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Assembly of Cell Mimicking Supported and Suspended Lipid Bilayer Models for the Study of Molecular Interactions
Published on: August 3, 2021
Alkyl esters of L-ascorbic acid: Stability, surface behaviour and interaction with phospholipid monolayers
Milagro Mottola1, Raquel V Vico2, Martín E Villanueva2
1Centro de Investigaciones en Química Biológica de Córdoba (CIQUIBIC-CONICET), Departamento de Química Biológica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Haya de la Torre y Medina Allende, Ciudad Universitaria, X5000HUA Córdoba, Argentina; Instituto de Investigaciones en Fisicoquímica de Córdoba (INFIQC-CONICET), Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Haya de la Torre y Medina Allende, Ciudad Universitaria, X5000HUA Córdoba, Argentina.
L-ascorbic acid alkyl esters (ASCn) are stable, amphiphilic compounds with pharmaceutical potential. Longer chain ASCn molecules exhibit significant surface activity and interact with lipid membranes, influencing their pharmacological effects.
Area of Science:
- Biochemistry
- Materials Science
- Pharmaceutical Chemistry
Background:
- L-ascorbic acid alkyl esters (ASCn) are amphiphilic molecules with potential antioxidant properties.
- ASCn exhibit greater stability against oxidation and tautomeric isomerization compared to L-ascorbic acid.
Purpose of the Study:
- To investigate the stability and surface properties of ASCn with varying acyl chain lengths.
- To explore the interaction of ASCn with phospholipid monolayers and understand their differential pharmacological activity.
Main Methods:
- Langmuir film formation and analysis.
- Brewster angle microscopy to observe two-dimensional domain structures.
- Investigation of ASCn penetration into phospholipid monolayers.
Main Results:
- ASC14 and ASC16 form stable monolayers at negative charge, while ASC10 and ASC12 do not.
- ASC16 films exhibit a liquid-expanded to liquid-condensed phase transition; ASC14 shows only a liquid-expanded phase.
- Longer chain ASCn (ASC16, ASC14, ASC12) display surface activity, form Gibbs monolayers, and penetrate phospholipid monolayers up to 45-50 mN/m.
- 1-palmitoyl-2-oleoylphosphatidylcholine/ASCn films show liquid-condensed and/or crystalline domains only with ASC16.
Conclusions:
- ASCn stability and surface behavior are dependent on acyl chain length and charge.
- ASCn demonstrate significant surface activity and membrane interaction capabilities.
- Understanding ASCn-lipid interactions is crucial for elucidating their distinct pharmacological profiles.
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