Cation Dependence of Chloride Ion Complexation by Open-Chained Receptor Molecules in Chloroform Solution

Pajewski, Robert; Ferdani, Riccardo; Pajewska, Jolanta; Li, Ruiqiong; Gokel, George W.

doi:10.1021/ja0558894

Cited by 36 publications

(37 citation statements)

References 56 publications

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“…13 All reactions were conducted under dry N 2 unless otherwise stated. All reagents were the best (non-LC) grade commercially available and were distilled, recrystallized, or used without further purification, as appropriate.…”

Section: Experimental Generalmentioning

confidence: 99%

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Transport of chloride and carboxyfluorescein through phospholipid vesicle membranes by heptapeptide amphiphiles

Ferdani¹,

Li²,

Pajewski³

et al. 2007

Org. Biomol. Chem.

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Seven synthetic anion transporters (SAT) of the general form R 2 N-COCH 2 OCH 2 CO-(Gly) 3 -Pro-(Gly) 3 -OR' were prepared. Three pairs of compounds each contained twin n-hexyl, n-decyl, and noctadecyl (R) groups at the N-terminus and one contained twin n-tetradecyl groups. Three of the compounds were C-terminated by benzyl and three by heptyl (R') residues. The ability of these compounds to mediate ion release from phospholipid vesicles was assessed. Chloride release was measured by ion selective electrode measurements and by chloride quenching of the fluorescent dye lucigenin. Transport of the anion carboxyfluorescein (CF) was measured by fluorescence dequenching. Differences in both the C-(R') and N-terminal (R) residues within the ionophores affected anion transport. The chloride release data acquired by ion selective electrode and fluorescence methods were similar but not identical. A possible carrier mechanism for Cl -transport was discredited. Both Cl -and CF anions were released from vesicles by these compounds. The results of CF and Cl -transport showed good consistency when the ionophore's N-terminal chains were either decyl or octadecyl but not when they were hexyl. The transport of CF and Cl -appears to be fundamentally different when R is C 6 compared to C 10 or C 18 . Differences between the behavior of SATs with Cl -and CF were also reflected in negative ion mass spectrometric studies.

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Section: Experimental Generalmentioning

confidence: 99%

“…10,11 In addition, Cl -complexation by 1 and several relatives was demonstrated by NMR methods. [12][13][14] Recently, an alternative method has been developed that is based on a fluorescent dye, lucigenin. 15 It has already found application in other transporter systems.…”

Section: Introductionmentioning

confidence: 99%

Transport of chloride and carboxyfluorescein through phospholipid vesicle membranes by heptapeptide amphiphiles

Ferdani¹,

Li²,

Pajewski³

et al. 2007

Org. Biomol. Chem.

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“…To establish that the synthetic anion transporters directly interact with Cl -, we conducted detailed NMR studies in CDCl 3 [66]. The first step in this study required the preparation of six amphiphilic, labeled peptides of the form (C 3 H 7 ) 2 N-COCH 2 OCH 2 CO-(Gly) 3 -Pro-(Gly) 3 OBn, each differing in the replacement of two H-atoms of a Gly residue with deuterium (D) atoms.…”

Section: Chloride Binding By Amphiphilic Heptapeptidesmentioning

confidence: 99%

Synthetic, Biologically Active Amphiphilic Peptides

Yamnitz

Gokel

2007

Chemistry & Biodiversity

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Amphiphilic peptides typically consist of a peptide portion that may be 5-25 (or more) amino acids in length. The hydrophobic portion may be a single fatty acid residue, but can also be more elaborate. The main focus of this article lies on the family of synthetic anion binders (SATs) of the general structure (R 1 ) 2 N-COCH 2 OCH 2 CO-(Aaa) n -OR 3 . The most-common R 1 groups are octadecyl (C 18 H 37 ). The most studied peptide sequence in this family is (Gly) 3 -Pro-(Gly) 3 , although different sequences (and longer and shorter peptides) have been prepared as well. The C-terminal ester residue providing the most effective anion release from liposomes is heptyl (C 7 H 15 ), although many others have been examined. The compound (C 18 H 37 ) 2 N-COCH 2 OCH 2 CO-(Gly) 3 -Pro-(Gly) 3 -OBn (Bn=benzyl) was found to mediate Cl -transport in mouse epithelial cells.

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“…[3][4][5][6][7][8][9][10][11] The bridging of a pair of NH groups by anionic or δ -atoms forming a nest is common within larger motifs like the Schellman loop and is a means of binding anionic groups such as phosphates and iron-sulfur centers. 2,[12][13][14][15][16][17] On the other hand, the bridging of two carbonyl groups by cationic or δ + atoms, though addressed by a number of authors, has not been fully explored. 3,[18][19][20][21] Much of the interesting work on main chain bridging has focused on water molecules.…”

Section: Introductionmentioning

confidence: 99%