Simultaneous replacements of triethyl phosphine and tetraacetyl thioglucose ligands from auranofin (an antiarthritic drug) with selenocyanate: 13C and 31P NMR studies

Abdul Rahman Al Arfaj; Ahmad A. Saeed; M. Naseem Akhtar; Anvarhusein A. Isab

doi:10.1080/00958979808022674

Simultaneous replacements of triethyl phosphine and tetraacetyl thioglucose ligands from auranofin (an antiarthritic drug) with selenocyanate: ¹³C and ³¹P NMR studies

Abdul Rahman Al Arfaj
, Ahmad A. Saeed
, M. Naseem Akhtar
, Anvarhusein A. Isab^*

^*Corresponding author for this work

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

9 Scopus citations

Abstract

The interaction of SeCN with a new gold-based antiarthritic drug auranofin (Et₃PAuSATg, where SATg^- = 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosato-S) in aqueous methanol has been studied by ¹³C and ³¹P NMR spectroscopy. It is observed that SeCN^- releases both ligands (i.e., SATg^- and Et₃P) to form [ATgS-Au-CN]^- and [Et₃P-Au-SeCN]. These newly generated species undergo further disproportionation and decomposition to generate species such as [(Et₃P)₂Au]⁺, [Au(CN)₂]^-, Et₃PO and metallic selenium. The formation of [(Et₃P)₂Au]⁺ and [Au(CN)₂]^- is found to be much faster for Et₃PAuNO₃ than for Et₃PAuSATg when reacted with SeCN^-. Exchange between unlabelled CN^- of Au(CN)₂^- and labelled Se¹³CN^- was observed without selenium being precipitated from Se¹³CN^-.

Original language	English
Pages (from-to)	257-272
Number of pages	16
Journal	Journal of Coordination Chemistry
Volume	43
Issue number	2-3
DOIs	https://doi.org/10.1080/00958979808022674
State	Published - 1998

Bibliographical note

Funding Information:
This research was supported by the King Fahd University of Petroleum and Minerals Research Committee under project No. CY/CYANIDE/I 75.

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Materials Chemistry

Access to Document

10.1080/00958979808022674

Cite this

@article{a205170953c4462a89f85312b175f146,

title = "Simultaneous replacements of triethyl phosphine and tetraacetyl thioglucose ligands from auranofin (an antiarthritic drug) with selenocyanate: 13C and 31P NMR studies",

abstract = "The interaction of SeCN with a new gold-based antiarthritic drug auranofin (Et3PAuSATg, where SATg- = 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosato-S) in aqueous methanol has been studied by 13C and 31P NMR spectroscopy. It is observed that SeCN- releases both ligands (i.e., SATg- and Et3P) to form [ATgS-Au-CN]- and [Et3P-Au-SeCN]. These newly generated species undergo further disproportionation and decomposition to generate species such as [(Et3P)2Au]+, [Au(CN)2]-, Et3PO and metallic selenium. The formation of [(Et3P)2Au]+ and [Au(CN)2]- is found to be much faster for Et3PAuNO3 than for Et3PAuSATg when reacted with SeCN-. Exchange between unlabelled CN- of Au(CN)2- and labelled Se13CN- was observed without selenium being precipitated from Se13CN-.",

author = "\{Al Arfaj\}, \{Abdul Rahman\} and Saeed, \{Ahmad A.\} and Akhtar, \{M. Naseem\} and Isab, \{Anvarhusein A.\}",

note = "Funding Information: This research was supported by the King Fahd University of Petroleum and Minerals Research Committee under project No. CY/CYANIDE/I 75.",

year = "1998",

doi = "10.1080/00958979808022674",

language = "English",

volume = "43",

pages = "257--272",

journal = "Journal of Coordination Chemistry",

issn = "0095-8972",

publisher = "Taylor and Francis Ltd.",

number = "2-3",

}

Simultaneous replacements of triethyl phosphine and tetraacetyl thioglucose ligands from auranofin (an antiarthritic drug) with selenocyanate: ¹³C and ³¹P NMR studies. / Al Arfaj, Abdul Rahman; Saeed, Ahmad A.; Akhtar, M. Naseem et al.
In: Journal of Coordination Chemistry, Vol. 43, No. 2-3, 1998, p. 257-272.

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

TY - JOUR

T1 - Simultaneous replacements of triethyl phosphine and tetraacetyl thioglucose ligands from auranofin (an antiarthritic drug) with selenocyanate

T2 - 13C and 31P NMR studies

AU - Al Arfaj, Abdul Rahman

AU - Saeed, Ahmad A.

AU - Akhtar, M. Naseem

AU - Isab, Anvarhusein A.

N1 - Funding Information: This research was supported by the King Fahd University of Petroleum and Minerals Research Committee under project No. CY/CYANIDE/I 75.

PY - 1998

Y1 - 1998

N2 - The interaction of SeCN with a new gold-based antiarthritic drug auranofin (Et3PAuSATg, where SATg- = 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosato-S) in aqueous methanol has been studied by 13C and 31P NMR spectroscopy. It is observed that SeCN- releases both ligands (i.e., SATg- and Et3P) to form [ATgS-Au-CN]- and [Et3P-Au-SeCN]. These newly generated species undergo further disproportionation and decomposition to generate species such as [(Et3P)2Au]+, [Au(CN)2]-, Et3PO and metallic selenium. The formation of [(Et3P)2Au]+ and [Au(CN)2]- is found to be much faster for Et3PAuNO3 than for Et3PAuSATg when reacted with SeCN-. Exchange between unlabelled CN- of Au(CN)2- and labelled Se13CN- was observed without selenium being precipitated from Se13CN-.

AB - The interaction of SeCN with a new gold-based antiarthritic drug auranofin (Et3PAuSATg, where SATg- = 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosato-S) in aqueous methanol has been studied by 13C and 31P NMR spectroscopy. It is observed that SeCN- releases both ligands (i.e., SATg- and Et3P) to form [ATgS-Au-CN]- and [Et3P-Au-SeCN]. These newly generated species undergo further disproportionation and decomposition to generate species such as [(Et3P)2Au]+, [Au(CN)2]-, Et3PO and metallic selenium. The formation of [(Et3P)2Au]+ and [Au(CN)2]- is found to be much faster for Et3PAuNO3 than for Et3PAuSATg when reacted with SeCN-. Exchange between unlabelled CN- of Au(CN)2- and labelled Se13CN- was observed without selenium being precipitated from Se13CN-.

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DO - 10.1080/00958979808022674

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JO - Journal of Coordination Chemistry

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