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Sulfonamide Porphyrins as Potent Photosensitizers against Multidrug-Resistant Staphylococcus aureus (MRSA): The Role of Co-Adjuvants
Sulfonamides are a conventional class of antibiotics that are well-suited to combat infections. However, their overuse leads to antimicrobial resistance. Porphyrins and analogs have demonstrated excellent photosensitizing properties and have been used as antimicrobial agents to photoinactivate micro...
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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2023-02, Vol.28 (5), p.2067 |
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| creator | Sarabando, Sofia N Dias, Cristina J Vieira, Cátia Bartolomeu, Maria Neves, Maria G P M S Almeida, Adelaide Monteiro, Carlos J P Faustino, Maria Amparo F |
| description | Sulfonamides are a conventional class of antibiotics that are well-suited to combat infections. However, their overuse leads to antimicrobial resistance. Porphyrins and analogs have demonstrated excellent photosensitizing properties and have been used as antimicrobial agents to photoinactivate microorganisms, including multiresistant
(MRSA) strains. It is well recognized that the combination of different therapeutic agents might improve the biological outcome. In this present work, a novel
-arylporphyrin and its Zn(II) complex functionalized with sulfonamide groups were synthesized and characterized and the antibacterial activity towards MRSA with and without the presence of the adjuvant KI was evaluated. For comparison, the studies were also extended to the corresponding sulfonated porphyrin TPP(SO
H)
. Photodynamic studies revealed that all porphyrin derivatives were effective in photoinactivating MRSA (>99.9% of reduction) at a concentration of 5.0 μM upon white light radiation with an irradiance of 25 mW cm
and a total light dose of 15 J cm
. The combination of the porphyrin photosensitizers with the co-adjuvant KI during the photodynamic treatment proved to be very promising allowing a significant reduction in the treatment time and photosensitizer concentration by six times and at least five times, respectively. The combined effect observed for TPP(SO
NHEt)
and ZnTPP(SO
NHEt)
with KI seems to be due to the formation of reactive iodine radicals. In the photodynamic studies with TPP(SO
H)
plus KI, the cooperative action was mainly due to the formation of free iodine (I
). |
| doi_str_mv | 10.3390/molecules28052067 |
| format | article |
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(MRSA) strains. It is well recognized that the combination of different therapeutic agents might improve the biological outcome. In this present work, a novel
-arylporphyrin and its Zn(II) complex functionalized with sulfonamide groups were synthesized and characterized and the antibacterial activity towards MRSA with and without the presence of the adjuvant KI was evaluated. For comparison, the studies were also extended to the corresponding sulfonated porphyrin TPP(SO
H)
. Photodynamic studies revealed that all porphyrin derivatives were effective in photoinactivating MRSA (>99.9% of reduction) at a concentration of 5.0 μM upon white light radiation with an irradiance of 25 mW cm
and a total light dose of 15 J cm
. The combination of the porphyrin photosensitizers with the co-adjuvant KI during the photodynamic treatment proved to be very promising allowing a significant reduction in the treatment time and photosensitizer concentration by six times and at least five times, respectively. The combined effect observed for TPP(SO
NHEt)
and ZnTPP(SO
NHEt)
with KI seems to be due to the formation of reactive iodine radicals. In the photodynamic studies with TPP(SO
H)
plus KI, the cooperative action was mainly due to the formation of free iodine (I
