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Nonquaternary poly(diallylammonium) polymers with different amine structure and their biocidal effect on Mycobacterium tuberculosis and Mycobacterium smegmatis
Mycobacteria, especially Mycobacterium tuberculosis, are one of the most dangerous types of microorganisms to cause diseases and mortality. Due to the known distinctive structure of their cell wall, mycobacteria are resistant to majority of antibiotics and common chemical disinfectants, including qu...
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Published in: | Applied microbiology and biotechnology 2015-03, Vol.99 (6), p.2557-2571 |
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description | Mycobacteria, especially Mycobacterium tuberculosis, are one of the most dangerous types of microorganisms to cause diseases and mortality. Due to the known distinctive structure of their cell wall, mycobacteria are resistant to majority of antibiotics and common chemical disinfectants, including quaternized low molecular weight and polymer biocides. In this work, nonquaternary protonated polydiallylamines (PDAAs) based on protonated monomers of the diallylamine (DAA) series have been synthesized, secondary s-PDAA and tertiary t-Me-PDAA and t-Et-PDAA (with Me and Et N-substituents). The antimicrobial actions of PDAAs on M. tuberculosis and Mycobacterium smegmatis have been studied, namely, dependences of the activity on the amine structure, length of alkyl N-substituents, Mwof polymers, treatment time, and cell concentration. All PDAAs examined at different conditions have been found to exhibit strong bactericidal effect on M. smegmatis and M. tuberculosis, including “nonculturable” dormant M. tuberculosis cells. The quaternary counterpart poly(diallyldimethylammonium chloride) (PDADMAC) and current antibiotics rifampicin and ciprofloxacin have been also tested and shown to be significantly less efficient or inactive at all (at the maximum tested concentration of 500 μg mL⁻¹). s-PDAA appeared to be the most effective or exhibited similar activity to t-Me-PDAA, while t-Et-PDAA appeared to be less active, especially against M. tuberculosis. The results obtained indicate a key role of the nonquaternary ammonium groups in the mycobactericidal action of PDAAs. Examination under an optical microscope in the epifluorescence mode has evidenced damage of the inner membrane permeability of M. smegmatis cells under the impact of PDAAs after 20 min. Studies on electrophoretic mobility (zeta-potential) of M. smegmatis cells and some model liposomes in the presence of PDAAs have revealed a small negative charge of mycobacteria outer surface and recharge in the presence of PDAAs. A conclusion was made that bactericidal activity of PDAAs is related to the disturbance of the integrity of the mycobacterial cell wall followed by damage of the inner membrane permeability. |
doi_str_mv | 10.1007/s00253-014-6331-1 |
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Due to the known distinctive structure of their cell wall, mycobacteria are resistant to majority of antibiotics and common chemical disinfectants, including quaternized low molecular weight and polymer biocides. In this work, nonquaternary protonated polydiallylamines (PDAAs) based on protonated monomers of the diallylamine (DAA) series have been synthesized, secondary s-PDAA and tertiary t-Me-PDAA and t-Et-PDAA (with Me and Et N-substituents). The antimicrobial actions of PDAAs on M. tuberculosis and Mycobacterium smegmatis have been studied, namely, dependences of the activity on the amine structure, length of alkyl N-substituents, Mwof polymers, treatment time, and cell concentration. All PDAAs examined at different conditions have been found to exhibit strong bactericidal effect on M. smegmatis and M. tuberculosis, including “nonculturable” dormant M. tuberculosis cells. The quaternary counterpart poly(diallyldimethylammonium chloride) (PDADMAC) and current antibiotics rifampicin and ciprofloxacin have been also tested and shown to be significantly