Zwitterionic fluorinated detergents: From design to membrane protein applications

Soulié, Marine; Deletraz, Anaïs; Wehbie, Moheddine; Mahler, Florian; Bouchemal, Ilham; Roy, Aline Le; Keller, Sandro; Meister, Annette; Pebay‐Peyroula, Eva; Breyton, Cécile; Ebel, Christine; Durand, Grégory

doi:10.1016/j.biochi.2022.11.003

Cited by 2 publications

(3 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More lately, fluorinated detergents were shown to be able to stabilize lipid nanodiscs [123] . Zwitter‐ionic and fluorinated detergents were shown to solubilize and stabilize membrane proteins [124] . Furthermore, fluorinated glycerol detergents are suitable for the preparation of highly stable water‐in‐fluorinated oil emulsions for microfluidics applications [9a] .…”

Section: Resultsmentioning

confidence: 99%

“…[123] Zwitter-ionic and fluorinated detergents were shown to solubilize and stabilize membrane proteins. [124] Furthermore, fluorinated glycerol detergents are suitable for the preparation of highly stable water-influorinated oil emulsions for microfluidics applications. [9a] Despite their environmental persistence and growing skepticism regarding their impact on human health and environment, [116,125] fluorinated detergents form an integral part within a growing research direction whose potential for future applications is under investigation.…”

Section: Linear and Branched Tailsmentioning

confidence: 99%

See 1 more Smart Citation

Trends in the Diversification of the Detergentome

Wycisk,

Wagner,

Urner

2023

ChemPlusChem

View full text Add to dashboard Cite

Detergents are amphiphilic molecules that serve as enabling steps for today’s world applications. The increasing diversity of the detergentome is key to applications enabled by detergent science. Regardless of the application, the optimal design of detergents is determined empirically, which leads to failed preparations, and raising costs. To facilitate project planning, here we review synthesis strategies that drive the diversification of the detergentome. Synthesis strategies relevant for industrial and academic applications include linear, modular, combinatorial, bio‐based, and metric‐assisted detergent synthesis. Scopes and limitations of individual synthesis strategies in context with industrial product development and academic research are discussed. Furthermore, when designing detergents, the selection of molecular building blocks, i.e., head, linker, tail, is as important as the employed synthesis strategy. To facilitate the design of safe‐to‐use and tailor‐made detergents, we provide an overview of established head, linker, and tail groups and highlight selected scopes and limitations for applications. It becomes apparent that most recent contributions to the increasing chemical diversity of detergent building blocks originate from the development of detergents for membrane protein studies. The overview of synthesis strategies and molecular blocks will bring us closer to the ability to predictably design and synthesize optimal detergents for challenging future applications.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Linear and Branched Tailsmentioning

confidence: 99%

Trends in the Diversification of the Detergentome

Wycisk,

Wagner,

Urner

2023

ChemPlusChem

View full text Add to dashboard Cite

show abstract

“…Such rigidification of the tail can be attained by substituting fluorine for hydrogen atoms, leading to fluorinated surfactants (FS, also called F -surfactants). F -surfactants are stabilizing toward fragile membrane proteins due to the bulkier and stiffer fluorinated alkyl chains, ,− but they can solubilize lipid membranes, extract membrane proteins from membranes, ,− and promote the formation of protein–lipid nanodiscs . Resorting to cyclic alkyl maltoside detergents is another promising strategy, as exemplified by the commercial Cymal series, where a β-maltoside polar head is linked to a hydrophobic tail made of a linear alkyl chain of n carbon atoms ended by a cyclohexyl group .…”

Section: Introductionmentioning

confidence: 99%

Rigid Cyclic Fluorinated Detergents: Fine-Tuning the Hydrophilic–Lipophilic Balance Controls Self-Assembling and Biochemical Properties

Soulié,

Deletraz,

Wehbie

et al. 2024

ACS Appl. Mater. Interfaces

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Zwitterionic fluorinated detergents: From design to membrane protein applications

Cited by 2 publications

References 43 publications

Trends in the Diversification of the Detergentome

Trends in the Diversification of the Detergentome

Rigid Cyclic Fluorinated Detergents: Fine-Tuning the Hydrophilic–Lipophilic Balance Controls Self-Assembling and Biochemical Properties

Contact Info

Product

Resources

About