{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T18:16:42Z","timestamp":1760897802588,"version":"3.37.3"},"reference-count":22,"publisher":"Wiley","license":[{"start":{"date-parts":[[2008,9,30]],"date-time":"2008-09-30T00:00:00Z","timestamp":1222732800000},"content-version":"unspecified","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Metal-Based Drugs"],"published-print":{"date-parts":[[2008,9,30]]},"abstract":"<jats:p>The porphyrazines (pzs), a class of porphyrin analogues, are being investigated for their potential use as tumor imaging\/therapeutic agents. We here examine six peripherally-functionalized M[pz(<mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\" id=\"E1\"><mml:msub><mml:mtext>A<\/mml:mtext><mml:mi>n<\/mml:mi><\/mml:msub><mml:msub><mml:mtext>B<\/mml:mtext><mml:mrow><mml:mn>4<\/mml:mn><mml:mtext>-<\/mml:mtext><mml:mi>n<\/mml:mi><\/mml:mrow><\/mml:msub><\/mml:math>)] pzs with <mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\" id=\"E2\"><mml:mrow><mml:mi>n<\/mml:mi><mml:mo>=<\/mml:mo><mml:mn>4<\/mml:mn><\/mml:mrow><\/mml:math>, 3, or 2 (in a <jats:italic>trans<\/jats:italic> conformation) and M = <mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\" id=\"E3\"><mml:msub><mml:mtext>H<\/mml:mtext><mml:mn>2<\/mml:mn><\/mml:msub><\/mml:math> or Zn, where A is an <mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\" id=\"E4\"><mml:msub><mml:mrow><mml:mo>[<\/mml:mo><mml:mrow><mml:mtext>S<\/mml:mtext><mml:msub><mml:mrow><mml:mrow><mml:mo>(<\/mml:mo><mml:mrow><mml:msub><mml:mrow><mml:mrow><mml:mo>(<\/mml:mo><mml:mrow><mml:msub><mml:mrow><mml:mtext>CH<\/mml:mtext><\/mml:mrow><mml:mn>2<\/mml:mn><\/mml:msub><\/mml:mrow><mml:mo>)<\/mml:mo><\/mml:mrow><\/mml:mrow><mml:mn>2<\/mml:mn><\/mml:msub><mml:mtext>O<\/mml:mtext><\/mml:mrow><mml:mo>)<\/mml:mo><\/mml:mrow><\/mml:mrow><mml:mn>4<\/mml:mn><\/mml:msub><mml:mtext>Me<\/mml:mtext><\/mml:mrow><mml:mo>]<\/mml:mo><\/mml:mrow><mml:mn>2<\/mml:mn><\/mml:msub><\/mml:math> unit and B is a fused <mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\" id=\"E5\"><mml:mi>\u03b2<\/mml:mi><mml:mo>,<\/mml:mo><mml:mi>\u03b2<\/mml:mi><mml:mo>\u2032<\/mml:mo><\/mml:math>-diisopropyloxybenzo group. Cell viability\/proliferation assays and fluorescence microscopy were carried out in both tumor and normal cells. Dark toxicity studies disclosed that four of the compounds exhibited toxicity in both normal and tumor cells; one was nontoxic in both normal and tumor cells, and one was selectively toxic to normal cells. Additionally, three of the pzs showed enhanced photo-induced toxicity with these effects in some cases being observed at treatment concentrations of up to ten-fold lower than that needed for a response in Photofrin. All six compounds were preferentially absorbed by tumor cells, suggesting that they have potential as \nin vitro diagnostic agents and as aids in the isolation and purification of aberrant cells from pathological specimens. In particular, two promising diagnostic candidates have been identified as part of this work.<\/jats:p>","DOI":"10.1155\/2008\/391418","type":"journal-article","created":{"date-parts":[[2007,10,4]],"date-time":"2007-10-04T14:56:33Z","timestamp":1191509793000},"page":"1-13","source":"Crossref","is-referenced-by-count":10,"title":["Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies"],"prefix":"10.1155","volume":"2008","author":[{"given":"Sangwan","family":"Lee","sequence":"first","affiliation":[{"name":"Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Benjamin J.","family":"Vesper","sequence":"additional","affiliation":[{"name":"Center for Molecular Biology of Oral Diseases, College of Dentistry, University of Illinois at Chicago, 801 S. Paulina Street, Chicago, IL 60612, USA"},{"name":"Jesse Brown VAMC, 820 South Damen Avenue, Chicago, IL 60612, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hong","family":"Zong","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Neal D.","family":"Hammer","sequence":"additional","affiliation":[{"name":"Center for Molecular Biology of Oral Diseases, College of Dentistry, University of Illinois at Chicago, 801 S. Paulina Street, Chicago, IL 60612, USA"},{"name":"Jesse Brown VAMC, 820 South Damen Avenue, Chicago, IL 