The Antibacterial Effects of New N-Alkylpyridinium Salts on Planktonic and Biofilm Bacteria
Status PubMed-not-MEDLINE Jazyk angličtina Země Švýcarsko Médium electronic-ecollection
Typ dokumentu časopisecké články
PubMed
33193183
PubMed Central
PMC7606276
DOI
10.3389/fmicb.2020.573951
Knihovny.cz E-zdroje
- Klíčová slova
- antimicrobial activity, bacteria, biofilm, photoacoustic irrigation, quaternary ammonium salts,
- Publikační typ
- časopisecké články MeSH
An increasing microbial resistance to known antibiotics raises a demand for new antimicrobials. In this study the antimicrobial properties of a series of new N-Alkylpyridinium quaternary ammonium compounds (QACs) with varying alkyl chain lengths were evaluated for several nosocomial pathogens. The chemical identities of the new QACs were determined by NMR, LC-MS, and HRMS. All the planktonic bacteria tested were susceptible to the new QACs as evaluated by MIC and MBC assays. The antimicrobial effect was most pronounced against Staphylococcus aureus clinical isolates. Live/dead staining CLSM was used to test the effectiveness of the QACs in biofilms. The effectiveness was up to 10-fold lower than in the plankton. When QACs were used as irrigants in Er:YAG - SSP photoacoustic steaming, their effectiveness significantly increased. The combined use of irrigants and photoacoustic streaming increased biofilm removal from the surface and increased the killing rate of the cells remaining on the surface. This may allow for a shorter chemical exposure time and lower dosage of QACs used in applications. The results demonstrate that the new QACs have potential to be applied as antibacterial compounds effective against planktonic and biofilm bacteria as well as irrigants in removal of difficult-to-reach biofilms.
Biomedical Research Centre University Hospital Hradec Kralove Hradec Kralove Czechia
Department of Microbiology Biotechnical Faculty University of Ljubljana Ljubljana Slovenia
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Akcay M., Arslan H., Mese M., Durmus N., Capar I. D. (2017). Effect of photon-initiated photoacoustic streaming, passive ultrasonic, and sonic irrigation techniques on dentinal tubule penetration of irrigation solution: a confocal microscopic study. Clin. Oral Investig. 21 2205–2212. 10.1007/s00784-016-2013-y PubMed DOI
ASTM International (2017). ASTM E2799-17, Standard Test Method for Testing Disinfectant Efficacy Against Pseudomonas aeruginosa Biofilm using the MBEC Assay. West Conshohocken, PA: ASTM International.
Bliss C. I. (1939). The toxicity of poisons applied jointly. Ann. Appl. Biol. 26 585–615. 10.1111/j.1744-7348.1939.tb06990.x DOI
Boutsioukis C., Verhaagen B., Versluis M., Kastrinakis E., Wesselink P. R., van der Sluis L. W. M. (2010). Evaluation of irrigant flow in the root canal using different needle types by an unsteady computational fluid dynamics model. J. Endod. 36 875–879. 10.1016/j.joen.2009.12.026 PubMed DOI
Brown P., Sresht V., Eral B. H., Fiore A., Fuente-Núñez C., O’Mahony M., et al. (2017). CO2 -reactive ionic liquid surfactants for the control of colloidal morphology. Langmuir 33 7633–7641. 10.1021/acs.langmuir.7b00679 PubMed DOI
Ceri H., Olson M. E., Stremick C., Read R. R., Morck D., Buret A. (1999). The calgary biofilm device: new technology for rapid determination of antibiotic susceptibilities of bacterial biofilms. J. Clin. Microbiol. 37 1771–1776. 10.1128/jcm.37.6.1771-1776.1999 PubMed DOI PMC
Christen V., Faltermann S., Brun N. R., Kunz P. Y., Fent K. (2017). Cytotoxicity and molecular effects of biocidal disinfectants (quaternary ammonia, glutaraldehyde, poly(hexamethylene biguanide) hydrochloride PHMB) and their mixtures in vitro and in zebrafish eleuthero-embryos. Sci. Total Environ. 586 1204–1218. 10.1016/j.scitotenv.2017.02.114 PubMed DOI
Clarkson R. M., Moule A. J. (1998). Sodium hypochlorite and its use as an endodontic irrigant. Aust. Dent. J. 43 250–256. 10.1111/j.1834-7819.1998.tb00173.x PubMed DOI
CLSI (2018). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically: CLSI Standard M07, 11th Edn Wayne, PA: Clinical and Laboratory Standards Institute.
