Synthesis, characterization, in vitro cytotoxicity and DNA interaction study of phosphanegold(I) complexes with dithiocarbamate ligands

Said S. Al-Jaroudi; Muhammad Altaf; Adam A. Seliman; Shipra Yadav; Farukh Arjmand; Ali Alhoshani; H. M. Korashy; Saeed Ahmad; Anvarhusein A. Isab

doi:10.1016/j.ica.2017.04.040

Synthesis, characterization, in vitro cytotoxicity and DNA interaction study of phosphanegold(I) complexes with dithiocarbamate ligands

Said S. Al-Jaroudi, Muhammad Altaf, Adam A. Seliman, Shipra Yadav, Farukh Arjmand, Ali Alhoshani, H. M. Korashy, Saeed Ahmad, Anvarhusein A. Isab^*

^*Corresponding author for this work

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

36 Scopus citations

Abstract

A new series of phosphanegold(I) dithiocarbamate complexes with general formula [Au(PR₃)(S₂CNR′₂)], 1–5 (Where R = Methyl, ethyl, isopropyl and R′ = Methyl, ethyl) were synthesized and characterized by elemental analysis, FTIR and multinuclear NMR spectroscopy. The molecular structure of one of them, [Au(PMe₃)(S₂CNMe₂)] (1) was determined by single crystal X-ray crystallography, which revealed linear geometry around the Au(I) metal center. The in vitro cytotoxicity of all Au(I) complexes was studied against two human cancer cell lines, A549 and HepG2. All the complexes showed significantly higher potency (4 to 6-fold for A549 and 3 to 5-fold for HepG2 cell line) than the commercial chemotherapeutic drug, cisplatin. The in vitro DNA binding abilities of Au(I) complexes 1–5 were examined by employing different biophysical techniques, viz., UV–Vis titrations, fluorescence spectroscopy and circular dichroism. The UV–Vis titration of Au(I) complexes with CT DNA revealed that the complexes bound to CT DNA via electrostatic interactions, and the intrinsic binding constant (K_b) values for 1–5 were found to be 3.90 × 10⁴, 4.74 × 10⁴, 6.81 × 10⁴, 8.53 × 10⁴ and 2.48 × 10⁴ M⁻¹ respectively, which suggested the highest binding propensity for complex 4. In addition, molecular docking studies of the Au(I) complexes were performed with B–DNA to visualize the preferential docking position, and the results showed the binding of complexes to the adenine–thymine residues in the minor groove of the DNA.

Original language	English
Pages (from-to)	37-48
Number of pages	12
Journal	Inorganica Chimica Acta
Volume	464
DOIs	https://doi.org/10.1016/j.ica.2017.04.040
State	Published - 2017

Bibliographical note

Publisher Copyright:
© 2017 Elsevier B.V.

Keywords

Anticancer
CT-DNA binding studies
Dithiocarbamates
Mononucleotide interaction and molecular docking
Phosphine Au(I) complexes

ASJC Scopus subject areas

Physical and Theoretical 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.ica.2017.04.040

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@article{a8e085e88fe24a9da5c341e7984e94d4,

title = "Synthesis, characterization, in vitro cytotoxicity and DNA interaction study of phosphanegold(I) complexes with dithiocarbamate ligands",

abstract = "A new series of phosphanegold(I) dithiocarbamate complexes with general formula [Au(PR3)(S2CNR′2)], 1–5 (Where R = Methyl, ethyl, isopropyl and R′ = Methyl, ethyl) were synthesized and characterized by elemental analysis, FTIR and multinuclear NMR spectroscopy. The molecular structure of one of them, [Au(PMe3)(S2CNMe2)] (1) was determined by single crystal X-ray crystallography, which revealed linear geometry around the Au(I) metal center. The in vitro cytotoxicity of all Au(I) complexes was studied against two human cancer cell lines, A549 and HepG2. All the complexes showed significantly higher potency (4 to 6-fold for A549 and 3 to 5-fold for HepG2 cell line) than the commercial chemotherapeutic drug, cisplatin. The in vitro DNA binding abilities of Au(I) complexes 1–5 were examined by employing different biophysical techniques, viz., UV–Vis titrations, fluorescence spectroscopy and circular dichroism. The UV–Vis titration of Au(I) complexes with CT DNA revealed that the complexes bound to CT DNA via electrostatic interactions, and the intrinsic binding constant (Kb) values for 1–5 were found to be 3.90 × 104, 4.74 × 104, 6.81 × 104, 8.53 × 104 and 2.48 × 104 M−1 respectively, which suggested the highest binding propensity for complex 4. In addition, molecular docking studies of the Au(I) complexes were performed with B–DNA to visualize the preferential docking position, and the results showed the binding of complexes to the adenine–thymine residues in the minor groove of the DNA.",