60612, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kim M.","family":"Elseth","sequence":"additional","affiliation":[{"name":"Center for Molecular Biology of Oral Diseases, College of Dentistry, University of Illinois at Chicago, 801 S. Paulina Street, Chicago, IL 60612, USA"},{"name":"Jesse Brown VAMC, 820 South Damen Avenue, Chicago, IL 60612, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anthony G. M.","family":"Barrett","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Natural Sciences, Imperial College London, Faculty Building, South Kensington Campus, London SW7 2AZ, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brian M.","family":"Hoffman","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4633-480X","authenticated-orcid":true,"given":"James A.","family":"Radosevich","sequence":"additional","affiliation":[{"name":"Center for Molecular Biology of Oral Diseases, College of Dentistry, University of Illinois at Chicago, 801 S. Paulina Street, Chicago, IL 60612, USA"},{"name":"Jesse Brown VAMC, 820 South Damen Avenue, Chicago, IL 60612, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","reference":[{"volume":"6","volume-title":"Porphyrins as photosensitizers in photodynamic therapy","year":"2000","key":"1"},{"issue":"5","key":"2","doi-asserted-by":"crossref","first-page":"807","DOI":"10.1007\/BF02498146","volume":"47","year":"1998","journal-title":"Russian Chemical Bulletin"},{"key":"3","doi-asserted-by":"publisher","DOI":"10.1016\/S1040-8428(84)80016-5"},{"key":"4","doi-asserted-by":"publisher","DOI":"10.1007\/BF00178119"},{"volume-title":"Synthetic strategies in designing porphyrin-based photosensitizers for photodynamic therapy","year":"2004","key":"5"},{"key":"6","doi-asserted-by":"publisher","DOI":"10.1002\/jpp.324"},{"issue":"1","key":"7","first-page":"13","volume":"6","year":"2003","journal-title":"Journal of Pharmacy and Pharmaceutical Sciences"},{"key":"8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200200561"},{"issue":"1","key":"9","first-page":"19","volume":"10","year":"1999","journal-title":"Reviews in Contemporary Pharmacotherapy"},{"key":"10","doi-asserted-by":"publisher","DOI":"10.1002\/0471227110.ch8"},{"key":"11","doi-asserted-by":"publisher","DOI":"10.1021\/jo001220y"},{"key":"12","doi-asserted-by":"publisher","DOI":"10.1562\/0031-8655(2003)077<0018:TTSOQY>2.0.CO;2"},{"key":"13","doi-asserted-by":"publisher","DOI":"10.1021\/ic0111583"},{"key":"14","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.09.060"},{"key":"15","doi-asserted-by":"publisher","DOI":"10.1021\/jm050466y"},{"key":"16","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotobiol.2005.11.006"},{"key":"17","doi-asserted-by":"publisher","DOI":"10.1002\/9780470132418.ch3"},{"key":"18","doi-asserted-by":"publisher","DOI":"10.1039\/jr9520004839"},{"key":"19","doi-asserted-by":"publisher","DOI":"10.1021\/jo971683c"},{"issue":"19","key":"20","doi-asserted-by":"crossref","first-page":"7416","DOI":"10.1021\/ja00045a013","volume":"114","year":"1992","journal-title":"Journal of the American Chemical Society"},{"key":"21","doi-asserted-by":"publisher","DOI":"10.1083\/jcb.109.4.1653"},{"issue":"7","key":"22","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1177\/002215540104900717","volume":"49","year":"2001","journal-title":"Journal of Histochemistry and Cytochemistry"}],"container-title":["Metal-Based Drugs"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/downloads.hindawi.com\/archive\/2008\/391418.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/downloads.hindawi.com\/archive\/2008\/391418.xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/downloads.hindawi.com\/archive\/2008\/391418.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2020,12,8]],"date-time":"2020-12-08T20:13:31Z","timestamp":1607458411000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.hindawi.com\/journals\/mbd\/2008\/391418\/"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,9,30]]},"references-count":22,"alternative-id":["391418","391418"],"URL":"https:\/\/doi.org\/10.1155\/2008\/391418","relation":{},"ISSN":["0793-0291","1687-5486"],"issn-type":[{"type":"print","value":"0793-0291"},{"type":"electronic","value":"1687-5486"}],"subject":[],"published":{"date-parts":[[2008,9,30]]}}}