Tensioactive properties of zwitterionic carboxybetaine amphiphiles

Chevalier, Yves; Storet, Yvan.; Pourchet, Sylvie; Perchec, P. Le

doi:10.1021/la00053a007

Cited by 120 publications

(110 citation statements)

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“…Furthermore, the formation of sodium chloride as the byproduct, which may tenaciously stick to the sulfobetaine moiety, required the purification of SHPP with a mixed bed ion exchanger, to obtain a monomer free of inorganic salt contamination. 28,29 Though reference data are missing, the 1 H-NMR spectra of SHPP (Fig. 2) fit well with the typical features of related sulfobetaine monomers.…”

Section: Resultssupporting

confidence: 57%

Modulating the solubility of zwitterionic poly((3-methacrylamidopropyl)ammonioalkane sulfonate)s in water and aqueous salt solutions via the spacer group separating the cationic and the anionic moieties

2016

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Modulating the solubility of zwitterionic poly((3-methacrylamidopropyl) ammonioalkane sulfonate)s in water and aqueous salt solutions via the spacer group separating the cationic and the anionic moieties Postprint Complementary to the well-established zwitterionic monomer 3-((3-methacrylamidopropyl)dimethylammonio)propane-1-sulfonate (SPP), the closely related monomers 2-hydroxy-3-((3-methacrylamidopropyl)dimethylammonio)propane-1-sulfonate (SHPP) and 4-((3-methacrylamidopropyl)dimethylammonio)-butane-1-sulfonate (SBP) were synthesised and polymerised by reversible addition-fragmentation chain transfer (RAFT) polymerisation, using a fluorophore labeled RAFT agent. The polyzwitterions of systematically varied molar masses were characterised with respect to their solubility in water and aqueous salt solutions. Both poly(sulfobetaine)s show thermoresponsive behaviour in water, exhibiting phase separation at low temperatures and upper critical solution temperatures (UCST). For both polySHPP and polySBP, cloud points depend notably on the molar mass, and are much higher in D 2 O than in H 2 O. Also, the cloud points are effectively modulated by the addition of salts. The individual effects can be in parts correlated to the Hofmeister series for the anions studied. Still, they depend in a complex way on the concentration and the nature of the added electrolytes, on the one hand, and on the detailed nature of the spacer group separating the anionic and the cationic charges of the betaine moiety, on the other hand. As anticipated, the cloud points of polySBP are much higher than the ones of the analogous polySPP of identical molar mass.Surprisingly, the cloud points of polySHPP are also somewhat higher than the ones of their polySPP analogues, despite the additional hydrophilic hydroxyl group present in the spacer separating the ammonium and the sulfonate moieties. These findings point to a complicated interplay of the various hydrophilic components in polyzwitterions with respect to their overall hydrophilicity. Thus, the spacer group in the betaine moiety proves to be an effective additional molecular design parameter, apparently small variations of which strongly influence the phase behaviour of the polyzwitterions in specific aqueous environments.

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Section: Resultssupporting

confidence: 57%

Modulating the solubility of zwitterionic poly((3-methacrylamidopropyl)ammonioalkane sulfonate)s in water and aqueous salt solutions via the spacer group separating the cationic and the anionic moieties

2016

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“…This problem has been remedied at least in parts by the use of ion exchange resins. Their use is particularly effective when inverting the second and third steps of the sequence shown in Scheme 6 [63,[86][87][88][89], so that the counterion X − in Im-2 becomes OH − and the final zwitterion is liberated without producing salts. However, this strategy cannot be applied universally due to the strongly alkaline conditions [86].…”

Section: Synthetic Strategies Towards Zwitterionic Moieties: Scope Anmentioning

confidence: 99%

“…This is particularly problematic at elevated temperatures or pH values. In fact, 3-ammoniopropionates have been described to be instable and to be in equilibrium with the ammonium acrylate salt that is formed after elimination [89,90,92]. This limits the usefulness of polyzwitterions bearing this motif severely, which has become rather popular these days due to their straightforward access.…”

