{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,6]],"date-time":"2026-03-06T19:34:29Z","timestamp":1772825669301,"version":"3.50.1"},"reference-count":51,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2017,10,25]],"date-time":"2017-10-25T00:00:00Z","timestamp":1508889600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Abstract: We designed three unsymmetrical meso-tetrasubstituted phenyl porphyrins for further development as theranostic agents for cancer photodynamic therapy (PDT): 5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin (P2.2), Zn(II)-5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin (Zn(II)2.2) and Cu(II)-5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin (Cu(II)2.2). The porphyrinic compounds were synthesized and their structures were confirmed by elemental analysis, FT-IR, UV-Vis, EPR and NMR. The compounds had a good solubility in polar\/nonpolar media. P2.2 and, to a lesser extent, Zn(II)2.2 were fluorescent, albeit with low fluoresence quantum yields. P2.2 and Zn(II)2.2 exhibited PDT-acceptable values of singlet oxygen generation. A \u201cdark\u201d cytotoxicity study was performed using cells that are relevant for the tumor niche (HT-29 colon carcinoma cells and L929 fibroblasts) and for blood (peripheral mononuclear cells). Cellular uptake of fluorescent compounds, cell viability\/proliferation and death were evaluated. P2.2 was highlighted as a promising theranostic agent for PDT in solid tumors considering that P2.2 generated PDT-acceptable singlet oxygen yields, accumulated into tumor cells and less in blood cells, exhibited good fluorescence within cells for imagistic detection, and had no significant cytotoxicity in vitro against tumor and normal cells. Complexing of P2.2 with Zn(II) or Cu(II) altered several of its PDT-relevant properties. These are consistent arguments for further developing P2.2 in animal models of solid tumors for in vivo PDT.<\/jats:p>","DOI":"10.3390\/molecules22111815","type":"journal-article","created":{"date-parts":[[2017,10,25]],"date-time":"2017-10-25T11:13:27Z","timestamp":1508930007000},"page":"1815","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Studies on the Synthesis, Photophysical and Biological Evaluation of Some Unsymmetrical Meso-Tetrasubstituted Phenyl Porphyrins"],"prefix":"10.3390","volume":"22","author":[{"given":"Rica","family":"Boscencu","sequence":"first","affiliation":[{"name":"Faculty of Pharmacy, \u201cCarol Davila\u201d University of Medicine and Pharmacy, 6 Traian Vuia St., 020956 Bucharest, Romania"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9706-1883","authenticated-orcid":false,"given":"Gina","family":"Manda","sequence":"additional","affiliation":[{"name":"\u201cVictor Babe\u015f\u201d National Institute of Pathology, 99-101 Splaiul Independentei, 050096 Bucharest, Romania"}]},{"given":"Natalia","family":"Radulea","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, \u201cCarol Davila\u201d University of Medicine and Pharmacy, 6 Traian Vuia St., 020956 Bucharest, Romania"}]},{"given":"Radu","family":"Socoteanu","sequence":"additional","affiliation":[{"name":"\u201cIlie Murgulescu\u201d Institute of Physical Chemistry, Romanian Academy, 202 Splaiul Independentei, 060021 Bucharest, Romania"}]},{"given":"Laura","family":"Ceafalan","sequence":"additional","affiliation":[{"name":"\u201cVictor Babe\u015f\u201d National Institute of Pathology, 99-101 Splaiul Independentei, 050096 Bucharest, Romania"}]},{"given":"Ionela","family":"Neagoe","sequence":"additional","affiliation":[{"name":"\u201cVictor Babe\u015f\u201d National Institute of Pathology, 99-101 Splaiul Independentei, 050096 Bucharest, Romania"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7527-9489","authenticated-orcid":false,"given":"Isabel","family":"Ferreira Machado","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica-F\u00edsica Molecular, Institute of Nanosciences and Nanotechnology, Instituto Superior T\u00e9cnico Av. Rovisco Pais 1049-001, Lisboa, Portugal"},{"name":"Polytechnic Institute of Portalegre, P-7300-110 Portalegre, Portugal"}]},{"given":"Selma Huveyda","family":"Basaga","sequence":"additional","affiliation":[{"name":"Dokumar, Teknopark Blvd No 1 Pendik 34906, Istanbul, Turkey"},{"name":"Molecular Biology Genetics & Bioengineering Program, Faculty of Engineering & Natural Sciences, Sabanci University, Orhanli 34956 Tuzla, Istanbul, Turkey"}]},{"given":"Lu\u00eds","family":"Vieira Ferreira","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica-F\u00edsica Molecular, Institute of Nanosciences and Nanotechnology, Instituto Superior T\u00e9cnico Av. Rovisco Pais 1049-001, Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,10,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"916","DOI":"10.7150\/thno.4571","article-title":"Unique diagnostic and therapeutic roles of porphyrins and phthalocyanines in photodynamic therapy, imaging and theranostics","volume":"2","author":"Josefsen","year":"2012","journal-title":"Theranostics"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1039\/B915149B","article-title":"The role of porphyrin chemistry in tumor imaging and photodynamic therapy","volume":"40","author":"Ethirajan","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1094","DOI":"10.1016\/j.addr.2010.09.002","article-title":"Development and applications of photo-triggered theranostic agents","volume":"62","author":"Rai","year":"2010","journal-title":"Adv. Drug Deliv. 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