{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,26]],"date-time":"2026-04-26T06:03:34Z","timestamp":1777183414493,"version":"3.51.4"},"reference-count":57,"publisher":"Public Library of Science (PLoS)","issue":"10","license":[{"start":{"date-parts":[[2017,10,10]],"date-time":"2017-10-10T00:00:00Z","timestamp":1507593600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","award":["UMO-2016\/22\/E\/NZ7\/00420"],"award-info":[{"award-number":["UMO-2016\/22\/E\/NZ7\/00420"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["www.plosone.org"],"crossmark-restriction":false},"short-container-title":["PLoS ONE"],"DOI":"10.1371\/journal.pone.0185984","type":"journal-article","created":{"date-parts":[[2017,10,10]],"date-time":"2017-10-10T13:33:14Z","timestamp":1507642394000},"page":"e0185984","update-policy":"https:\/\/doi.org\/10.1371\/journal.pone.corrections_policy","source":"Crossref","is-referenced-by-count":72,"title":["Properties of halogenated and sulfonated porphyrins relevant for the selection of photosensitizers in anticancer and antimicrobial therapies"],"prefix":"10.1371","volume":"12","author":[{"given":"Barbara","family":"Pucelik","sequence":"first","affiliation":[]},{"given":"Robert","family":"Paczy\u0144ski","sequence":"additional","affiliation":[]},{"given":"Grzegorz","family":"Dubin","sequence":"additional","affiliation":[]},{"given":"Mariette M.","family":"Pereira","sequence":"additional","affiliation":[]},{"given":"Luis G.","family":"Arnaut","sequence":"additional","affiliation":[]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8791-7035","authenticated-orcid":true,"given":"Janusz M.","family":"D\u0105browski","sequence":"additional","affiliation":[]}],"member":"340","published-online":{"date-parts":[[2017,10,10]]},"reference":[{"issue":"10","key":"ref1","doi-asserted-by":"crossref","first-page":"1765","DOI":"10.1039\/C5PP00132C","article-title":"Photodynamic therapy (PDT) of cancer: from local to systemic treatment","volume":"14","author":"JM D\u0105browski","year":"2015","journal-title":"Photochemical & Photobiological Sciences"},{"issue":"3","key":"ref2","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1177\/039463200401700304","article-title":"Photodynamic therapy targeted to pathogens","volume":"17","author":"T Demidova","year":"2004","journal-title":"International journal of immunopathology and pharmacology"},{"issue":"5","key":"ref3","doi-asserted-by":"crossref","first-page":"436","DOI":"10.1039\/b311900a","article-title":"Photodynamic therapy: a new antimicrobial approach to infectious disease?","volume":"3","author":"MR Hamblin","year":"2004","journal-title":"Photochemical & Photobiological Sciences"},{"key":"ref4","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.ccr.2016.06.007","article-title":"Engineering of relevant photodynamic processes through structural modifications of metallotetrapyrrolic photosensitizers","volume":"325","author":"JM D\u0105browski","year":"2016","journal-title":"Coordination Chemistry Reviews"},{"key":"ref5","article-title":"Bioinorganic antimicrobial strategies in the resistance era","author":"A Regiel-Futyra","year":"2017","journal-title":"Coordination Chemistry Reviews"},{"key":"ref6","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1016\/j.jphotobiol.2015.05.010","article-title":"Strategies to optimize photosensitizers for photodynamic inactivation of bacteria","volume":"150","author":"T Maisch","year":"2015","journal-title":"Journal of Photochemistry and Photobiology B: Biology"},{"issue":"3","key":"ref7","doi-asserted-by":"crossref","first-page":"e0174627","DOI":"10.1371\/journal.pone.0174627","article-title":"5-aminolevulinic acid-mediated photodynamic therapy and its strain-dependent combined effect with antibiotics on Staphylococcus aureus biofilm","volume":"12","author":"Q-Z Zhang","year":"2017","journal-title":"PloS one"},{"issue":"6","key":"ref8","doi-asserted-by":"crossref","first-page":"941","DOI":"10.1093\/jac\/dkf053","article-title":"Polycationic photosensitizer conjugates: effects of chain length and Gram classification on the photodynamic inactivation of bacteria","volume":"49","author":"MR Hamblin","year":"2002","journal-title":"Journal of Antimicrobial Chemotherapy"},{"issue":"7","key":"ref9","doi-asserted-by":"crossref","first-page":"e11674","DOI":"10.1371\/journal.pone.0011674","article-title":"Efficient