Preparation, stability, and molecular modeling of nitro-oleic acid/cyclodextrin complexes under aqueous conditions

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388980%3A_____%2F23%3A00572514" target="_blank" >RIV/61388980:_____/23:00572514 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60076658:12310/23:43906654

Výsledek na webu

<a href="https://doi.org/10.1016/j.molliq.2023.122020" target="_blank" >https://doi.org/10.1016/j.molliq.2023.122020</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molliq.2023.122020" target="_blank" >10.1016/j.molliq.2023.122020</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Preparation, stability, and molecular modeling of nitro-oleic acid/cyclodextrin complexes under aqueous conditions

Popis výsledku v původním jazyce

Nitro-oleic acid (NO2-OA) is an endogenously produced pleiotropic modulator involved in cell redox homeostasis. The intrinsic property of NO2-OA is a decay reaction under aqueous conditions. This aqueous instability is simultaneously a problematic issue for NO2-OA sample handling and NO2-OA application in general. In this work NO2-OA (eq. mol. 9/10-NO2 isomers) was encapsulated with β-cyclodextrin (β-CD). The formation of the β-CD/NO2-OA complex was determined based on 1H NMR. The QM calculations revealed that dispersion forces are crucial for the stability of the complex. Based on thermogravimetry–differential scanning calorimetry, free NO2-OA was less thermally stable than its inclusion β-CD complex. The electrochemical reduction of the nitro group was investigated to determine the degradation kinetics of β-CD/NO2-OA. Under aqueous conditions, β-CD/NO2-OA degrades at a similar rate to NO2-OA alone. However, when β-CD/NO2-OA is stored in solid (lyophilized) form, no degradation was observed for a one-month period.

Název v anglickém jazyce

Preparation, stability, and molecular modeling of nitro-oleic acid/cyclodextrin complexes under aqueous conditions

Popis výsledku anglicky

Nitro-oleic acid (NO2-OA) is an endogenously produced pleiotropic modulator involved in cell redox homeostasis. The intrinsic property of NO2-OA is a decay reaction under aqueous conditions. This aqueous instability is simultaneously a problematic issue for NO2-OA sample handling and NO2-OA application in general. In this work NO2-OA (eq. mol. 9/10-NO2 isomers) was encapsulated with β-cyclodextrin (β-CD). The formation of the β-CD/NO2-OA complex was determined based on 1H NMR. The QM calculations revealed that dispersion forces are crucial for the stability of the complex. Based on thermogravimetry–differential scanning calorimetry, free NO2-OA was less thermally stable than its inclusion β-CD complex. The electrochemical reduction of the nitro group was investigated to determine the degradation kinetics of β-CD/NO2-OA. Under aqueous conditions, β-CD/NO2-OA degrades at a similar rate to NO2-OA alone. However, when β-CD/NO2-OA is stored in solid (lyophilized) form, no degradation was observed for a one-month period.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

<a href="/cs/project/LM2018124" target="_blank" >LM2018124: Nanomateriály a nanotechnologie pro ochranu životního prostředí a udržitelnou budoucnost</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

Journal of Molecular Liquids

ISSN

0167-7322

e-ISSN

1873-3166

Svazek periodika

383

Číslo periodika v rámci svazku

AUG

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

122020

Kód UT WoS článku

001013072800001

EID výsledku v databázi Scopus

2-s2.0-85159771995