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Compared to purpurinimides, the pyropheophorbide containing an iodobenzyl group showed enhanced PDT efficacy and tumor imaging (124I-PET) ability.

Abstract
Two positional isomers of purpurinimide, 3-[1'-(3-iodobenzyloxyethyl)] purpurin-18-N-hexylimide methyl ester 4, in which the iodobenzyl group is present at the top half of the molecule (position-3), and a 3-(1'-hexyloxyethy)purpurin-18-N-(3-iodo-benzylimide)] methyl ester 5, where the iodobenzyl group is introduced at the bottom half (N-substitued cyclicimide) of the molecule, were derived from chlorophyll-a. The tumor uptake and phototherapeutic abilities of these isomers were compared with the pyropheophorbide analogue 1 (lead compound). These compounds were then converted into the corresponding 124I-labeled PET imaging agents with specific activity >1 Ci/micromol. Among the positional isomers 4 and 5, purpurinimide 5 showed enhanced imaging and therapeutic potential. However, the lead compound 1 derived from pyropheophorbide-a exhibited the best PET imaging and PDT efficacy. For investigating the overall lipophilicity of the molecule, the 3-O-hexyl ether group present at position-3 of purpurinimide 5 was replaced with a methyl ether substituent, and the resulting product 10 showed improved tumor uptake, but due to its significantly higher uptake in the liver, spleen, and other organs, a poor tumor contrast in whole-body tumor imaging was observed.
AuthorsSuresh K Pandey, Munawwar Sajjad, Yihui Chen, Anupam Pandey, Joseph R Missert, Carrie Batt, Rutao Yao, Hani A Nabi, Allan R Oseroff, Ravindra K Pandey
JournalBioconjugate chemistry (Bioconjug Chem) Vol. 20 Issue 2 Pg. 274-82 (Feb 2009) ISSN: 1520-4812 [Electronic] United States
PMID19191565 (Publication Type: Comparative Study, Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)
Chemical References
  • Anthraquinones
  • Iodine Radioisotopes
  • Iodobenzenes
  • Photosensitizing Agents
  • Chlorophyll
  • iodobenzene
  • purpurin
  • Chlorophyll A
Topics
  • Animals
  • Anthraquinones (chemistry, pharmacokinetics, therapeutic use)
  • Chlorophyll (chemistry, pharmacokinetics, therapeutic use)
  • Chlorophyll A
  • Iodine Radioisotopes (chemistry)
  • Iodobenzenes (chemistry)
  • Isomerism
  • Mice
  • Neoplasms (diagnostic imaging, drug therapy, metabolism)
  • Photochemotherapy
  • Photosensitizing Agents (chemistry, pharmacokinetics, therapeutic use)
  • Positron-Emission Tomography
  • Tissue Distribution

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