Comparative 13C and 31P NMR studies of the ligand exchange reactions of auranofin with ergothionine, imidazolidine-2-thione and diazinane-2-thione

Anvarhusein A. Isab; Saeed Ahmad

doi:10.1016/S0162-0134(01)00304-X

Comparative ¹³C and ³¹P NMR studies of the ligand exchange reactions of auranofin with ergothionine, imidazolidine-2-thione and diazinane-2-thione

Anvarhusein A. Isab^*, Saeed Ahmad

^*Corresponding author for this work

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

13 Scopus citations

Abstract

The interaction of auranofin (Et₃PAuSATg) with ergothionine (ErS), imidazolidine-2-thione (Imt) and diazinane-2-thione (Diaz) has been studied using ¹³C and ³¹P NMR spectroscopy. It is observed that these thiones are able to replace both Et₃P and SATg^- ligands simultaneously from gold(I) in auranofin forming >C=S-Au-SATg and [Et₃P-Au-S=C<]⁺ type complexes. The displaced SATg^- is oxidized to its disulfide (SATg)₂. However, some of the displaced Et₃P is oxidized to Et₃PO while the remaining reacts with thiones to form Et₃P-S=C< species characterized by δ ³¹P NMR of 1.0-1.5 ppm. The Et₃PO resonance appeared in the ³¹P NMR spectrum, after 10 days of the addition of ErS, after 19 days of the addition of Imt and after 6 days of the addition of Diaz, to auranofin solution showing that the thiones react with auranofin very slowly.

Original language	English
Pages (from-to)	53-60
Number of pages	8
Journal	Journal of Inorganic Biochemistry
Volume	88
Issue number	1
DOIs	https://doi.org/10.1016/S0162-0134(01)00304-X
State	Published - 1 Jan 2002

Bibliographical note

Funding Information:
This research was supported by the KFUPM Research Committee under project no. CY/NMR-STUDIES/214.

Keywords

Auranofin
Diazinane-2-thione
Ergothionine
Gold(I)
Imidazolidine-2-thione
NMR

ASJC Scopus subject areas

Biochemistry
Inorganic Chemistry

Access to Document

10.1016/S0162-0134(01)00304-X

Cite this

@article{4ccd2d03a8f9474992a6c1f72d4cc6b6,

title = "Comparative 13C and 31P NMR studies of the ligand exchange reactions of auranofin with ergothionine, imidazolidine-2-thione and diazinane-2-thione",

abstract = "The interaction of auranofin (Et3PAuSATg) with ergothionine (ErS), imidazolidine-2-thione (Imt) and diazinane-2-thione (Diaz) has been studied using 13C and 31P NMR spectroscopy. It is observed that these thiones are able to replace both Et3P and SATg- ligands simultaneously from gold(I) in auranofin forming >C=S-Au-SATg and [Et3P-Au-S=C<]+ type complexes. The displaced SATg- is oxidized to its disulfide (SATg)2. However, some of the displaced Et3P is oxidized to Et3PO while the remaining reacts with thiones to form Et3P-S=C< species characterized by δ 31P NMR of 1.0-1.5 ppm. The Et3PO resonance appeared in the 31P NMR spectrum, after 10 days of the addition of ErS, after 19 days of the addition of Imt and after 6 days of the addition of Diaz, to auranofin solution showing that the thiones react with auranofin very slowly.",

keywords = "Auranofin, Diazinane-2-thione, Ergothionine, Gold(I), Imidazolidine-2-thione, NMR",

author = "Isab, {Anvarhusein A.} and Saeed Ahmad",

note = "Funding Information: This research was supported by the KFUPM Research Committee under project no. CY/NMR-STUDIES/214. ",

year = "2002",

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doi = "10.1016/S0162-0134(01)00304-X",

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T1 - Comparative 13C and 31P NMR studies of the ligand exchange reactions of auranofin with ergothionine, imidazolidine-2-thione and diazinane-2-thione

AU - Isab, Anvarhusein A.

AU - Ahmad, Saeed

N1 - Funding Information: This research was supported by the KFUPM Research Committee under project no. CY/NMR-STUDIES/214.

PY - 2002/1/1

Y1 - 2002/1/1

N2 - The interaction of auranofin (Et3PAuSATg) with ergothionine (ErS), imidazolidine-2-thione (Imt) and diazinane-2-thione (Diaz) has been studied using 13C and 31P NMR spectroscopy. It is observed that these thiones are able to replace both Et3P and SATg- ligands simultaneously from gold(I) in auranofin forming >C=S-Au-SATg and [Et3P-Au-S=C<]+ type complexes. The displaced SATg- is oxidized to its disulfide (SATg)2. However, some of the displaced Et3P is oxidized to Et3PO while the remaining reacts with thiones to form Et3P-S=C< species characterized by δ 31P NMR of 1.0-1.5 ppm. The Et3PO resonance appeared in the 31P NMR spectrum, after 10 days of the addition of ErS, after 19 days of the addition of Imt and after 6 days of the addition of Diaz, to auranofin solution showing that the thiones react with auranofin very slowly.

AB - The interaction of auranofin (Et3PAuSATg) with ergothionine (ErS), imidazolidine-2-thione (Imt) and diazinane-2-thione (Diaz) has been studied using 13C and 31P NMR spectroscopy. It is observed that these thiones are able to replace both Et3P and SATg- ligands simultaneously from gold(I) in auranofin forming >C=S-Au-SATg and [Et3P-Au-S=C<]+ type complexes. The displaced SATg- is oxidized to its disulfide (SATg)2. However, some of the displaced Et3P is oxidized to Et3PO while the remaining reacts with thiones to form Et3P-S=C< species characterized by δ 31P NMR of 1.0-1.5 ppm. The Et3PO resonance appeared in the 31P NMR spectrum, after 10 days of the addition of ErS, after 19 days of the addition of Imt and after 6 days of the addition of Diaz, to auranofin solution showing that the thiones react with auranofin very slowly.

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KW - Gold(I)

KW - Imidazolidine-2-thione

KW - NMR

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