photodynamic therapy against gram-positive and gram-negative bacteria using THPTS, a cationic photosensitizer excited by infrared wavelength","volume":"5","author":"S Schastak","year":"2010","journal-title":"PloS one"},{"issue":"4","key":"ref10","doi-asserted-by":"crossref","first-page":"1402","DOI":"10.1128\/AAC.50.4.1402-1410.2006","article-title":"Protease-stable polycationic photosensitizer conjugates between polyethyleneimine and chlorin (e6) for broad-spectrum antimicrobial photoinactivation","volume":"50","author":"GP Tegos","year":"2006","journal-title":"Antimicrobial agents and chemotherapy"},{"issue":"9","key":"ref11","doi-asserted-by":"crossref","first-page":"3834","DOI":"10.1128\/AAC.00125-10","article-title":"Stable synthetic cationic bacteriochlorins as selective antimicrobial photosensitizers","volume":"54","author":"L Huang","year":"2010","journal-title":"Antimicrobial agents and chemotherapy"},{"key":"ref12","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.jphotobiol.2014.09.016","article-title":"Stable synthetic mono-substituted cationic bacteriochlorins mediate selective broad-spectrum photoinactivation of drug-resistant pathogens at nanomolar concentrations","volume":"141","author":"L Huang","year":"2014","journal-title":"Journal of Photochemistry and Photobiology B: Biology"},{"issue":"5","key":"ref13","doi-asserted-by":"crossref","first-page":"e0176529","DOI":"10.1371\/journal.pone.0176529","article-title":"Photodynamic antimicrobial chemotherapy with the novel amino acid-porphyrin conjugate 4I: In vitro and in vivo studies","volume":"12","author":"Y Yuan","year":"2017","journal-title":"PloS one"},{"issue":"9","key":"ref14","doi-asserted-by":"crossref","first-page":"4031","DOI":"10.1007\/s00253-015-6539-8","article-title":"Antimicrobial photodynamic therapy with fulleropyrrolidine: photoinactivation mechanism of Staphylococcus aureus, in vitro and in vivo studies","volume":"99","author":"M Grinholc","year":"2015","journal-title":"Applied microbiology and biotechnology"},{"issue":"6","key":"ref15","doi-asserted-by":"crossref","first-page":"e0129301","DOI":"10.1371\/journal.pone.0129301","article-title":"Photodynamic inactivation of candida albicans with imidazoacridinones: influence of irradiance, photosensitizer uptake and reactive oxygen species generation","volume":"10","author":"A Taraszkiewicz","year":"2015","journal-title":"PloS one"},{"issue":"17","key":"ref16","doi-asserted-by":"crossref","first-page":"5291","DOI":"10.1021\/jm060153i","article-title":"Synthesis and properties of benzo [a] phenoxazinium chalcogen analogues as novel broad-spectrum antimicrobial photosensitizers","volume":"49","author":"JW Foley","year":"2006","journal-title":"Journal of medicinal chemistry"},{"issue":"1","key":"ref17","doi-asserted-by":"crossref","first-page":"e54387","DOI":"10.1371\/journal.pone.0054387","article-title":"Effect of virulence factors on the photodynamic inactivation of Cryptococcus neoformans","volume":"8","author":"RA Prates","year":"2013","journal-title":"PloS one"},{"issue":"12","key":"ref18","doi-asserted-by":"crossref","first-page":"e111792","DOI":"10.1371\/journal.pone.0111792","article-title":"Fast and effective photodynamic inactivation of multiresistant bacteria by cationic riboflavin derivatives","volume":"9","author":"T Maisch","year":"2014","journal-title":"PloS one"},{"issue":"30","key":"ref19","doi-asserted-by":"crossref","first-page":"9273","DOI":"10.1002\/chem.201000111","article-title":"Mechanisms of Singlet\u2010Oxygen and Superoxide\u2010Ion Generation by Porphyrins and Bacteriochlorins and their Implications","volume":"16","author":"EF Silva","year":"2010","journal-title":"Photodynamic Therapy. Chemistry-A European Journal"},{"key":"ref20","doi-asserted-by":"crossref","DOI":"10.1016\/bs.adioch.2017.03.002","article-title":"Reactive Oxygen Species in Photodynamic Therapy: Mechanisms of Their Generation and Potentiation","author":"JM D\u0105browski","year":"2017","journal-title":"Advances in Inorganic Chemistry"},{"issue":"12","key":"ref21","doi-asserted-by":"crossref","first-page":"2155","DOI":"10.1002\/cmdc.201200351","article-title":"Stable synthetic bacteriochlorins for photodynamic therapy: role of dicyano