Courvalin P. (2016). Why is antibiotic resistance a deadly emerging disease? Clin. Microbiol. Infect. 22 405–407. 10.1016/j.cmi.2016.01.012 PubMed DOI
Datta S., Baudouin C., Brignole-Baudouin F., Denoyer A., Cortopassi G. A. (2017). The eye drop preservative benzalkonium chloride potently induces mitochondrial dysfunction and preferentially affects LHON mutant cells. Investig. Opthalmology Vis. Sci. 58:2406. 10.1167/iovs.16-20903 PubMed DOI PMC
Dolezal R., Soukup O., Malinak D., Savedra R. M. L., Marek J., Dolezalova M., et al. (2016). Towards understanding the mechanism of action of antibacterial N-alkyl-3-hydroxypyridinium salts: biological activities, molecular modeling and QSAR studies. Eur. J. Med. Chem. 121 699–711. 10.1016/j.ejmech.2016.05.058 PubMed DOI
Foucquier J., Guedj M. (2015). Analysis of drug combinations: current methodological landscape. Pharmacol. Res. Perspect. 3:e00149. 10.1002/prp2.149 PubMed DOI PMC
Fuente-Nunez C., Brown P., Torres M. D. T., Cao J., Lu T. K. (2018). Magnetic surfactant ionic liquids and polymers with tetrahaloferrate (III) anions as antimicrobial agents with low cytotoxicity. Colloid Interface Sci. Commun. 22 11–13. 10.1016/j.colcom.2017.11.002 DOI
Gerba C. P. (2015). Quaternary ammonium biocides: efficacy in application. Appl. Environ. Microbiol. 81 464–469. 10.1128/AEM.02633-14 PubMed DOI PMC
Jennings M. C., Ator L. E., Paniak T. J., Minbiole K. P. C., Wuest W. M. (2014). Biofilm-eradicating properties of quaternary ammonium amphiphiles: simple mimics of antimicrobial peptides. ChemBioChem 15 2211–2215. 10.1002/cbic.201402254 PubMed DOI
Khan H. A., Baig F. K., Mehboob R. (2017). Nosocomial infections: epidemiology, prevention, control and surveillance. Asian Pac. J. Trop. Biomed. 7 478–482. 10.1016/j.apjtb.2017.01.019 DOI
Kurzmann C., Meire M. A., Lettner S., Farmakis E. T. R., Moritz A., De Moor R. J. G. (2019). The efficacy of ultrasonic and PIPS (photon-induced acoustic streaming) irrigation to remove artificially placed dentine debris plugs out of an artificial and natural root model. Lasers Med. Sci. 35 719–728. 10.1007/s10103-019-02912-3 PubMed DOI
Kwon D., Lim Y., Kwon J., Shim I., Kim E., Lee D., et al. (2019). Evaluation of pulmonary toxicity of benzalkonium chloride and triethylene glycol mixtures using in vitro and in vivo systems. Environ. Toxicol. 34 561–572. 10.1002/tox.22722 PubMed DOI PMC
Li F., Weir M. D., Xu H. H. K. (2013). Effects of quaternary ammonium chain length on antibacterial bonding agents. J. Dent. Res. 92 932–938. 10.1177/0022034513502053 PubMed DOI PMC
López Pérez D., Baker P. J., Pintar A. L., Sun J., Lin N. J., Lin-Gibson S. (2017). Experimental and statistical methods to evaluate antibacterial activity of a quaternary pyridinium salt on planktonic, biofilm-forming, and biofilm states. Biofouling 33 222–234. 10.1080/08927014.2017.1286476 PubMed DOI
