A,B,D,F-tetrasubstituted β-cyclodextrin as artificial channel compound

Tabushi, Iwao; Kuroda, Yasuhisa; Yokota, Kan-ichi

doi:10.1016/s0040-4039(00)85664-6

Cited by 229 publications

(135 citation statements)

References 13 publications

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“…For example, Tabushi and colleagues made a ␤CD carrying hydrophobic chains on four of the seven 6-positions (41). It was claimed that two of these molecule form a transmembrane pore.…”

Section: Discussionmentioning

confidence: 99%

Reversal of charge selectivity in transmembrane protein pores by using noncovalent molecular adapters

Gu¹,

Serra²,

Vincent³

et al. 2000

Proc. Natl. Acad. Sci. U.S.A.

143

163

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In this study, the charge selectivity of staphylococcal ␣-hemolysin (␣HL), a bacterial pore-forming toxin, is manipulated by using cyclodextrins as noncovalent molecular adapters. Anionselective versions of ␣HL, including the wild-type pore and various mutants, become more anion selective when ␤-cyclodextrin (␤CD) is lodged within the channel lumen. By contrast, the negatively charged adapter, hepta-6-sulfato-␤-cyclodextrin (s7␤CD), produces cation selectivity. The cyclodextrin adapters have similar effects when placed in cation-selective mutant ␣HL pores. Most probably, hydrated Cl ؊ ions partition into the central cavity of ␤CD more readily than K ؉ ions, whereas s7␤CD introduces a charged ring near the midpoint of the channel lumen and confers cation selectivity through electrostatic interactions. The molecular adapters generate permeability ratios (P K؉/PCl؊) over a 200-fold range and should be useful in the de novo design of membrane channels both for basic studies of ion permeation and for applications in biotechnology.

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“…For example, Tabushi and colleagues made a ␤CD carrying hydrophobic chains on four of the seven 6-positions (41). It was claimed that two of these molecule form a transmembrane pore.…”

Section: Discussionmentioning

confidence: 99%

Reversal of charge selectivity in transmembrane protein pores by using noncovalent molecular adapters

Gu¹,

Serra²,

Vincent³

et al. 2000

Proc. Natl. Acad. Sci. U.S.A.

143

163

View full text Add to dashboard Cite

show abstract

“…A good example is the pioneering effort of Tabushi and coworkers who reported the preparation of an artificial cation channel in 1982 [29]. Their channel was based on a modified cyclodextrin and its efficacy was demonstrated by measuring Co 2+ transport.…”

Section: Function In Artificial Model Systemsmentioning

confidence: 99%

“…When we began our studies, no solid state structure of a channel protein was available so no cue could be taken from it. The only synthetic channel model that was available was that of Tabushi et al [29], which had about the same length dimension as a phospholipid monomer. Of course, even the length of a phospholipid monomer is highly variable because the fatty acid chains can range from about 12 carbons to 24 or more.…”

Section: Design Criteria For Hydraphilesmentioning

confidence: 99%

Coordination and transport of alkali metal cations through phospholipid bilayer membranes by hydraphile channels

Gokel

Daschbach

2008

Coordination Chemistry Reviews

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Hydraphiles are synthetic ionophores that were designed to mimic some properties of protein channels that conduct such cations as sodium. They use macrocyclic (crown) polyethers as amphiphilic headgroups and as entry and exit portals. Their overall length is controlled by covalent links between the two headgroups (distal macrocycles) and the "central relay" unit, typically also an azacrown. The hydraphiles insert in the bilayer membranes of synthetic phospholipid vesicles or vital cells and mediate the transport of cations. The hydraphiles were intended to be models but they are functional channels. Because they are symmetric, they are non-rectifying but they show open-close behavior characteristic of natural channels. Because they are non-rectifying, when they insert into a microbial membrane, they lead to a rapid change in osmotic balance that proves fatal to bacteria.

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“…By far, the lowest Cl -transport activity is observed for the compounds having octadecyl C-terminal groups (18,19), whether one or two chains are present. More active, but less active than 17, are the 2°-decyl (16) and 3° diheptyl (15) heptapeptides.…”

Section: C-terminal Secondary and Tertiary Amides As Secondary Anchorsmentioning

confidence: 99%

The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers

et al. 2005

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The synthetic peptide, R 2 N-COCH 2 OCH 2 CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR', was shown to be selective for Cl -over K + when R is n-octadecyl and R' is benzyl. Nineteen heptapeptides have now been prepared in which the N-terminal and C-terminal residues have been varied. All of the Nterminal residues are dialkyl but the C-terminal chains are esters, 2° amides, or 3° amides. The compounds having varied N-terminal anchors and C-terminal benzyl groups are as follows: 1, R = n-propyl; 2, R = n-hexyl; 3, R = n-octyl; 4, R = n-decyl; 5, R = n-dodecyl; 6, R = n-tetradecyl; 7, R = n-hexadecyl; 8, R = n-octadecyl. Compounds 9-19 have R = n-octadecyl and C-terminal residues as follows: 9, OR' = OCH 2 CH 3 ; 10, OR' = OCH(CH 3 ) 2 ; 11, OR' = O(CH 2 ) 6 CH 3 ; 12, OR' = OCH 2 -c-C 6 H 11 ; 13, OR' = O(CH 2 ) 9 CH 3 ; 14, OR' = O (CH 2 ) 17

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A,B,D,F-tetrasubstituted β-cyclodextrin as artificial channel compound

Cited by 229 publications

References 13 publications

Reversal of charge selectivity in transmembrane protein pores by using noncovalent molecular adapters

Reversal of charge selectivity in transmembrane protein pores by using noncovalent molecular adapters

Coordination and transport of alkali metal cations through phospholipid bilayer membranes by hydraphile channels

The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers

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