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CC-BY-NC-ND - Uznanie autorstwa - Użycie niekomercyjne - Bez utworów zależnychAn X-ray and Natural Bond Orbital (NBO) structural study of α-tocopheryl and 2,2,5,7,8-pentamethylchroman-6-yl succinates
| cris.lastimport.scopus | 2024-02-12T19:36:01Z |
| dc.abstract.en | α-Tocopheryl succinate (α-TOS) is a very promising anticancer agent; however, the mechanism of its action and the role of the succinic moiety in biological activity still remains unclear. This paper, presents the first determination of the X-ray structure of α-TOS and 2,2,5,7,8-pentamethylchroman-6-yl succinate (PMCS). The X-ray data indicated high out of planarity deformation of the aryl ring in the chroman-6-ol system. α-TOS and PMCS differed in angle θ value (28.4° vs. 21.5°, respectively) and in their heterocyclic ring conformations: 2-endo-3-exo in PMCS, and 2-endo-3-exo and 2-exo-3-endo in α-TOS. Due to their strong intermolecular hydrogen bonds, both succinates form cyclically repeated dimeric structures in well assembled crystal supramolecular structures. A population analysis of α-tocopherol (α-TOC), 2,2,5,7,8-pentamethylchroman-6-ol (PMC) and their acyl derivatives was performed at B3LYP/6-31G(d,p)/CPCM level of theory using a natural bond orbital (NBO) analysis within the Gaussian 09 program package. For all compounds, relaxed scans were performed along torsion angle γ, and for low-energy conformers the Fukui functions were calculated: electron donor (ƒ−(r)), electron acceptor (ƒ+(r)), free radical (ƒo(r)) and dual descriptor (ƒ2(r)). In general, the differences observed between α-TOC and its acyl derivative structures result from the non-bonding lone pair of the phenolic oxygen and its interaction with aromatic system π electrons. |
| dc.affiliation | Uniwersytet Warszawski |
| dc.contributor.author | Ratkiewicz, Artur |
| dc.contributor.author | Socha, Paweł |
| dc.contributor.author | Cyrański, Michał |
| dc.contributor.author | Wałejko, Piotr |
| dc.contributor.author | Dobrzycki, Łukasz |
| dc.contributor.author | Witkowski, Stanisław |
| dc.date.accessioned | 2024-01-24T16:43:58Z |
| dc.date.available | 2024-01-24T16:43:58Z |
| dc.date.copyright | 2018-09-04 |
| dc.date.issued | 2019 |
| dc.description.accesstime | AT_PUBLICATION |
| dc.description.finance | Nie dotyczy |
| dc.description.number | 3 |
| dc.description.version | FINAL_PUBLISHED |
| dc.description.volume | 23 |
| dc.identifier.doi | 10.1016/J.JSCS.2018.08.010 |
| dc.identifier.issn | 1319-6103 |
| dc.identifier.uri | https://repozytorium.uw.edu.pl//handle/item/100957 |
| dc.language | eng |
| dc.pbn.affiliation | chemical sciences |
| dc.relation.ispartof | Journal of Saudi Chemical Society |
| dc.relation.pages | 365-377 |
| dc.rights | CC-BY-NC-ND |
| dc.sciencecloud | nosend |
| dc.subject.en | α-Tocopheryl succinate |
| dc.subject.en | X-ray |
| dc.subject.en | Natural Bond Orbital |
| dc.subject.en | DFT calculation |
| dc.subject.en | Fukui function |
| dc.title | An X-ray and Natural Bond Orbital (NBO) structural study of α-tocopheryl and 2,2,5,7,8-pentamethylchroman-6-yl succinates |
| dc.type | JournalArticle |
| dspace.entity.type | Publication |