Synthesis, characterization and cytotoxicity of new gold(III) complexes with 1,2-diaminocyclohexane: Influence of stereochemistry on antitumor activity

Said S. Al-Jaroudi; Mohammed Fettouhi; Mohammed I.M. Wazeer; Anvarhusein A. Isab; Saleh Altuwaijri

doi:10.1016/j.poly.2012.11.034

Synthesis, characterization and cytotoxicity of new gold(III) complexes with 1,2-diaminocyclohexane: Influence of stereochemistry on antitumor activity

Said S. Al-Jaroudi
, Mohammed Fettouhi
, Mohammed I.M. Wazeer
, Anvarhusein A. Isab^*
, Saleh Altuwaijri

^*Corresponding author for this work

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

30 Scopus citations

Abstract

Gold(III) complexes of the type [(DACH)AuCl₂]Cl, derived from sodium tetrachloroaurate(III) dihydrate NaAuCl₄·2H ₂O, where DACH is diaminocyclohexane, have been synthesized. These potential metallodrug compounds were characterized using various spectroscopic and analytical techniques, including elemental analysis, UV-Vis, infrared spectroscopy, solution as well as solid NMR spectroscopy and X-ray crystallography. The potential of the synthesized gold(III) complexes as anti-cancer agents was investigated by measuring some relevant physicochemical and biochemical properties, such as the stability of the Au-N bonds by vibrational stretching from far-IR as well as cytotoxicity and the stomach cancer cell inhibiting effect. The solid-state ¹³C NMR chemical shift shows that the ligand is strongly bound to the gold(III) center via N atoms. An X-ray crystallography study of the complexes shows that the cyclohexyl ring adopts a chair conformation and the gold coordination sphere adopts a distorted square planar geometry. The cis isomer in solution showed higher activity towards the inhibitory effect of human cancer cell lines such as prostate cancer (PC-3) and gastric carcinoma (SGC-7901) than that of the trans isomer. The cytotoxicity of the cis isomer complex has also been estimated in PC-3 and SGC-7901 cells.

Original language	English
Pages (from-to)	434-442
Number of pages	9
Journal	Polyhedron
Volume	50
Issue number	1
DOIs	https://doi.org/10.1016/j.poly.2012.11.034
State	Published - 13 Feb 2013

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. 10-BIO1368-04 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

1,2-Diaminocyclohexane
Anticancer
Gastric carcinogenesis (SGC-7901)
Gold(III) complex
Prostate (PC-3)

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.poly.2012.11.034

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@article{b8f33f925ecc4bd98ed46f048dda25af,

title = "Synthesis, characterization and cytotoxicity of new gold(III) complexes with 1,2-diaminocyclohexane: Influence of stereochemistry on antitumor activity",

abstract = "Gold(III) complexes of the type [(DACH)AuCl2]Cl, derived from sodium tetrachloroaurate(III) dihydrate NaAuCl4·2H 2O, where DACH is diaminocyclohexane, have been synthesized. These potential metallodrug compounds were characterized using various spectroscopic and analytical techniques, including elemental analysis, UV-Vis, infrared spectroscopy, solution as well as solid NMR spectroscopy and X-ray crystallography. The potential of the synthesized gold(III) complexes as anti-cancer agents was investigated by measuring some relevant physicochemical and biochemical properties, such as the stability of the Au-N bonds by vibrational stretching from far-IR as well as cytotoxicity and the stomach cancer cell inhibiting effect. The solid-state 13C NMR chemical shift shows that the ligand is strongly bound to the gold(III) center via N atoms. An X-ray crystallography study of the complexes shows that the cyclohexyl ring adopts a chair conformation and the gold coordination sphere adopts a distorted square planar geometry. The cis isomer in solution showed higher activity towards the inhibitory effect of human cancer cell lines such as prostate cancer (PC-3) and gastric carcinoma (SGC-7901) than that of the trans isomer. The cytotoxicity of the cis isomer complex has also been estimated in PC-3 and SGC-7901 cells.",

keywords = "1,2-Diaminocyclohexane, Anticancer, Gastric carcinogenesis (SGC-7901), Gold(III) complex, Prostate (PC-3)",

author = "Al-Jaroudi, \{Said S.\} and Mohammed Fettouhi and Wazeer, \{Mohammed I.M.\} and Isab, \{Anvarhusein A.\} and Saleh Altuwaijri",

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. 10-BIO1368-04 as part of the National Science, Technology and Innovation Plan. ",

year = "2013",

month = feb,

day = "13",

doi = "10.1016/j.poly.2012.11.034",

language = "English",

volume = "50",

pages = "434--442",

journal = "Polyhedron",

issn = "0277-5387",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Synthesis, characterization and cytotoxicity of new gold(III) complexes with 1,2-diaminocyclohexane

T2 - Influence of stereochemistry on antitumor activity

AU - Al-Jaroudi, Said S.

