Synthesis, X-ray structures, spectroscopic analysis and anticancer activity of novel gold(I) carbene complexes

Muhammad Altaf; M. Monim-Ul-Mehboob; Adam A.A. Seliman; Anvarhusein A. Isab; Vikram Dhuna; Gaurav Bhatia; Kshitija Dhuna

doi:10.1016/j.jorganchem.2014.04.029

Synthesis, X-ray structures, spectroscopic analysis and anticancer activity of novel gold(I) carbene complexes

Muhammad Altaf, M. Monim-Ul-Mehboob, Adam A.A. Seliman, Anvarhusein A. Isab^*, Vikram Dhuna, Gaurav Bhatia, Kshitija Dhuna

^*Corresponding author for this work

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

34 Scopus citations

Abstract

Three new linear gold(I) complexes of the formulas [(Ipr)Au(S ₂CN(CH₃)₂)] (1), [(Ipr)Au (S ₂CN(C₂H₅)₂)] (2) and [(Ipr)Au(S ₂CN(C₇H₇)₂)] (3) [where Ipr = 1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold] have been prepared by the reaction of equimolar amounts of 1,3-bis(2,6-di-isopropylphenyl)imidazol-2- ylidenegold(I)chloride, [(Ipr)Au(Cl)] with sodium dimethyldithiocarbamate monohydrate, sodium diethyl dithiocarbamatetrihydrate and dibenzyl dithiocarbamate, respectively. The structures of the complexes have been determined by single X-ray crystallography. All gold(I) complexes (1-3) are iso-structural i.e. linear geometry. The complex (1) crystallizes in monoclinic space group 'P2₁/a', while the complexes (2) and (3) crystallize in orthorhombic space group 'Pna2₁'. The IR spectra and ¹H as well as ¹³C NMR measurements of the Au(I) complexes (1-3) corroborate well with their single crystal X-ray structure analysis. These gold(I) complexes show moderate potential anti-cancer activities against A549 (human lung carcinoma), HCT15 (human colon cancer), and HeLa (human cervical cancer) cell lines.

Original language	English
Pages (from-to)	68-79
Number of pages	12
Journal	Journal of Organometallic Chemistry
Volume	765
DOIs	https://doi.org/10.1016/j.jorganchem.2014.04.029
State	Published - 15 Aug 2014

Bibliographical note

Funding Information:
The author(s) would like to acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science & Technology Unit at King Fahd University of Petroleum & Minerals (KFUPM) for funding this work through project No. 11-MED1670-04 as part of the National Science, Technology and Innovation Plan.

Keywords

1,3-Bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold
Dithiocarbamate gold(I) complexes
IR and NMR spectroscopic studies
In vitro cytotoxicity

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.jorganchem.2014.04.029

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title = "Synthesis, X-ray structures, spectroscopic analysis and anticancer activity of novel gold(I) carbene complexes",

abstract = "Three new linear gold(I) complexes of the formulas [(Ipr)Au(S 2CN(CH3)2)] (1), [(Ipr)Au (S 2CN(C2H5)2)] (2) and [(Ipr)Au(S 2CN(C7H7)2)] (3) [where Ipr = 1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold] have been prepared by the reaction of equimolar amounts of 1,3-bis(2,6-di-isopropylphenyl)imidazol-2- ylidenegold(I)chloride, [(Ipr)Au(Cl)] with sodium dimethyldithiocarbamate monohydrate, sodium diethyl dithiocarbamatetrihydrate and dibenzyl dithiocarbamate, respectively. The structures of the complexes have been determined by single X-ray crystallography. All gold(I) complexes (1-3) are iso-structural i.e. linear geometry. The complex (1) crystallizes in monoclinic space group 'P21/a', while the complexes (2) and (3) crystallize in orthorhombic space group 'Pna21'. The IR spectra and 1H as well as 13C NMR measurements of the Au(I) complexes (1-3) corroborate well with their single crystal X-ray structure analysis. These gold(I) complexes show moderate potential anti-cancer activities against A549 (human lung carcinoma), HCT15 (human colon cancer), and HeLa (human cervical cancer) cell lines.",

keywords = "1,3-Bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold, Dithiocarbamate gold(I) complexes, IR and NMR spectroscopic studies, In vitro cytotoxicity",

