Computational insight into the structure-activity relationship of novel N -substituted phthalimides with gibberellin-like activity
| LEADER | caa a22 4500 | ||
|---|---|---|---|
| 001 | 605512248 | ||
| 003 | CHVBK | ||
| 005 | 20210128100654.0 | ||
| 007 | cr unu---uuuuu | ||
| 008 | 210128e20151001xx s 000 0 eng | ||
| 024 | 7 | 0 | |a 10.1007/s00894-015-2817-8 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2817-8 | ||
| 245 | 0 | 0 | |a Computational insight into the structure-activity relationship of novel N -substituted phthalimides with gibberellin-like activity |h [Elektronische Daten] |c [Dongling Li, Shaoqing Du, Weiming Tan, Hongxia Duan] |
| 520 | 3 | |a N-substituted phthalimides (NSPs) that show multiple gibberellin (GA)-like effects on the growth and development of higher plants have been reported. These NSPs may represent a potential alternative to commercial GAs. Therefore, in this work, molecular docking and molecular dynamics simulations were used to explore the mode of interaction between some NSPs and the GA receptor GID1A in order to clarify the relationship between structure and GA-like activity in the NSPs. The results obtained demonstrate that both a multiple-hydrogen-bond network and a "hat-shaped” hydrophobic interaction play important roles in the binding of the NSPs to GID1A. The carbonyl group of a phthalimide fragment in the NSPs acted in a similar manner to the pharmacophore group 6-COOH in GAs, forming multiple-hydrogen-bond interactions with residues Ser191 and Tyr322 in the binding domain of GID1A. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were used to further study the 3D quantitative structure-activity relationship (3D-QSAR) of the NSPs. It was confirmed that the GA-like activity of these NSPs is strongly linked to a few H-bond donor and acceptor field contributions of the NSPs to the H-bond interactions with GID1A. Five new NSP molecules D1-D5 were designed using the binding domain of GID1A and then docked into the receptor. D1 and D4 were shown to have good docking scores due to enhanced hydrophobic contact. We hope that these results will provide useful guidance in the rational design of new NSPs. Graphical Abstract Molecular docking and molecular dynamics simulations were used to explore the interaction mode between N-substituted phthalimides (NSPs) and the gibberellin (GA) receptor GID1A to clarify the relationship between structure and GA-like activity for the NSPs. A multiple-hydrogen-bond network and a "hat-shaped” hydrophobic interaction were found to play important roles in the binding of NSPs to GID1A. These H-bond interactions were further shown to influence the GA-like activity of the NSPs via some H-bond donor and acceptor molecular fields | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a NSPs |2 nationallicence | |
| 690 | 7 | |a GAs |2 nationallicence | |
| 690 | 7 | |a GID1A |2 nationallicence | |
| 690 | 7 | |a Structural-activity relationship |2 nationallicence | |
| 690 | 7 | |a Plant growth regulators |2 nationallicence | |
| 700 | 1 | |a Li |D Dongling |u Department of Applied Chemistry, College of Science, China Agricultural University, 100193, Beijing, China |4 aut | |
| 700 | 1 | |a Du |D Shaoqing |u Department of Applied Chemistry, College of Science, China Agricultural University, 100193, Beijing, China |4 aut | |
| 700 | 1 | |a Tan |D Weiming |u Engineering Research Center of Plant Growth Regulators, Ministry of Education, College of Agronomy and Biotechnology, China Agricultural University, 100193, Beijing, China |4 aut | |
| 700 | 1 | |a Duan |D Hongxia |u Department of Applied Chemistry, College of Science, China Agricultural University, 100193, Beijing, China |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/10(2015-10-01), 1-10 |x 1610-2940 |q 21:10<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2817-8 |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/s00894-015-2817-8 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Li |D Dongling |u Department of Applied Chemistry, College of Science, China Agricultural University, 100193, Beijing, China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Du |D Shaoqing |u Department of Applied Chemistry, College of Science, China Agricultural University, 100193, Beijing, China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Tan |D Weiming |u Engineering Research Center of Plant Growth Regulators, Ministry of Education, College of Agronomy and Biotechnology, China Agricultural University, 100193, Beijing, China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Duan |D Hongxia |u Department of Applied Chemistry, College of Science, China Agricultural University, 100193, Beijing, China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/10(2015-10-01), 1-10 |x 1610-2940 |q 21:10<1 |1 2015 |2 21 |o 894 | ||