AU - Fettouhi, Mohammed

AU - Wazeer, Mohammed I.M.

AU - Isab, Anvarhusein A.

AU - Altuwaijri, Saleh

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. 10-BIO1368-04 as part of the National Science, Technology and Innovation Plan.

PY - 2013/2/13

Y1 - 2013/2/13

N2 - Gold(III) complexes of the type [(DACH)AuCl2]Cl, derived from sodium tetrachloroaurate(III) dihydrate NaAuCl4·2H 2O, where DACH is diaminocyclohexane, have been synthesized. These potential metallodrug compounds were characterized using various spectroscopic and analytical techniques, including elemental analysis, UV-Vis, infrared spectroscopy, solution as well as solid NMR spectroscopy and X-ray crystallography. The potential of the synthesized gold(III) complexes as anti-cancer agents was investigated by measuring some relevant physicochemical and biochemical properties, such as the stability of the Au-N bonds by vibrational stretching from far-IR as well as cytotoxicity and the stomach cancer cell inhibiting effect. The solid-state 13C NMR chemical shift shows that the ligand is strongly bound to the gold(III) center via N atoms. An X-ray crystallography study of the complexes shows that the cyclohexyl ring adopts a chair conformation and the gold coordination sphere adopts a distorted square planar geometry. The cis isomer in solution showed higher activity towards the inhibitory effect of human cancer cell lines such as prostate cancer (PC-3) and gastric carcinoma (SGC-7901) than that of the trans isomer. The cytotoxicity of the cis isomer complex has also been estimated in PC-3 and SGC-7901 cells.

AB - Gold(III) complexes of the type [(DACH)AuCl2]Cl, derived from sodium tetrachloroaurate(III) dihydrate NaAuCl4·2H 2O, where DACH is diaminocyclohexane, have been synthesized. These potential metallodrug compounds were characterized using various spectroscopic and analytical techniques, including elemental analysis, UV-Vis, infrared spectroscopy, solution as well as solid NMR spectroscopy and X-ray crystallography. The potential of the synthesized gold(III) complexes as anti-cancer agents was investigated by measuring some relevant physicochemical and biochemical properties, such as the stability of the Au-N bonds by vibrational stretching from far-IR as well as cytotoxicity and the stomach cancer cell inhibiting effect. The solid-state 13C NMR chemical shift shows that the ligand is strongly bound to the gold(III) center via N atoms. An X-ray crystallography study of the complexes shows that the cyclohexyl ring adopts a chair conformation and the gold coordination sphere adopts a distorted square planar geometry. The cis isomer in solution showed higher activity towards the inhibitory effect of human cancer cell lines such as prostate cancer (PC-3) and gastric carcinoma (SGC-7901) than that of the trans isomer. The cytotoxicity of the cis isomer complex has also been estimated in PC-3 and SGC-7901 cells.

KW - 1,2-Diaminocyclohexane

KW - Anticancer

KW - Gastric carcinogenesis (SGC-7901)

KW - Gold(III) complex

KW - Prostate (PC-3)

UR - https://www.scopus.com/pages/publications/84871444045

U2 - 10.1016/j.poly.2012.11.034

DO - 10.1016/j.poly.2012.11.034

M3 - Article

AN - SCOPUS:84871444045

SN - 0277-5387

VL - 50

SP - 434

EP - 442

JO - Polyhedron

JF - Polyhedron

IS - 1

ER -

Synthesis, characterization and cytotoxicity of new gold(III) complexes with 1,2-diaminocyclohexane: Influence of stereochemistry on antitumor activity

Abstract

Bibliographical note

UN SDGs

Keywords

ASJC Scopus subject areas

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