Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies
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(AnB4-n)] pzs with n=4, 3, or 2 (in a trans conformation) and M = H2 or Zn, where A is an [S((CH2)2O)4Me]2...
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Hindawi Publishing Corporation
2008
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| Online Access: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2225588/ |
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pubmed-22255882008-02-14 Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies Lee, Sangwan Vesper, Benjamin J. Zong, Hong Hammer, Neal D. Elseth, Kim M. Barrett, Anthony G. M. Hoffman, Brian M. Radosevich, James A. Research Article 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(AnB4-n)] pzs with n=4, 3, or 2 (in a trans conformation) and M = H2 or Zn, where A is an [S((CH2)2O)4Me]2 unit and B is a fused β,β′-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 in 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. Hindawi Publishing Corporation 2008 2007-10-01 /pmc/articles/PMC2225588/ /pubmed/18274661 http://dx.doi.org/10.1155/2008/391418 Text en Copyright © 2008 Sangwan Lee et al. https://creativecommons.org/licenses/by/3.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
| repository_type |
Open Access Journal |
| institution_category |
Foreign Institution |
| institution |
US National Center for Biotechnology Information |
| building |
NCBI PubMed |
| collection |
Online Access |
| language |
English |
| format |
Online |
| author |
Lee, Sangwan Vesper, Benjamin J. Zong, Hong Hammer, Neal D. Elseth, Kim M. Barrett, Anthony G. M. Hoffman, Brian M. Radosevich, James A. |
| spellingShingle |
Lee, Sangwan Vesper, Benjamin J. Zong, Hong Hammer, Neal D. Elseth, Kim M. Barrett, Anthony G. M. Hoffman, Brian M. Radosevich, James A. Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies |
| author_facet |
Lee, Sangwan Vesper, Benjamin J. Zong, Hong Hammer, Neal D. Elseth, Kim M. Barrett, Anthony G. M. Hoffman, Brian M. Radosevich, James A. |
| author_sort |
Lee, Sangwan |
| title |
Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies |
| title_short |
Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies |
| title_full |
Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies |
| title_fullStr |
Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies |
| title_full_unstemmed |
Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies |
| title_sort |
synthesis and biological analysis of thiotetra(ethylene glycol) monomethyl ether-functionalized porphyrazines: cellular uptake and toxicity studies |
| description |
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(AnB4-n)] pzs with n=4, 3, or 2 (in a trans conformation) and M = H2 or Zn, where A is an [S((CH2)2O)4Me]2 unit and B is a fused β,β′-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
in 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. |
| publisher |
Hindawi Publishing Corporation |
| publishDate |
2008 |
| url |
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2225588/ |
| _version_ |
1611436690833932288 |