Comparative stability, toxicity and anti-leishmanial activity of triphenyl antimony(v) and bismuth(v) α-hydroxy carboxylato complexes

Rebekah N. Duffin, Victoria L. Blair, Lukasz Kedzierski, Philip C. Andrews

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3 Citations (Scopus)

Abstract

A series of triphenyl Sb(v) and Bi(v) α-hydroxy carboxylato complexes of the general formula [MPh3(O2CROH)2] and [MPh3(O2CRO)] have been successfully synthesised and characterised, and subsequently assayed for their comparative activity towards Leishmania parasites and human fibroblast cells. Four complexes are novel; [SbPh3Gly], [BiPh3(GlyH)2], [SbPh3(R-ManH)2] and [SbPh3(S-ManH)2], and have been structurally characterised through X-ray diffraction. These were combined in the study with the known complexes; ([SbPh3(R-Man)], [SbPh3(S-Man)], [BiPh3(R-ManH)2], [BiPh3(R-ManH)2], [SbPh3(BenzH)2], [BiPh3(BenzH)2], for which the crystal structures of [BiPh3(S-ManH)2] and [BiPh3(R-Man)2] have now been authenticated (GlyH2 = glycolic acid, R/S-ManH2 = mandelic acid, BenzH2 = benzilic acid). The complexes adopt a typical bipyramidal 7-coordinate geometry with the phenyl rings occupying the equatorial plane, and the ligands on the axial. In contrast to previous studies the Bi(v) compounds show a relatively high degree of stability in DMEM culture media. Promastigote and human fibroblast cell assays showed the Bi(v) analogues to be non-selectively toxic with a respective IC50 range of 3.58-6.33 μM and 5.83-7.01 μM. In contrast, the Sb(v) analogues provided much greater selectivity (promastigotes 12.5-20.7; fibroblasts 72.8-≥100 μM). Assessment of the Sb(v) complexes against amastigotes at 10 μM showed them to be effective with % infection values ranging from 9.5 ± 0.5-30 ± 1.3.

Original languageEnglish
Pages (from-to)971-980
Number of pages10
JournalDalton Transactions
Volume47
Issue number3
DOIs
Publication statusPublished - 2018

Cite this

@article{5414a5fd4a1548089f80778037fda12a,
title = "Comparative stability, toxicity and anti-leishmanial activity of triphenyl antimony(v) and bismuth(v) α-hydroxy carboxylato complexes",
abstract = "A series of triphenyl Sb(v) and Bi(v) α-hydroxy carboxylato complexes of the general formula [MPh3(O2CROH)2] and [MPh3(O2CRO)] have been successfully synthesised and characterised, and subsequently assayed for their comparative activity towards Leishmania parasites and human fibroblast cells. Four complexes are novel; [SbPh3Gly], [BiPh3(GlyH)2], [SbPh3(R-ManH)2] and [SbPh3(S-ManH)2], and have been structurally characterised through X-ray diffraction. These were combined in the study with the known complexes; ([SbPh3(R-Man)], [SbPh3(S-Man)], [BiPh3(R-ManH)2], [BiPh3(R-ManH)2], [SbPh3(BenzH)2], [BiPh3(BenzH)2], for which the crystal structures of [BiPh3(S-ManH)2] and [BiPh3(R-Man)2] have now been authenticated (GlyH2 = glycolic acid, R/S-ManH2 = mandelic acid, BenzH2 = benzilic acid). The complexes adopt a typical bipyramidal 7-coordinate geometry with the phenyl rings occupying the equatorial plane, and the ligands on the axial. In contrast to previous studies the Bi(v) compounds show a relatively high degree of stability in DMEM culture media. Promastigote and human fibroblast cell assays showed the Bi(v) analogues to be non-selectively toxic with a respective IC50 range of 3.58-6.33 μM and 5.83-7.01 μM. In contrast, the Sb(v) analogues provided much greater selectivity (promastigotes 12.5-20.7; fibroblasts 72.8-≥100 μM). Assessment of the Sb(v) complexes against amastigotes at 10 μM showed them to be effective with {\%} infection values ranging from 9.5 ± 0.5-30 ± 1.3.",
author = "Duffin, {Rebekah N.} and Blair, {Victoria L.} and Lukasz Kedzierski and Andrews, {Philip C.}",
year = "2018",
doi = "10.1039/c7dt04171c",
language = "English",
volume = "47",
pages = "971--980",
journal = "Journal of the Chemical Society. Dalton Transactions",
issn = "1477-9226",
publisher = "The Royal Society of Chemistry",
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}

Comparative stability, toxicity and anti-leishmanial activity of triphenyl antimony(v) and bismuth(v) α-hydroxy carboxylato complexes. / Duffin, Rebekah N.; Blair, Victoria L.; Kedzierski, Lukasz; Andrews, Philip C.