less efficient or inactive at all (at the maximum tested concentration of 500 μg mL⁻¹). s-PDAA appeared to be the most effective or exhibited similar activity to t-Me-PDAA, while t-Et-PDAA appeared to be less active, especially against M. tuberculosis. The results obtained indicate a key role of the nonquaternary ammonium groups in the mycobactericidal action of PDAAs. Examination under an optical microscope in the epifluorescence mode has evidenced damage of the inner membrane permeability of M. smegmatis cells under the impact of PDAAs after 20 min. Studies on electrophoretic mobility (zeta-potential) of M. smegmatis cells and some model liposomes in the presence of PDAAs have revealed a small negative charge of mycobacteria outer surface and recharge in the presence of PDAAs. A conclusion was made that bactericidal activity of PDAAs is related to the disturbance of the integrity of the mycobacterial cell wall followed by damage of the inner membrane permeability.</description><identifier>ISSN: 0175-7598</identifier><identifier>EISSN: 1432-0614</identifier><identifier>DOI: 10.1007/s00253-014-6331-1</identifier><identifier>PMID: 25557627</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>Acids ; Allyl Compounds - chemical synthesis ; Allyl Compounds - pharmacology ; Amines ; Ammonium ; Anti-Bacterial Agents - pharmacology ; antibacterial properties ; Antibiotics ; Antimicrobial agents ; Bacteria ; Biocides ; Biomedical and Life Sciences ; Biotechnological Products and Process Engineering ; Biotechnology ; Cell Wall ; cell walls ; ciprofloxacin ; Damage ; Disinfectants ; Disinfectants - chemistry ; Drug resistance ; Drug therapy ; electrophoresis ; Infections ; Life Sciences ; Lipids ; Magnetic Resonance Spectroscopy ; membrane permeability ; Membranes ; Microbial Genetics and Genomics ; Microbial Viability - drug effects ; Microbiology ; Microorganisms ; Molecular weight ; Mortality ; Mycobacterium smegmatis ; Mycobacterium smegmatis - drug effects ; Mycobacterium smegmatis - growth & development ; Mycobacterium tuberculosis ; Mycobacterium tuberculosis - drug effects ; Mycobacterium tuberculosis - growth & development ; Pathogenesis ; Permeability ; Polyamines ; Polyethylenes - chemical synthesis ; Polyethylenes - pharmacology ; Polymers ; Polymers - chemistry ; Quaternary Ammonium Compounds - chemical synthesis ; Quaternary Ammonium Compounds - pharmacology ; rifampicin ; Rifampin - pharmacology ; Studies ; Tuberculosis ; Zeta potential</subject><ispartof>Applied microbiology and biotechnology, 2015-03, Vol.99 (6), p.2557-2571</ispartof><rights>Springer-Verlag Berlin Heidelberg 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c569t-869b2c2761fb551a20c1f35e92bff5668dd8ff202ed8eae02f86678fc4ab82b43</citedby><cites>FETCH-LOGICAL-c569t-869b2c2761fb551a20c1f35e92bff5668dd8ff202ed8eae02f86678fc4ab82b43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1658840750/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1658840750?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,780,784,11688,27924,27925,36060,36061,44363,74895</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25557627$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Timofeeva, Larisa M</creatorcontrib><creatorcontrib>Kleshcheva, Natalia A</creatorcontrib><creatorcontrib>Shleeva, Margarita O</creatorcontrib><creatorcontrib>Filatova, Marina P</creatorcontrib><creatorcontrib>Simonova, Yulia A</creatorcontrib><creatorcontrib>Ermakov, Yury A</creatorcontrib><creatorcontrib>Kaprelyants, Arseny S</creatorcontrib><title>Nonquaternary poly(diallylammonium) polymers with different amine structure and their biocidal effect on Mycobacterium tuberculosis and Mycobacterium smegmatis</title><title>Applied microbiology and biotechnology</title><addtitle>Appl Microbiol Biotechnol</addtitle><addtitle>Appl Microbiol Biotechnol</addtitle><description>Mycobacteria, especially Mycobacterium tuberculosis, are one of the most dangerous types of microorganisms to cause diseases and mortality. Due to the known distinctive structure of their cell wall, mycobacteria