Structural influences on the activity of bismuth(III) indole-carboxylato complexes towards Helicobacter pylori and Leishmania

Amita Pathak, Victoria Blair, Richard L. Ferrero, Lukasz Kedzierski, Philip C. Andrews

Research output: Contribution to journalArticleResearchpeer-review

4 Citations (Scopus)

Abstract

Seven new bismuth(III) complexes derived from indole-carboxylic acids have been synthesised: five are homoleptic; [Bi(IAA)3] B1, [Bi(IPA)3] B2, [Bi(IBA)3] B3, [Bi(MICA)3] B4, [Bi(IGA)3] B6, and two are heteroleptic [BiPh(MICA)2] B5 (where IAA-H =2-(1H-indol-3-yl)acetic acid, IPA-H =3-(1H-indol-3-yl)propanoic acid, IBA-H =4-(1H-indol-3-yl)butanoic acid, IGA-H =2-(1H-indol-3-yl)-2-oxoacetic acid, and MICA-H =1-methyl-1H-indole-3-carboxylic acid). All complexes were fully characterised by elemental analysis, infrared and mass-spectroscopy, and nuclear magnetic resonance (1H, 13C) spectroscopy. Complex [BiPh(IGA)2] B7 is structurally authenticated by X-ray crystallography as a dimer in the solid-state. The in-vitro anti-bacterial activity of the indole-carboxylic acids and their bismuth(III) complexes was assessed against Helicobacter pylori. While the acids were non-toxic at <100μgmL-1, all the bismuth compounds showed an MIC of 6.25μgmL-1, indicating that the anti-bacterial activity is insensitive to the degree of substitution at the Bi(III) centre or the composition of the indole-carboxylate ligands. All compounds were further tested for their anti-parasitic activity against Leishmania major and for their toxicity towards mammalian cells. From the anti-parasitic studies, it was found that the heteroleptic bismuth(III) complexes are the most active, with B5 and B7 showing comparable activity to Amphotericin B, without any toxicity towards the mammalian cells at their effective concentration.

Original languageEnglish
Pages (from-to)266-275
Number of pages10
JournalJournal of Inorganic Biochemistry
Volume177
DOIs
Publication statusPublished - Dec 2017

Cite this

@article{dd85c63c44584572910e448245b7452a,
title = "Structural influences on the activity of bismuth(III) indole-carboxylato complexes towards Helicobacter pylori and Leishmania",
abstract = "Seven new bismuth(III) complexes derived from indole-carboxylic acids have been synthesised: five are homoleptic; [Bi(IAA)3] B1, [Bi(IPA)3] B2, [Bi(IBA)3] B3, [Bi(MICA)3] B4, [Bi(IGA)3] B6, and two are heteroleptic [BiPh(MICA)2] B5 (where IAA-H =2-(1H-indol-3-yl)acetic acid, IPA-H =3-(1H-indol-3-yl)propanoic acid, IBA-H =4-(1H-indol-3-yl)butanoic acid, IGA-H =2-(1H-indol-3-yl)-2-oxoacetic acid, and MICA-H =1-methyl-1H-indole-3-carboxylic acid). All complexes were fully characterised by elemental analysis, infrared and mass-spectroscopy, and nuclear magnetic resonance (1H, 13C) spectroscopy. Complex [BiPh(IGA)2] B7 is structurally authenticated by X-ray crystallography as a dimer in the solid-state. The in-vitro anti-bacterial activity of the indole-carboxylic acids and their bismuth(III) complexes was assessed against Helicobacter pylori. While the acids were non-toxic at <100μgmL-1, all the bismuth compounds showed an MIC of 6.25μgmL-1, indicating that the anti-bacterial activity is insensitive to the degree of substitution at the Bi(III) centre or the composition of the indole-carboxylate ligands. All compounds were further tested for their anti-parasitic activity against Leishmania major and for their toxicity towards mammalian cells. From the anti-parasitic studies, it was found that the heteroleptic bismuth(III) complexes are the most active, with B5 and B7 showing comparable activity to Amphotericin B, without any toxicity towards the mammalian cells at their effective concentration.",
author = "Amita Pathak and Victoria Blair and Ferrero, {Richard L.} and Lukasz Kedzierski and Andrews, {Philip C.}",
year = "2017",
month = "12",
doi = "10.1016/j.jinorgbio.2017.05.014",
language = "English",
volume = "177",
pages = "266--275",
journal = "Journal of Inorganic Biochemistry",
issn = "0162-0134",
publisher = "Elsevier",

}

Structural influences on the activity of bismuth(III) indole-carboxylato complexes towards Helicobacter pylori and Leishmania. / Pathak, Amita; Blair, Victoria; Ferrero, Richard L.; Kedzierski, Lukasz; Andrews, Philip C.