).</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules28052067</identifier><identifier>PMID: 36903314</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acids ; Adjuvants ; Adjuvants, Immunologic - pharmacology ; Adjuvants, Pharmaceutic - pharmacology ; Anti-Bacterial Agents - pharmacology ; Antibacterial activity ; Antibiotics ; Antimicrobial agents ; Antimicrobial resistance ; Bacteria ; Chemical compounds ; Humans ; Iodine ; Iodine - pharmacology ; Irradiance ; Methicillin-Resistant Staphylococcus aureus ; Microorganisms ; MRSA ; Multidrug resistance ; Multidrug resistant organisms ; Pharmacology ; Photochemotherapy ; photodynamic therapy ; Photosensitization ; photosensitizer ; Photosensitizing Agents - pharmacology ; Porphyrins ; Porphyrins - pharmacology ; Radiation ; Staphylococcal Infections ; Staphylococcus aureus ; Staphylococcus infections ; Sulfanilamide - pharmacology ; Sulfonamides ; White light ; Zinc</subject><ispartof>Molecules (Basel, Switzerland), 2023-02, Vol.28 (5), p.2067</ispartof><rights>2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2023 by the authors. 2023</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c494t-bef92293fdf25a982990f007b750d3af787e00c959a6bda62b941f0fe544a57f3</citedby><cites>FETCH-LOGICAL-c494t-bef92293fdf25a982990f007b750d3af787e00c959a6bda62b941f0fe544a57f3</cites><orcidid>0000-0003-2986-2088 ; 0000-0002-8422-8664 ; 0000-0002-7773-3902 ; 0000-0003-4423-3802 ; 0000-0003-3421-0383 ; 0000-0002-7953-8166</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2785216563/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2785216563?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36903314$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sarabando, Sofia N</creatorcontrib><creatorcontrib>Dias, Cristina J</creatorcontrib><creatorcontrib>Vieira, Cátia</creatorcontrib><creatorcontrib>Bartolomeu, Maria</creatorcontrib><creatorcontrib>Neves, Maria G P M S</creatorcontrib><creatorcontrib>Almeida, Adelaide</creatorcontrib><creatorcontrib>Monteiro, Carlos J P</creatorcontrib><creatorcontrib>Faustino, Maria Amparo F</creatorcontrib><title>Sulfonamide Porphyrins as Potent Photosensitizers against Multidrug-Resistant Staphylococcus aureus (MRSA): The Role of Co-Adjuvants</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>Sulfonamides are a conventional class of antibiotics that are well-suited to combat infections. However, their overuse leads to antimicrobial resistance. Porphyrins and analogs have demonstrated excellent photosensitizing properties and have been used as antimicrobial agents to photoinactivate microorganisms, including multiresistant
(MRSA) strains. It is well recognized that the combination of different therapeutic agents might improve the biological outcome. In this present work, a novel
-arylporphyrin and its Zn(II) complex functionalized with sulfonamide groups were synthesized and characterized and the antibacterial activity towards MRSA with and without the presence of the adjuvant KI was evaluated. For comparison, the studies were also extended to the corresponding sulfonated porphyrin TPP(SO
H)
. Photodynamic studies revealed that all porphyrin derivatives were effective in photoinactivating MRSA (>99.9% of reduction) at a concentration of 5.0 μM upon white light radiation with an irradiance of 25 mW cm
and a total light dose of 15 J cm
. The combination of the porphyrin photosensitizers with the co-adjuvant KI during the photodynamic treatment proved to be very promising allowing a significant reduction in the treatment time and photosensitizer concentration by six times and at least five times, respectively. The combined effect observed for TPP(SO
NHEt)
and ZnTPP(SO
NHEt)
with KI seems to be due to the formation of reactive iodine radicals. In the photodynamic studies with TPP(SO
H)
plus KI, the cooperative action was mainly due to the formation of free iodine (I
).</description><subject>Acids</subject><subject>Adjuvants</subject><subject>Adjuvants, Immunologic - pharmacology</subject><subject>Adjuvants, Pharmaceutic - pharmacology</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial activity</subject><subject>Antibiotics</subject><subject>Antimicrobial agents</subject><subject>Antimicrobial resistance</subject><subject>Bacteria</subject><subject>Chemical compounds</subject><subject>Humans</subject><subject>Iodine</subject><subject>Iodine - pharmacology</subject><subject>Irradiance</subject><subject>Methicillin-Resistant Staphylococcus aureus</subject><subject>Microorganisms</subject><subject>MRSA</subject><subject>Multidrug