Synthesis and structural characterisation of bismuth(III) hydroxamates and their activity against Helicobacter pylori

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Abstract

Seven new bismuth(iii) hydroxamate complexes derived from the hydroxamic acids N-methylfurohydroxamic acid (H-MFHA), N-benzoyl-N-phenylhydroxamic acid (H-BPHA), salicylhydroxamic acid (H2-SHA), benzohydroxamic acid (H2-BHA), and acetohydroxamic acid (H2-AHA) have been synthesized and characterized. The complexes formed are either tris-hydroxamato complexes containing only mono-anionic ligands, [Bi(H-SHA)3], [Bi(MFHA)3] and [Bi(BPHA)3]; mixed-anion complexes, [Bi(SHA)(H-SHA)] and [Bi(AHA)(H-AHA)]; and potassium bismuthate complexes, K[Bi(SHA)2] and K[Bi(BHA)2]. The solid-state structure of three complexes has been determined through single crystal X-ray diffraction; [Bi(MFHA)3]2·Me2CO, {[Bi(SHA)(H-SHA)(DMSO)2][Bi(SHA)(H-SHA)(DMSO)]·DMSO}∞ and [Bi(BPHA)3]2·2EtOH. All the complexes and their parent acids were assessed for the bactericidal activity against three strains of Helicobacter pylori (26695, B128 and 251). Of the acids, only acetohydroxamic acid showed any activity at low concentrations (MIC 6.25 μg mL-1; 83.26 μM) while the others were not toxic below 25 μg mL-1. In contrast, their bismuth(iii) complexes all showed excellent activity across all three strains (e.g. 0.28 μM for [Bi(H-SHA)3] to 6.01 μM for K[Bi(BHA)2] against strain 251) with only minor variations in activity being both ligand and composition dependant
Original languageEnglish
Pages (from-to)16903-16913
Number of pages11
JournalDalton Transactions
Volume44
Issue number38
DOIs
Publication statusPublished - 2015

Cite this

@article{8fdc569b930b43db9baad24e59408913,
title = "Synthesis and structural characterisation of bismuth(III) hydroxamates and their activity against Helicobacter pylori",
abstract = "Seven new bismuth(iii) hydroxamate complexes derived from the hydroxamic acids N-methylfurohydroxamic acid (H-MFHA), N-benzoyl-N-phenylhydroxamic acid (H-BPHA), salicylhydroxamic acid (H2-SHA), benzohydroxamic acid (H2-BHA), and acetohydroxamic acid (H2-AHA) have been synthesized and characterized. The complexes formed are either tris-hydroxamato complexes containing only mono-anionic ligands, [Bi(H-SHA)3], [Bi(MFHA)3] and [Bi(BPHA)3]; mixed-anion complexes, [Bi(SHA)(H-SHA)] and [Bi(AHA)(H-AHA)]; and potassium bismuthate complexes, K[Bi(SHA)2] and K[Bi(BHA)2]. The solid-state structure of three complexes has been determined through single crystal X-ray diffraction; [Bi(MFHA)3]2·Me2CO, {[Bi(SHA)(H-SHA)(DMSO)2][Bi(SHA)(H-SHA)(DMSO)]·DMSO}∞ and [Bi(BPHA)3]2·2EtOH. All the complexes and their parent acids were assessed for the bactericidal activity against three strains of Helicobacter pylori (26695, B128 and 251). Of the acids, only acetohydroxamic acid showed any activity at low concentrations (MIC 6.25 μg mL-1; 83.26 μM) while the others were not toxic below 25 μg mL-1. In contrast, their bismuth(iii) complexes all showed excellent activity across all three strains (e.g. 0.28 μM for [Bi(H-SHA)3] to 6.01 μM for K[Bi(BHA)2] against strain 251) with only minor variations in activity being both ligand and composition dependant",
author = "Amita Pathak and Blair, {Victoria Louise} and Ferrero, {Richard Louis} and Junk, {Peter Courtney} and Tabor, {Richard Francis} and Andrews, {Philip Craig}",
year = "2015",
doi = "10.1039/c5dt02259b",
language = "English",
volume = "44",
pages = "16903--16913",
journal = "Journal of the Chemical Society. Dalton Transactions",
issn = "1477-9226",
publisher = "The Royal Society of Chemistry",
number = "38",

}

Synthesis and structural characterisation of bismuth(III) hydroxamates and their activity against Helicobacter pylori. / Pathak, Amita; Blair, Victoria Louise; Ferrero, Richard Louis; Junk, Peter Courtney; Tabor, Richard Francis; Andrews, Philip Craig.