are resistant to majority of antibiotics and common chemical disinfectants, including quaternized low molecular weight and polymer biocides. In this work, nonquaternary protonated polydiallylamines (PDAAs) based on protonated monomers of the diallylamine (DAA) series have been synthesized, secondary s-PDAA and tertiary t-Me-PDAA and t-Et-PDAA (with Me and Et N-substituents). The antimicrobial actions of PDAAs on M. tuberculosis and Mycobacterium smegmatis have been studied, namely, dependences of the activity on the amine structure, length of alkyl N-substituents, Mwof polymers, treatment time, and cell concentration. All PDAAs examined at different conditions have been found to exhibit strong bactericidal effect on M. smegmatis and M. tuberculosis, including “nonculturable” dormant M. tuberculosis cells. The quaternary counterpart poly(diallyldimethylammonium chloride) (PDADMAC) and current antibiotics rifampicin and ciprofloxacin have been also tested and shown to be significantly less efficient or inactive at all (at the maximum tested concentration of 500 μg mL⁻¹). s-PDAA appeared to be the most effective or exhibited similar activity to t-Me-PDAA, while t-Et-PDAA appeared to be less active, especially against M. tuberculosis. The results obtained indicate a key role of the nonquaternary ammonium groups in the mycobactericidal action of PDAAs. Examination under an optical microscope in the epifluorescence mode has evidenced damage of the inner membrane permeability of M. smegmatis cells under the impact of PDAAs after 20 min. Studies on electrophoretic mobility (zeta-potential) of M. smegmatis cells and some model liposomes in the presence of PDAAs have revealed a small negative charge of mycobacteria outer surface and recharge in the presence of PDAAs. A conclusion was made that bactericidal activity of PDAAs is related to the disturbance of the integrity of the mycobacterial cell wall followed by damage of the inner membrane permeability.</description><subject>Acids</subject><subject>Allyl Compounds - chemical synthesis</subject><subject>Allyl Compounds - pharmacology</subject><subject>Amines</subject><subject>Ammonium</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>antibacterial properties</subject><subject>Antibiotics</subject><subject>Antimicrobial agents</subject><subject>Bacteria</subject><subject>Biocides</subject><subject>Biomedical and Life Sciences</subject><subject>Biotechnological Products and Process Engineering</subject><subject>Biotechnology</subject><subject>Cell Wall</subject><subject>cell walls</subject><subject>ciprofloxacin</subject><subject>Damage</subject><subject>Disinfectants</subject><subject>Disinfectants - chemistry</subject><subject>Drug resistance</subject><subject>Drug therapy</subject><subject>electrophoresis</subject><subject>Infections</subject><subject>Life Sciences</subject><subject>Lipids</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>membrane permeability</subject><subject>Membranes</subject><subject>Microbial Genetics and Genomics</subject><subject>Microbial Viability - drug effects</subject><subject>Microbiology</subject><subject>Microorganisms</subject><subject>Molecular weight</subject><subject>Mortality</subject><subject>Mycobacterium smegmatis</subject><subject>Mycobacterium smegmatis - drug effects</subject><subject>Mycobacterium smegmatis - growth & development</subject><subject>Mycobacterium tuberculosis</subject><subject>Mycobacterium tuberculosis - drug effects</subject><subject>Mycobacterium tuberculosis - growth & development</subject><subject>Pathogenesis</subject><subject>Permeability</subject><subject>Polyamines</subject><subject>Polyethylenes - chemical synthesis</subject><subject>Polyethylenes - pharmacology</subject><subject>Polymers</subject><subject>Polymers - chemistry</subject><subject>Quaternary Ammonium Compounds - chemical synthesis</subject><subject>Quaternary Ammonium Compounds - pharmacology</subject><subject>rifampicin</subject><subject>Rifampin - pharmacology</subject><subject>Studies</subject><subject>Tuberculosis</subject><subject>Zeta