In: Dalton Transactions, Vol. 47, No. 3, 2018, p. 971-980.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Comparative stability, toxicity and anti-leishmanial activity of triphenyl antimony(v) and bismuth(v) α-hydroxy carboxylato complexes

AU - Duffin, Rebekah N.

AU - Blair, Victoria L.

AU - Kedzierski, Lukasz

AU - Andrews, Philip C.

PY - 2018

Y1 - 2018

N2 - A series of triphenyl Sb(v) and Bi(v) α-hydroxy carboxylato complexes of the general formula [MPh3(O2CROH)2] and [MPh3(O2CRO)] have been successfully synthesised and characterised, and subsequently assayed for their comparative activity towards Leishmania parasites and human fibroblast cells. Four complexes are novel; [SbPh3Gly], [BiPh3(GlyH)2], [SbPh3(R-ManH)2] and [SbPh3(S-ManH)2], and have been structurally characterised through X-ray diffraction. These were combined in the study with the known complexes; ([SbPh3(R-Man)], [SbPh3(S-Man)], [BiPh3(R-ManH)2], [BiPh3(R-ManH)2], [SbPh3(BenzH)2], [BiPh3(BenzH)2], for which the crystal structures of [BiPh3(S-ManH)2] and [BiPh3(R-Man)2] have now been authenticated (GlyH2 = glycolic acid, R/S-ManH2 = mandelic acid, BenzH2 = benzilic acid). The complexes adopt a typical bipyramidal 7-coordinate geometry with the phenyl rings occupying the equatorial plane, and the ligands on the axial. In contrast to previous studies the Bi(v) compounds show a relatively high degree of stability in DMEM culture media. Promastigote and human fibroblast cell assays showed the Bi(v) analogues to be non-selectively toxic with a respective IC50 range of 3.58-6.33 μM and 5.83-7.01 μM. In contrast, the Sb(v) analogues provided much greater selectivity (promastigotes 12.5-20.7; fibroblasts 72.8-≥100 μM). Assessment of the Sb(v) complexes against amastigotes at 10 μM showed them to be effective with % infection values ranging from 9.5 ± 0.5-30 ± 1.3.

AB - A series of triphenyl Sb(v) and Bi(v) α-hydroxy carboxylato complexes of the general formula [MPh3(O2CROH)2] and [MPh3(O2CRO)] have been successfully synthesised and characterised, and subsequently assayed for their comparative activity towards Leishmania parasites and human fibroblast cells. Four complexes are novel; [SbPh3Gly], [BiPh3(GlyH)2], [SbPh3(R-ManH)2] and [SbPh3(S-ManH)2], and have been structurally characterised through X-ray diffraction. These were combined in the study with the known complexes; ([SbPh3(R-Man)], [SbPh3(S-Man)], [BiPh3(R-ManH)2], [BiPh3(R-ManH)2], [SbPh3(BenzH)2], [BiPh3(BenzH)2], for which the crystal structures of [BiPh3(S-ManH)2] and [BiPh3(R-Man)2] have now been authenticated (GlyH2 = glycolic acid, R/S-ManH2 = mandelic acid, BenzH2 = benzilic acid). The complexes adopt a typical bipyramidal 7-coordinate geometry with the phenyl rings occupying the equatorial plane, and the ligands on the axial. In contrast to previous studies the Bi(v) compounds show a relatively high degree of stability in DMEM culture media. Promastigote and human fibroblast cell assays showed the Bi(v) analogues to be non-selectively toxic with a respective IC50 range of 3.58-6.33 μM and 5.83-7.01 μM. In contrast, the Sb(v) analogues provided much greater selectivity (promastigotes 12.5-20.7; fibroblasts 72.8-≥100 μM). Assessment of the Sb(v) complexes against amastigotes at 10 μM showed them to be effective with % infection values ranging from 9.5 ± 0.5-30 ± 1.3.

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U2 - 10.1039/c7dt04171c

DO - 10.1039/c7dt04171c

M3 - Article

VL - 47

SP - 971

EP - 980

JO - Journal of the Chemical Society. Dalton Transactions

JF - Journal of the Chemical Society. Dalton Transactions

SN - 1477-9226

IS - 3

ER -