Antistaphylococcal Activities and ADME-Related Properties of
Chlorinated Arylcarbamoylnaphthalenylcarbamates

J 2022

Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates

GONĚC, Tomáš, D. PINDJAKOVA, L. VRABLOVA, Tomáš STRHÁRSKY, H. MICHNOVA et. al.

Basic information

Original name

Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates

Authors

GONĚC, Tomáš (203 Czech Republic, guarantor, belonging to the institution), D. PINDJAKOVA, L. VRABLOVA, Tomáš STRHÁRSKY (703 Slovakia, belonging to the institution), H. MICHNOVA, Tereza KAUEROVÁ (203 Czech Republic, belonging to the institution), Peter KOLLÁR (203 Czech Republic, belonging to the institution), M. ORAVEC, I. JENDRZEJEWSKA, A. CIZEK and J. JAMPILEK

Edition

Pharmaceuticals, BASEL, MDPI, 2022, 1424-8247

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.600

RIV identification code

RIV/00216224:14160/22:00126255

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.3390/ph15060715

UT WoS

000816677300001

Keywords in English

hydroxynaphthalenes; carbamates; antistaphylococcal activity; cytotoxicity; lipophilicity; structure-activity relationships

Abstract

V originále

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.

Citovat

GONĚC, Tomáš, D. PINDJAKOVA, L. VRABLOVA, Tomáš STRHÁRSKY, H. MICHNOVA, Tereza KAUEROVÁ, Peter KOLLÁR, M. ORAVEC, I. JENDRZEJEWSKA, A. CIZEK and J. JAMPILEK. Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates. Pharmaceuticals. BASEL: MDPI, 2022, vol. 15, No 6, p. 1-19. ISSN 1424-8247. Available from: https://dx.doi.org/10.3390/ph15060715.

@article{1874631,
   author = {Goněc, Tomáš and Pindjakova, D. and Vrablova, L. and Strhársky, Tomáš and Michnova, H. and Kauerová, Tereza and Kollár, Peter and Oravec, M. and Jendrzejewska, I. and Cizek, A. and Jampilek, J.},
   article_location = {BASEL},
   article_number = {6},
   doi = {http://dx.doi.org/10.3390/ph15060715},
   keywords = {hydroxynaphthalenes; carbamates; antistaphylococcal activity; cytotoxicity; lipophilicity; structure-activity relationships},
   language = {eng},
   issn = {1424-8247},
   journal = {Pharmaceuticals},
   title = {Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates},
   url = {https://www.mdpi.com/1424-8247/15/6/715/htm},
   volume = {15},
   year = {2022}
}

TY  - JOUR
ID  - 1874631
AU  - Goněc, Tomáš - Pindjakova, D. - Vrablova, L. - Strhársky, Tomáš - Michnova, H. - Kauerová, Tereza - Kollár, Peter - Oravec, M. - Jendrzejewska, I. - Cizek, A. - Jampilek, J.
PY  - 2022
TI  - Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates
JF  - Pharmaceuticals
VL  - 15
IS  - 6
SP  - 1-19
EP  - 1-19
PB  - MDPI
SN  - 14248247
KW  - hydroxynaphthalenes
KW  - carbamates
KW  - antistaphylococcal activity
KW  - cytotoxicity
KW  - lipophilicity
KW  - structure-activity relationships
UR  - https://www.mdpi.com/1424-8247/15/6/715/htm
N2  - 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.
ER  -

GONĚC, Tomáš, D. PINDJAKOVA, L. VRABLOVA, Tomáš STRHÁRSKY, H. MICHNOVA, Tereza KAUEROVÁ, Peter KOLLÁR, M. ORAVEC, I. JENDRZEJEWSKA, A. CIZEK and J. JAMPILEK. Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates. \textit{Pharmaceuticals}. BASEL: MDPI, 2022, vol.~15, No~6, p.~1-19. ISSN~1424-8247. Available from: https://dx.doi.org/10.3390/ph15060715.

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