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Calixpyrroles-based antitumor compounds

Antineoplastic agentsCalixpyrrolesChemotherapiesGenotoxicitySupramolecular systems


Anticancer compounds based on calixpirroles are derivatized to obtain passive transport on tumor masses through the Enhanced Permeation and Retention effect of the neoplastic vasculature. The anti-tumor compounds can be conjugated with peptides/antibodies for an active transport to cancer cells. Moreover, these compounds can be inserted in formulations adapted to perform a selective delivery to tumor cells.

Technical features

The discovery of cytoxicity of certain calixpyrrole derivatives (i.e. compounds 1 and 2 in figure) against specific cancer cell lines (in particularA549 lung cancer) is at the best of this technology. These compounds seem to act via the formation of covalent adducts with DNA, where the genetic damage induces cell death by apoptosis. The formation of covalent adducts was detected using ‘32P post-labelling’. We believe these adducts are formed by the initial complexation of the DNA phosphate unit by the calixpyrrole fragment and/or intercalation of the DNA major groove as shown in ‘in silico’ trials, and subsequently the by the reaction with the nucleobases of compounds 1 and 2 (or their activated metabolites). Preliminary pharmacokinetic tests (A/J mice) showed 1 and 2 to have extremely low toxicity in vivo and also their ability to cross the blood-brain barrier.

Possible Applications

  • Brain tumors;
  • Brain metastases;
  • Ovary tumors;
  • Lung tumors,
  • Estrogen depending tumors;
  • Tumors of neuro-endocrine origin.


  • Activity against several tumor cell types;
  • Preliminary in vivo tests showed low toxicity.