author = "Muhammad Altaf and M. Monim-Ul-Mehboob and Seliman, \{Adam A.A.\} and Isab, \{Anvarhusein A.\} and Vikram Dhuna and Gaurav Bhatia and Kshitija Dhuna",

note = "Funding Information: The author(s) would like to acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science \& Technology Unit at King Fahd University of Petroleum \& Minerals (KFUPM) for funding this work through project No. 11-MED1670-04 as part of the National Science, Technology and Innovation Plan. ",

year = "2014",

month = aug,

day = "15",

doi = "10.1016/j.jorganchem.2014.04.029",

language = "English",

volume = "765",

pages = "68--79",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

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TY - JOUR

T1 - Synthesis, X-ray structures, spectroscopic analysis and anticancer activity of novel gold(I) carbene complexes

AU - Altaf, Muhammad

AU - Monim-Ul-Mehboob, M.

AU - Seliman, Adam A.A.

AU - Isab, Anvarhusein A.

AU - Dhuna, Vikram

AU - Bhatia, Gaurav

AU - Dhuna, Kshitija

N1 - Funding Information: The author(s) would like to acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science & Technology Unit at King Fahd University of Petroleum & Minerals (KFUPM) for funding this work through project No. 11-MED1670-04 as part of the National Science, Technology and Innovation Plan.

PY - 2014/8/15

Y1 - 2014/8/15

N2 - Three new linear gold(I) complexes of the formulas [(Ipr)Au(S 2CN(CH3)2)] (1), [(Ipr)Au (S 2CN(C2H5)2)] (2) and [(Ipr)Au(S 2CN(C7H7)2)] (3) [where Ipr = 1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold] have been prepared by the reaction of equimolar amounts of 1,3-bis(2,6-di-isopropylphenyl)imidazol-2- ylidenegold(I)chloride, [(Ipr)Au(Cl)] with sodium dimethyldithiocarbamate monohydrate, sodium diethyl dithiocarbamatetrihydrate and dibenzyl dithiocarbamate, respectively. The structures of the complexes have been determined by single X-ray crystallography. All gold(I) complexes (1-3) are iso-structural i.e. linear geometry. The complex (1) crystallizes in monoclinic space group 'P21/a', while the complexes (2) and (3) crystallize in orthorhombic space group 'Pna21'. The IR spectra and 1H as well as 13C NMR measurements of the Au(I) complexes (1-3) corroborate well with their single crystal X-ray structure analysis. These gold(I) complexes show moderate potential anti-cancer activities against A549 (human lung carcinoma), HCT15 (human colon cancer), and HeLa (human cervical cancer) cell lines.

AB - Three new linear gold(I) complexes of the formulas [(Ipr)Au(S 2CN(CH3)2)] (1), [(Ipr)Au (S 2CN(C2H5)2)] (2) and [(Ipr)Au(S 2CN(C7H7)2)] (3) [where Ipr = 1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold] have been prepared by the reaction of equimolar amounts of 1,3-bis(2,6-di-isopropylphenyl)imidazol-2- ylidenegold(I)chloride, [(Ipr)Au(Cl)] with sodium dimethyldithiocarbamate monohydrate, sodium diethyl dithiocarbamatetrihydrate and dibenzyl dithiocarbamate, respectively. The structures of the complexes have been determined by single X-ray crystallography. All gold(I) complexes (1-3) are iso-structural i.e. linear geometry. The complex (1) crystallizes in monoclinic space group 'P21/a', while the complexes (2) and (3) crystallize in orthorhombic space group 'Pna21'. The IR spectra and 1H as well as 13C NMR measurements of the Au(I) complexes (1-3) corroborate well with their single crystal X-ray structure analysis. These gold(I) complexes show moderate potential anti-cancer activities against A549 (human lung carcinoma), HCT15 (human colon cancer), and HeLa (human cervical cancer) cell lines.

KW - 1,3-Bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold

KW - Dithiocarbamate gold(I) complexes

KW - IR and NMR spectroscopic studies

KW - In vitro cytotoxicity

UR - https://www.scopus.com/pages/publications/84902133702

U2 - 10.1016/j.jorganchem.2014.04.029

DO - 10.1016/j.jorganchem.2014.04.029

M3 - Article

AN - SCOPUS:84902133702

SN - 0022-328X

VL - 765

SP - 68

EP - 79

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Synthesis, X-ray structures, spectroscopic analysis and anticancer activity of novel gold(I) carbene complexes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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