Amphiphilic cationic Zn-porphyrins with high photodynamic antimicrobial activity
Photodynamic inactivation of microbes can efficiently eradicate antibiotic-resistant strains. Systematic structural modification was used to investigate how porphyrin-based photosensitizers (PSs) could be designed for improved antibacterial activity. Zinc(II)5,10,15,20-tetrakis( -alkylpyridinium-2(3...
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| Veröffentlicht in: | Future microbiology 2015-05, Vol.10 (5), p.709-724 |
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| container_title | Future microbiology |
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| creator | Thomas, Milini Craik, James D Tovmasyan, Artak Batinic-Haberle, Ines Benov, Ludmil T |
| description | Photodynamic inactivation of microbes can efficiently eradicate antibiotic-resistant strains. Systematic structural modification was used to investigate how porphyrin-based photosensitizers (PSs) could be designed for improved antibacterial activity.
Zinc(II)5,10,15,20-tetrakis(
-alkylpyridinium-2(3,4)-yl)porphyrins presenting systematic modifications at the periphery of the porphyrin ring were evaluated for toxicity and antimicrobial photodynamic activity by measuring metabolic activity, cell membrane integrity and viability using antibiotic-sensitive and resistant
strains as model Gram-negative targets.
Maximal sensitizer uptake, and, upon illumination, decrease of viable bacteria by >6 log
were achieved by positively charged amphiphilic PSs with longer (six to eight carbon) alkyl substituents.
Antibacterial photoefficiency (throughout the text photoefficiency has been used as equivalent of photocytotoxic efficacy) can be increased by orders of magnitude by increasing the lipophilicity of cationic alkylmetalloporphyrin PSs. |
| doi_str_mv | 10.2217/fmb.14.148 |
| format | Article |
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Zinc(II)5,10,15,20-tetrakis(
-alkylpyridinium-2(3,4)-yl)porphyrins presenting systematic modifications at the periphery of the porphyrin ring were evaluated for toxicity and antimicrobial photodynamic activity by measuring metabolic activity, cell membrane integrity and viability using antibiotic-sensitive and resistant
strains as model Gram-negative targets.
Maximal sensitizer uptake, and, upon illumination, decrease of viable bacteria by >6 log
were achieved by positively charged amphiphilic PSs with longer (six to eight carbon) alkyl substituents.
Antibacterial photoefficiency (throughout the text photoefficiency has been used as equivalent of photocytotoxic efficacy) can be increased by orders of magnitude by increasing the lipophilicity of cationic alkylmetalloporphyrin PSs.</description><identifier>ISSN: 1746-0913</identifier><identifier>EISSN: 1746-0921</identifier><identifier>DOI: 10.2217/fmb.14.148</identifier><identifier>PMID: 26000647</identifier><language>eng</language><publisher>England: Future Medicine Ltd</publisher><subject>Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibiotics ; Antimicrobial agents ; antimicrobial photodynamic therapy ; Cations - chemistry ; Cations - pharmacology ; Cell Membrane - drug effects ; Cell Membrane - physiology ; E coli ; Escherichia coli - cytology ; Escherichia coli - drug effects ; Escherichia coli - metabolism ; Escherichia coli - physiology ; Flow cytometry ; Health aspects ; Metabolism ; Methods ; Microbial Viability - drug effects ; Molecular Structure ; Photochemotherapy ; photosensitizer ; Photosensitizing Agents - chemistry ; Photosensitizing Agents - pharmacology ; porphyrin ; Porphyrins ; Porphyrins - chemistry ; Porphyrins - pharmacology ; reactive oxygen species ; singlet oxygen ; Structure-Activity Relationship ; Zinc (Nutrient) ; Zinc Compounds - chemistry ; Zinc Compounds - pharmacology</subject><ispartof>Future microbiology, 2015-05, Vol.10 (5), p.709-724</ispartof><rights>Future Medicine Ltd</rights><rights>COPYRIGHT 2015 Future Medicine Ltd.</rights><rights>2015 Future Medicine Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-593b521f90a30a821d5170a97ff099649aa060d90bd4ff82f84e4e42b87696323</citedby><cites>FETCH-LOGICAL-c429t-593b521f90a30a821d5170a97ff099649aa060d90bd4ff82f84e4e42b87696323</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26000647$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Thomas, Milini</creatorcontrib><creatorcontrib>Craik, James D</creatorcontrib><creatorcontrib>Tovmasyan, Artak</creatorcontrib><creatorcontrib>Batinic-Haberle, Ines</creatorcontrib><creatorcontrib>Benov, Ludmil T</creatorcontrib><title>Amphiphilic cationic Zn-porphyrins with high photodynamic antimicrobial activity</title><title>Future microbiology</title><addtitle>Future Microbiol</addtitle><description>Photodynamic inactivation of microbes can efficiently eradicate antibiotic-resistant strains. Systematic structural modification was used to investigate how porphyrin-based photosensitizers (PSs) could be designed for improved antibacterial activity.