resistance</subject><subject>Multidrug resistant organisms</subject><subject>Pharmacology</subject><subject>Photochemotherapy</subject><subject>photodynamic therapy</subject><subject>Photosensitization</subject><subject>photosensitizer</subject><subject>Photosensitizing Agents - pharmacology</subject><subject>Porphyrins</subject><subject>Porphyrins - pharmacology</subject><subject>Radiation</subject><subject>Staphylococcal Infections</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus infections</subject><subject>Sulfanilamide - pharmacology</subject><subject>Sulfonamides</subject><subject>White light</subject><subject>Zinc</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplkktv1DAQgCMEoqXwA7igSFzKITB-JTEXtFrxqNSKarecLccZ73qVjbe2U6mc-eF42VK1cBrb882n8WiK4jWB94xJ-LD1A5ppwEhbEBTq5klxTDiFigGXTx-cj4oXMW4AKOFEPC-OWC2BMcKPi1_LabB-1FvXY3npw259G9wYSx3zLeGYysu1Tz7iGF1yPzHk1EpnIpUX05BcH6ZVtcDoYtIZXiadDYM33pgpo1PAHE4vFsvZu4_l1RrLRe659Lac-2rWb6abXBVfFs-sHiK-uosnxY8vn6_m36rz71_P5rPzynDJU9WhlZRKZntLhZYtlRIsQNM1AnqmbdM2CGCkkLruel3TTnJiwaLgXIvGspPi7ODtvd6oXXBbHW6V1079efBhpXRIzgyoqMS2bltuZN3zhshWtsB6ixYJI9Sw7Pp0cO2mbou9yaMKengkfZwZ3Vqt_I0iAMCpgGw4vTMEfz1hTGrrosFh0CP6KSratDVIUQuR0bf_oBs_hTHPak8JSmpR71siB8oEH2NAe98NAbVfGPXfwuSaNw-_cV_xd0PYb39iwDM</recordid><startdate>20230222</startdate><enddate>20230222</enddate><creator>Sarabando, Sofia N</creator><creator>Dias, Cristina J</creator><creator>Vieira, Cátia</creator><creator>Bartolomeu, Maria</creator><creator>Neves, Maria G P M S</creator><creator>Almeida, Adelaide</creator><creator>Monteiro, Carlos J P</creator><creator>Faustino, Maria Amparo F</creator><general>MDPI AG</general><general>MDPI</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>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0003-2986-2088</orcidid><orcidid>https://orcid.org/0000-0002-8422-8664</orcidid><orcidid>https://orcid.org/0000-0002-7773-3902</orcidid><orcidid>https://orcid.org/0000-0003-4423-3802</orcidid><orcidid>https://orcid.org/0000-0003-3421-0383</orcidid><orcidid>https://orcid.org/0000-0002-7953-8166</orcidid></search><sort><creationdate>20230222</creationdate><title>Sulfonamide Porphyrins as Potent Photosensitizers against Multidrug-Resistant Staphylococcus aureus (MRSA): The Role of Co-Adjuvants</title><author>Sarabando, Sofia N ; Dias, Cristina J ; Vieira, Cátia ; Bartolomeu, Maria ; Neves, Maria G P M S ; Almeida, Adelaide ; Monteiro, Carlos J P ; Faustino, Maria Amparo F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c494t-bef92293fdf25a982990f007b750d3af787e00c959a6bda62b941f0fe544a57f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acids</topic><topic>Adjuvants</topic><topic>Adjuvants, Immunologic - pharmacology</topic><topic>Adjuvants, Pharmaceutic - pharmacology</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial activity</topic><topic>Antibiotics</topic><topic>Antimicrobial agents</topic><topic>Antimicrobial resistance</topic><topic>Bacteria</topic><topic>Chemical compounds</topic><topic>Humans</topic><topic>Iodine</topic><topic>Iodine - pharmacology</topic><topic>Irradiance</topic><topic>Methicillin-Resistant Staphylococcus aureus</topic><topic>Microorganisms</topic><topic>MRSA</topic><topic>Multidrug resistance</topic><topic>Multidrug resistant organisms</topic><topic>Pharmacology</topic><topic>Photochemotherapy</topic><topic>photodynamic therapy</topic><topic>Photosensitization</topic><topic>photosensitizer</topic><topic>Photosensitizing Agents - pharmacology</topic><topic>Porphyrins</topic><topic>Porphyrins - pharmacology</topic><topic>Radiation</topic><topic>Staphylococcal Infections</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus infections</topic><topic>Sulfanilamide - pharmacology</topic><topic>Sulfonamides</topic><topic>White light</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sarabando, Sofia N</creatorcontrib><creatorcontrib>Dias, Cristina J</creatorcontrib><creatorcontrib>Vieira, Cátia</creatorcontrib><creatorcontrib>Bartolomeu, Maria</creatorcontrib><creatorcontrib>Neves, Maria G P M S</creatorcontrib><creatorcontrib>Almeida, Adelaide</creatorcontrib><creatorcontrib>Monteiro, Carlos J P</creatorcontrib><creatorcontrib>Faustino, Maria Amparo