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.

Základní údaje

Originální název

Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates

Autoři

GONĚC, Tomáš (203 Česká republika, garant, domácí), D. PINDJAKOVA, L. VRABLOVA, Tomáš STRHÁRSKY (703 Slovensko, domácí), H. MICHNOVA, Tereza KAUEROVÁ (203 Česká republika, domácí), Peter KOLLÁR (203 Česká republika, domácí), M. ORAVEC, I. JENDRZEJEWSKA, A. CIZEK a J. JAMPILEK

Vydání

Pharmaceuticals, BASEL, MDPI, 2022, 1424-8247

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.600

Kód RIV

RIV/00216224:14160/22:00126255

Organizační jednotka

Farmaceutická fakulta

DOI

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

UT WoS

000816677300001

Klíčová slova anglicky

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

Štítky

rivok, ÚChL, ÚFTo

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 14. 7. 2022 09:26, JUDr. Sabina Krejčiříková

Anotace

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 a J. JAMPILEK. Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates. Pharmaceuticals. BASEL: MDPI, 2022, roč. 15, č. 6, s. 1-19. ISSN 1424-8247. Dostupné z: 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 a J. JAMPILEK. Antistaphylococcal Activities and ADME-Related Properties of Chlorinated Arylcarbamoylnaphthalenylcarbamates. \textit{Pharmaceuticals}. BASEL: MDPI, 2022, roč.~15, č.~6, s.~1-19. ISSN~1424-8247. Dostupné z: https://dx.doi.org/10.3390/ph15060715.

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