Ethylene glycol and amino acid derivatives of 5-aminolevulinic acid as new photosensitizing precursors of protoporphyrin IX in cells

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State: Public
Version: Final published version
License: All rights reserved
Serval ID
serval:BIB_0B2B04E9FA52
Type
Article: article from journal or magazin.
Collection
Publications
Institution
Title
Ethylene glycol and amino acid derivatives of 5-aminolevulinic acid as new photosensitizing precursors of protoporphyrin IX in cells
Journal
Journal of Medicinal Chemistry
Author(s)
Berger Y., Greppi A., Siri O., Neier R., Juillerat-Jeanneret L.
ISSN
0022-2623 (Print)
Publication state
Published
Issued date
2000
Volume
43
Number
25
Pages
4738-4746
Language
english
Notes
PT - Journal Article PT - Research Support, Non-U.S. Gov't
Abstract
Protoporphyrin IX (PpIX) is used as a photosensitizing agent in photodynamic detection and therapy (PDT) of cancer and is synthesized intracellularly from aminolevulinic acid (ALA) precursors. To evaluate means to specifically target ALA derivatives to defined cells, we have synthesized and characterized ethylene glycol esters and amino acid pseudodipeptide derivatives of ALA as potential specific substrates for cellular esterases and aminopeptidases, respectively. The PpIX formation induced by these products was investigated using cultures of human and rat cell lines of carcinoma and endothelial origins. The cytotoxicity of these compounds in the absence of light was also controlled. The results have shown that ethylenglycol esters can induce high levels of PpIX and are useful at concentrations below their cytotoxicity threshold. From the ALA-amino acid derivatives which were evaluated, the highest PpIX production was obtained using ALA derivatives of neutral amino acids, as compared to acidic or basic amino acids
Keywords
Amino Acids/chemistry/Aminolevulinic Acid/analogs & derivatives/chemical synthesis/metabolism/Aminopeptidases/Animals/Dipeptides/Ethylene Glycols/Fluorescence/Glutamyl Aminopeptidase/Humans/Photosensitizing Agents/Protein Precursors/Protoporphyrins/biosynthesis/Rats/Tumor Cells,Cultured
Pubmed
Web of science
Create date
29/01/2008 19:33
Last modification date
15/07/2020 7:08
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