potential</subject><issn>0175-7598</issn><issn>1432-0614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>M0C</sourceid><recordid>eNqNks1u1TAQhSMEopfCA7ABS2zKImA78U-WqCo_UoEFdG05zvjWlR3f2o7QfRpetb5NQcACdWXJ850zo5nTNM8JfkMwFm8zxpR1LSZ9y7uOtORBsyF9R1vMSf-w2WAiWCvYII-aJzlfYUyo5Pxxc0QZY4JTsWl-fonz9aILpFmnPdpFvz-ZnPZ-73UIcXZLeH37GyBl9MOVSzQ5ayHBXJAObgaUS1pMWRIgPU-oXIJLaHTRuEl7BJU1BcUZfd6bOGpTO1VPVJYRkll8zC7f6v4u5wDboIvLT5tHVvsMz-7e4-bi_dn304_t-dcPn07fnbeG8aG0kg8jNVRwYkfGiKbYENsxGOhoLeNcTpO0lmIKkwQNmNq6CCGt6fUo6dh3x83J6rtL8XqBXFRw2YD3eoa4ZEW4EENfdynugXJJ-4GI7j5oPeHA5WGAV_-gV3GpR_EHiknZY8FwpchKmRRzTmDVLrlQL6cIVodMqDUTqmZCHTKhSNW8uHNexgDTb8WvEFSArkCupXkL6Y_W_3F9uYqsjkpvk8vq4hvFhNWU9UySobsBv6TOOQ</recordid><startdate>20150301</startdate><enddate>20150301</enddate><creator>Timofeeva, Larisa M</creator><creator>Kleshcheva, Natalia A</creator><creator>Shleeva, Margarita O</creator><creator>Filatova, Marina P</creator><creator>Simonova, Yulia A</creator><creator>Ermakov, Yury A</creator><creator>Kaprelyants, Arseny S</creator><general>Springer-Verlag</general><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7QL</scope><scope>7T7</scope><scope>7WY</scope><scope>7WZ</scope><scope>7X7</scope><scope>7XB</scope><scope>87Z</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8FL</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BEZIV</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FRNLG</scope><scope>FYUFA</scope><scope>F~G</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K60</scope><scope>K6~</scope><scope>K9.</scope><scope>L.-</scope><scope>LK8</scope><scope>M0C</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PQBIZ</scope><scope>PQBZA</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope><scope>7QO</scope><scope>7SR</scope><scope>7U5</scope><scope>F28</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150301</creationdate><title>Nonquaternary poly(diallylammonium) polymers with different amine structure and their biocidal effect on Mycobacterium tuberculosis and Mycobacterium smegmatis</title><author>Timofeeva, Larisa M ; Kleshcheva, Natalia A ; Shleeva, Margarita O ; Filatova, Marina P ; Simonova, Yulia A ; Ermakov, Yury A ; Kaprelyants, Arseny S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c569t-869b2c2761fb551a20c1f35e92bff5668dd8ff202ed8eae02f86678fc4ab82b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acids</topic><topic>Allyl Compounds - chemical synthesis</topic><topic>Allyl Compounds - pharmacology</topic><topic>Amines</topic><topic>Ammonium</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>antibacterial properties</topic><topic>Antibiotics</topic><topic>Antimicrobial agents</topic><topic>Bacteria</topic><topic>Biocides</topic><topic>Biomedical and Life Sciences</topic><topic>Biotechnological Products and Process Engineering</topic><topic>Biotechnology</topic><topic>Cell Wall</topic><topic>cell walls</topic><topic>ciprofloxacin</topic><topic>Damage</topic><topic>Disinfectants</topic><topic>Disinfectants - chemistry</topic><topic>Drug resistance</topic><topic>Drug therapy</topic><topic>electrophoresis</topic><topic>Infections</topic><topic>Life Sciences</topic><topic>Lipids</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>membrane permeability</topic><topic>Membranes</topic><topic>Microbial Genetics and Genomics</topic><topic>Microbial Viability - drug effects</topic><topic>Microbiology</topic><topic>Microorganisms</topic><topic>Molecular weight</topic><topic>Mortality</topic><topic>Mycobacterium smegmatis</topic><topic>Mycobacterium smegmatis - 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Due to the known distinctive structure of their cell wall, mycobacteria are resistant to majority of antibiotics and common chemical disinfectants, including quaternized low molecular weight and polymer biocides. In this work, nonquaternary protonated polydiallylamines (PDAAs) based on protonated monomers of the diallylamine (DAA) series have been synthesized, secondary s-PDAA and tertiary t-Me-PDAA and t-Et-PDAA (with Me and Et N-substituents). The