LAPSE:2020.0770
Published Article
LAPSE:2020.0770
Synthesis and Characterization of New Fluoro/Trifluoromethyl-Substituted Acylthiourea Derivatives with Promising Activity against Planktonic and Biofilm-Embedded Microbial Cells
Carmen Limban, Diana Camelia Nuta, Alexandru Vasile Missir, Roxana Roman, Miron Teodor Caproiu, Florea Dumitrascu, Lucia Pintilie, Amalia Stefaniu, Mariana Carmen Chifiriuc, Marcela Popa, Irina Zarafu, Andreea Letiția Arsene, Cristina Elena Dinu Pirvu, Denisa Ioana Udeanu, Ioana Raluca Papacocea
July 2, 2020
The aim of this study was preparation of new derivatives based on 2-((4-chlorophenoxy)methyl)-N-(arylcarbamothioyl)benzamide structure; the new compounds were characterized by IR, NMR (1H, 13C) spectroscopy, and elemental analysis. The obtained compounds were evaluated for their in vitro antimicrobial activity against planktonic and biofilm-embedded microbial cells (Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans), by qualitative and quantitative assays. Some of the compounds revealed promising antibacterial and antifungal activities, with low minimum inhibitory concentration values between 0.15 and 2.5 mg/mL and minimal biofilm eradication concentrations of 0.019−2.5 mg/mL. To investigate the potential target of their antibacterial activity, in silico drug-likeness and molecular docking screenings on Staphylococcus aureus DNA gyrase were performed. The compound with the best antibacterial activity (1g) was docked into topoisomerase II DNA gyrase enzymes (PDB ID: 2XCS) and showed valuable interactions with the target protein along with good docking scores, suggesting that it can act by the inhibition of DNA replication. The tested compounds exhibited only a poor antioxidant activity, as revealed by the in vitro assay using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay.
Keywords
13C-NMR, 1H-NMR, anti-biofilm activity, antimicrobial activity, antioxidant activity, benzamides, IR spectroscopy, thiourea derivatives
Subject
Suggested Citation
Limban C, Nuta DC, Missir AV, Roman R, Caproiu MT, Dumitrascu F, Pintilie L, Stefaniu A, Chifiriuc MC, Popa M, Zarafu I, Arsene AL, Dinu Pirvu CE, Udeanu DI, Papacocea IR. Synthesis and Characterization of New Fluoro/Trifluoromethyl-Substituted Acylthiourea Derivatives with Promising Activity against Planktonic and Biofilm-Embedded Microbial Cells. (2020). LAPSE:2020.0770
Author Affiliations
Limban C: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no.6, Bucharest 020956, Romania
Nuta DC: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no.6, Bucharest 020956, Romania
Missir AV: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no.6, Bucharest 020956, Romania
Roman R: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no.6, Bucharest 020956, Romania
Caproiu MT: The Organic Chemistry Center of Romanian Academy “C. D. Neniţescu”, Splaiul Independenţei no. 202B, Bucharest 060023, Romania
Dumitrascu F: The Organic Chemistry Center of Romanian Academy “C. D. Neniţescu”, Splaiul Independenţei no. 202B, Bucharest 060023, Romania
Pintilie L: National Institute of Chemical-Pharmaceutical Research & Development, Vitan Av. 112, Bucharest 031299, Romania [ORCID]
Stefaniu A: National Institute of Chemical-Pharmaceutical Research & Development, Vitan Av. 112, Bucharest 031299, Romania
Chifiriuc MC: Research Institute of the University of Bucharest (ICUB) and the Department of Microbiology, Faculty of Biology, University of Bucharest, Aleea Portocalelor no. 1-3, Bucharest 060101, Romania [ORCID]
Popa M: Research Institute of the University of Bucharest (ICUB) and the Department of Microbiology, Faculty of Biology, University of Bucharest, Aleea Portocalelor no. 1-3, Bucharest 060101, Romania
Zarafu I: Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, Regina Elisabeta no. 4-12, Bucharest 030018, Romania [ORCID]
Arsene AL: Department of Pharmaceutical Microbiology, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no.6, Bucharest 020956, Romania [ORCID]
Dinu Pirvu CE: Department of Physical and Colloidal Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no.6, Bucharest 020956, Romania
Udeanu DI: Department of Clinical Laboratory and Food Safety, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, Traian Vuia no.6, Bucharest 020956, Romania [ORCID]
Papacocea IR: Department of Physiology I, Faculty of Medicine, “Carol Davila” University of Medicine and Pharmacy, Bdul Eroilor Sanitari no. 8, Bucharest 050474, Romania
Journal Name
Processes
Volume
8
Issue
5
Article Number
E503
Year
2020
Publication Date
2020-04-26
Published Version
ISSN
2227-9717
Version Comments
Original Submission
Other Meta
PII: pr8050503, Publication Type: Journal Article
Record Map
Published Article

LAPSE:2020.0770
This Record
External Link

doi:10.3390/pr8050503
Publisher Version
Download
Files
[Download 1v1.pdf] (4.1 MB)
Jul 2, 2020
Main Article
License
CC BY 4.0
Meta
Record Statistics
Record Views
370
Version History
[v1] (Original Submission)
Jul 2, 2020
 
Verified by curator on
Jul 2, 2020
This Version Number
v1
Citations
Most Recent
This Version
URL Here
https://psecommunity.org/LAPSE:2020.0770
 
Original Submitter
Calvin Tsay
Links to Related Works
Directly Related to This Work
Publisher Version