Evaluation of the Specific Interactions between Glycodendrimetic Porphyrins, Free or Incorporated into Liposomes, and Concanavaline A by Fluorescence Spectroscopy, Surface Pressure, and QCM-D Measurements

A. Makky (1, 2) , J.P. Michel (1, 2) , A. Kasselouri (3) , E. Briand (1, 2) , Ph. Maillard (2, 4) , V. Rosilio (1, 2)

1 LPCS - Laboratoire de Physico-Chimie des Surfaces
2 PHOTOMED - Médicaments Photoactivables - Photochimiothérapie
3 Groupe de Chimie Analytique de Paris-Sud
4 Institut Curie [Paris]

In photodynamic therapy, the specificity of a photosensitizer and its penetration into tumor cells are crucial. We have analyzed the ability of newly synthesized meso-(tetraphenyl)porphyrins to be recognized by a model of mannose-specific proteins overexpressed at the surface of retinoblastoma cells. The specific interaction of porphyrin with Con A was studied by surface pressure measurements, fluorescence spectroscopy, dynamic light scattering, and QCM-D. The extent of porphyrins binding to Con A was highly dependent upon their chemical structure. Glycodendrimeric porphyrins showed the higher binding constant to Con A. The length of the spacer separating the sugar from the tetrapyrrolic ring appeared to be crucial in controlling the interaction of the compounds with the lectin in solution or immobilized onto a solid substrate. The methodology used proved to be efficient for the selection of potentially active compounds. The glycodendrimeric porphyrins, especially the derivative having the longer spacer, interacted more significantly with the lectin than the compound devoid of any sugar.

Domaines: Chimie organique

A. Makky, J.P. Michel, A. Kasselouri, E. Briand, Ph. Maillard, et al.. Evaluation of the Specific Interactions between Glycodendrimetic Porphyrins, Free or Incorporated into Liposomes, and Concanavaline A by Fluorescence Spectroscopy, Surface Pressure, and QCM-D Measurements. Langmuir, 2010, 26 (15), pp.12761-12768. ⟨10.1021/la101260t⟩. ⟨hal-00509827⟩