keywords = "Anticancer, CT-DNA binding studies, Dithiocarbamates, Mononucleotide interaction and molecular docking, Phosphine Au(I) complexes",

author = "Al-Jaroudi, \{Said S.\} and Muhammad Altaf and Seliman, \{Adam A.\} and Shipra Yadav and Farukh Arjmand and Ali Alhoshani and Korashy, \{H. M.\} and Saeed Ahmad and Isab, \{Anvarhusein A.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier B.V.",

year = "2017",

doi = "10.1016/j.ica.2017.04.040",

language = "English",

volume = "464",

pages = "37--48",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

}

TY - JOUR

T1 - Synthesis, characterization, in vitro cytotoxicity and DNA interaction study of phosphanegold(I) complexes with dithiocarbamate ligands

AU - Al-Jaroudi, Said S.

AU - Altaf, Muhammad

AU - Seliman, Adam A.

AU - Yadav, Shipra

AU - Arjmand, Farukh

AU - Alhoshani, Ali

AU - Korashy, H. M.

AU - Ahmad, Saeed

AU - Isab, Anvarhusein A.

PY - 2017

Y1 - 2017

N2 - A new series of phosphanegold(I) dithiocarbamate complexes with general formula [Au(PR3)(S2CNR′2)], 1–5 (Where R = Methyl, ethyl, isopropyl and R′ = Methyl, ethyl) were synthesized and characterized by elemental analysis, FTIR and multinuclear NMR spectroscopy. The molecular structure of one of them, [Au(PMe3)(S2CNMe2)] (1) was determined by single crystal X-ray crystallography, which revealed linear geometry around the Au(I) metal center. The in vitro cytotoxicity of all Au(I) complexes was studied against two human cancer cell lines, A549 and HepG2. All the complexes showed significantly higher potency (4 to 6-fold for A549 and 3 to 5-fold for HepG2 cell line) than the commercial chemotherapeutic drug, cisplatin. The in vitro DNA binding abilities of Au(I) complexes 1–5 were examined by employing different biophysical techniques, viz., UV–Vis titrations, fluorescence spectroscopy and circular dichroism. The UV–Vis titration of Au(I) complexes with CT DNA revealed that the complexes bound to CT DNA via electrostatic interactions, and the intrinsic binding constant (Kb) values for 1–5 were found to be 3.90 × 104, 4.74 × 104, 6.81 × 104, 8.53 × 104 and 2.48 × 104 M−1 respectively, which suggested the highest binding propensity for complex 4. In addition, molecular docking studies of the Au(I) complexes were performed with B–DNA to visualize the preferential docking position, and the results showed the binding of complexes to the adenine–thymine residues in the minor groove of the DNA.

AB - A new series of phosphanegold(I) dithiocarbamate complexes with general formula [Au(PR3)(S2CNR′2)], 1–5 (Where R = Methyl, ethyl, isopropyl and R′ = Methyl, ethyl) were synthesized and characterized by elemental analysis, FTIR and multinuclear NMR spectroscopy. The molecular structure of one of them, [Au(PMe3)(S2CNMe2)] (1) was determined by single crystal X-ray crystallography, which revealed linear geometry around the Au(I) metal center. The in vitro cytotoxicity of all Au(I) complexes was studied against two human cancer cell lines, A549 and HepG2. All the complexes showed significantly higher potency (4 to 6-fold for A549 and 3 to 5-fold for HepG2 cell line) than the commercial chemotherapeutic drug, cisplatin. The in vitro DNA binding abilities of Au(I) complexes 1–5 were examined by employing different biophysical techniques, viz., UV–Vis titrations, fluorescence spectroscopy and circular dichroism. The UV–Vis titration of Au(I) complexes with CT DNA revealed that the complexes bound to CT DNA via electrostatic interactions, and the intrinsic binding constant (Kb) values for 1–5 were found to be 3.90 × 104, 4.74 × 104, 6.81 × 104, 8.53 × 104 and 2.48 × 104 M−1 respectively, which suggested the highest binding propensity for complex 4. In addition, molecular docking studies of the Au(I) complexes were performed with B–DNA to visualize the preferential docking position, and the results showed the binding of complexes to the adenine–thymine residues in the minor groove of the DNA.

KW - Anticancer

KW - CT-DNA binding studies

KW - Dithiocarbamates

KW - Mononucleotide interaction and molecular docking

KW - Phosphine Au(I) complexes

UR - https://www.scopus.com/pages/publications/85018362905

U2 - 10.1016/j.ica.2017.04.040

DO - 10.1016/j.ica.2017.04.040

M3 - Article

AN - SCOPUS:85018362905

SN - 0020-1693

VL - 464

SP - 37

EP - 48

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

ER -

Synthesis, characterization, in vitro cytotoxicity and DNA interaction study of phosphanegold(I) complexes with dithiocarbamate ligands

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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