On the interactions of leflunomide and teriflunomide within receptor cavity — NMR studies and energy calculations
| LEADER | caa a22 4500 | ||
|---|---|---|---|
| 001 | 605513317 | ||
| 003 | CHVBK | ||
| 005 | 20210128100659.0 | ||
| 007 | cr unu---uuuuu | ||
| 008 | 210128e20150501xx s 000 0 eng | ||
| 024 | 7 | 0 | |a 10.1007/s00894-015-2643-z |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2643-z | ||
| 245 | 0 | 0 | |a On the interactions of leflunomide and teriflunomide within receptor cavity — NMR studies and energy calculations |h [Elektronische Daten] |c [Jacek Kujawski, Marek Bernard, Elżbieta Jodłowska, Kornelia Czaja, Beata Drabińska] |
| 520 | 3 | |a Leflunomide is a disease-modifying antirheumatic drug with antiinflammatory and immunosuppressive activity used for the treatment of psoriatic and rheumatoid arthritis. It undergoes rapid metabolization to teriflunomide, a metabolite that is responsible for the biological activity of leflunomide. Continuing our investigations on the interactions of biologically important azahetarenes with the environment, we focused on leflunomide and its active metabolite, teriflunomide, considering the interactions teriflunomide-amino acid within the target protein (dihydroorotate dehydrogenase) using density functional theory, as well as ONIOM techniques. The results of theoretical studies have shown that the interactions of teriflunomide with tyrosine and arginine involve principally the amide fragment of teriflunomide. The presence of the internal hydrogen bond between (Z)-teriflunomide carbonyl oxygen and enolic hydroxyl decreases the interaction strength between teriflunomide and tyrosine or arginine. Even the E isomer of teriflunomide would usually provide a stronger interaction teriflunomide—amino acid than the Z isomer with the internal hydrogen bond. Graphical Abstract The interactions of leflunomide and teriflunomide within receptor cavityᅟ | |
| 540 | |a The Author(s), 2015 | ||
| 690 | 7 | |a DFT calculations |2 nationallicence | |
| 690 | 7 | |a Hydrogen bond |2 nationallicence | |
| 690 | 7 | |a Leflunomide |2 nationallicence | |
| 690 | 7 | |a NMR calculations |2 nationallicence | |
| 690 | 7 | |a Teriflunomide |2 nationallicence | |
| 700 | 1 | |a Kujawski |D Jacek |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | |
| 700 | 1 | |a Bernard |D Marek |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | |
| 700 | 1 | |a Jodłowska |D Elżbieta |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | |
| 700 | 1 | |a Czaja |D Kornelia |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | |
| 700 | 1 | |a Drabińska |D Beata |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/5(2015-05-01), 1-12 |x 1610-2940 |q 21:5<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2643-z |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2643-z |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Kujawski |D Jacek |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Bernard |D Marek |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Jodłowska |D Elżbieta |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Czaja |D Kornelia |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Drabińska |D Beata |u Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka 6 street, 60-780, Poznań, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/5(2015-05-01), 1-12 |x 1610-2940 |q 21:5<1 |1 2015 |2 21 |o 894 | ||