Section: Synthetic Strategies Towards Zwitterionic Moieties: Scope Anmentioning

confidence: 99%

Structures and Synthesis of Zwitterionic Polymers

2014

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Abstract:The structures and synthesis of polyzwitterions ("polybetaines") are reviewed, emphasizing the literature of the past decade. Particular attention is given to the general challenges faced, and to successful strategies to obtain polymers with a true balance of permanent cationic and anionic groups, thus resulting in an overall zero charge. Also, the progress due to applying new methodologies from general polymer synthesis, such as controlled polymerization methods or the use of "click" chemical reactions is presented. Furthermore, the emerging topic of responsive ("smart") polyzwitterions is addressed. The considerations and critical discussions are illustrated by typical examples.

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“…However, this trajectory is just a suggestion, as it is difficult to follow each peak unambiguously. (33,34,51)). Line broadening can be seen at intermediate detergent concentrations (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Our study focuses on TRP3 accommodation at the hydrophilic/ hydrophobic interface of micelles and subsequent events. The structure and dynamics of TRP3 were examined in the presence of micelles of different chemical nature: zwitterionic (lysolauroylphosphatidylcholine 1-lauroyl-2-hydroxy-sn-glycero-3-phosphocholine (LLPC), n-dodecylphosphocholine (DPC), and N-dodecyl-N,N-(dimethylammonio) butyrate (DDMAB), anionic 1-myristoyl-2-hydroxy-sn-glycero-3-phospho-(1 0 -rac-glycerol) (LMPG), and nonionic (octylglucoside (OG)) (23,24,(31)(32)(33)(34)(35). The conformational ensemble was evaluated during detergent titration and it was found that the peptide interacts via conformational selection.…”

Section: Introductionmentioning

confidence: 99%

Structural and Dynamic Insights of the Interaction between Tritrpticin and Micelles: An NMR Study

Santos

Moraes

Nakaie

et al. 2016

Biophysical Journal

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A large number of antimicrobial peptides (AMPs) acts with high selectivity and specificity through interactions with membrane lipid components. These peptides undergo complex conformational changes in solution; upon binding to an interface, one major conformation is stabilized. Here we describe a study of the interaction between tritrpticin (TRP3), a cathelicidin AMP, and micelles of different chemical composition. The peptide's structure and dynamics were examined using one-dimensional and two-dimensional NMR. Our data showed that the interaction occurred by conformational selection and the peptide acquired similar structures in all systems studied, despite differences in detergent headgroup charge or dipole orientation. Fluorescence and paramagnetic relaxation enhancement experiments showed that the peptide is located in the interface region and is slightly more deeply inserted in 1-myristoyl-2-hydroxy-sn-glycero-3-phospho-1 0 -rac-glycerol (LMPG, anionic) than in 1-lauroyl-2-hydroxy-sn-glycero-3-phosphocholine (LLPC, zwitterionic) micelles. Moreover, the tilt angle of an assumed helical portion of the peptide is similar in both systems. In previous work we proposed that TRP3 acts by a toroidal pore mechanism. In view of the high hydrophobic core exposure, hydration, and curvature presented by micelles, the conformation of TRP3 in these systems could be related to the peptide's conformation in the toroidal pore.

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Tensioactive properties of zwitterionic carboxybetaine amphiphiles

Cited by 120 publications

References 0 publications

Modulating the solubility of zwitterionic poly((3-methacrylamidopropyl)ammonioalkane sulfonate)s in water and aqueous salt solutions via the spacer group separating the cationic and the anionic moieties

Modulating the solubility of zwitterionic poly((3-methacrylamidopropyl)ammonioalkane sulfonate)s in water and aqueous salt solutions via the spacer group separating the cationic and the anionic moieties

Structures and Synthesis of Zwitterionic Polymers

Structural and Dynamic Insights of the Interaction between Tritrpticin and Micelles: An NMR Study

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