title: [Interfacial behaviour of glycoconjugated tetraphenylporphyrins and their interaction with biomimetic models of the cell membrane].
abstract: BACKGROUND
  Porphyrins are photosensitizers usable in photodynamic therapy. Although these molecules are clinically effective, their low water solubility and their lack of specificity are major drawbacks to their development. Our study was aimed at analysing the interfacial behaviour of glycoconjugated tetraphenylporphyrins newly synthesized at the Curie Institute, and their interaction with model membranes bearing a specific lectin mimicking a mannose membrane receptor in retinoblastoma.
  
  
  METHODS
  The interfacial behaviour of the porphyrins was analysed by surface pressure measurements, and their specific interaction with the lectin, by dynamic light scattering (liposomes) and the quartz crystal microbalance technique (supported bilayers).
  
  
  RESULTS
  All porphyrin derivatives were able to organize at the air/liquid interface. The dendrimeric compounds formed more stable monolayers than the others, and generally showed good mixing properties with the phospholipid used for liposome preparation. In the presence of concanavalin A, the porphyrin bearing-liposomes behaved differently depending on the nature (mannosylated or not) of the porphyrins.
  
  
  CONCLUSIONS
  The interfacial behaviour of the tetraphenylporphyrins is directly related to the orientation of the tetrapyrrolic macrocycle controlled by the grafted groups. Incorporated into a liposome bilayer, glycodendrimeric porphyrins expose their sugar moieties at the vesicle surface. The spacer length plays a crucial role by increasing sugars freedom and enhancing glycosylated liposomes interaction with the lectin.
  
  
  CONCLUSIONS
  Compared to the other studied compounds, the glycodendrimeric porphyrins seem very promising compounds and are now evaluated on cell cultures.
authors: UMR CNRS 8612, laboratoire de physicochimie des surfaces, faculté de pharmacie, université Paris-Sud 11, 5, rue J.-B.-Clément, 92296 Châtenay-Malabry cedex, France. veronique.rosilio@u-psud.fr
authors: V
authors: V
authors: Rosilio
authors: A
authors: A
authors: Makky
authors: J-P
authors: JP
authors: Michel
authors: P
authors: P
authors: Maillard
mesh_terms: D032701:Biomimetics; D045744:Cell Line, Tumor; D002462:Cell Membrane / Q000187:drug effects*; D003208:Concanavalin A / Q000737:chemistry; D050091:Dendrimers; D006001:Glycoconjugates / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D037102:Lectins; D008567:Membranes, Artificial; D010743:Phospholipids / Q000737:chemistry; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000737:chemistry / Q000494:pharmacology*; D011166:Porphyrins / Q000737:chemistry / Q000494:pharmacology*; D019572:Retinal Neoplasms / Q000378:metabolism; D012175:Retinoblastoma / Q000378:metabolism; D013499:Surface Properties
chemical_list: D050091:Dendrimers; D006001:Glycoconjugates; D037102:Lectins; D008567:Membranes, Artificial; D010743:Phospholipids; D017319:Photosensitizing Agents; D011166:Porphyrins; C409084:tetraphenylporphyrin; D003208:Concanavalin A