Liquid membrane transport of cytochrome c using a calix[6]arene carboxylic acid derivative as a carrier

Oshima, Tatsuya; Suetsugu, Akinori; Baba, Yoshihiro; Shikaze, Yuka; Ohto, Keisuke; Inoue, Katsutoshi

doi:10.1016/j.memsci.2007.09.033

Cited by 24 publications

(8 citation statements)

References 31 publications

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“…Probably, this effect is caused by the increase of the positive charges at the surface due to protonated amino groups of lysines (ÀNH 3 + ) that did not enter the calixarene cavity. This interpretation is in accordance with the observation that the interaction of cyt c with the CALIX involves only 19 lysine residues at the surface of cyt c [26,27].…”

Section: Resultssupporting

confidence: 92%

Electrochemical Impedance Spectroscopy for Assessing the Recognition of Cytochrome c by Immobilized Calixarenes

et al. 2011

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We developed a biosensor based on supported lipid films (sBLM) with incorporated calixarenes for detection of cytochrome c (cyt c) using electrochemical impedance spectroscopy (EIS). Calix[6]arene (CALIX) was incorporated into soybean phosphatidylcholine (SBPC) liposomes in different molar ratios (SBPC:CALIX = 10 : 1, 30 : 1 and 100 : 1). The lipid layer containing calixarenes has been formed on the surface of a gold electrode previously covered with an octadecanethiol monolayer. Both the sBLM capacitance and the electron transfer resistance showed noticeable modification at a cyt c concentration as low as 10 nM. However, a much higher concentration of free lysine (> 30 mM) was necessary to induce a similar effect. Nonspecific interaction of cyt c with sBLM without CALIX was negligible.

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Section: Resultssupporting

confidence: 92%

Electrochemical Impedance Spectroscopy for Assessing the Recognition of Cytochrome c by Immobilized Calixarenes

et al. 2011

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“…As reported phosphonic acid 1 24,25 could effect transport across a bulk liquid membrane without a pH gradient, whereas lower rim functionalized carboxylates calix[4]arene 2 26 and calix[6]arene 3 27 responded favorably to an inverse acid gradient (Fig. 1).…”

Section: Introductionsupporting

confidence: 54%

Calixarene-mediated liquid membrane transport of choline conjugates 3: The effect of handle variation on neurotransmitter transport

Collins

Fujii

Roshandel

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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Upper rim phosphonic acid functionalized calix[4]arene affects selective transport of multiple molecular payloads through a liquid membrane. The secret is in the attachment of a receptor-complementary handle to the payload. We find that the trimethylammonium ethylene group present in choline is one of several general handles for the transport of drug and drug-like species. Herein we compare the effect of handle variation against the transport of serotonin and dopamine. We find that several ionizable amine termini handles are sufficient for transport and identify two ideal candidates. Their performance is significantly enhanced in HEPES buffered solutions. This inquiry completes a series of 3 studies aimed at optimization of this strategy. In completion a new approach towards synthetic receptor mediated selective small molecule transport has emerged; future work in vesicular and cellular systems will follow.

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“…Calix[6]arenecarboxylic acids have previously been shown to transport cationic amino acids [20] through liquid membranes, and more interestingly multiple calixarenes facilitate the transport of polycationic cytochrome C. [21] Under acidic conditions, calix[6]arene hexacarboxylic acid 5 transports 4.7 times more guest 9 than 6 . More interesting to us is the ability of 4 and 6 to carry out transport under neutral conditions.…”

Section: Discussionmentioning

confidence: 99%

Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

2014

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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.

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Liquid membrane transport of cytochrome c using a calix[6]arene carboxylic acid derivative as a carrier

Cited by 24 publications

References 31 publications

Electrochemical Impedance Spectroscopy for Assessing the Recognition of Cytochrome c by Immobilized Calixarenes

Electrochemical Impedance Spectroscopy for Assessing the Recognition of Cytochrome c by Immobilized Calixarenes

Calixarene-mediated liquid membrane transport of choline conjugates 3: The effect of handle variation on neurotransmitter transport

Calixarene‐Mediated Liquid‐Membrane Transport of Choline Conjugates

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