In: Journal of Inorganic Biochemistry, Vol. 177, 12.2017, p. 266-275.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Structural influences on the activity of bismuth(III) indole-carboxylato complexes towards Helicobacter pylori and Leishmania

AU - Pathak, Amita

AU - Blair, Victoria

AU - Ferrero, Richard L.

AU - Kedzierski, Lukasz

AU - Andrews, Philip C.

PY - 2017/12

Y1 - 2017/12

N2 - Seven new bismuth(III) complexes derived from indole-carboxylic acids have been synthesised: five are homoleptic; [Bi(IAA)3] B1, [Bi(IPA)3] B2, [Bi(IBA)3] B3, [Bi(MICA)3] B4, [Bi(IGA)3] B6, and two are heteroleptic [BiPh(MICA)2] B5 (where IAA-H =2-(1H-indol-3-yl)acetic acid, IPA-H =3-(1H-indol-3-yl)propanoic acid, IBA-H =4-(1H-indol-3-yl)butanoic acid, IGA-H =2-(1H-indol-3-yl)-2-oxoacetic acid, and MICA-H =1-methyl-1H-indole-3-carboxylic acid). All complexes were fully characterised by elemental analysis, infrared and mass-spectroscopy, and nuclear magnetic resonance (1H, 13C) spectroscopy. Complex [BiPh(IGA)2] B7 is structurally authenticated by X-ray crystallography as a dimer in the solid-state. The in-vitro anti-bacterial activity of the indole-carboxylic acids and their bismuth(III) complexes was assessed against Helicobacter pylori. While the acids were non-toxic at <100μgmL-1, all the bismuth compounds showed an MIC of 6.25μgmL-1, indicating that the anti-bacterial activity is insensitive to the degree of substitution at the Bi(III) centre or the composition of the indole-carboxylate ligands. All compounds were further tested for their anti-parasitic activity against Leishmania major and for their toxicity towards mammalian cells. From the anti-parasitic studies, it was found that the heteroleptic bismuth(III) complexes are the most active, with B5 and B7 showing comparable activity to Amphotericin B, without any toxicity towards the mammalian cells at their effective concentration.

AB - Seven new bismuth(III) complexes derived from indole-carboxylic acids have been synthesised: five are homoleptic; [Bi(IAA)3] B1, [Bi(IPA)3] B2, [Bi(IBA)3] B3, [Bi(MICA)3] B4, [Bi(IGA)3] B6, and two are heteroleptic [BiPh(MICA)2] B5 (where IAA-H =2-(1H-indol-3-yl)acetic acid, IPA-H =3-(1H-indol-3-yl)propanoic acid, IBA-H =4-(1H-indol-3-yl)butanoic acid, IGA-H =2-(1H-indol-3-yl)-2-oxoacetic acid, and MICA-H =1-methyl-1H-indole-3-carboxylic acid). All complexes were fully characterised by elemental analysis, infrared and mass-spectroscopy, and nuclear magnetic resonance (1H, 13C) spectroscopy. Complex [BiPh(IGA)2] B7 is structurally authenticated by X-ray crystallography as a dimer in the solid-state. The in-vitro anti-bacterial activity of the indole-carboxylic acids and their bismuth(III) complexes was assessed against Helicobacter pylori. While the acids were non-toxic at <100μgmL-1, all the bismuth compounds showed an MIC of 6.25μgmL-1, indicating that the anti-bacterial activity is insensitive to the degree of substitution at the Bi(III) centre or the composition of the indole-carboxylate ligands. All compounds were further tested for their anti-parasitic activity against Leishmania major and for their toxicity towards mammalian cells. From the anti-parasitic studies, it was found that the heteroleptic bismuth(III) complexes are the most active, with B5 and B7 showing comparable activity to Amphotericin B, without any toxicity towards the mammalian cells at their effective concentration.

UR - http://www.scopus.com/inward/record.url?scp=85020118728&partnerID=8YFLogxK

U2 - 10.1016/j.jinorgbio.2017.05.014

DO - 10.1016/j.jinorgbio.2017.05.014

M3 - Article

VL - 177

SP - 266

EP - 275

JO - Journal of Inorganic Biochemistry

JF - Journal of Inorganic Biochemistry

SN - 0162-0134

ER -