peripheral groups, central metal substitution (2H, Zn, Pd), and Cremophor EL delivery","volume":"7","author":"YY Huang","year":"2012","journal-title":"ChemMedChem"},{"issue":"1","key":"ref22","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.canlet.2009.02.054","article-title":"Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: role of molecular charge, central metal and hydroxyl radical production","volume":"282","author":"P Mroz","year":"2009","journal-title":"Cancer letters"},{"issue":"1","key":"ref23","doi-asserted-by":"crossref","first-page":"236","DOI":"10.1016\/j.cplett.2005.03.100","article-title":"Effect of protonation on the photophysical properties of meso-tetra (sulfonatophenyl) porphyrin","volume":"407","author":"P Gon\u00e7alves","year":"2005","journal-title":"Chemical physics letters"},{"issue":"17\u201318","key":"ref24","doi-asserted-by":"crossref","first-page":"3116","DOI":"10.1080\/00958972.2015.1073723","article-title":"Towards tuning PDT relevant photosensitizer properties: comparative study for the free and Zn2+ coordinated meso-tetrakis [2, 6-difluoro-5-(N-methylsulfamylo) phenyl] porphyrin","volume":"68","author":"JM D\u0105browski","year":"2015","journal-title":"Journal of Coordination Chemistry"},{"key":"ref25","article-title":"Handbook of Photochemistry","author":"SL Murov","year":"1993"},{"issue":"25","key":"ref26","doi-asserted-by":"crossref","first-page":"12809","DOI":"10.1021\/jp061010a","article-title":"Intra-and intermolecular heavy-atom effects on the fluorescence properties of brominated C60 polyads","volume":"110","author":"M Rae","year":"2006","journal-title":"The Journal of Physical Chemistry B"},{"key":"ref27","first-page":"10","article-title":"Boron-Fluorine Photosensitizers for Photodynamic Therapy","volume":"2013","author":"L Yao","year":"2013","journal-title":"Journal of Chemistry"},{"key":"ref28","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1016\/j.cplett.2015.05.040","article-title":"Influence of halogen atoms and protonation on the photophysical properties of sulfonated porphyrins","volume":"633","author":"L De Boni","year":"2015","journal-title":"Chemical Physics Letters"},{"issue":"49","key":"ref29","doi-asserted-by":"crossref","first-page":"9545","DOI":"10.1016\/j.tet.2010.09.106","article-title":"Synthesis and photophysical characterization of a library of photostable halogenated bacteriochlorins: an access to near infrared chemistry","volume":"66","author":"MM Pereira","year":"2010","journal-title":"Tetrahedron"},{"issue":"15","key":"ref30","doi-asserted-by":"crossref","first-page":"5806","DOI":"10.1021\/jo800736c","article-title":"Tailoring a bacteriochlorin building block with cationic, amphipathic, or lipophilic substituents","volume":"73","author":"C Ruzi\u00e9","year":"2008","journal-title":"The Journal of organic chemistry"},{"issue":"18","key":"ref31","doi-asserted-by":"crossref","first-page":"6897","DOI":"10.1039\/c3dt53410c","article-title":"Modulation of the electronic and spectroscopic properties of Zn (II) phthalocyanines by their substitution pattern","volume":"43","author":"SZ Topal","year":"2014","journal-title":"Dalton Transactions"},{"issue":"5","key":"ref32","doi-asserted-by":"crossref","first-page":"e97894","DOI":"10.1371\/journal.pone.0097894","article-title":"Improved photodynamic efficacy of Zn (II) phthalocyanines via glycerol substitution","volume":"9","author":"Y Chin","year":"2014","journal-title":"PloS one"},{"issue":"9","key":"ref33","doi-asserted-by":"crossref","first-page":"e108500","DOI":"10.1371\/journal.pone.0108500","article-title":"Photodynamic antimicrobial polymers for infection control","volume":"9","author":"CP McCoy","year":"2014","journal-title":"PloS one"},{"issue":"34","key":"ref34","doi-asserted-by":"crossref","first-page":"22039","DOI":"10.1021\/acsami.6b07031","article-title":"Design of Pluronic-based formulation for enhanced redaporfin-photodynamic therapy against pigmented melanoma","volume":"8","author":"B Pucelik","year":"2016","journal-title":"ACS applied materials & interfaces"},{"issue":"2","key":"ref35","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.jphotobiol.2009.01.005","article-title":"Drug delivery strategies for photodynamic antimicrobial chemotherapy: from benchtop to clinical