Insight into antimicrobial activity of substituted
phenylcarbamoyloxypiperazinylpropanols

J 2020

Insight into antimicrobial activity of substituted phenylcarbamoyloxypiperazinylpropanols

POSPISILOVA, S., I. MALIK, J. CURILLOVA, H. MICHNOVA, L. CERNA et. al.

Basic information

Original name

Insight into antimicrobial activity of substituted phenylcarbamoyloxypiperazinylpropanols

Authors

POSPISILOVA, S., I. MALIK, J. CURILLOVA, H. MICHNOVA, L. CERNA, Tereza PADRTOVÁ (203 Czech Republic, belonging to the institution), J. HOSEK, D. PECHER, A. CIZEK and J. JAMPILEK

Edition

Bioorganic Chemistry, SAN DIEGO, ACADEMIC PRESS INC ELSEVIER SCIENCE, 2020, 0045-2068

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.275

RIV identification code

RIV/00216224:14160/20:00118183

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.1016/j.bioorg.2020.104060

UT WoS

000567809600011

Keywords in English

Piperazine; Carbamate; Antibacterial; Antimycobacterial; Synergy; Antibiofilm activity; Antiproliferative effect

Abstract

V originále

3-[4-(Substituted)phenyl-/4-(diphenylmethyl)phenylpiperazin-1-yl]-2-hydroxypropyl-1-[(substituted)phenyl] carbamates and their salts with hydrochloric acid were synthesized, characterized, and tested in vitro against Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 as reference and quality control strains, against three methicillin-resistant isolates of S. aureus, and three isolates of vancomycin-resistant E. faecalis. All the compounds were evaluated against Mycobacterium tuberculosis H37Ra/ATCC 25177, M. kansasii DSM 44162, and M. smegmatis ATCC 700084. All of the tested compounds demonstrated very good activity against all the tested strains/isolates comparable with or better than that of clinically used drugs (ampicillin, ciprofloxacin, vancomycin, isoniazid). 1-[{(3-Trifluoromethyl)phenyl}carbamoyloxy-2-hydroxypropyl]-4-(3,4-dichlorophenyl)piperazin-1-ium chloride demonstrated the highest potency against all the tested strains/isolates (MICs ranged from 3.78 to 30.2 mu M), and 1-[{(3-trifluoromethyl)phenyl}carbamoyloxy-2-hydroxypropyl]-4-(diphenylmethyl)piperazin-1-ium chloride was the most effective against all the screened mycobacterial strains (MICs ranged from 3.64 to 14.5 mu M). All the investigated derivatives had strong antibiofilm activity against S. aureus ATCC 29123 and a synergistic or additive effect with gentamicin against isolates of E. faecalis with both intrinsic and acquired resistance to gentamicin. The screening of the cytotoxicity of the compounds was performed using human monocytic leukemia THP-1 cells. The IC50 values of the most effective compounds ranged from ca. 2.8 to 7.3 mu M; thus, it can be stated that the antimicrobial effect is closely connected with their cytotoxicity. These observations disqualify these compounds from further development as antimicrobial agents, but they can be considered potential multi-target drugs with a preferred anticancer effect with good water solubility and additional anti-infectious activity.

Citovat

POSPISILOVA, S., I. MALIK, J. CURILLOVA, H. MICHNOVA, L. CERNA, Tereza PADRTOVÁ, J. HOSEK, D. PECHER, A. CIZEK and J. JAMPILEK. Insight into antimicrobial activity of substituted phenylcarbamoyloxypiperazinylpropanols. Bioorganic Chemistry. SAN DIEGO: ACADEMIC PRESS INC ELSEVIER SCIENCE, 2020, vol. 102, SEP 2020, p. 1-13. ISSN 0045-2068. Available from: https://dx.doi.org/10.1016/j.bioorg.2020.104060.

