Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity

Ahmad Luqman; Victoria L Blair; Rajini Brammananth; Paul K Crellin; Ross L Coppel; Lukasz Kedzierski; Philip C Andrews

doi:10.1002/ejic.201402958

Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity

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

Research output: Contribution to journal › Article › Research › peer-review

31 Citations (Scopus)

Abstract

Two new homo- and heteroleptic bismuth thiazole-thiolato complexes derived from 4-phenylthiazole-2-thiol MBT(H) have been synthesised and structurally characterised, [BiPh(MBT)₂]₂ and [Bi(MBT)₃]₂. Syntheses were achieved using BiPh₃ or Bi(OtBu)₃ in protolysis reactions with MBT(H), or by salt metathesis with BiCl₃ or BiPhCl₂ and the sodium thiolate, [NaMBT]. The complexes were obtained under both standard solvent-free and solvent-mediated conditions, and by microwave irradiation. The solid-state structures of [BiPh(MBT)₂]₂ and [Bi(MBT)₃]₂, were determined using single-crystal X-ray diffraction, showing them to be dimeric. The bactericidal properties of the complexes against Mycobacterium smegmatis, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, vancomycin-resistant Enterococcus (VRE) and Escherichia coli revealed [BiPh(MBT)₂]₂ to be the most effective against all the bacteria with MIC values of 0.6 μg/mL (0.25 μM) against S. aureus and 0.9 μg/mL (0.27 μM) against E. faecalis. [Bi(MBT)₃]₂ was less active overall. However, comparisons with the analogous complex [Bi(4-BrMTD)₃], revealed a significant hundred-fold enhanced activity against S. aureus, MRSA, VRE, and E. faecalis. Both complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. [BiPh(MBT)₂]₂ also was found to display good antileishmanial activity with an IC₅₀ value of 0.11 μg/mL (0.17 μM), at which concentration the complex was non-toxic to human fibroblast cells.

Original language	English
Pages (from-to)	725-733
Number of pages	9
Journal	European Journal of Inorganic Chemistry
Volume	2015
Issue number	4
DOIs	https://doi.org/10.1002/ejic.201402958
Publication status	Published - 2015

Keywords

Antibiotics
Antiparasitic agents
Bismuth
Medicinal chemistry
S ligands

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10.1002/ejic.201402958

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@article{bbc76408cc674588aec3387c23e39bab,

title = "Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity",

abstract = "Two new homo- and heteroleptic bismuth thiazole-thiolato complexes derived from 4-phenylthiazole-2-thiol MBT(H) have been synthesised and structurally characterised, [BiPh(MBT)2]2 and [Bi(MBT)3]2. Syntheses were achieved using BiPh3 or Bi(OtBu)3 in protolysis reactions with MBT(H), or by salt metathesis with BiCl3 or BiPhCl2 and the sodium thiolate, [NaMBT]. The complexes were obtained under both standard solvent-free and solvent-mediated conditions, and by microwave irradiation. The solid-state structures of [BiPh(MBT)2]2 and [Bi(MBT)3]2, were determined using single-crystal X-ray diffraction, showing them to be dimeric. The bactericidal properties of the complexes against Mycobacterium smegmatis, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, vancomycin-resistant Enterococcus (VRE) and Escherichia coli revealed [BiPh(MBT)2]2 to be the most effective against all the bacteria with MIC values of 0.6 μg/mL (0.25 μM) against S. aureus and 0.9 μg/mL (0.27 μM) against E. faecalis. [Bi(MBT)3]2 was less active overall. However, comparisons with the analogous complex [Bi(4-BrMTD)3], revealed a significant hundred-fold enhanced activity against S. aureus, MRSA, VRE, and E. faecalis. Both complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. [BiPh(MBT)2]2 also was found to display good antileishmanial activity with an IC50 value of 0.11 μg/mL (0.17 μM), at which concentration the complex was non-toxic to human fibroblast cells.",

keywords = "Antibiotics, Antiparasitic agents, Bismuth, Medicinal chemistry, S ligands",

author = "Ahmad Luqman and Blair, {Victoria L} and Rajini Brammananth and Crellin, {Paul K} and Coppel, {Ross L} and Lukasz Kedzierski and Andrews, {Philip C}",

year = "2015",

doi = "10.1002/ejic.201402958",

language = "English",

volume = "2015",

pages = "725--733",

journal = "European Journal of Inorganic Chemistry",

issn = "1434-1948",

publisher = "Wiley-VCH Verlag GmbH & Co. KGaA",

number = "4",

}

Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity. / Luqman, Ahmad; Blair, Victoria L; Brammananth, Rajini et al.
In: European Journal of Inorganic Chemistry, Vol. 2015, No. 4, 2015, p. 725-733.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity

AU - Luqman, Ahmad

AU - Blair, Victoria L

AU - Brammananth, Rajini

AU - Crellin, Paul K

AU - Coppel, Ross L

AU - Kedzierski, Lukasz

AU - Andrews, Philip C

PY - 2015

Y1 - 2015

N2 - Two new homo- and heteroleptic bismuth thiazole-thiolato complexes derived from 4-phenylthiazole-2-thiol MBT(H) have been synthesised and structurally characterised, [BiPh(MBT)2]2 and [Bi(MBT)3]2. Syntheses were achieved using BiPh3 or Bi(OtBu)3 in protolysis reactions with MBT(H), or by salt metathesis with BiCl3 or BiPhCl2 and the sodium thiolate, [NaMBT]. The complexes were obtained under both standard solvent-free and solvent-mediated conditions, and by microwave irradiation. The solid-state structures of [BiPh(MBT)2]2 and [Bi(MBT)3]2, were determined using single-crystal X-ray diffraction, showing them to be dimeric. The bactericidal properties of the complexes against Mycobacterium smegmatis, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, vancomycin-resistant Enterococcus (VRE) and Escherichia coli revealed [BiPh(MBT)2]2 to be the most effective against all the bacteria with MIC values of 0.6 μg/mL (0.25 μM) against S. aureus and 0.9 μg/mL (0.27 μM) against E. faecalis. [Bi(MBT)3]2 was less active overall. However, comparisons with the analogous complex [Bi(4-BrMTD)3], revealed a significant hundred-fold enhanced activity against S. aureus, MRSA, VRE, and E. faecalis. Both complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. [BiPh(MBT)2]2 also was found to display good antileishmanial activity with an IC50 value of 0.11 μg/mL (0.17 μM), at which concentration the complex was non-toxic to human fibroblast cells.

AB - Two new homo- and heteroleptic bismuth thiazole-thiolato complexes derived from 4-phenylthiazole-2-thiol MBT(H) have been synthesised and structurally characterised, [BiPh(MBT)2]2 and [Bi(MBT)3]2. Syntheses were achieved using BiPh3 or Bi(OtBu)3 in protolysis reactions with MBT(H), or by salt metathesis with BiCl3 or BiPhCl2 and the sodium thiolate, [NaMBT]. The complexes were obtained under both standard solvent-free and solvent-mediated conditions, and by microwave irradiation. The solid-state structures of [BiPh(MBT)2]2 and [Bi(MBT)3]2, were determined using single-crystal X-ray diffraction, showing them to be dimeric. The bactericidal properties of the complexes against Mycobacterium smegmatis, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, vancomycin-resistant Enterococcus (VRE) and Escherichia coli revealed [BiPh(MBT)2]2 to be the most effective against all the bacteria with MIC values of 0.6 μg/mL (0.25 μM) against S. aureus and 0.9 μg/mL (0.27 μM) against E. faecalis. [Bi(MBT)3]2 was less active overall. However, comparisons with the analogous complex [Bi(4-BrMTD)3], revealed a significant hundred-fold enhanced activity against S. aureus, MRSA, VRE, and E. faecalis. Both complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. [BiPh(MBT)2]2 also was found to display good antileishmanial activity with an IC50 value of 0.11 μg/mL (0.17 μM), at which concentration the complex was non-toxic to human fibroblast cells.

KW - Antibiotics

KW - Antiparasitic agents

KW - Bismuth

KW - Medicinal chemistry

KW - S ligands

UR - http://www.scopus.com/inward/record.url?scp=85027933369&partnerID=8YFLogxK

U2 - 10.1002/ejic.201402958

DO - 10.1002/ejic.201402958

M3 - Article

AN - SCOPUS:85027933369

SN - 1434-1948

VL - 2015

SP - 725

EP - 733

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 4

ER -

Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity

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Keywords

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Bio-inspired Chemistry of Novel Metal-Organic Bismuth Compounds

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Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity

Abstract

Keywords

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Bio-inspired Chemistry of Novel Metal-Organic Bismuth Compounds

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