practice","volume":"95","author":"CM Cassidy","year":"2009","journal-title":"Journal of Photochemistry and Photobiology B: Biology"},{"issue":"3","key":"ref36","doi-asserted-by":"crossref","first-page":"e0150295","DOI":"10.1371\/journal.pone.0150295","article-title":"Photodynamic Effect of Ni Nanotubes on an HeLa Cell Line","volume":"11","author":"MH Aziz","year":"2016","journal-title":"PloS one"},{"issue":"19","key":"ref37","first-page":"7155","article-title":"Pegylation of a chlorine6 polymer conjugate increases tumor targeting of photosensitizer","volume":"61","author":"MR Hamblin","year":"2001","journal-title":"Cancer research"},{"issue":"2","key":"ref38","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1016\/j.jphotochem.2005.12.023","article-title":"Effects of interaction with CTAB micelles on photophysical characteristics of meso-tetrakis (sulfonatophenyl) porphyrin","volume":"181","author":"P Gon\u00e7alves","year":"2006","journal-title":"Journal of Photochemistry and Photobiology A: Chemistry"},{"key":"ref39","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1016\/j.jphotobiol.2016.05.026","article-title":"Photodynamic inactivation of planktonic and biofilm growing bacteria mediated by a meso-substituted porphyrin bearing four basic amino groups","volume":"161","author":"L Mamone","year":"2016","journal-title":"Journal of Photochemistry and Photobiology B: Biology"},{"key":"ref40","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1016\/j.ejmech.2016.08.035","article-title":"Fluorination of phthalocyanine substituents: Improved photoproperties and enhanced photodynamic efficacy after optimal micellar formulations","volume":"124","author":"B Pucelik","year":"2016","journal-title":"European Journal of Medicinal Chemistry"},{"issue":"18","key":"ref41","doi-asserted-by":"crossref","first-page":"5346","DOI":"10.1002\/chem.201304202","article-title":"Photodynamic therapy efficacy enhanced by dynamics: the role of charge transfer and photostability in the selection of photosensitizers","volume":"20","author":"LG Arnaut","year":"2014","journal-title":"Chemistry-A European Journal"},{"issue":"22","key":"ref42","doi-asserted-by":"crossref","first-page":"5132","DOI":"10.1016\/j.tet.2008.03.055","article-title":"Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol\/water partition coefficients","volume":"64","author":"CJ Monteiro","year":"2008","journal-title":"Tetrahedron"},{"issue":"3","key":"ref43","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1002\/jhet.5570280317","article-title":"Some new aspects related to the synthesis of meso\u2010substituted porphyrins","volume":"28","author":"A Gonsalves","year":"1991","journal-title":"Journal of heterocyclic chemistry"},{"issue":"43","key":"ref44","first-page":"1423","article-title":"Improved syntheses of 5, 10, 15, 20-tetrakisaryl-and tetrakisalkylporphyrins","volume":"7","author":"RA Johnstone","year":"1996","journal-title":"Heterocycles"},{"issue":"50","key":"ref45","doi-asserted-by":"crossref","first-page":"6571","DOI":"10.1039\/C4CC01100G","article-title":"Size and ability do matter! Influence of acidity and pore size on the synthesis of hindered halogenated meso-phenyl porphyrins catalysed by porous solid oxides","volume":"50","author":"M Silva","year":"2014","journal-title":"Chemical Communications"},{"issue":"1","key":"ref46","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/S0301-0104(02)00485-8","article-title":"Heavy-atom effects on metalloporphyrins and polyhalogenated porphyrins","volume":"280","author":"ElG Azenha","year":"2002","journal-title":"Chemical physics"},{"key":"ref47","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1016\/j.jphotobiol.2015.02.006","article-title":"Synthesis, spectroscopic, and in vitro investigations of 2, 6-diiodo-BODIPYs with PDT and bioimaging applications","volume":"145","author":"JH Gibbs","year":"2015","journal-title":"Journal of Photochemistry and Photobiology B: Biology"},{"issue":"5","key":"ref48","doi-asserted-by":"crossref","first-page":"1177","DOI":"10.1111\/j.1751-1097.2009.00555.x","article-title":"Monitoring singlet oxygen and hydroxyl radical formation with fluorescent probes during photodynamic therapy","volume":"85","author":"M Price","year":"2009","journal-title":"Photochemistry and