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Related Concept Videos

Electron Carriers01:24

Electron Carriers

Electron carriers can be thought of as electron shuttles. These compounds can easily accept electrons (i.e., be reduced) or lose them (i.e., be oxidized). They play an essential role in energy production because cellular respiration is contingent on the flow of electrons.
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Transcellular transport of solutes is the movement of substances like monosaccharides and amino acids through polarized cells. This transport mechanism is primarily seen in epithelial and endothelial cells aided by membrane transport proteins such as channels and transporters. The tight junctions between these cells confine the membrane proteins to the two sides of the cell. The epithelial cells have distinct apical and basolateral domains. In contrast, the endothelial cells show the luminal...
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The energy released from the breakdown of the chemical bonds within nutrients can be stored either through the reduction of electron carriers or in the bonds of adenosine triphosphate (ATP). In living systems, a small class of compounds functions as mobile electron carriers, molecules that bind to and shuttle high-energy electrons between compounds in pathways. The principal electron carriers that will be considered originate from the B vitamin group and are derivatives of nucleotides; they are...
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Electron Transport Chain Components

The electron transport chain (ETC) is a crucial metabolic pathway that facilitates energy conversion in prokaryotic and eukaryotic cells. In eukaryotes, the ETC comprises four membrane-associated protein complexes in the inner mitochondrial membrane. In prokaryotes, the ETC in the plasma membrane can vary in composition, with fewer or different complexes depending on the organism and environmental conditions. These complexes transfer electrons from electron donors, such as NADH and FADH2, to...
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Host-[2]rotaxanes as cellular transport agents.

Vadims Dvornikovs1, Brian E House, Marcia Kaetzel

  • 1Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, USA.

Journal of the American Chemical Society
|July 3, 2003
PubMed
Summary

Host-[2]rotaxanes, featuring a dibenzo-24-crown-8 ether ring, act as effective cell transport agents. They efficiently bind amino acids and fluorophores, facilitating cellular uptake, including nuclear transport.

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Biology
  • Materials Science

Background:

  • Host-[2]rotaxanes are designed supramolecular structures with potential applications in molecular transport.
  • Dibenzo-24-crown-8 (DB24C8) ether and cyclophane moieties are key components influencing host-guest interactions.
  • Understanding the binding affinities and transport capabilities of these rotaxanes is crucial for their development.

Purpose of the Study:

  • To investigate the binding affinities of host-[2]rotaxanes with various guests in different solvent systems.
  • To evaluate the cell transport efficiency of these rotaxanes for biologically relevant molecules.
  • To compare the transport capabilities of different rotaxane architectures.

Main Methods:

  • Synthesis and characterization of host-[2]rotaxanes with cyclophane or aromatic cleft blocking groups.
  • Spectroscopic determination of association constants (K(A)) for guest binding in aqueous buffer, DMSO, and mixed solvent systems.
  • Cellular uptake studies using fluorescently labeled guests and COS-7 cells to assess transport efficiency.

Main Results:

  • Host-[2]rotaxanes exhibit strong association constants (10^4 to 10^5 M^-1) for peptidic guests and fluorophores across tested solvents.
  • The rotaxane architecture enhances guest binding compared to the cyclophane component alone.
  • Cyclophane-[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-PKC inhibitor into COS-7 cells, including the nucleus.
  • Cleft-[2]rotaxane 2 shows less efficient fluorescein transport despite similar binding affinity, indicating architecture-dependent cellular delivery.

Conclusions:

  • Host-[2]rotaxanes are effective molecular transporters capable of binding diverse guests with high affinity.
  • The rotaxane structure is advantageous for molecular recognition and binding.
  • The specific rotaxane architecture significantly influences cellular uptake efficiency, highlighting the importance of structural design for targeted delivery.