antimicrobial actions of PDAAs on M. tuberculosis and Mycobacterium smegmatis have been studied, namely, dependences of the activity on the amine structure, length of alkyl N-substituents, Mwof polymers, treatment time, and cell concentration. All PDAAs examined at different conditions have been found to exhibit strong bactericidal effect on M. smegmatis and M. tuberculosis, including “nonculturable” dormant M. tuberculosis cells. The quaternary counterpart poly(diallyldimethylammonium chloride) (PDADMAC) and current antibiotics rifampicin and ciprofloxacin have been also tested and shown to be significantly less efficient or inactive at all (at the maximum tested concentration of 500 μg mL⁻¹). s-PDAA appeared to be the most effective or exhibited similar activity to t-Me-PDAA, while t-Et-PDAA appeared to be less active, especially against M. tuberculosis. The results obtained indicate a key role of the nonquaternary ammonium groups in the mycobactericidal action of PDAAs. Examination under an optical microscope in the epifluorescence mode has evidenced damage of the inner membrane permeability of M. smegmatis cells under the impact of PDAAs after 20 min. Studies on electrophoretic mobility (zeta-potential) of M. smegmatis cells and some model liposomes in the presence of PDAAs have revealed a small negative charge of mycobacteria outer surface and recharge in the presence of PDAAs. A conclusion was made that bactericidal activity of PDAAs is related to the disturbance of the integrity of the mycobacterial cell wall followed by damage of the inner membrane permeability.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><pmid>25557627</pmid><doi>10.1007/s00253-014-6331-1</doi><tpages>15</tpages></addata></record> |
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recordid | cdi_proquest_miscellaneous_1677947597 |
source | ABI/INFORM Global; Springer Link |
subjects | Acids Allyl Compounds - chemical synthesis Allyl Compounds - pharmacology Amines Ammonium Anti-Bacterial Agents - pharmacology antibacterial properties Antibiotics Antimicrobial agents Bacteria Biocides Biomedical and Life Sciences Biotechnological Products and Process Engineering Biotechnology Cell Wall cell walls ciprofloxacin Damage Disinfectants Disinfectants - chemistry Drug resistance Drug therapy electrophoresis Infections Life Sciences Lipids Magnetic Resonance Spectroscopy membrane permeability Membranes Microbial Genetics and Genomics Microbial Viability - drug effects Microbiology Microorganisms Molecular weight Mortality Mycobacterium smegmatis Mycobacterium smegmatis - drug effects Mycobacterium smegmatis - growth & development Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects Mycobacterium tuberculosis - growth & development Pathogenesis Permeability Polyamines Polyethylenes - chemical synthesis Polyethylenes - pharmacology Polymers Polymers - chemistry Quaternary Ammonium Compounds - chemical synthesis Quaternary Ammonium Compounds - pharmacology rifampicin Rifampin - pharmacology Studies Tuberculosis Zeta potential |
title | Nonquaternary poly(diallylammonium) polymers with different amine structure and their biocidal effect on Mycobacterium tuberculosis and Mycobacterium smegmatis |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T09%3A51%3A09IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Nonquaternary%20poly(diallylammonium)%20polymers%20with%20different%20amine%20structure%20and%20their%20biocidal%20effect%20on%20Mycobacterium%20tuberculosis%20and%20Mycobacterium%20smegmatis&rft.jtitle=Applied%20microbiology%20and%20biotechnology&rft.au=Timofeeva,%20Larisa%20M&rft.date=2015-03-01&rft.volume=99&rft.issue=6&rft.spage=2557&rft.epage=2571&rft.pages=2557-2571&rft.issn=0175-7598&rft.eissn=1432-0614&rft_id=info:doi/10.1007/s00253-014-6331-1&rft_dat=%3Cproquest_cross%3E1660029684%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c569t-869b2c2761fb551a20c1f35e92bff5668dd8ff202ed8eae02f86678fc4ab82b43%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1658840750&rft_id=info:pmid/25557627&rfr_iscdi=true |