Trifluoromethylcinnamanilide Michael Acceptors for Treatment of
Resistant Bacterial Infections

J 2022

Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections

STRHÁRSKY, Tomáš, Dominika PINDJAKOVA, Jiří KOS, Lucia VRABLOVA, Pavel ŠMAK et. al.

Základní údaje

Originální název

Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections

Autoři

STRHÁRSKY, Tomáš (703 Slovensko, domácí), Dominika PINDJAKOVA, Jiří KOS (203 Česká republika, garant, domácí), Lucia VRABLOVA, Pavel ŠMAK (203 Česká republika, domácí), Hana MICHNOVA, Tomáš GONĚC (203 Česká republika, domácí), Jan HOŠEK (203 Česká republika), Michal ORAVEC, Izabela JENDRZEJEWSKA, Alois ČÍŽEK (203 Česká republika) a Josef JAMPILEK

Vydání

International Journal of Molecular Sciences, Basel, Multidisciplinary Digital Publishing Institute, 2022, 1422-0067

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: 5.600

Kód RIV

RIV/00216224:14110/22:00127694

Organizační jednotka

Lékařská fakulta

DOI

http://dx.doi.org/10.3390/ijms232315090

UT WoS

000897240400001

Klíčová slova anglicky

cinnamamides; Michael acceptors; antimicrobial activity; cytotoxicity; lipophilicity; structure-activity relationships; docking study

Štítky

14110512, podil, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 30. 1. 2023 12:13, Mgr. Tereza Miškechová

Anotace

V originále

A series of thirty-two anilides of 3-(trifluoromethyl)cinnamic acid (series 1) and 4-(trifluoromethyl)cinnamic acid (series 2) was prepared by microwave-assisted synthesis. All the compounds were tested against reference strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 and resistant clinical isolates of methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (VRE). All the compounds were evaluated in vitro against Mycobacterium smegmatis ATCC 700084 and M. marinum CAMP 5644. (2E)-3-[3-(Trifluoromethyl)phenyl]-N-[4-(trifluoromethyl)phenyl]prop-2-enamide (1j), (2E)-N-(3,5-dichlorophenyl)-3-[3-(trifluoromethyl)phenyl]prop-2-enamide (1o) and (2E)-N-[3-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)-phenyl]prop-2-enamide (2i), (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]-prop-2-enamide (2p) showed antistaphylococcal (MICs/MBCs 0.15-5.57 mu M) as well as anti-enterococcal (MICs/MBCs 2.34-44.5 mu M) activity. The growth of M. marinum was strongly inhibited by compounds 1j and 2p in a MIC range from 0.29 to 2.34 mu M, while all the agents of series 1 showed activity against M. smegnatis (MICs ranged from 9.36 to 51.7 mu M). The performed docking study demonstrated the ability of the compounds to bind to the active site of the mycobacterial enzyme InhA. The compounds had a significant effect on the inhibition of bacterial respiration, as demonstrated by the MTT assay. The compounds showed not only bacteriostatic activity but also bactericidal activity. Preliminary in vitro cytotoxicity screening was assessed using the human monocytic leukemia cell line THP-1 and, except for compound 2p, all effective agents did show insignificant cytotoxic effect. Compound 2p is an interesting anti-invasive agent with dual (cytotoxic and antibacterial) activity, while compounds 1j and 1o are the most interesting purely antibacterial compounds within the prepared molecules.

Návaznosti

90123, velká výzkumná infrastruktura

Název: CzeCOS III

Citovat

STRHÁRSKY, Tomáš, Dominika PINDJAKOVA, Jiří KOS, Lucia VRABLOVA, Pavel ŠMAK, Hana MICHNOVA, Tomáš GONĚC, Jan HOŠEK, Michal ORAVEC, Izabela JENDRZEJEWSKA, Alois ČÍŽEK a Josef JAMPILEK. Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections. International Journal of Molecular Sciences. Basel: Multidisciplinary Digital Publishing Institute, 2022, roč. 23, č. 23, s. 1-22. ISSN 1422-0067. Dostupné z: https://dx.doi.org/10.3390/ijms232315090.

