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

0572514 - ÚACH 2024 RIV NL eng J - Journal Article
Novák, D. - Zatloukalová, M. - Jedinák, L. - Komárková, Bára - Kabeláč, M. - Vacek, J.
Preparation, stability, and molecular modeling of nitro-oleic acid/cyclodextrin complexes under aqueous conditions.
Journal of Molecular Liquids. Roč. 383, AUG (2023), č. článku 122020. ISSN 0167-7322. E-ISSN 1873-3166
R&D Projects: GA MŠMT(CZ) LM2018124
Research Infrastructure: e-INFRA CZ - 90140
Institutional support: RVO:61388980
Keywords : Cyclodextrin * Encapsulation * Fatty acid * Nitric oxide * Nitroalkene * Oleic acid
OECD category: Inorganic and nuclear chemistry
Impact factor: 6, year: 2022
Method of publishing: Limited access
https://doi.org/10.1016/j.molliq.2023.122020

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.
Permanent Link: https://hdl.handle.net/11104/0343176