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Joanna Mazurkiewicz1,2, Ewa Stanek2,3, Pedro Maximiano4

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Summary
This summary is machine-generated.

Albumin binds astaxanthin (AXT) enantioselectively, favoring the S,S form over the R,R form, but only when AXT is racemic. This enantiopreference is explained by distinct binding modes and energies.

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Area of Science:

  • Biochemistry
  • Structural Biology
  • Pharmacology

Background:

  • Albumin is a key transport protein with known binding sites for various ligands.
  • Astaxanthin (AXT) is a carotenoid with potential therapeutic applications, existing as different stereoisomers.
  • Understanding stereoisomer-protein interactions is crucial for drug development and bioavailability.

Purpose of the Study:

  • To investigate the enantiopreference in astaxanthin (AXT) binding to albumin.
  • To elucidate the molecular mechanisms underlying AXT enantioselectivity in protein binding.
  • To correlate binding characteristics with AXT stereochemistry.

Main Methods:

  • Chiroptical spectroscopies (e.g., Circular Dichroism) were employed.
  • Computational methods including molecular docking and molecular dynamics simulations were utilized.
  • Quantum-chemical calculations were performed to assess interaction energies.

Main Results:

  • Enantiopreference for (3S,3'S)-AXT over (3R,3'R)-AXT binding to albumin was observed specifically for racemic AXT.
  • A unique binding mode for (3S,3'S)-AXT was identified, contrasting with multiple possibilities for (3R,3'R)-AXT.
  • Higher interaction energy was calculated for the (3R,3'R)-AXT enantiomer with albumin.

Conclusions:

  • Albumin exhibits enantioselectivity towards astaxanthin, favoring the S,S isomer in racemic mixtures.
  • The observed enantiopreference is driven by distinct binding modes and differential interaction energies.
  • These findings provide molecular insights into stereoselective drug-protein interactions.