F</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>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</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)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Publicly Available Content Database</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><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sarabando, Sofia N</au><au>Dias, Cristina J</au><au>Vieira, Cátia</au><au>Bartolomeu, Maria</au><au>Neves, Maria G P M S</au><au>Almeida, Adelaide</au><au>Monteiro, Carlos J P</au><au>Faustino, Maria Amparo F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sulfonamide Porphyrins as Potent Photosensitizers against Multidrug-Resistant Staphylococcus aureus (MRSA): The Role of Co-Adjuvants</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2023-02-22</date><risdate>2023</risdate><volume>28</volume><issue>5</issue><spage>2067</spage><pages>2067-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Sulfonamides are a conventional class of antibiotics that are well-suited to combat infections. However, their overuse leads to antimicrobial resistance. Porphyrins and analogs have demonstrated excellent photosensitizing properties and have been used as antimicrobial agents to photoinactivate microorganisms, including multiresistant
(MRSA) strains. It is well recognized that the combination of different therapeutic agents might improve the biological outcome. In this present work, a novel
-arylporphyrin and its Zn(II) complex functionalized with sulfonamide groups were synthesized and characterized and the antibacterial activity towards MRSA with and without the presence of the adjuvant KI was evaluated. For comparison, the studies were also extended to the corresponding sulfonated porphyrin TPP(SO
H)
. Photodynamic studies revealed that all porphyrin derivatives were effective in photoinactivating MRSA (>99.9% of reduction) at a concentration of 5.0 μM upon white light radiation with an irradiance of 25 mW cm
and a total light dose of 15 J cm
. The combination of the porphyrin photosensitizers with the co-adjuvant KI during the photodynamic treatment proved to be very promising allowing a significant reduction in the treatment time and photosensitizer concentration by six times and at least five times, respectively. The combined effect observed for TPP(SO
NHEt)
and ZnTPP(SO
NHEt)
with KI seems to be due to the formation of reactive iodine radicals. In the photodynamic studies with TPP(SO
H)
plus KI, the cooperative action was mainly due to the formation of free iodine (I
).</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>36903314</pmid><doi>10.3390/molecules28052067</doi><orcidid>https://orcid.org/0000-0003-2986-2088</orcidid><orcidid>https://orcid.org/0000-0002-8422-8664</orcidid><orcidid>https://orcid.org/0000-0002-7773-3902</orcidid><orcidid>https://orcid.org/0000-0003-4423-3802</orcidid><orcidid>https://orcid.org/0000-0003-3421-0383</orcidid><orcidid>https://orcid.org/0000-0002-7953-8166</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Molecules (Basel, Switzerland), 2023-02, Vol.28 (5), p.2067 |
| issn | 1420-3049 1420-3049 |
| language | eng |
| recordid | cdi_doaj_primary_oai_doaj_org_article_29e86884c96d471989803dfefe1312c3 |
| source | Publicly Available Content Database; PubMed Central |
| subjects | Acids Adjuvants Adjuvants, Immunologic - pharmacology Adjuvants, Pharmaceutic - pharmacology Anti-Bacterial Agents - pharmacology Antibacterial activity Antibiotics Antimicrobial agents Antimicrobial resistance Bacteria Chemical compounds Humans Iodine Iodine - pharmacology Irradiance Methicillin-Resistant Staphylococcus aureus Microorganisms MRSA Multidrug resistance Multidrug resistant organisms Pharmacology Photochemotherapy photodynamic therapy Photosensitization photosensitizer Photosensitizing Agents - pharmacology Porphyrins Porphyrins - pharmacology Radiation Staphylococcal Infections Staphylococcus aureus Staphylococcus infections Sulfanilamide - pharmacology Sulfonamides White light Zinc |
| title | Sulfonamide Porphyrins as Potent Photosensitizers against Multidrug-Resistant Staphylococcus aureus (MRSA): The Role of Co-Adjuvants |
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