Lukač N., Jezeršek M. (2018). Amplification of pressure waves in laser-assisted endodontics with synchronized delivery of Er:YAG laser pulses. Lasers Med. Sci. 33 823–833. 10.1007/s10103-017-2435-z PubMed DOI PMC
Marek J., Malinak D., Dolezal R., Soukup O., Pasdiorova M., Dolezal M., et al. (2015). Synthesis and disinfection effect of the pyridine-4-aldoxime based salts. Molecules 20 3681–3696. 10.3390/molecules20033681 PubMed DOI PMC
Marek J., Stodulka P., Cabal J., Soukup O., Pohanka M., Korabecny J., et al. (2010). Preparation of the pyridinium salts differing in the length of the N-Alkyl substituent. Molecules 15 1967–1972. 10.3390/molecules15031967 PubMed DOI PMC
Olivi G., DiVito E., Peters O., Kaitsas V., Angiero F., Signore A., et al. (2014). Disinfection efficacy of photon-induced photoacoustic streaming on root canals infected with Enterococcus faecalis. J. Am. Dent. Assoc. 145 843–848. 10.14219/jada.2014.46 PubMed DOI
Olson M. E., Ceri H., Morck D. W., Buret A. G., Read R. R. (2002). Biofilm bacteria: formation and comparative susceptibility to antibiotics. Can. J. Vet. Res. 66 86–92. PubMed PMC
Paz L. E. C., Bergenholtz G., Svensäter G. (2010). The effects of antimicrobials on endodontic biofilm bacteria. J. Endod. 36 70–77. 10.1016/j.joen.2009.09.017 PubMed DOI
Rémy B., Mion S., Plener L., Elias M., Chabrière E., Daudé D. (2018). Interference in bacterial quorum sensing: a biopharmaceutical perspective. Front. Pharmacol. 9:203. 10.3389/fphar.2018.00203 PubMed DOI PMC
Shtyrlin N. V., Sapozhnikov S. V., Galiullina A. S., Kayumov A. R., Bondar O. V., Mirchink E. P., et al. (2016). Synthesis and antibacterial activity of quaternary ammonium 4-deoxypyridoxine derivatives. BioMed Res. Int. 2016:3864193. 10.1155/2016/3864193 PubMed DOI PMC
Soukup O., Benkova M., Dolezal R., Sleha R., Malinak D., Salajkova S., et al. (2020). The wide-spectrum antimicrobial effect of novel N-alkyl monoquaternary ammonium salts and their mixtures; the QSAR study against bacteria. Eur. J. Med. Chem. 206:112584. 10.1016/j.ejmech.2020.112584 PubMed DOI
Tischer M., Pradel G., Ohlsen K., Holzgrabe U. (2012). Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions? ChemMedChem 7 22–31. 10.1002/cmdc.201100404 PubMed DOI
Watkins K. (2018). Emerging infectious diseases: a review. Curr. Emerg. Hosp. Med. Rep. 6 86–93. 10.1007/s40138-018-0162-9 PubMed DOI PMC
Zehnder M. (2006). Root canal irrigants. J. Endod. 32 389–398. 10.1016/j.joen.2005.09.014 PubMed DOI
Zhang K., Cheng L., Weir M. D., Bai Y.-X., Xu H. H. (2016). Effects of quaternary ammonium chain length on the antibacterial and remineralizing effects of a calcium phosphate nanocomposite. Int. J. Oral Sci. 8 45–53. 10.1038/ijos.2015.33 PubMed DOI PMC
Zhang Y., Chen Y., Hu Y., Huang F., Xiao Y. (2018). Quaternary ammonium compounds in dental restorative materials. Dent. Mater. J. 37 183–191. 10.4012/dmj.2017-096 PubMed DOI