@article{1742756,
   author = {Pospisilova, S. and Malik, I. and Curillova, J. and Michnova, H. and Cerna, L. and Padrtová, Tereza and Hosek, J. and Pecher, D. and Cizek, A. and Jampilek, J.},
   article_location = {SAN DIEGO},
   article_number = {SEP 2020},
   doi = {http://dx.doi.org/10.1016/j.bioorg.2020.104060},
   keywords = {Piperazine; Carbamate; Antibacterial; Antimycobacterial; Synergy; Antibiofilm activity; Antiproliferative effect},
   language = {eng},
   issn = {0045-2068},
   journal = {Bioorganic Chemistry},
   title = {Insight into antimicrobial activity of substituted phenylcarbamoyloxypiperazinylpropanols},
   url = {https://reader.elsevier.com/reader/sd/pii/S0045206820313572?token=DE099DA7E310024FB4EEB6D343EBC53C275E3AC051EF2B629BA5C1E5F9F6C1E6EDE799168A968020ECE398A9052AEEC3},
   volume = {102},
   year = {2020}
}

TY  - JOUR
ID  - 1742756
AU  - Pospisilova, S. - Malik, I. - Curillova, J. - Michnova, H. - Cerna, L. - Padrtová, Tereza - Hosek, J. - Pecher, D. - Cizek, A. - Jampilek, J.
PY  - 2020
TI  - Insight into antimicrobial activity of substituted phenylcarbamoyloxypiperazinylpropanols
JF  - Bioorganic Chemistry
VL  - 102
IS  - SEP 2020
SP  - 1-13
EP  - 1-13
PB  - ACADEMIC PRESS INC ELSEVIER SCIENCE
SN  - 00452068
KW  - Piperazine
KW  - Carbamate
KW  - Antibacterial
KW  - Antimycobacterial
KW  - Synergy
KW  - Antibiofilm activity
KW  - Antiproliferative effect
UR  - https://reader.elsevier.com/reader/sd/pii/S0045206820313572?token=DE099DA7E310024FB4EEB6D343EBC53C275E3AC051EF2B629BA5C1E5F9F6C1E6EDE799168A968020ECE398A9052AEEC3
L2  - https://reader.elsevier.com/reader/sd/pii/S0045206820313572?token=DE099DA7E310024FB4EEB6D343EBC53C275E3AC051EF2B629BA5C1E5F9F6C1E6EDE799168A968020ECE398A9052AEEC3
N2  - 3-[4-(Substituted)phenyl-/4-(diphenylmethyl)phenylpiperazin-1-yl]-2-hydroxypropyl-1-[(substituted)phenyl] carbamates and their salts with hydrochloric acid were synthesized, characterized, and tested in vitro against Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 as reference and quality control strains, against three methicillin-resistant isolates of S. aureus, and three isolates of vancomycin-resistant E. faecalis. All the compounds were evaluated against Mycobacterium tuberculosis H37Ra/ATCC 25177, M. kansasii DSM 44162, and M. smegmatis ATCC 700084. All of the tested compounds demonstrated very good activity against all the tested strains/isolates comparable with or better than that of clinically used drugs (ampicillin, ciprofloxacin, vancomycin, isoniazid). 1-[{(3-Trifluoromethyl)phenyl}carbamoyloxy-2-hydroxypropyl]-4-(3,4-dichlorophenyl)piperazin-1-ium chloride demonstrated the highest potency against all the tested strains/isolates (MICs ranged from 3.78 to 30.2 mu M), and 1-[{(3-trifluoromethyl)phenyl}carbamoyloxy-2-hydroxypropyl]-4-(diphenylmethyl)piperazin-1-ium chloride was the most effective against all the screened mycobacterial strains (MICs ranged from 3.64 to 14.5 mu M). All the investigated derivatives had strong antibiofilm activity against S. aureus ATCC 29123 and a synergistic or additive effect with gentamicin against isolates of E. faecalis with both intrinsic and acquired resistance to gentamicin. The screening of the cytotoxicity of the compounds was performed using human monocytic leukemia THP-1 cells. The IC50 values of the most effective compounds ranged from ca. 2.8 to 7.3 mu M; thus, it can be stated that the antimicrobial effect is closely connected with their cytotoxicity. These observations disqualify these compounds from further development as antimicrobial agents, but they can be considered potential multi-target drugs with a preferred anticancer effect with good water solubility and additional anti-infectious activity.
ER  -

POSPISILOVA, S., I. MALIK, J. CURILLOVA, H. MICHNOVA, L. CERNA, Tereza PADRTOVÁ, J. HOSEK, D. PECHER, A. CIZEK and J. JAMPILEK. Insight into antimicrobial activity of substituted phenylcarbamoyloxypiperazinylpropanols. \textit{Bioorganic Chemistry}. SAN DIEGO: ACADEMIC PRESS INC ELSEVIER SCIENCE, 2020, vol.~102, SEP 2020, p.~1-13. ISSN~0045-2068. Available from: https://dx.doi.org/10.1016/j.bioorg.2020.104060.

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