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

doi:10.1039/c7dt04171c

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

School of Chemistry

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

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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 language	English
Pages (from-to)	971-980
Number of pages	10
Journal	Dalton Transactions
Volume	47
Issue number	3
DOIs	https://doi.org/10.1039/c7dt04171c
Publication status	Published - 2018

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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",

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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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DO - 10.1039/c7dt04171c

M3 - Article

AN - SCOPUS:85041825323

SN - 1477-9226

VL - 47

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JO - Dalton Transactions

JF - Dalton Transactions

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

Abstract

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