An artificial ionophore based on a polyhydroxylated steroid dimer

Riccardis, Francesco De; Filippo, Marcello Di; Garrisi, Davide; Izzo, Irene; Mancin, Fabrizio; Pasquato, Lucia; Scrimin, Paolo; Tecilla, Paolo

doi:10.1039/b208943b

Cited by 25 publications

(21 citation statements)

References 16 publications

(14 reference statements)

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“…10). 95 According to Na NMR kinetics, dimeric steroid 46 mediates the influx of sodium cations into PC/PG vesicles (95:5). The concentration dependence of this activity is in agreement with endergonic formation of a trimeric barrel-stave supramolecule as the active structure.…”

Section: Barrel-stave Supramoleculesmentioning

confidence: 99%

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Recent synthetic ion channels and pores

2004

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Section: Barrel-stave Supramoleculesmentioning

confidence: 99%

“…Synthetic ion channels and pores formed by ionophoric(85,86), 'smart'(88,89) and cationic(90)(91)(92)(93)(94)(95)(96)(97)(98)(99)(100)(101)(102)(103)(104)(105) polymers of interest as antibiotics(90 -105) and for drug delivery with triggered endosomal escape(88,89).…”

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confidence: 99%

Recent synthetic ion channels and pores

2004

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“…Recently, the synthesis of a tail-to-tail triad of (20S)-5-23,24bisnorchol-16-en-3,6,7,22-tetrol derivative with the terephthalate linker has been presented by Di Filippo and coworkers (Di Filippo et al, 2003). The triad compound was active as a Na + -transporting trans-membrane channel (De Riccardis et al, 2002). Among steroids, bile acids are the most frequently used for the synthesis of dimeric and oligomeric artificial receptors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characteristics of lithocholate triads: steroid-type channels occupied by spacer fragments

Rychłewska

Warżajtis

Joachimiak

et al. 2008

Acta Crystallogr Sect B

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Reported in this paper are the syntheses and X-ray investigations of C(2) symmetrical molecular A-B-A triads consisting of two steroid units (lithocholic acid or its methyl ester) joined together by linkers derived from bifunctional molecules such as terephthalic acid or N,N'-dicarboxypiperazine. Unlike their monomeric analogues, some of these compounds form inclusion complexes. All steroidal triads form crystals that are highly pseudo-centrosymmetric, in which the constituting molecules are held together either exclusively by van der Waals forces or form lattice inclusion complexes, with guest molecules hydrogen bonded to the host. The presence of carboxyl groups promotes the inclusion of pyridine molecules and the formation of the well known carboxylic acid...pyridine hydrogen bonds. Combined with pairwise face-to-face pi-stacking between pyridine rings, these hydrogen-bond interactions lead to the formation of extended supramolecular tapes, analogous to polymers. The co-crystals of pyridine and a lithocholic acid triad undergo a symmetry-lowering phase transition from a P1 cell with Z = 1 to a P1 cell with Z = 2. The two structures are virtually the same, the two independent molecules in the larger cell being related by pseudo-translation. Changes in the type of spacer between two methyl lithocholate units from planar aromatic (terephthalic acid) to highly puckered aliphatic six-membered ring (N,N'-dicarboxypiperazine) bring about inclusion properties and changes in side-chain conformation in a crystal. Although the efficient packing of these highly elongated molecules is hindered, as indicated by low values of crystal density, ranging from 1.16 to 1.19 g cm(-3), several very short C...O and H...H contacts are present in the crystals.

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“…For an organic chemist entering the field without BLMs, [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] LUVs provide a user friendly and, according to the comparative studies discussed below, valid alternative. Among several possible methods to determine anion/cation selectivity of synthetic ion channels in vesicles, the HPTS assay worked best in our hands (Fig.…”

Section: Determination Of Anion/cation Selectivity In Vesicles For Symentioning

confidence: 99%

The determination of the ion selectivity of synthetic ion channels and pores in vesicles

Sakai

Matile

2006

J of Physical Organic Chem

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Organic chemists entering the field of synthetic ion channels and pores are often restricted to the characterization of their creation by fluorescence kinetics in vesicles and do not have access to conductance experiments in planar bilayer membranes. This limitation excludes the application of methods to evaluate key characteristics such as ion selectivity or voltage gating that are routine in the membrane biophysics community.

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An artificial ionophore based on a polyhydroxylated steroid dimer

Abstract: The Na+ transporting properties of the first member of a new class of artificial ionophores, based on a C2-symmetric polyhydroxylated steroid dimer, are described.

Cited by 25 publications

References 16 publications

Recent synthetic ion channels and pores

Recent synthetic ion channels and pores

Synthesis and structural characteristics of lithocholate triads: steroid-type channels occupied by spacer fragments

The determination of the ion selectivity of synthetic ion channels and pores in vesicles

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