Synthetic Organic Chemical Models for Transmembrane Channels

Gokel, George W.; Murillo, Óscar

doi:10.1021/ar9601353

Cited by 191 publications

(127 citation statements)

References 67 publications

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“…Some early attempts to design channels involved the preparation of cylindrical structures or compounds that looked cylindrical [26]. In some of these early studies, only the conceptualization and synthesis were presented.…”

Section: The Elements Of Channel Designmentioning

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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Section: The Elements Of Channel Designmentioning

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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“…Synthetic organic channels 2 are more amenable to structure-activity studies because of their smaller size and the fact that the most successful ones were designed to be modular. 3 In previous work, we developed a successful cation-transporting channel compound. 4 Although it was designed to be a model for proteins, it is a true channel.…”

Section: Introductionmentioning

confidence: 99%

“…It was constructed from four key modules. The central element is a heptapeptide that has the sequence (Gly) 3 Pro(Gly) 3 . The sequence was based on the conserved Gly-Xxx-Xxx-Pro sequence identified in the CLC family of chloride transporters.…”

Section: Introductionmentioning

confidence: 99%

“…The amphiphilic peptide 7 (C 18 H 37 ) 2 NCOCH 2 OCH 2 CONH-(Gly) 3 Pro(Gly) 3 OCH 2 Ph 8 showed remarkable properties when it inserted into phospholipid bilayers. 9 In a previous study reported in this Journal, we showed that changing the central amino acid in the heptapeptide from proline to pipecolic acid dramatically altered the ion transport profile of this compound.…”

Section: Introductionmentioning

confidence: 99%

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Anion transport in liposomes responds to variations in the anchor chains and the fourth amino acid of heptapeptide ion channels

et al. 2005

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Seven heptapeptide derivatives have been prepared. The peptide structure is (Gly) 3 Xxx(Gly) 3 in which Xxx stands for a variable amino acid. The amino acid variations include azetidine carboxylic acid, pipecolic acid, meta-aminobenzoic acid, proline, and leucine. All seven compounds have a Cterminal benzyl group. In all cases, the heptapeptide's N-terminus was linked to diglycolic acid and a dialkylamine. In five cases, the N-terminal group was didecylamine and in two cases, N-ethyl-Ndecyl. Chloride and carboxyfluorescein release from phospholipid vesicles was studied with the result that C 10 H 21 N(C 2 H 5 ) COCH 2 OCH 2 CO-NH-(Gly) 3 Leu(Gly) 3 -OCH 2 Ph was the most active. Hill analysis showed that this compound involves pore formation by four monomer units rather than two, as previously found for other members of this family.

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“…[1,2] A particular interest presents modification of crown macrocycles that involves fusing them with small nitrogenous pharmacophore moieties such as derivatives of pyrrole, pyridine, piperidine, etc. Recently we have developed a modified Petrenko-Kritschenko type cascade condensation of 1,5-bis(2-formylphenoxy)-3-oxapentane (1) with dialkylketones and ammonium acetate, which afforded high yields of azacrown ethers which include a piperidine subunit.…”

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confidence: 99%

Unexpected Formation of [(Δ3-Piperideino)pyrimidino]-14-crown-4 Ethers in a Petrenko-Kritschenko Type Condensation

Hieu¹,

Anh²,

Солдатенков³

et al. 2013

MHC

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Synthetic Organic Chemical Models for Transmembrane Channels

Cited by 191 publications

References 67 publications

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

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

Anion transport in liposomes responds to variations in the anchor chains and the fourth amino acid of heptapeptide ion channels

Unexpected Formation of [(Δ3-Piperideino)pyrimidino]-14-crown-4 Ethers in a Petrenko-Kritschenko Type Condensation

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