Charge dependence of cellular uptake and selective antitumor activity of porphyrazines

Neal D. Hammer, Sangwan Lee, Benjamin J. Vesper, Kim M. Elseth, Brian M. Hoffman, Anthony G.M. Barrett, James A. Radosevich*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Scopus citations


Porphyrazines (pzs), or tetraazaporphyrins, can be viewed as porphyrinic macrocycles in which the porphyrin meso (CH) groups are replaced by nitrogen atoms; as such, it can be anticipated that pzs would show similar biocompatibility and biodistribution to those of porphyrins. However, distinctive chemical and physical features of the pzs differentiate them from either the porphyrins or phthalocyanines, in particular making them excellent candidates as optical imaging/therapeutic agents. The novelty of the pzs requires that we first determine how specific structures selectively alter biological function, leading to the development of "rules" that will be used to predict future biologically functional pzs. In the first of these studies, we present here a correlation of pz charge with biocompatibility for a suite of three pzs-neutral, negative, and positive. Confocal fluorescence microscopy and proliferation/viability measurements disclose that the three pzs differ in their toxicity, uptake, and localization in A549 human lung adenocarcinoma cells and WI-38 VA13 normal cells. Interestingly, the negatively charged pz exhibits selective dark toxicity in pulmonary adenocarcinoma cells.

Original languageEnglish (US)
Pages (from-to)8125-8133
Number of pages9
JournalJournal of Medicinal Chemistry
Issue number26
StatePublished - Dec 29 2005

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


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