@article{2243548,
   author = {Strhársky, Tomáš and Pindjakova, Dominika and Kos, Jiří and Vrablova, Lucia and Šmak, Pavel and Michnova, Hana and Goněc, Tomáš and Hošek, Jan and Oravec, Michal and Jendrzejewska, Izabela and Čížek, Alois and Jampilek, Josef},
   article_location = {Basel},
   article_number = {23},
   doi = {http://dx.doi.org/10.3390/ijms232315090},
   keywords = {cinnamamides; Michael acceptors; antimicrobial activity; cytotoxicity; lipophilicity; structure-activity relationships; docking study},
   language = {eng},
   issn = {1422-0067},
   journal = {International Journal of Molecular Sciences},
   title = {Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections},
   url = {https://www.mdpi.com/1422-0067/23/23/15090},
   volume = {23},
   year = {2022}
}

TY  - JOUR
ID  - 2243548
AU  - Strhársky, Tomáš - Pindjakova, Dominika - Kos, Jiří - Vrablova, Lucia - Šmak, Pavel - Michnova, Hana - Goněc, Tomáš - Hošek, Jan - Oravec, Michal - Jendrzejewska, Izabela - Čížek, Alois - Jampilek, Josef
PY  - 2022
TI  - Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections
JF  - International Journal of Molecular Sciences
VL  - 23
IS  - 23
SP  - 1-22
EP  - 1-22
PB  - Multidisciplinary Digital Publishing Institute
SN  - 14220067
KW  - cinnamamides
KW  - Michael acceptors
KW  - antimicrobial activity
KW  - cytotoxicity
KW  - lipophilicity
KW  - structure-activity relationships
KW  - docking study
UR  - https://www.mdpi.com/1422-0067/23/23/15090
N2  - A series of thirty-two anilides of 3-(trifluoromethyl)cinnamic acid (series 1) and 4-(trifluoromethyl)cinnamic acid (series 2) was prepared by microwave-assisted synthesis. All the compounds were tested against reference strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 and resistant clinical isolates of methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (VRE). All the compounds were evaluated in vitro against Mycobacterium smegmatis ATCC 700084 and M. marinum CAMP 5644. (2E)-3-[3-(Trifluoromethyl)phenyl]-N-[4-(trifluoromethyl)phenyl]prop-2-enamide (1j), (2E)-N-(3,5-dichlorophenyl)-3-[3-(trifluoromethyl)phenyl]prop-2-enamide (1o) and (2E)-N-[3-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)-phenyl]prop-2-enamide (2i), (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]-prop-2-enamide (2p) showed antistaphylococcal (MICs/MBCs 0.15-5.57 mu M) as well as anti-enterococcal (MICs/MBCs 2.34-44.5 mu M) activity. The growth of M. marinum was strongly inhibited by compounds 1j and 2p in a MIC range from 0.29 to 2.34 mu M, while all the agents of series 1 showed activity against M. smegnatis (MICs ranged from 9.36 to 51.7 mu M). The performed docking study demonstrated the ability of the compounds to bind to the active site of the mycobacterial enzyme InhA. The compounds had a significant effect on the inhibition of bacterial respiration, as demonstrated by the MTT assay. The compounds showed not only bacteriostatic activity but also bactericidal activity. Preliminary in vitro cytotoxicity screening was assessed using the human monocytic leukemia cell line THP-1 and, except for compound 2p, all effective agents did show insignificant cytotoxic effect. Compound 2p is an interesting anti-invasive agent with dual (cytotoxic and antibacterial) activity, while compounds 1j and 1o are the most interesting purely antibacterial compounds within the prepared molecules.
ER  -

STRHÁRSKY, Tomáš, Dominika PINDJAKOVA, Jiří KOS, Lucia VRABLOVA, Pavel ŠMAK, Hana MICHNOVA, Tomáš GONĚC, Jan HOŠEK, Michal ORAVEC, Izabela JENDRZEJEWSKA, Alois ČÍŽEK a Josef JAMPILEK. Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections. \textit{International Journal of Molecular Sciences}. Basel: Multidisciplinary Digital Publishing Institute, 2022, roč.~23, č.~23, s.~1-22. ISSN~1422-0067. Dostupné z: https://dx.doi.org/10.3390/ijms232315090.

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