In: Dalton Transactions, Vol. 44, No. 38, 2015, p. 16903-16913.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Synthesis and structural characterisation of bismuth(III) hydroxamates and their activity against Helicobacter pylori

AU - Pathak, Amita

AU - Blair, Victoria Louise

AU - Ferrero, Richard Louis

AU - Junk, Peter Courtney

AU - Tabor, Richard Francis

AU - Andrews, Philip Craig

PY - 2015

Y1 - 2015

N2 - Seven new bismuth(iii) hydroxamate complexes derived from the hydroxamic acids N-methylfurohydroxamic acid (H-MFHA), N-benzoyl-N-phenylhydroxamic acid (H-BPHA), salicylhydroxamic acid (H2-SHA), benzohydroxamic acid (H2-BHA), and acetohydroxamic acid (H2-AHA) have been synthesized and characterized. The complexes formed are either tris-hydroxamato complexes containing only mono-anionic ligands, [Bi(H-SHA)3], [Bi(MFHA)3] and [Bi(BPHA)3]; mixed-anion complexes, [Bi(SHA)(H-SHA)] and [Bi(AHA)(H-AHA)]; and potassium bismuthate complexes, K[Bi(SHA)2] and K[Bi(BHA)2]. The solid-state structure of three complexes has been determined through single crystal X-ray diffraction; [Bi(MFHA)3]2·Me2CO, {[Bi(SHA)(H-SHA)(DMSO)2][Bi(SHA)(H-SHA)(DMSO)]·DMSO}∞ and [Bi(BPHA)3]2·2EtOH. All the complexes and their parent acids were assessed for the bactericidal activity against three strains of Helicobacter pylori (26695, B128 and 251). Of the acids, only acetohydroxamic acid showed any activity at low concentrations (MIC 6.25 μg mL-1; 83.26 μM) while the others were not toxic below 25 μg mL-1. In contrast, their bismuth(iii) complexes all showed excellent activity across all three strains (e.g. 0.28 μM for [Bi(H-SHA)3] to 6.01 μM for K[Bi(BHA)2] against strain 251) with only minor variations in activity being both ligand and composition dependant

AB - Seven new bismuth(iii) hydroxamate complexes derived from the hydroxamic acids N-methylfurohydroxamic acid (H-MFHA), N-benzoyl-N-phenylhydroxamic acid (H-BPHA), salicylhydroxamic acid (H2-SHA), benzohydroxamic acid (H2-BHA), and acetohydroxamic acid (H2-AHA) have been synthesized and characterized. The complexes formed are either tris-hydroxamato complexes containing only mono-anionic ligands, [Bi(H-SHA)3], [Bi(MFHA)3] and [Bi(BPHA)3]; mixed-anion complexes, [Bi(SHA)(H-SHA)] and [Bi(AHA)(H-AHA)]; and potassium bismuthate complexes, K[Bi(SHA)2] and K[Bi(BHA)2]. The solid-state structure of three complexes has been determined through single crystal X-ray diffraction; [Bi(MFHA)3]2·Me2CO, {[Bi(SHA)(H-SHA)(DMSO)2][Bi(SHA)(H-SHA)(DMSO)]·DMSO}∞ and [Bi(BPHA)3]2·2EtOH. All the complexes and their parent acids were assessed for the bactericidal activity against three strains of Helicobacter pylori (26695, B128 and 251). Of the acids, only acetohydroxamic acid showed any activity at low concentrations (MIC 6.25 μg mL-1; 83.26 μM) while the others were not toxic below 25 μg mL-1. In contrast, their bismuth(iii) complexes all showed excellent activity across all three strains (e.g. 0.28 μM for [Bi(H-SHA)3] to 6.01 μM for K[Bi(BHA)2] against strain 251) with only minor variations in activity being both ligand and composition dependant

UR - http://pubs.rsc.org.ezproxy.lib.monash.edu.au/en/content/articlepdf/2015/dt/c5dt02259b

U2 - 10.1039/c5dt02259b

DO - 10.1039/c5dt02259b

M3 - Article

VL - 44

SP - 16903

EP - 16913

JO - Journal of the Chemical Society. Dalton Transactions

JF - Journal of the Chemical Society. Dalton Transactions

SN - 1477-9226

IS - 38

ER -