photobiology"},{"issue":"11","key":"ref49","doi-asserted-by":"crossref","first-page":"1359","DOI":"10.1016\/S0891-5849(03)00142-4","article-title":"Superoxide reacts with hydroethidine but forms a fluorescent product that is distinctly different from ethidium: potential implications in intracellular fluorescence detection of superoxide","volume":"34","author":"H Zhao","year":"2003","journal-title":"Free Radical Biology and Medicine"},{"issue":"9","key":"ref50","doi-asserted-by":"crossref","first-page":"836","DOI":"10.1002\/cbic.201500573","article-title":"Pro\u2010oxidant and Antioxidant Effects in Photodynamic Therapy: Cells Recognise that Not All Exogenous ROS Are Alike","volume":"17","author":"HT Soares","year":"2016","journal-title":"ChemBioChem"},{"issue":"2","key":"ref51","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/j.jphotochem.2009.08.009","article-title":"The effect of porphyrin structure on binding to human serum albumin by fluorescence spectroscopy","volume":"208","author":"O Rinco","year":"2009","journal-title":"Journal of Photochemistry and Photobiology A: Chemistry"},{"issue":"S1","key":"ref52","doi-asserted-by":"crossref","first-page":"787","DOI":"10.1111\/j.1751-1097.1987.tb07883.x","article-title":"Tumor localization and photosensitization by sulfonated derivatives of tetraphenylporphine","volume":"45","author":"D Kessel","year":"1987","journal-title":"Photochemistry and photobiology"},{"issue":"2","key":"ref53","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1124\/jpet.102.043307","article-title":"Optimal structure requirements for pluronic block copolymers in modifying P-glycoprotein drug efflux transporter activity in bovine brain microvessel endothelial cells","volume":"304","author":"EV Batrakova","year":"2003","journal-title":"Journal of Pharmacology and Experimental Therapeutics"},{"issue":"35","key":"ref54","doi-asserted-by":"crossref","first-page":"4341","DOI":"10.1016\/j.vaccine.2015.04.051","article-title":"Dynamics of antigen delivery and the functional roles of L121-adjuvant","volume":"33","author":"S-S Shen","year":"2015","journal-title":"Vaccine"},{"issue":"10","key":"ref55","doi-asserted-by":"crossref","first-page":"3291","DOI":"10.1039\/C4PY00039K","article-title":"Pluronic\u00ae block-copolymers in medicine: from chemical and biological versatility to rationalisation and clinical advances","volume":"5","author":"A Pitto-Barry","year":"2014","journal-title":"Polymer Chemistry"},{"issue":"3","key":"ref56","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1016\/1011-1344(95)07147-4","article-title":"Meso-substituted cationic porphyrins as efficient photosensitizers of gram-positive and gram-negative bacteria","volume":"32","author":"M Merchat","year":"1996","journal-title":"Journal of Photochemistry and Photobiology B: Biology"},{"issue":"3","key":"ref57","doi-asserted-by":"crossref","first-page":"518","DOI":"10.1111\/php.12421","article-title":"Formulation of Aluminum Chloride Phthalocyanine in Pluronic\u2122 P\u2010123 and F\u2010127 Block Copolymer Micelles: Photophysical properties and Photodynamic Inactivation of Microorganisms","volume":"91","author":"BH Vilsinski","year":"2015","journal-title":"Photochemistry and photobiology"}],"updated-by":[{"DOI":"10.1371\/journal.pone.0191777","type":"correction","label":"Correction","source":"publisher","updated":{"date-parts":[[2018,1,19]],"date-time":"2018-01-19T00:00:00Z","timestamp":1516320000000}}],"container-title":["PLOS ONE"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/dx.plos.org\/10.1371\/journal.pone.0185984","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2018,10,23]],"date-time":"2018-10-23T02:51:51Z","timestamp":1540263111000},"score":1,"resource":{"primary":{"URL":"https:\/\/dx.plos.org\/10.1371\/journal.pone.0185984"}},"subtitle":[],"editor":[{"given":"Michael","family":"Hamblin","sequence":"first","affiliation":[]}],"short-title":[],"issued":{"date-parts":[[2017,10,10]]},"references-count":57,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2017,10,10]]}},"URL":"https:\/\/doi.org\/10.1371\/journal.pone.0185984","relation":{"correction":[{"id-type":"doi","id":"10.1371\/journal.pone.0191777","asserted-by":"object"}]},"ISSN":["1932-6203"],"issn-type":[{"value":"1932-6203","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,10,10]]}}}