Two- and Three-Dimensional Physical-Chemical Characterization of CER[AP]: A Study of Stereochemistry and Chain Symmetry

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F21%3A10433995" target="_blank" >RIV/00216208:11160/21:10433995 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=GCqliRMPzI" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=GCqliRMPzI</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.jpcb.1c05572" target="_blank" >10.1021/acs.jpcb.1c05572</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Two- and Three-Dimensional Physical-Chemical Characterization of CER[AP]: A Study of Stereochemistry and Chain Symmetry

Popis výsledku v původním jazyce

The stratum corneum represents the first skin barrier against chemical and physical damage. These unique properties are based on its peculiar lipid composition with ceramides (CERs) as the main protagonists. In this study, the structural and chemical properties of the alpha-OH phytosphingosine [AP] CER class have been investigated. alpha-OH CERs are present in the stratum corneum in their D-forms; however, in most model systems the diastereomer mixture with the synthetically produced L-form is used. The D-form is well-known to form a hydrogen bonding network that helps to reduce the permeability of the lipid matrix, while the L-form does not show any hydrogen bonding network formation. In this paper, 2D (monolayers) and 3D (aqueous dispersions) models have been used to thoroughly study the physical-chemical behaviors of CER[AP] diastereomers taking into account how the symmetry of the chain pattern influences the behavior of the molecules. The chains of both diastereomers arrange in an oblique unit cell, but only the D-CER[AP] forms a supramolecular lattice (subgel phase) in both model systems. Interestingly, the chain pattern does not play any role in structure formation since the hydrogen bonding network dictates the packing properties. The 1:1 mixture of the diastereomers phase separates into two domains: one is composed of practically pure D-form and the other one is composed of a mixture of the L-form with a certain amount of D-form molecules.

Název v anglickém jazyce

Two- and Three-Dimensional Physical-Chemical Characterization of CER[AP]: A Study of Stereochemistry and Chain Symmetry

Popis výsledku anglicky

The stratum corneum represents the first skin barrier against chemical and physical damage. These unique properties are based on its peculiar lipid composition with ceramides (CERs) as the main protagonists. In this study, the structural and chemical properties of the alpha-OH phytosphingosine [AP] CER class have been investigated. alpha-OH CERs are present in the stratum corneum in their D-forms; however, in most model systems the diastereomer mixture with the synthetically produced L-form is used. The D-form is well-known to form a hydrogen bonding network that helps to reduce the permeability of the lipid matrix, while the L-form does not show any hydrogen bonding network formation. In this paper, 2D (monolayers) and 3D (aqueous dispersions) models have been used to thoroughly study the physical-chemical behaviors of CER[AP] diastereomers taking into account how the symmetry of the chain pattern influences the behavior of the molecules. The chains of both diastereomers arrange in an oblique unit cell, but only the D-CER[AP] forms a supramolecular lattice (subgel phase) in both model systems. Interestingly, the chain pattern does not play any role in structure formation since the hydrogen bonding network dictates the packing properties. The 1:1 mixture of the diastereomers phase separates into two domains: one is composed of practically pure D-form and the other one is composed of a mixture of the L-form with a certain amount of D-form molecules.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

<a href="/cs/project/GA19-09600S" target="_blank" >GA19-09600S: Integrovaná metodologie návrhu nanoformulačních procesů pro (trans-)dermální doručování účinných látek</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Physical Chemistry B

ISSN

1520-6106

e-ISSN

—

Svazek periodika

125

Číslo periodika v rámci svazku

35

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

10

Strana od-do

9960-9969

Kód UT WoS článku

000696174500005

EID výsledku v databázi Scopus

2-s2.0-85114853109