Zinc(II)5,10,15,20-tetrakis(
-alkylpyridinium-2(3,4)-yl)porphyrins presenting systematic modifications at the periphery of the porphyrin ring were evaluated for toxicity and antimicrobial photodynamic activity by measuring metabolic activity, cell membrane integrity and viability using antibiotic-sensitive and resistant
strains as model Gram-negative targets.
Maximal sensitizer uptake, and, upon illumination, decrease of viable bacteria by >6 log
were achieved by positively charged amphiphilic PSs with longer (six to eight carbon) alkyl substituents.
Antibacterial photoefficiency (throughout the text photoefficiency has been used as equivalent of photocytotoxic efficacy) can be increased by orders of magnitude by increasing the lipophilicity of cationic alkylmetalloporphyrin PSs.</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibiotics</subject><subject>Antimicrobial agents</subject><subject>antimicrobial photodynamic therapy</subject><subject>Cations - chemistry</subject><subject>Cations - pharmacology</subject><subject>Cell Membrane - drug effects</subject><subject>Cell Membrane - physiology</subject><subject>E coli</subject><subject>Escherichia coli - cytology</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - metabolism</subject><subject>Escherichia coli - physiology</subject><subject>Flow cytometry</subject><subject>Health aspects</subject><subject>Metabolism</subject><subject>Methods</subject><subject>Microbial Viability - drug effects</subject><subject>Molecular Structure</subject><subject>Photochemotherapy</subject><subject>photosensitizer</subject><subject>Photosensitizing Agents - chemistry</subject><subject>Photosensitizing Agents - pharmacology</subject><subject>porphyrin</subject><subject>Porphyrins</subject><subject>Porphyrins - chemistry</subject><subject>Porphyrins - pharmacology</subject><subject>reactive oxygen species</subject><subject>singlet oxygen</subject><subject>Structure-Activity Relationship</subject><subject>Zinc (Nutrient)</subject><subject>Zinc Compounds - chemistry</subject><subject>Zinc Compounds - pharmacology</subject><issn>1746-0913</issn><issn>1746-0921</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNptkV2L1TAQhoMo7rp64w-Qgjci9JhJ07S5PCx-wYJe6I03IU2TbZY2qUm6cv69czjrirLMCzMJzzsMM4S8BLpjDLp3bhl2wFH9I3IOHRc1lQwe39fQnJFnOd9Q2vYg4Sk5Y4JSKnh3Tr7ul3XyqNmbyujiY8DiR6jXmNbpkHzI1S9fpmry11O1TrHE8RD0gpAOxWNOcfB6rrQp_taXw3PyxOk52xd3-YJ8__D-2-Wn-urLx8-X-6vacCZL3cpmaBk4SXVDdc9gbKGjWnbOUSkFl1pTQUdJh5E71zPXc4vBhr4TUjSsuSBvTn3XFH9uNhe1-GzsPOtg45YViL6hnRCtQPT1f-hN3FLA6Y4UE00nKfylrvVslQ8ulqTNsanac-CtBKAcqd0DFMZocRcxWOfx_x_D25MBF5Vzsk6tyS86HRRQdTyfwvMp4Kge4Vd3k27DYsd79M-9EBAnwG1lSzYbb4Ox6vRChzc-2Ic6_wbJoKX6</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Thomas, Milini</creator><creator>Craik, James D</creator><creator>Tovmasyan, Artak</creator><creator>Batinic-Haberle, Ines</creator><creator>Benov, Ludmil T</creator><general>Future Medicine Ltd</general><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>7RV</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>EHMNL</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB0</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>NAPCQ</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>7X8</scope></search><sort><creationdate>20150501</creationdate><title>Amphiphilic cationic Zn-porphyrins with high photodynamic antimicrobial activity</title><author>Thomas, Milini ; Craik, James D ; Tovmasyan, Artak ; Batinic-Haberle, Ines ; Benov, Ludmil T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-593b521f90a30a821d5170a97ff099649aa060d90bd4ff82f84e4e42b87696323</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibiotics</topic><topic>Antimicrobial agents</topic><topic>antimicrobial photodynamic therapy</topic><topic>Cations - chemistry</topic><topic>Cations - pharmacology</topic><topic>Cell Membrane - drug effects</topic><topic>Cell Membrane - physiology</topic><topic>E coli</topic><topic>Escherichia coli - cytology</topic><topic>Escherichia coli - drug effects</topic><topic>Escherichia coli - metabolism</topic><topic>Escherichia coli - physiology</topic><topic>Flow cytometry</topic><topic>Health aspects</topic><topic>Metabolism</topic><topic>Methods</topic><topic>Microbial Viability - drug effects</topic><topic>Molecular Structure</topic><topic>Photochemotherapy</topic><topic>photosensitizer</topic><topic>Photosensitizing Agents - chemistry</topic><topic>Photosensitizing Agents - pharmacology</topic><topic>porphyrin</topic><topic>Porphyrins</topic><topic>Porphyrins - chemistry</topic><topic>Porphyrins - pharmacology</topic><topic>reactive oxygen species</topic><topic>singlet oxygen</topic><topic>Structure-Activity Relationship</topic><topic>Zinc (Nutrient)</topic><topic>Zinc Compounds - chemistry</topic><topic>Zinc Compounds - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thomas, Milini</creatorcontrib><creatorcontrib>Craik, James D</creatorcontrib><creatorcontrib>Tovmasyan, Artak</creatorcontrib><creatorcontrib>Batinic-Haberle, Ines</creatorcontrib><creatorcontrib>Benov, Ludmil T</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Proquest Nursing & Allied Health Source</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>UK & Ireland Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Biological Science Database</collection><collection>Nursing & Allied Health Premium</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>MEDLINE - Academic</collection><jtitle>Future microbiology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thomas, Milini</au><au>Craik, James D</au><au>Tovmasyan, Artak</au><au>Batinic-Haberle, Ines</au><au>Benov, Ludmil T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Amphiphilic cationic Zn-porphyrins with high photodynamic antimicrobial activity</atitle><jtitle>Future microbiology</jtitle><addtitle>Future Microbiol</addtitle><date>2015-05-01</date><risdate>2015</risdate><volume>10</volume><issue>5</issue><spage>709</spage><epage>724</epage><pages>709-724</pages><issn>1746-0913</issn><eissn>1746-0921</eissn><abstract>Photodynamic inactivation of microbes can efficiently eradicate antibiotic-resistant strains. Systematic structural modification was used to investigate how porphyrin-based photosensitizers (PSs) could be designed for improved antibacterial activity.
Zinc(II)5,10,15,20-tetrakis(
-alkylpyridinium-2(3,4)-yl)porphyrins presenting systematic modifications at the periphery of the porphyrin ring were evaluated for toxicity and antimicrobial photodynamic activity by measuring metabolic activity, cell membrane integrity and viability using antibiotic-sensitive and resistant
strains as model Gram-negative targets.
Maximal sensitizer uptake, and, upon illumination, decrease of viable bacteria by >6 log
were achieved by positively charged amphiphilic PSs with longer (six to eight carbon) alkyl substituents.
Antibacterial photoefficiency (throughout the text photoefficiency has been used as equivalent of photocytotoxic efficacy) can be increased by orders of magnitude by increasing the lipophilicity of cationic alkylmetalloporphyrin PSs.</abstract><cop>England</cop><pub>Future Medicine Ltd</pub><pmid>26000647</pmid><doi>10.2217/fmb.14.148</doi><tpages>16</tpages></addata></record> |
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| subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibiotics Antimicrobial agents antimicrobial photodynamic therapy Cations - chemistry Cations - pharmacology Cell Membrane - drug effects Cell Membrane - physiology E coli Escherichia coli - cytology Escherichia coli - drug effects Escherichia coli - metabolism Escherichia coli - physiology Flow cytometry Health aspects Metabolism Methods Microbial Viability - drug effects Molecular Structure Photochemotherapy photosensitizer Photosensitizing Agents - chemistry Photosensitizing Agents - pharmacology porphyrin Porphyrins Porphyrins - chemistry Porphyrins - pharmacology reactive oxygen species singlet oxygen Structure-Activity Relationship Zinc (Nutrient) Zinc Compounds - chemistry Zinc Compounds - pharmacology |
| title | Amphiphilic cationic Zn-porphyrins with high photodynamic antimicrobial activity |
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