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.

UN SDGs

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

SDG 3 Good Health and Well-being

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

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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",

publisher = "Elsevier BV",

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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

UN SDGs

Keywords

ASJC Scopus subject areas

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