Synthesis and Spectrum of Biological Activities of Novel
N-arylcinnamamides

J 2018

Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides

POSPÍŠILOVÁ, Šárka, Jiří KOS, Hana MICHNOVÁ, Iva KAPUSTÍKOVÁ, Tomáš STRHÁRSKY et. al.

Základní údaje

Originální název

Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides

Autoři

POSPÍŠILOVÁ, Šárka, Jiří KOS, Hana MICHNOVÁ, Iva KAPUSTÍKOVÁ, Tomáš STRHÁRSKY, Michal ORAVEC, Agnes M. MORICZ, Jozsef BAKONYI, Tereza KAUEROVÁ, Peter KOLLÁR a Alois ČÍŽEK

Vydání

International Journal of Molecular Sciences, Basel, MDPI, 2018, 1422-0067

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.183

DOI

http://dx.doi.org/10.3390/ijms19082318

UT WoS

000442869800170

Klíčová slova česky

cinnamamidy; antistafylokoková aktivita; test time-kill; biofilm; antituberkulózní aktivita; MTT test; antifungální aktivita; Inhibice PET; toxicita; vztah struktura-účinek

Klíčová slova anglicky

cinnamamides; antistaphylococcal activity; time-kill assay; biofilm; antitubercular activity; MTT assay; antifungal activity; PET inhibition; toxicity; structure-activity relationship

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 28. 8. 2020 19:33, doc. PharmDr. Peter Kollár, Ph.D.

Anotace

V originále

A series of sixteen ring-substituted N-arylcinnamamides was prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra, Fusarium avenaceum, and Bipolaris sorokiniana. Several of the tested compounds showed antistaphylococcal, antitubercular, and antifungal activities comparable with or higher than those of ampicillin, isoniazid, and benomyl. (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-phenylprop-2-enamide and (2E)-3-phenyl-N-[3-(trifluoromethyl)phenyl]prop-2-enamide showed the highest activities (MICs = 22.27 and 27.47 mu M, respectively) against all four staphylococcal strains and against M. tuberculosis. These compounds showed an activity against biofilm formation of S. aureus ATCC 29213 in concentrations close to MICs and an ability to increase the activity of clinically used antibiotics with different mechanisms of action (vancomycin, ciprofloxacin, and tetracycline). In time-kill studies, a decrease of CFU/mL of >99% after 8 h from the beginning of incubation was observed. (2E)-N-(3,5-Dichlorophenyl)- and (2E)-N-(3,4-dichlorophenyl)-3-phenylprop-2-enamide had a MIC = 27.38 mu M against M. tuberculosis, while a significant decrease (22.65%) of mycobacterial cell metabolism determined by the MTT assay was observed for the 3,5-dichlorophenyl derivative. (2E)-N-(3-Fluorophenyl)- and (2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide exhibited MICs = 16.58 and 33.71 mu M, respectively, against B. sorokiniana. The screening of the cytotoxicity of the most effective antimicrobial compounds was performed using THP-1 cells, and these chosen compounds did not shown any significant lethal effect. The compounds were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. (2E)-N-(3,5-dichlorophenyl)-3-phenylprop-2-enamide (IC50 = 5.1 mu M) was the most active PET inhibitor. Compounds with fungicide potency did not show any in vivo toxicity against Nicotiana tabacum var. Samsun. The structure-activity relationships are discussed.

Citovat

POSPÍŠILOVÁ, Šárka, Jiří KOS, Hana MICHNOVÁ, Iva KAPUSTÍKOVÁ, Tomáš STRHÁRSKY, Michal ORAVEC, Agnes M. MORICZ, Jozsef BAKONYI, Tereza KAUEROVÁ, Peter KOLLÁR a Alois ČÍŽEK. Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides. International Journal of Molecular Sciences. Basel: MDPI, 2018, roč. 19, č. 8, 25 s. ISSN 1422-0067. Dostupné z: https://dx.doi.org/10.3390/ijms19082318.

