Rigid cyclic fluorinated detergents: fine-tuning the hydrophilic–lipophilic balance controls self-assembling and biochemical properties - Groupe Membrane et pathogènes / Membrane and Pathogens Group (IBS-MP)
Article Dans Une Revue ACS Applied Materials & Interfaces Année : 2024

Rigid cyclic fluorinated detergents: fine-tuning the hydrophilic–lipophilic balance controls self-assembling and biochemical properties

Résumé

We report herein the synthesis of three detergents bearing a perfluorinated cyclohexyl group connected through a short, hydrogenated spacer (i.e., propyl, butyl, or pentyl) to a β-maltoside polar head that are, respectively, called FCymal-3, FCymal-4, and FCymal-5. Increasing the length of the spacer decreased the critical micellar concentration (CMC), as demonstrated by surface tension (SFT) and isothermal titration calorimetry (ITC), from 5 mM for FCymal-3 to 0.7 mM for FCymal-5. The morphology of the micelles was studied by dynamic light scattering (DLS), analytical ultracentrifugation (AUC), and small-angle X-ray scattering (SAXS), indicating heterogeneous rod-like shapes. While micelles of FCymal-3 and -4 have similar hydrodynamic diameters of ∼10 nm, those of FCymal-5 were twice as large. We also investigated the ability of the detergents to solubilize lipid membranes made of 1-palmitoyl-2-oleyl-sn-glycero-3-phosphocholine (POPC). Molecular modeling indicated that the FCymal detergents generate disorder in lipid bilayers, with FCymal-3 being inserted more deeply into bilayers than FCymal-4 and -5. This was experimentally confirmed using POPC vesicles that were completely solubilized within 2 h with FCymal-3, whereas FCymal-5 required >8 h. A similar trend was noticed for the direct extraction of membrane proteins from E. coli membranes, with FCymal-3 being more potent than FCymal-5. An opposite trend was observed in terms of stabilization of the two model membrane proteins bacteriorhodopsin (bR) and SpNOX. In all three FCymal detergents, bR was stable for at least 2 months with no signs of aggregation. However, while the structural integrity of bR was fully preserved in FCymal-4 and -5, minor bleaching was observed in FCymal-3. Similarly, SpNOX exhibited the least activity in FCymal-3 and the highest activity in FCymal-5. By combining solubilizing and stabilizing potency, FCymal detergents push forward our expectations of the usefulness of fluorinated detergents for handling and investigating membrane proteins.
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Dates et versions

hal-04637060 , version 1 (05-07-2024)

Identifiants

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Marine Soulié, Anais Deletraz, Moheddine Wehbie, Florian Mahler, Benjamin Chantemargue, et al.. Rigid cyclic fluorinated detergents: fine-tuning the hydrophilic–lipophilic balance controls self-assembling and biochemical properties. ACS Applied Materials & Interfaces, 2024, 16 (26), pp.32971-32982. ⟨10.1021/acsami.4c03359⟩. ⟨hal-04637060⟩
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