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Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives

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2020
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Authors
Obradović, Dragiša
Nikolić, Stefan
Milenković, Ivana
Milenković, Marina
Jovanović, Predrag M.
Savić, Vladimir
Roller, Alexander
Đorđi Crnogorac, Marija
Stanojković, Tatjana
Grgurić-Šipka, Sanja
Article (Accepted Version)
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Abstract
Three new ruthenium(II)-arene complexes, [Ru(η6-p-cymene)(L1)Cl2] (C1) where L1 is N-((4 methoxyphenyl)carbamothioyl)benzamide; [Ru(η6-p-cymene)(L2)Cl2] (C2) where L2 is 4-(3-benzoylthioureido)benzoic acid and[Ru(η6-p-cymene)(L3)Cl2] (C3) where L3 is methyl 4-(3- benzoylthioureido)benzoate have been synthetized,characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performedusing 1H and 13C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Raydiffraction analysis. X-Ray diffraction analysis of C1 showed typical expected “piano-stool” geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, inherein described complex, upon coordination the four-membered ring was formed, instead of six-memberedchelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma(HeLa) cell line and IC50 values ranged from 29.68 to... 52.36 μM and the complexes were more active than relatedligands (except in case of C2 where it is found that IC50 value is close to IC50 value of related ligand). Complex[Ru(η6-p-cymene)(L1)Cl2] (C1) expressed the highest cytotoxic activity with IC50 value of 29.7 μM. Complexesand ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans.Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well.Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans toover 1000 μg/ml for several bacterial species.

Keywords:
Antimicrobial activity / Benzylthiourea derivatives / Cytotoxic activity / Ruthenium(II) complexes
Source:
Journal of Inorganic Biochemistry, 2020, 210, 111164-
Publisher:
  • Elsevier
Funding / projects:
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200288 (Innovation Center of the Faculty of Chemistry) (RS-200288)
Note:
  • This is the peer-reviewed version of the article: Obradović, D.; Nikolić, S.; Milenković, I.; Milenković, M.; Jovanović, P.; Savić, V.; Roller, A.; Đorđi Crnogorac, M.; Stanojković, T.; Grgurić-Šipka, S. Synthesis, Characterization, Antimicrobial and Cytotoxic Activity of Novel Half-Sandwich Ru(II) Arene Complexes with Benzoylthiourea Derivatives. Journal of Inorganic Biochemistry 2020, 210, 111164. https://doi.org/10.1016/j.jinorgbio.2020.111164.
  • Published version: https://cherry.chem.bg.ac.rs/handle/123456789/5137
Related info:
  • Version of
    https://doi.org/10.1016/j.jinorgbio.2020.111164
  • Version of
    https://cherry.chem.bg.ac.rs/handle/123456789/5137

DOI: 10.1016/j.jinorgbio.2020.111164

ISSN: 0162-0134

WoS: 000564740000011

Scopus: 2-s2.0-85087360793
[ Google Scholar ]
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URI
http://cherry.chem.bg.ac.rs/handle/123456789/5138
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Obradović, Dragiša
AU  - Nikolić, Stefan
AU  - Milenković, Ivana
AU  - Milenković, Marina
AU  - Jovanović, Predrag M.
AU  - Savić, Vladimir
AU  - Roller, Alexander
AU  - Đorđi Crnogorac, Marija
AU  - Stanojković, Tatjana
AU  - Grgurić-Šipka, Sanja
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5138
AB  - Three new ruthenium(II)-arene complexes, [Ru(η6-p-cymene)(L1)Cl2] (C1) where L1 is N-((4 methoxyphenyl)carbamothioyl)benzamide; [Ru(η6-p-cymene)(L2)Cl2] (C2) where L2 is 4-(3-benzoylthioureido)benzoic acid and[Ru(η6-p-cymene)(L3)Cl2] (C3) where L3 is methyl 4-(3- benzoylthioureido)benzoate have been synthetized,characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performedusing 1H and 13C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Raydiffraction analysis. X-Ray diffraction analysis of C1 showed typical expected “piano-stool” geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, inherein described complex, upon coordination the four-membered ring was formed, instead of six-memberedchelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma(HeLa) cell line and IC50 values ranged from 29.68 to 52.36 μM and the complexes were more active than relatedligands (except in case of C2 where it is found that IC50 value is close to IC50 value of related ligand). Complex[Ru(η6-p-cymene)(L1)Cl2] (C1) expressed the highest cytotoxic activity with IC50 value of 29.7 μM. Complexesand ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans.Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well.Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans toover 1000 μg/ml for several bacterial species.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives
VL  - 210
SP  - 111164
DO  - 10.1016/j.jinorgbio.2020.111164
ER  - 
@article{
author = "Obradović, Dragiša and Nikolić, Stefan and Milenković, Ivana and Milenković, Marina and Jovanović, Predrag M. and Savić, Vladimir and Roller, Alexander and Đorđi Crnogorac, Marija and Stanojković, Tatjana and Grgurić-Šipka, Sanja",
year = "2020",
abstract = "Three new ruthenium(II)-arene complexes, [Ru(η6-p-cymene)(L1)Cl2] (C1) where L1 is N-((4 methoxyphenyl)carbamothioyl)benzamide; [Ru(η6-p-cymene)(L2)Cl2] (C2) where L2 is 4-(3-benzoylthioureido)benzoic acid and[Ru(η6-p-cymene)(L3)Cl2] (C3) where L3 is methyl 4-(3- benzoylthioureido)benzoate have been synthetized,characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performedusing 1H and 13C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Raydiffraction analysis. X-Ray diffraction analysis of C1 showed typical expected “piano-stool” geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, inherein described complex, upon coordination the four-membered ring was formed, instead of six-memberedchelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma(HeLa) cell line and IC50 values ranged from 29.68 to 52.36 μM and the complexes were more active than relatedligands (except in case of C2 where it is found that IC50 value is close to IC50 value of related ligand). Complex[Ru(η6-p-cymene)(L1)Cl2] (C1) expressed the highest cytotoxic activity with IC50 value of 29.7 μM. Complexesand ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans.Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well.Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans toover 1000 μg/ml for several bacterial species.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives",
volume = "210",
pages = "111164",
doi = "10.1016/j.jinorgbio.2020.111164"
}
Obradović, D., Nikolić, S., Milenković, I., Milenković, M., Jovanović, P. M., Savić, V., Roller, A., Đorđi Crnogorac, M., Stanojković, T.,& Grgurić-Šipka, S.. (2020). Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives. in Journal of Inorganic Biochemistry
Elsevier., 210, 111164.
https://doi.org/10.1016/j.jinorgbio.2020.111164
Obradović D, Nikolić S, Milenković I, Milenković M, Jovanović PM, Savić V, Roller A, Đorđi Crnogorac M, Stanojković T, Grgurić-Šipka S. Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives. in Journal of Inorganic Biochemistry. 2020;210:111164.
doi:10.1016/j.jinorgbio.2020.111164 .
Obradović, Dragiša, Nikolić, Stefan, Milenković, Ivana, Milenković, Marina, Jovanović, Predrag M., Savić, Vladimir, Roller, Alexander, Đorđi Crnogorac, Marija, Stanojković, Tatjana, Grgurić-Šipka, Sanja, "Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives" in Journal of Inorganic Biochemistry, 210 (2020):111164,
https://doi.org/10.1016/j.jinorgbio.2020.111164 . .

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