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Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates
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SYSNO ASEP 0558879 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates Author(s) Gonec, T. (CZ)
Pindjakova, D. (SK)
Vrablova, L. (SK)
Strharsky, T. (CZ)
Michnova, H. (CZ)
Kauerová, T. (CZ)
Kollár, P. (CZ)
Oravec, Michal (UEK-B) RID, ORCID, SAI
Jendrzejewska, I. (PL)
Čížek, A. (CZ)
Jampílek, J. (CZ)Number of authors 11 Article number 715 Source Title Pharmaceuticals. - : MDPI
Roč. 15, č. 6 (2022)Number of pages 19 s. Language eng - English Country CH - Switzerland Keywords antimicrobial activity ; staphylococcus-aureus ; biological-activity ; resistance ; derivatives ; permeability ; mechanisms ; spectrum ; design ; oxides ; hydroxynaphthalenes ; carbamates ; antistaphylococcal activity ; cytotoxicity ; lipophilicity ; structure-activity relationships Subject RIV FR - Pharmacology ; Medidal Chemistry OECD category Pharmacology and pharmacy R&D Projects LM2018123 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) EF16_019/0000797 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UEK-B - RVO:86652079 UT WOS 000816677300001 EID SCOPUS 85132033562 DOI 10.3390/ph15060715 Annotation Pattern 1-hydroxy-N-(2,4,5-trichlorophenyl)-2-naphthamide and the thirteen original carbamates derived from it were prepared and characterized. All the compounds were tested against Staphylococcus aureus ATCC 29213 as a reference and quality control strain and in addition against three clinical isolates of methicillin-resistant S. aureus (MRSA). Moreover, the compounds were evaluated against Enterococcus faecalis ATCC 29212, and preliminary in vitro cytotoxicity of the compounds was assessed using the human monocytic leukemia cell line (THP-1). The lipophilicity of the prepared compounds was experimentally determined and correlated with biological activity. While pattern anilide had no antibacterial activity, the prepared carbamates demonstrated high antistaphylococcal activity comparable to the used standards (ampicillin and ciprofloxacin), which unfortunately were ineffective against E. feacalis. 2-[(2,4,5-Trichlorophenyl)carba- moyl]naphthalen-1-yl ethylcarbamate (2) and 2-[(2,4,5-trichlorophenyl)carbamoyl]naphthalen-1-yl butylcarbamate (4) expressed the nanomolar minimum inhibitory concentrations (MICs 0.018-0.064 mu M) against S. aureus and at least two other MRSA isolates. Microbicidal effects based on the minimum bactericidal concentrations (MBCs) against all the tested staphylococci were found for nine carbamates, while 2-[(2,4,5-trichlorophenyl)carbamoyl]naphthalen-1-yl heptylcarbamate (7) and 2-[(2,4,5-trichlorophenyl)carbamoyl]naphthalen-1-yl (4-phenylbutyl)carbamate (14) demonstrated MBCs in the range of 0.124-0.461 mu M. The selectivity index (SI) for most investigated carbamates was >20 and for some derivatives even >100. The performed tests did not show an effect on the damage to the bacterial membrane, while the compounds were able to inhibit the respiratory chain of S. aureus. Workplace Global Change Research Institute Contact Nikola Šviková, svikova.n@czechglobe.cz, Tel.: 511 192 268 Year of Publishing 2023 Electronic address https://www.mdpi.com/1424-8247/15/6/715
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