PBN Derived Amphiphilic Spin-Traps. I/Synthesis and Study of Their Miscibility with Polyunsaturated Phospholipids

• Published in: Langmuir 2003-11, Vol.19 (23), p.9699-9705
• Main Authors: Morandat, Sandrine, Durand, Grégory, Polidori, Ange, Desigaux, Léa, Bortolato, Muriel, Roux, Bernard, Pucci, Bernard
• Format: Article
• Language: English
• ISSN: 0743-7463; 1520-5827
• DOI: 10.1021/la034470t

The synthesis of new amphiphilic α-phenyl-N-tert-butylnitrone (PBN) derivatives bearing two hydrocarbon tails with 17 carbon atoms (compound A 17 ) or 11 carbon atoms (compound B 11 ) is reported. The amphiphilic and morphological properties of these potential antioxidant compounds were investigated at the air−water interface. The analyses were conducted using Langmuir film balance and Brewster angle microscopy. As it is possible to obtain pressure−area (π−A) isotherms from pure A 17 and B 11 , this means that they can form stable monomolecular films at the air−water interface. Monolayers of pure PBN derivatives exhibited different interface behavior. Indeed, along with compression, the B 11 monolayer showed only a liquid-expanded phase and the A 17 monolayer showed a liquid-condensed phase. Brewster angle microscopy showed the presence of condensed domains within the A 17 monolayer. The lateral interactions of these compounds with the polyunsaturated phospholipids, 1,2-dilinoleoyl-sn-glycero-3-phosphocholine (DLoPC) and 1,2-dilinoleoyl-sn-glycero-3-phosphoethanolamine (DLoPE), were evaluated by analysis of π−A isotherms and excess free energy of mixing. Each PBN derivative was miscible with DLoPC or DLoPE and formed nonideal mixed monolayers at the air−water interface. Only the A 17 molecules exhibited favorable interactions at high surface pressures (over 20 mN/m) with both DLoPC and DLoPE, however. Under these conditions, A 17 should be a better antioxidant than B 11 .