Insights into the Structural Requirements of Potent Brassinosteroids as Vegetable Growth Promoters Using Second-Internode Elongation as Biological Activity: CoMFA and CoMSIA Studies

Ferrer, Karoll; Espinoza, Luis; Mella, Jaime

doi:10.3390/ijms18122734

Cited by 8 publications

(8 citation statements)

References 47 publications

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“…Additionally, BRs analogues obtained from deoxycholic and hyodeoxycholic acids have turned out to show excellent bioactivity in the rice lamina inclination assay [ 72 , 73 ]. Using a 3D-QSAR it has been possible to establish a structure-activity relationship which indicates that activity is favored by the following structural parameters: presence of hydroxyl groups at C22 and voluminous group in the end of alkyl chain; the hydroxyl group in C3 of ring A is indispensable [ 74 ]. The 3D contour maps showed that the growth promoting activity of the compounds was influenced mainly by electrostatic properties and the presence of hydrogen-bond acceptor groups [ 74 ].…”

Section: Design and Synthesis Of Molecules For The Exogenous Stimumentioning

confidence: 99%

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Figueroa-Macías

García

Núñez

et al. 2021

IJMS

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In order to survive in a hostile habitat, plants have to manage the available resources to reach a delicate balance between development and defense processes, setting up what plant scientists call a trade-off. Most of these processes are basically responses to stimuli sensed by plant cell receptors and are influenced by the environmental features, which can incredibly modify such responses and even cause changes upon both molecular and phenotypic level. Therefore, significant differences can be detected between plants of the same species living in different environments. The comprehension of plant growth-defense trade-offs from the molecular basis to the phenotypic expression is one of the fundamentals for developing sustainable agriculture, so with this review we intend to contribute to the increasing of knowledge on this topic, which have a great importance for future development of agricultural crop production.

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Section: Design and Synthesis Of Molecules For The Exogenous Stimumentioning

confidence: 99%

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Figueroa-Macías

García

Núñez

et al. 2021

IJMS

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“…In this way, BRs analogs with shorter side chains [19][20][21][22] and/or including a variety of substituents [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] have been reported. The biological activity of these synthetic BRs analogs seems to depend on the spatial distribution of oxygen atoms instead of the presence or absence of one specific functional group in the molecule [11,18], and consequently some new SAR have been proposed [40][41][42].…”

Section: Introductionmentioning

confidence: 99%

Biological Activities and Molecular Docking of Brassinosteroids 24-Norcholane Type Analogs

Díaz

Espinoza

Carvajal

et al. 2020

IJMS

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The quest and design of new brassinosteroids analogs is a matter of current interest. Herein, the effect of short alkyl side chains and the configuration at C22 on the growth-promoting activity of a series of new brassinosteroid 24-norcholan-type analogs have been evaluated by the rice leaf inclination test using brassinolide as positive control. The highest activities were found for triol 3 with a C22(S) configuration and monobenzoylated derivatives. A docking study of these compounds into the active site of the Brassinosteroid Insensitive 1(BRI1)–ligand–BRI1-Associated Receptor Kinase 1 (BAK1) complex was performed using AutoDock Vina, and protein–ligand contacts were analyzed using LigPlot+. The results suggest that the hydrophobic interactions of ligands with the receptor BRI1LRR and hydrogen bonding with BAK1 in the complex are important for ligand recognition. For monobenzoylated derivatives, the absence of the hydrophobic end in the alkyl chain seems to be compensated by the benzoyl group. Thus, it would be interesting to determine if this result depends on the nature of the substituent group. Finally, mixtures of S/R triols 3/4 exhibit activities that are comparable or even better than those found for brassinolide. Thus, these compounds are potential candidates for application in agriculture to improve the growth and yield of plants against various types of biotic and abiotic stress.

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“…Partial least squares (PLS) is an extension of the multiple regression (MR). It was applied to linearly correlate the variance in CoMSIA and CoMFA fields to variations in pIC 50 values of compounds [ 40 ]. In this study, PLS was performed in two stages including the first with leave-one-out (LOO) cross-validation to obtain the optimal number of components (ONC), which represents the complexity level of a model and corresponds to the highest cross-validated r 2 (called q 2 ) [ 41 , 42 ].…”

Section: Methodsmentioning

confidence: 99%

Molecular Modeling and Design Studies of Purine Derivatives as Novel CDK2 Inhibitors

Zhang

Ren

2018

Molecules

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Cyclin-dependent kinase 2 (CDK2) is a potential target for treating cancer. Purine heterocycles have attracted particular attention as the scaffolds for the development of CDK2 inhibitors. To explore the interaction mechanism and the structure–activity relationship (SAR) and to design novel candidate compounds as potential CDK2 inhibitors, a systematic molecular modeling study was conducted on 35 purine derivatives as CDK2 inhibitors by combining three-dimensional quantitative SAR (3D-QSAR), virtual screening, molecular docking, and molecular dynamics (MD) simulations. The predictive CoMFA model (q2 = 0.743, rpred2 = 0.991), the CoMSIA model (q2 = 0.808, rpred2 = 0.990), and the Topomer CoMFA model (q2 = 0.779, rpred2 = 0.962) were obtained. Contour maps revealed that the electrostatic, hydrophobic, hydrogen bond donor and steric fields played key roles in the QSAR models. Thirty-one novel candidate compounds with suitable predicted activity (predicted pIC50 > 8) were designed by using the results of virtual screening. Molecular docking indicated that residues Asp86, Glu81, Leu83, Lys89, Lys33, and Gln131 formed hydrogen bonds with the ligand, which affected activity of the ligand. Based on the QSAR model prediction and molecular docking, two candidate compounds, I13 and I60 (predicted pIC50 > 8, docking score > 10), with the most potential research value were further screened out. MD simulations of the corresponding complexes of these two candidate compounds further verified their stability. This study provided valuable information for the development of new potential CDK2 inhibitors.

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Insights into the Structural Requirements of Potent Brassinosteroids as Vegetable Growth Promoters Using Second-Internode Elongation as Biological Activity: CoMFA and CoMSIA Studies

Cited by 8 publications

References 47 publications

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Biological Activities and Molecular Docking of Brassinosteroids 24-Norcholane Type Analogs

Molecular Modeling and Design Studies of Purine Derivatives as Novel CDK2 Inhibitors

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