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Pore Transport and Ion-Pair Transport

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Pore transport and ion-pair formation are critical mechanisms for the absorption and distribution of drugs in the body.
Pore transport, also known as convective transport, is a process where small molecules like urea, water, and sugars rapidly cross cell membranes as though there were channels or pores in the membrane. Although direct microscopic evidence is limited  but the concept of pores or channels is widely accepted based on physiological evidence. Despite the lack of direct...
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Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Anion transport with halogen bonds.

Andreas Vargas Jentzsch1, Stefan Matile

  • 1Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.

Topics in Current Chemistry
|April 4, 2014
PubMed
Summary
This summary is machine-generated.

Halogen bonds enable potent anion transport across lipid membranes, outperforming anion-π interactions. This review highlights macrocyclic and linear scaffolds, including a gas-phase transporter, showcasing halogen bonds

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Area of Science:

  • Supramolecular Chemistry
  • Membrane Transport
  • Chemical Biology

Background:

  • Biological and synthetic systems facilitate ion transport across lipid bilayers.
  • Anion recognition often involves interactions beyond simple coordination or hydrogen bonds, such as cation-π and anion-π interactions.
  • Halogen bonds offer unique properties for designing anion transporters.

Purpose of the Study:

  • To review the application of halogen bonds in transporting anions across lipid bilayer membranes.
  • To emphasize structural motifs and interactions relevant for halogen-bond-mediated anion transport.
  • To compare the efficacy of halogen bonds with other interaction types for anion transport.

Main Methods:

  • Utilizing macrocyclic and linear scaffolds incorporating halogen-bond donors.
  • Employing fluorogenic vesicles to study anion binding in solution and transport across membranes.
  • Conductance experiments in planar bilayer membranes for ion selectivity measurements.
  • Investigating gas-phase anion transport using small organic molecules like trifluoroiodomethane.

Main Results:

  • Macrocyclic scaffolds, particularly calixarene derivatives with cyclic arrays of halogen-bond donors, facilitate anion transport.
  • Monomeric halogen-bond donors, including gaseous trifluoroiodomethane, demonstrate efficient anion transport.
  • Linear scaffolds, such as hydrophobically matching p-oligophenyl rods, act as effective transmembrane transporters.
  • The first synthetic ion channel utilizing cooperative multi-ion hopping via transmembrane halogen-bonding cascades was described.
  • Halogen-bond-mediated anion transport is shown to be more powerful than anion-π interactions.

Conclusions:

  • Halogen bonds are powerful tools for designing efficient synthetic anion transporters.
  • The lipophilicity and directionality of halogen bonds contribute to their effectiveness in membrane transport.
  • Diverse scaffolds, from macrocycles to linear channels, can be engineered for halogen-bond-driven anion transport.