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Novel boronated derivatives of 5,10,15,20-tetraphenylporphyrin: synthesis and toxicity for drug-resistant tumor cells.

Abstract
We have developed the synthesis of boronated porphyrins for potential application in cancer treatment, based on the functional derivatives of 5,10,15,20-tetraphenylporphyrin. Boronated amide derivatives starting from 5,10,15,20-tetra(p-aminophenyl)porphyrin and 9-o- and 9-m-carborane carboxylic acid chlorides were prepared. Also, the reaction of 2-formyl-5,10,15,20-tetraphenylporphyrin with closo-C-lithium-o- and m-carboranes, as well as with closo-C-lithium monocarbon carborane, yielded neutral and anionic boronated hydroxy derivatives of 5,10,15,20-tetraphenylporphyrin, respectively. Water-soluble forms of neutral compounds were prepared by deboronation of closo-polyhedra with Bu4NF into nido-7,8- and nido-7,9-dicarbaundecaborate anions. Monocarbon carborane conjugated with copper (II) complex of 5,10,15,20-tetraphenylporphyrin was active for a variety of tumor cell lines (IC50 approximately 5 microM after 48-72 h of exposure) but was inert for non-malignant fibroblasts at up to 100 microM. At low micromolar concentrations, this compound caused the death of cells that express P-glycoprotein and other mechanisms of resistance to conventional anticancer drugs.
AuthorsValentina A Ol'shevskaya, Andrei V Zaitsev, Valentina N Luzgina, Tatyana T Kondratieva, Oleg G Ivanov, Elena G Kononova, Pavel V Petrovskii, Andrei F Mironov, Valery N Kalinin, Johann Hofmann, Alexander A Shtil
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 14 Issue 1 Pg. 109-20 (Jan 01 2006) ISSN: 0968-0896 [Print] England
PMID16185886 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • 5,10,15,20-tetraphenylporphyrin
  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Antineoplastic Agents
  • Boron Compounds
  • Porphyrins
Topics
  • ATP Binding Cassette Transporter, Subfamily B, Member 1 (analysis)
  • Antineoplastic Agents (chemical synthesis, toxicity)
  • Boron Compounds (chemistry)
  • Cell Line, Tumor
  • Drug Resistance, Neoplasm
  • Humans
  • Porphyrins (chemical synthesis, chemistry, toxicity)

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