@article{1675890,
   author = {Pospíšilová, Šárka and Kos, Jiří and Michnová, Hana and Kapustíková, Iva and Strhársky, Tomáš and Oravec, Michal and Moricz, Agnes M. and Bakonyi, Jozsef and Kauerová, Tereza and Kollár, Peter and Čížek, Alois},
   article_location = {Basel},
   article_number = {8},
   doi = {http://dx.doi.org/10.3390/ijms19082318},
   keywords = {cinnamamides; antistaphylococcal activity; time-kill assay; biofilm; antitubercular activity; MTT assay; antifungal activity; PET inhibition; toxicity; structure-activity relationship},
   language = {eng},
   issn = {1422-0067},
   journal = {International Journal of Molecular Sciences},
   title = {Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides},
   url = {https://www.mdpi.com/1422-0067/19/8/2318/htm},
   volume = {19},
   year = {2018}
}

TY  - JOUR
ID  - 1675890
AU  - Pospíšilová, Šárka - Kos, Jiří - Michnová, Hana - Kapustíková, Iva - Strhársky, Tomáš - Oravec, Michal - Moricz, Agnes M. - Bakonyi, Jozsef - Kauerová, Tereza - Kollár, Peter - Čížek, Alois
PY  - 2018
TI  - Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides
JF  - International Journal of Molecular Sciences
VL  - 19
IS  - 8
PB  - MDPI
SN  - 14220067
KW  - cinnamamides
KW  - antistaphylococcal activity
KW  - time-kill assay
KW  - biofilm
KW  - antitubercular activity
KW  - MTT assay
KW  - antifungal activity
KW  - PET inhibition
KW  - toxicity
KW  - structure-activity relationship
UR  - https://www.mdpi.com/1422-0067/19/8/2318/htm
L2  - https://www.mdpi.com/1422-0067/19/8/2318/htm
N2  - A series of sixteen ring-substituted N-arylcinnamamides was prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra, Fusarium avenaceum, and Bipolaris sorokiniana. Several of the tested compounds showed antistaphylococcal, antitubercular, and antifungal activities comparable with or higher than those of ampicillin, isoniazid, and benomyl. (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-phenylprop-2-enamide and (2E)-3-phenyl-N-[3-(trifluoromethyl)phenyl]prop-2-enamide showed the highest activities (MICs = 22.27 and 27.47 mu M, respectively) against all four staphylococcal strains and against M. tuberculosis. These compounds showed an activity against biofilm formation of S. aureus ATCC 29213 in concentrations close to MICs and an ability to increase the activity of clinically used antibiotics with different mechanisms of action (vancomycin, ciprofloxacin, and tetracycline). In time-kill studies, a decrease of CFU/mL of >99% after 8 h from the beginning of incubation was observed. (2E)-N-(3,5-Dichlorophenyl)- and (2E)-N-(3,4-dichlorophenyl)-3-phenylprop-2-enamide had a MIC = 27.38 mu M against M. tuberculosis, while a significant decrease (22.65%) of mycobacterial cell metabolism determined by the MTT assay was observed for the 3,5-dichlorophenyl derivative. (2E)-N-(3-Fluorophenyl)- and (2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide exhibited MICs = 16.58 and 33.71 mu M, respectively, against B. sorokiniana. The screening of the cytotoxicity of the most effective antimicrobial compounds was performed using THP-1 cells, and these chosen compounds did not shown any significant lethal effect. The compounds were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. (2E)-N-(3,5-dichlorophenyl)-3-phenylprop-2-enamide (IC50 = 5.1 mu M) was the most active PET inhibitor. Compounds with fungicide potency did not show any in vivo toxicity against Nicotiana tabacum var. Samsun. The structure-activity relationships are discussed.
ER  -

POSPÍŠILOVÁ, Šárka, Jiří KOS, Hana MICHNOVÁ, Iva KAPUSTÍKOVÁ, Tomáš STRHÁRSKY, Michal ORAVEC, Agnes M. MORICZ, Jozsef BAKONYI, Tereza KAUEROVÁ, Peter KOLLÁR a Alois ČÍŽEK. Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides. \textit{International Journal of Molecular Sciences}. Basel: MDPI, 2018, roč.~19, č.~8, 25 s. ISSN~1422-0067. Dostupné z: https://dx.doi.org/10.3390/ijms19082318.

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