1-MMTZ)2{1-MMTZ(H)}(2-MMI){2-MMI(H)2}] (5) were synthesised from imidazole-, thiazole-, thiadiazole-, triazole-, tetrazole- and pyrimidine-based heterocyclic thiones. Four of these complexes 1–4 were synthesized from BiPh3, while complex 5 was obtained from Bi[4-(MeO)Ph]3. Complexes 1–5 were structurally characterised by XRD. Evaluation of the antibacterial properties against Mycobacterium smegmatis, Staphylococcus aureus, Methicillin-resistant S. aureus (MRSA), Vancomycin-resistant Enterococcus (VRE), Enterococcus faecalis and Escherichia coli showed that mixed thiolato complexes containing the anionic thiazole-based ligands MBT and 4-BrMTD are most effective. The mixed thiolato complexes [Bi(MBT)2(5-MMTD)] (3) having thiazole- and thiadiazole- and [Bi(4-BrMBT)3{2-MMI(H)}] (4) containing thiazole- and imidazole-based ligands proved to be more efficient, with low minimum inhibitory concentrations of 1.73 and 3.45 µm for 3 against VRE and E. faecalis, respectively, and 2.20 µm for 4 against M. smegmatis and E. faecalis. All complexes showed little or no toxicity towards mammalian COS-7 cell lines at 20 µg mL–1.

Original languageEnglish
Pages (from-to)2738-2749
Number of pages12
JournalEuropean Journal of Inorganic Chemistry
Volume2016
Issue number17
DOIs
Publication statusPublished - 2016

Keywords

  • Antibiotics
  • Bismuth
  • Drug design
  • Heteroleptic complexes
  • Medicinal chemistry
  • S ligands

Cite this

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title = "The importance of heterolepticity in improving the antibacterial activity of bismuth(III) thiolates",
abstract = "Five mixed thiolatobismuth(III) complexes [BiPh(5-MMTD)2{4-MMT(H)}] (1), [Bi(1-MMTZ)2{(PYM)(PYM(H))2}] (2), [Bi(MBT)2(5-MMTD)] (3), [Bi(4-BrMTD)3{2-MMI(H)}] (4) and [Bi(1-MMTZ)2{1-MMTZ(H)}(2-MMI){2-MMI(H)2}] (5) were synthesised from imidazole-, thiazole-, thiadiazole-, triazole-, tetrazole- and pyrimidine-based heterocyclic thiones. Four of these complexes 1–4 were synthesized from BiPh3, while complex 5 was obtained from Bi[4-(MeO)Ph]3. Complexes 1–5 were structurally characterised by XRD. Evaluation of the antibacterial properties against Mycobacterium smegmatis, Staphylococcus aureus, Methicillin-resistant S. aureus (MRSA), Vancomycin-resistant Enterococcus (VRE), Enterococcus faecalis and Escherichia coli showed that mixed thiolato complexes containing the anionic thiazole-based ligands MBT and 4-BrMTD are most effective. The mixed thiolato complexes [Bi(MBT)2(5-MMTD)] (3) having thiazole- and thiadiazole- and [Bi(4-BrMBT)3{2-MMI(H)}] (4) containing thiazole- and imidazole-based ligands proved to be more efficient, with low minimum inhibitory concentrations of 1.73 and 3.45 µm for 3 against VRE and E. faecalis, respectively, and 2.20 µm for 4 against M. smegmatis and E. faecalis. All complexes showed little or no toxicity towards mammalian COS-7 cell lines at 20 µg mL–1.",
keywords = "Antibiotics, Bismuth, Drug design, Heteroleptic complexes, Medicinal chemistry, S ligands",
author = "Ahmad Luqman and Blair, {Victoria L} and Rajini Brammananth and Crellin, {Paul K} and Coppel, {Ross L} and Andrews, {Philip C}",
year = "2016",
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The importance of heterolepticity in improving the antibacterial activity of bismuth(III) thiolates. / Luqman, Ahmad; Blair, Victoria L; Brammananth, Rajini; Crellin, Paul K; Coppel, Ross L; Andrews, Philip C.

In: European Journal of Inorganic Chemistry, Vol. 2016, No. 17, 2016, p. 2738-2749.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - The importance of heterolepticity in improving the antibacterial activity of bismuth(III) thiolates

AU - Luqman, Ahmad

AU - Blair, Victoria L

AU - Brammananth, Rajini

AU - Crellin, Paul K

AU - Coppel, Ross L

AU - Andrews, Philip C

PY - 2016

Y1 - 2016

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AB - Five mixed thiolatobismuth(III) complexes [BiPh(5-MMTD)2{4-MMT(H)}] (1), [Bi(1-MMTZ)2{(PYM)(PYM(H))2}] (2), [Bi(MBT)2(5-MMTD)] (3), [Bi(4-BrMTD)3{2-MMI(H)}] (4) and [Bi(1-MMTZ)2{1-MMTZ(H)}(2-MMI){2-MMI(H)2}] (5) were synthesised from imidazole-, thiazole-, thiadiazole-, triazole-, tetrazole- and pyrimidine-based heterocyclic thiones. Four of these complexes 1–4 were synthesized from BiPh3, while complex 5 was obtained from Bi[4-(MeO)Ph]3. Complexes 1–5 were structurally characterised by XRD. Evaluation of the antibacterial properties against Mycobacterium smegmatis, Staphylococcus aureus, Methicillin-resistant S. aureus (MRSA), Vancomycin-resistant Enterococcus (VRE), Enterococcus faecalis and Escherichia coli showed that mixed thiolato complexes containing the anionic thiazole-based ligands MBT and 4-BrMTD are most effective. The mixed thiolato complexes [Bi(MBT)2(5-MMTD)] (3) having thiazole- and thiadiazole- and [Bi(4-BrMBT)3{2-MMI(H)}] (4) containing thiazole- and imidazole-based ligands proved to be more efficient, with low minimum inhibitory concentrations of 1.73 and 3.45 µm for 3 against VRE and E. faecalis, respectively, and 2.20 µm for 4 against M. smegmatis and E. faecalis. All complexes showed little or no toxicity towards mammalian COS-7 cell lines at 20 µg mL–1.

KW - Antibiotics

KW - Bismuth

KW - Drug design

KW - Heteroleptic complexes

KW - Medicinal chemistry

KW - S ligands

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DO - 10.1002/ejic.201600076

M3 - Article

VL - 2016

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EP - 2749

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

SN - 1434-1948

IS - 17

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