Embedding resorcinarene cavitands in lipid vesicles

Feher, Katie M.; Hoang, Hai; Schramm, Michael

doi:10.1039/c2nj20961f

Cited by 12 publications

(8 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[8] We know too that fluorescently tagged cavitands distribute regularly in giant unilamellar vesicles (GUVs), and that these vesicles remain viable and non-permeable to their surroundings. [9] New hosts have emerged that are capable of self-micelle formation and compartmentalization of payloads. [10] Resorcinarenes have also formed ion channels in lipid environments.…”

Section: Introductionmentioning

confidence: 99%

Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

2014

Self Cite

View full text Add to dashboard Cite

A series of supramolecular calixarenes efficiently transport distinct molecular species through a liquid membrane when attached to a receptor-complementary choline handle. Calix-[6]arene hexacarboxylic acid was highly effective at transporting different target molecules against a pH gradient. Both carboxylic- and phosphonic-acid-functionalized calix[4]arenes effect transport without requiring a pH or ion gradient. NMR binding studies, two-phase solvent extraction, and three-phase transport experiments reveal the necessary and subtle parameters to effect the transport of molecules attached to a choline “handle”. On the other hand, rescorin[4]arene cavitands, which have similar guest recognition profiles, did not transport guest molecules. These developments reveal new approaches towards attempting synthetic-receptor-mediated selective small-molecule transport in vesicular and cellular systems.

show abstract

Section: Introductionmentioning

confidence: 99%

Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

2014

Self Cite

View full text Add to dashboard Cite

show abstract

“…[11,25] We know that supramolecular receptors are compatible with cells and we can monitor their localization tendencies in giant unilamellar vesicles. [9] A final report on the behavior of guests in buffer as well as a comparison of trimethylammonium vs. ammonium vs. ammonium dicarboxylate species will be reported in due course. Our first report using vesicles to visualize and quantitate transport will follow shortly thereafter.…”

Section: Discussionmentioning

confidence: 99%

“…[6] We have discovered that these systems function in aqueous lipid systems as hosts, [7] and as platforms for switching, [8] and we know too that these molecules distribute themselves evenly in lipid bilayer systems. [9] Our colleagues have demonstrated remarkable functions for these systems as surface bound receptors for protein sensing [10] and, most interestingly, as facilitators of endocytosis for guest molecules! [11] These properties have been developed under constraints of the host, as they are largely incompatible with pure water environments.…”

Section: Introductionmentioning

confidence: 99%

Calixarene‐Mediated Liquid Membrane Transport of Choline Conjugates 2: Transport of Drug‐Choline Conjugates and Neurotransmitters

et al. 2015

Self Cite

View full text Add to dashboard Cite

Lower rim carboxylic acid calix[n]arenes and upper rim phosphonic acid functionalized calix[4]arenes effect selective transport of distinct molecular payloads through a liquid membrane. The secret to this success lies in the attachment of a receptor-complementary handle. We find that the trimethylammonium ethylene group present in choline is a general handle for the transport of drug and drug-like species. Furthermore, neurotransmitters possessing ionizable amine termini are also transported. Some limitations to this strategy have been uncovered as payloads become increasingly lipophilic. These developments reveal new approaches to synthetic receptor-mediated selective small molecule transport in vesicular and cellular systems.

show abstract

“…6 A few examples exist that show these intriguing properties can be maintained in water. 7,8 The same applies to some deep cavitands incorporated into micelles [9][10][11] and bilayer structures, 12,13 mimicking biological membranes. However, this approach of embedding cavitands into phospholipids is limited, especially in terms of cavitand concentration.…”

mentioning

confidence: 93%