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Enantiorecognition in a multi-component environment.
Joanna Mazurkiewicz1,2, Ewa Stanek2,3, Pedro Maximiano4
1Faculty of Chemistry, Jagiellonian University, 2 Gronostajowa Str., Krakow 30-387, Poland. agnieszka.kaczor@uj.edu.pl.
Physical Chemistry Chemical Physics : PCCP
|February 17, 2025
Summary
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.
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.
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