Polyamine conjugates of meso-tritolylporphyrin and protoporphyrin IX: potential agents for photodynamic therapy of cancers.

Vincent Sol (1) , François Lamarche , Michaela Enache , Guillaume Garcia , Robert Granet (1) , M. Guilloton (1) , Jean-Claude Blais (2) , Pierre Krausz (1)

1 LCSN - Laboratoire de Chimie des Substances Naturelles
2 SSFMB - Synthèse, Structure et Fonction de Molécules Bioactives

An efficient five-step synthesis method was developed to obtain tritolylporphyrin and protoporphyrin IX polyamine conjugates. These compounds were composed of either one polyamine unit (spermidine or spermine) covalently tethered to monocarboxyphenyl tritolylporphyrin or two molecules of polyamines borne by protoporphyrin IX. In each compound, an aliphatic spacer arm is linked to the N(4) polyamine position. Photocytotoxicity of these new compounds was evaluated against K562 human chronic myelogenous leukemia cells and compared to Photofrin II; protoporphyrin IX polyamine conjugates exhibited much stronger photocytocicity than Photofrin II and were shown to readily induce necrosis in treated cells.

Domaines: Chimie organique

Vincent Sol, François Lamarche, Michaela Enache, Guillaume Garcia, Robert Granet, et al.. Polyamine conjugates of meso-tritolylporphyrin and protoporphyrin IX: potential agents for photodynamic therapy of cancers.. Bioorganic and Medicinal Chemistry, 2006, 14 (5), pp.1364-1377. ⟨10.1016/j.bmc.2005.09.071⟩. ⟨hal-00684447⟩