Wide-Antimicrobial Spectrum of Picolinium Salts
Nosocomial infections, which greatly increase morbidity among hospitalized patients, together with growing antibiotic resistance still encourage many researchers to search for novel antimicrobial compounds. Picolinium salts with different lengths of alkyl chains (C<sub>12</sub>, C<sub...
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-05-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/9/2254 |
| _version_ | 1827717131110711296 |
|---|---|
| author | Sarka Salajkova Marketa Benkova Jan Marek Radek Sleha Lukas Prchal David Malinak Rafael Dolezal Kristina Sepčić Nina Gunde-Cimerman Kamil Kuca Ondrej Soukup |
| author_facet | Sarka Salajkova Marketa Benkova Jan Marek Radek Sleha Lukas Prchal David Malinak Rafael Dolezal Kristina Sepčić Nina Gunde-Cimerman Kamil Kuca Ondrej Soukup |
| author_sort | Sarka Salajkova |
| collection | DOAJ |
| description | Nosocomial infections, which greatly increase morbidity among hospitalized patients, together with growing antibiotic resistance still encourage many researchers to search for novel antimicrobial compounds. Picolinium salts with different lengths of alkyl chains (C<sub>12</sub>, C<sub>14</sub>, C<sub>16</sub>) were prepared by Menshutkin-like reaction and evaluated with respect to their biological activity, i.e., lipophilicity and critical micellar concentration. Picolinium salts with C<sub>14</sub> and C<sub>16</sub> side chains achieved similar or even better results when in terms of antimicrobial efficacy than benzalkoniums; notably, their fungicidal efficiency was substantially more potent. The position of the methyl substituent on the aromatic ring does not seem to affect antimicrobial activity, in contrast to the effect of length of the <i>N</i>-alkyl chain. Concurrently, picolinium salts exhibited satisfactory low cytotoxicity against mammalian cells, i.e., lower than that of benzalkonium compounds, which are considered as safe. |
| first_indexed | 2024-03-10T19:55:23Z |
| format | Article |
| id | doaj.art-4cd878c40b944f69ad4c9d84c9b6eb82 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:55:23Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4cd878c40b944f69ad4c9d84c9b6eb822023-11-20T00:00:51ZengMDPI AGMolecules1420-30492020-05-01259225410.3390/molecules25092254Wide-Antimicrobial Spectrum of Picolinium SaltsSarka Salajkova0Marketa Benkova1Jan Marek2Radek Sleha3Lukas Prchal4David Malinak5Rafael Dolezal6Kristina Sepčić7Nina Gunde-Cimerman8Kamil Kuca9Ondrej Soukup10Biomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicBiomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicBiomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicDepartment of Epidemiology, University of Defence in Brno, Trebesska 1575, 500 05 Hradec Kralove, Czech RepublicBiomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicBiomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicBiomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicDepartment of Biology, Biotechnical Faculty, University of Ljubljana, Jamnikarjeva 101, 1000 Ljubljana, SloveniaDepartment of Biology, Biotechnical Faculty, University of Ljubljana, Jamnikarjeva 101, 1000 Ljubljana, SloveniaBiomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicBiomedical Research Center, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech RepublicNosocomial infections, which greatly increase morbidity among hospitalized patients, together with growing antibiotic resistance still encourage many researchers to search for novel antimicrobial compounds. Picolinium salts with different lengths of alkyl chains (C<sub>12</sub>, C<sub>14</sub>, C<sub>16</sub>) were prepared by Menshutkin-like reaction and evaluated with respect to their biological activity, i.e., lipophilicity and critical micellar concentration. Picolinium salts with C<sub>14</sub> and C<sub>16</sub> side chains achieved similar or even better results when in terms of antimicrobial efficacy than benzalkoniums; notably, their fungicidal efficiency was substantially more potent. The position of the methyl substituent on the aromatic ring does not seem to affect antimicrobial activity, in contrast to the effect of length of the <i>N</i>-alkyl chain. Concurrently, picolinium salts exhibited satisfactory low cytotoxicity against mammalian cells, i.e., lower than that of benzalkonium compounds, which are considered as safe.https://www.mdpi.com/1420-3049/25/9/2254picolinium saltsquaternary ammonium compoundssurfactantcritical micellar concentrationantimicrobial activitycytotoxicity |
| spellingShingle | Sarka Salajkova Marketa Benkova Jan Marek Radek Sleha Lukas Prchal David Malinak Rafael Dolezal Kristina Sepčić Nina Gunde-Cimerman Kamil Kuca Ondrej Soukup Wide-Antimicrobial Spectrum of Picolinium Salts Molecules picolinium salts quaternary ammonium compounds surfactant critical micellar concentration antimicrobial activity cytotoxicity |
| title | Wide-Antimicrobial Spectrum of Picolinium Salts |
| title_full | Wide-Antimicrobial Spectrum of Picolinium Salts |
| title_fullStr | Wide-Antimicrobial Spectrum of Picolinium Salts |
| title_full_unstemmed | Wide-Antimicrobial Spectrum of Picolinium Salts |
| title_short | Wide-Antimicrobial Spectrum of Picolinium Salts |
| title_sort | wide antimicrobial spectrum of picolinium salts |
| topic | picolinium salts quaternary ammonium compounds surfactant critical micellar concentration antimicrobial activity cytotoxicity |
| url | https://www.mdpi.com/1420-3049/25/9/2254 |
| work_keys_str_mv | AT sarkasalajkova wideantimicrobialspectrumofpicoliniumsalts AT marketabenkova wideantimicrobialspectrumofpicoliniumsalts AT janmarek wideantimicrobialspectrumofpicoliniumsalts AT radeksleha wideantimicrobialspectrumofpicoliniumsalts AT lukasprchal wideantimicrobialspectrumofpicoliniumsalts AT davidmalinak wideantimicrobialspectrumofpicoliniumsalts AT rafaeldolezal wideantimicrobialspectrumofpicoliniumsalts AT kristinasepcic wideantimicrobialspectrumofpicoliniumsalts AT ninagundecimerman wideantimicrobialspectrumofpicoliniumsalts AT kamilkuca wideantimicrobialspectrumofpicoliniumsalts AT ondrejsoukup wideantimicrobialspectrumofpicoliniumsalts |