Drug delivery with a calixpyrrole-trans -Pt(II) complex

Grazia Cafeo, Grazia Carbotti, Angela Cuzzola, Marina Fabbi, Silvano Ferrini, Franz H. Kohnke, Georgia Papanikolaou, Maria Rosaria Plutino, Camillo Rosano, Andrew J P White

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Abstract

A meso-p-nitroaniline-calix[4]pyrrole derivative trans-coordinated to a Pt(II) center was synthesized and its structure solved by X-ray analysis. Adenosine monophosphate (AMP) was used as a model compound to evaluate the potential for the assisted delivery of the metal to the DNA nucleobases via the phosphate anion-binding properties of the calix[4]pyrrole unit. An NMR investigation of the kinetics of AMP complexation in the absence of an H-bonding competing solvent (dry CD3CN) was consistent with this hypothesis, but we could not detect the interaction of the calix[4]pyrrole with phosphate in the presence of water. However, in vitro tests of the new trans-calixpyrrole- Pt(II) complex on different cancer cell lines indicate a cytotoxic activity that is unquestionably derived from the coexistence of both the trans-Pt(II) fragment and the calix[4]pyrrole unit.

Original languageEnglish
Pages (from-to)2544-2551
Number of pages8
JournalJournal of the American Chemical Society
Volume135
Issue number7
DOIs
Publication statusPublished - Feb 20 2013

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ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Cafeo, G., Carbotti, G., Cuzzola, A., Fabbi, M., Ferrini, S., Kohnke, F. H., Papanikolaou, G., Plutino, M. R., Rosano, C., & White, A. J. P. (2013). Drug delivery with a calixpyrrole-trans -Pt(II) complex. Journal of the American Chemical Society, 135(7), 2544-2551. https://doi.org/10.1021/ja307791j