{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T21:58:57Z","timestamp":1790805537354,"version":"4.1.0"},"reference-count":90,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2019,12,6]],"date-time":"2019-12-06T00:00:00Z","timestamp":1575590400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001823","name":"The Ministry of Education, Youth and Sports","doi-asserted-by":"publisher","award":["LO1220, LO1601, LM2015063"],"award-info":[{"award-number":["LO1220, LO1601, LM2015063"]}],"id":[{"id":"10.13039\/501100001823","id-type":"DOI","asserted-by":"publisher"}]},{"name":"CZ.02.1.01\/0.0\/0.0\/16_013\/0001799","award":["CZ.02.1.01\/0.0\/0.0\/16_013\/0001799"],"award-info":[{"award-number":["CZ.02.1.01\/0.0\/0.0\/16_013\/0001799"]}]},{"name":"OP VVV [2.16\/3.1.00\/24503]","award":["OP VVV [2.16\/3.1.00\/24503]"],"award-info":[{"award-number":["OP VVV [2.16\/3.1.00\/24503]"]}]},{"name":"Specific university research MSMT","award":["No 21-SVV\/2019"],"award-info":[{"award-number":["No 21-SVV\/2019"]}]},{"DOI":"10.13039\/501100015267","name":"Martina Roeselov\u00e1 foundation","doi-asserted-by":"publisher","award":["Martina Roeselov\u00e1 foundation"],"award-info":[{"award-number":["Martina Roeselov\u00e1 foundation"]}],"id":[{"id":"10.13039\/501100015267","id-type":"DOI","asserted-by":"publisher"}]},{"name":"L'Or\u00e9al -UNESCO for Women in Science 2019","award":["L'Or\u00e9al -UNESCO for Women in Science 2019"],"award-info":[{"award-number":["L'Or\u00e9al -UNESCO for Women in Science 2019"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Purpurin 18 derivatives with a polyethylene glycol (PEG) linker were synthesized as novel photosensitizers (PSs) with the goal of using them in photodynamic therapy (PDT) for cancer. These compounds, derived from a second-generation PS, exhibit absorption at long wavelengths; considerable singlet oxygen generation and, in contrast to purpurin 18, have higher hydrophilicity due to decreased logP. Together, these properties make them potentially ideal PSs. To verify this, we screened the developed compounds for cell uptake, intracellular localization, antitumor activity and induced cell death type. All of the tested compounds were taken up into cancer cells of various origin and localized in organelles known to be important PDT targets, specifically, mitochondria and the endoplasmic reticulum. The incorporation of a zinc ion and PEGylation significantly enhanced the photosensitizing efficacy, decreasing IC50 (half maximal inhibitory compound concentration) in HeLa cells by up to 170 times compared with the parental purpurin 18. At effective PDT concentrations, the predominant type of induced cell death was apoptosis. Overall, our results show that the PEGylated derivatives presented have significant potential as novel PSs with substantially augmented phototoxicity for application in the PDT of cervical, prostate, pancreatic and breast cancer.<\/jats:p>","DOI":"10.3390\/molecules24244477","type":"journal-article","created":{"date-parts":[[2019,12,6]],"date-time":"2019-12-06T10:41:44Z","timestamp":1575628904000},"page":"4477","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1055-4026","authenticated-orcid":false,"given":"Vladim\u00edra","family":"Pavl\u00ed\u010dkov\u00e1","sequence":"first","affiliation":[{"name":"Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technick\u00e1 3, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3008-1396","authenticated-orcid":false,"given":"Silvie","family":"Rimpelov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technick\u00e1 3, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5069-9716","authenticated-orcid":false,"given":"Michal","family":"Jur\u00e1\u0161ek","sequence":"additional","affiliation":[{"name":"Department of Chemistry of Natural Compounds, University of Chemistry and Technology in Prague, Technick\u00e1 5, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3988-2261","authenticated-orcid":false,"given":"Kamil","family":"Z\u00e1ruba","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, University of Chemistry and Technology in Prague, Technick\u00e1 5, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jan","family":"F\u00e4hnrich","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, University of Chemistry and Technology in Prague, Technick\u00e1 5, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0497-4924","authenticated-orcid":false,"given":"Ivana","family":"K\u0159\u00ed\u017eov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, University of Chemistry and Technology in Prague, Technick\u00e1 5, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji\u0159\u00ed","family":"Bej\u010dek","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technick\u00e1 3, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zde\u0148ka","family":"Rottnerov\u00e1","sequence":"additional","affiliation":[{"name":"Central laboratories, University of Chemistry and Technology in Prague, Technick\u00e1 5, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8108-2033","authenticated-orcid":false,"given":"Vojt\u011bch","family":"Spiwok","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technick\u00e1 3, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0093-7007","authenticated-orcid":false,"given":"Pavel","family":"Dra\u0161ar","sequence":"additional","affiliation":[{"name":"Department of Chemistry of Natural Compounds, University of Chemistry and Technology in Prague, Technick\u00e1 5, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5698-4366","authenticated-orcid":false,"given":"Tom\u00e1\u0161","family":"Ruml","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technick\u00e1 3, 166 28 Prague 6, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,12,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3164","DOI":"10.1021\/mp500351s","article-title":"Photodynamic characterization of amino acid conjugated 15(1)-hydroxypurpurin-7-lactone for cancer treatment","volume":"11","author":"Lim","year":"2014","journal-title":"Mol. 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