Synthesis, characterization, DFT optimization and anticancer evaluation of phosphanegold(I) dithiocarbamates

Adam A. Sulaiman; Wiktor Zierkiewicz; Mariusz Michalczyk; Magdalena Malik-Gajewska; Saeed Ahmad; Ali Alhoshani; Homood M. As Sobeai; Dariusz Bieńko; Anvarhusein A. Isab

doi:10.1016/j.molstruc.2020.128486

Synthesis, characterization, DFT optimization and anticancer evaluation of phosphanegold(I) dithiocarbamates

Adam A. Sulaiman
, Wiktor Zierkiewicz
, Mariusz Michalczyk
, Magdalena Malik-Gajewska
, Saeed Ahmad
, Ali Alhoshani
, Homood M. As Sobeai
, Dariusz Bieńko^*
, Anvarhusein A. Isab

^*Corresponding author for this work

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

10 Scopus citations

Abstract

Six phosphanegold(I)-dithiocarbamate complexes (1–6) of general formula [Au(L)(S₂CNR₂)] (where L = 2-(di-isopropylphosphanyl)-1-aminoethane (AEP) and 3-(di-isopropylphosphanyl)-1-aminopropane (APP), and R = methyl, ethyl, benzyl) were prepared by the reactions of equimolar amounts of (CH₃)₂S–AuCl, phosphanes and dithiocarbamates (S₂CNR₂) in dichloromethane. The complexes were characterized by elemental analysis, FTIR and NMR spectroscopy. The structures of the complexes were predicted theoretically in the gas phase as well as in chloroform solution using the DFT (density functional theory) methodology. The in vitro cytotoxicity of the complexes was investigated against three human cancer cell lines; A549, HeLa and HepG2. In most of the cases, the inhibition effect of the complexes is less than that of cisplatin. Two of the six tested complexes (3 and 5) showed excellent in vitro cytotoxicity for HepG2 and A549 cells respectively.

Original language	English
Article number	128486
Journal	Journal of Molecular Structure
Volume	1218
DOIs	https://doi.org/10.1016/j.molstruc.2020.128486
State	Published - 15 Oct 2020

Bibliographical note

Publisher Copyright:
© 2020 Elsevier B.V.

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Aminophosphanes
Anticancer activity
DFT calculations
Dithiocarbamates
Gold(I)

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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@article{dfb29e0210484b7e88bf40689ade1178,

title = "Synthesis, characterization, DFT optimization and anticancer evaluation of phosphanegold(I) dithiocarbamates",

abstract = "Six phosphanegold(I)-dithiocarbamate complexes (1–6) of general formula [Au(L)(S2CNR2)] (where L = 2-(di-isopropylphosphanyl)-1-aminoethane (AEP) and 3-(di-isopropylphosphanyl)-1-aminopropane (APP), and R = methyl, ethyl, benzyl) were prepared by the reactions of equimolar amounts of (CH3)2S–AuCl, phosphanes and dithiocarbamates (S2CNR2) in dichloromethane. The complexes were characterized by elemental analysis, FTIR and NMR spectroscopy. The structures of the complexes were predicted theoretically in the gas phase as well as in chloroform solution using the DFT (density functional theory) methodology. The in vitro cytotoxicity of the complexes was investigated against three human cancer cell lines; A549, HeLa and HepG2. In most of the cases, the inhibition effect of the complexes is less than that of cisplatin. Two of the six tested complexes (3 and 5) showed excellent in vitro cytotoxicity for HepG2 and A549 cells respectively.",

keywords = "Aminophosphanes, Anticancer activity, DFT calculations, Dithiocarbamates, Gold(I)",

author = "Sulaiman, \{Adam A.\} and Wiktor Zierkiewicz and Mariusz Michalczyk and Magdalena Malik-Gajewska and Saeed Ahmad and Ali Alhoshani and \{As Sobeai\}, \{Homood M.\} and Dariusz Bie{\'n}ko and Isab, \{Anvarhusein A.\}",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier B.V.",

year = "2020",

month = oct,

day = "15",

doi = "10.1016/j.molstruc.2020.128486",

language = "English",

volume = "1218",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - Synthesis, characterization, DFT optimization and anticancer evaluation of phosphanegold(I) dithiocarbamates

AU - Sulaiman, Adam A.

AU - Zierkiewicz, Wiktor

AU - Michalczyk, Mariusz

AU - Malik-Gajewska, Magdalena

AU - Ahmad, Saeed

AU - Alhoshani, Ali

AU - As Sobeai, Homood M.

AU - Bieńko, Dariusz

AU - Isab, Anvarhusein A.

PY - 2020/10/15

Y1 - 2020/10/15

N2 - Six phosphanegold(I)-dithiocarbamate complexes (1–6) of general formula [Au(L)(S2CNR2)] (where L = 2-(di-isopropylphosphanyl)-1-aminoethane (AEP) and 3-(di-isopropylphosphanyl)-1-aminopropane (APP), and R = methyl, ethyl, benzyl) were prepared by the reactions of equimolar amounts of (CH3)2S–AuCl, phosphanes and dithiocarbamates (S2CNR2) in dichloromethane. The complexes were characterized by elemental analysis, FTIR and NMR spectroscopy. The structures of the complexes were predicted theoretically in the gas phase as well as in chloroform solution using the DFT (density functional theory) methodology. The in vitro cytotoxicity of the complexes was investigated against three human cancer cell lines; A549, HeLa and HepG2. In most of the cases, the inhibition effect of the complexes is less than that of cisplatin. Two of the six tested complexes (3 and 5) showed excellent in vitro cytotoxicity for HepG2 and A549 cells respectively.

AB - Six phosphanegold(I)-dithiocarbamate complexes (1–6) of general formula [Au(L)(S2CNR2)] (where L = 2-(di-isopropylphosphanyl)-1-aminoethane (AEP) and 3-(di-isopropylphosphanyl)-1-aminopropane (APP), and R = methyl, ethyl, benzyl) were prepared by the reactions of equimolar amounts of (CH3)2S–AuCl, phosphanes and dithiocarbamates (S2CNR2) in dichloromethane. The complexes were characterized by elemental analysis, FTIR and NMR spectroscopy. The structures of the complexes were predicted theoretically in the gas phase as well as in chloroform solution using the DFT (density functional theory) methodology. The in vitro cytotoxicity of the complexes was investigated against three human cancer cell lines; A549, HeLa and HepG2. In most of the cases, the inhibition effect of the complexes is less than that of cisplatin. Two of the six tested complexes (3 and 5) showed excellent in vitro cytotoxicity for HepG2 and A549 cells respectively.

KW - Aminophosphanes

KW - Anticancer activity

KW - DFT calculations

KW - Dithiocarbamates

KW - Gold(I)

UR - https://www.scopus.com/pages/publications/85085658408

U2 - 10.1016/j.molstruc.2020.128486

DO - 10.1016/j.molstruc.2020.128486

M3 - Article

AN - SCOPUS:85085658408

SN - 0022-2860

VL - 1218

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 128486

ER -

Synthesis, characterization, DFT optimization and anticancer evaluation of phosphanegold(I) dithiocarbamates

Abstract

Bibliographical note

UN SDGs

Keywords

ASJC Scopus subject areas

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