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3. Synthesis, Biological Activity, and Molecular-Docking Studies of New Brassinosteroid Analogs.

Author

Nuñez, María, Wang, Yaowei, Russinova, Eugenia, Estévez-Braun, Ana, Amesty, Angel, Olea, Andrés F., Mellado, Marco, Díaz, Katy, and Espinoza Catalán, Luis

Subjects
ALKYL group, MOLECULAR dynamics, RUMEX, HYDROXYL group, PHENYL group
Abstract

Much work has been dedicated to the quest to determine the structure–activity relationship in synthetic brassinosteroid (BR) analogs. Recently, it has been reported that analogs with phenyl or benzoate groups in the alkyl chain present activities comparable to those shown by natural BRs, depending on the nature of the substituent in the aromatic ring. However, as it is well known that the activity depends on the structure of the whole molecule, in this work, we have synthesized a series of compounds with the same substituted benzoate in the alkyl chain and a hydroxyl group at C3. The main goal was to compare the activities with analogs with -OH at C2 and C3. Additionally, a molecular-docking study and molecular dynamics simulations were performed to establish a correlation between the experimental and theoretical results. The synthesis of eight new BR analogs was described. All the analogs were fully characterized by spectroscopical methods. The bioactivity of these analogs was assessed using the rice lamina inclination test (RLIT) and the inhibition of the root and hypocotyl elongation of Arabidopsis thaliana. The results of the RLIT indicate that at the lowest tested concentration (1 × 10−8 M), in the BR analogs in which the aromatic ring was substituted at the para position with methoxy, the I and CN substituents were more active than brassinolide (50–72%) and 2–3 times more active than those analogs in which the substituent group was F, Cl or Br atoms. However, at the highest concentrations, brassinolide was the most active compound, and the structure–activity relationship changed. On the other hand, the results of the A. thaliana root sensitivity assay show that brassinolide and the analogs with I and CN as substituents on the benzoyl group were the most active compounds. These results are in line with those obtained via the RLIT. A comparison of these results with those obtained for similar analogs that had a hydroxyl group at C2 indicates the importance of considering the whole structure. The molecular-docking results indicate that all the analogs adopted a brassinolide-like orientation, while the stabilizing effect of the benzoate group on the interactions with the receptor complex provided energy binding values ranging between −10.17 and −13.17 kcal mol−1, where the analog with a nitrile group was the compound that achieved better contact with the amino acids present in the active site. [ABSTRACT FROM AUTHOR]

Published
2024
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7. SEC14-like condensate phase transitions at plasma membranes regulate root growth in Arabidopsis

Author

Liu, Chen, primary, Mentzelopoulou, Andriani, additional, Papagavriil, Fotini, additional, Ramachandran, Prashanth, additional, Perraki, Artemis, additional, Claus, Lucas, additional, Barg, Sebastian, additional, Dörmann, Peter, additional, Jaillais, Yvon, additional, Johnen, Philipp, additional, Russinova, Eugenia, additional, Gizeli, Electra, additional, Schaaf, Gabriel, additional, and Moschou, Panagiotis Nikolaou, additional

Published
2023
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9. Nonselective Chemical Inhibition of Sec7 Domain-Containing ARF GTPase Exchange Factors

Author

Mishev, Kiril, Lu, Qing, BramDenoo, Peurois, François, WimDejonghe, JanHullaert, RietDeRycke, Boeren, Sjef, Bretou, Marine, De Munck, Steven, Sharma, Isha, Goodman, Kaija, Kalinowska, Kamila, Storme, Veronique, Nguyen, Le Son Long, Drozdzecki, Andrzej, Martins, Sara, Nerinckx, Wim, Audenaert, Dominique, AnnemiekeMadder, Isono, Erika, Savvides, Savvas N., Annaert, Wim, De Vries, Sacco, Cherfils, Jacqueline, JohanWinne, and Russinova, Eugenia

Published
2018

15. Cell type–specific attenuation of brassinosteroid signaling precedes stomatal asymmetric cell division

Author

Kim, Eun-Ji, primary, Zhang, Cheng, additional, Guo, Boyu, additional, Eekhout, Thomas, additional, Houbaert, Anaxi, additional, Wendrich, Jos R., additional, Vandamme, Niels, additional, Tiwari, Manish, additional, Simon--Vezo, Claire, additional, Vanhoutte, Isabelle, additional, Saeys, Yvan, additional, Wang, Kun, additional, Zhu, Yuxian, additional, De Rybel, Bert, additional, and Russinova, Eugenia, additional

Published
2023
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17. POLAR-guided signalling complex assembly and localization drive asymmetric cell division

Author

Houbaert, Anaxi, Zhang, Cheng, Tiwari, Manish, Wang, Kun, de Marcos Serrano, Alberto, Savatin, Daniel V., Urs, Mounashree J., Zhiponova, Miroslava K., Gudesblat, Gustavo E., Vanhoutte, Isabelle, Eeckhout, Dominique, Boeren, Sjef, Karimi, Mansour, Betti, Camilla, Jacobs, Thomas, Fenoll, Carmen, Mena, Montaña, de Vries, Sacco, De Jaeger, Geert, and Russinova, Eugenia

Published
2018
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18. SEC14-like condensate phase transitions at plasma membranes regulate root growth in Arabidopsis

Author

Liu, Chen, Mentzelopoulou, Andriani, Papagavriil, Fotini, Ramachandran, Prashanth, Perraki, Artemis, Claus, Lucas, Barg, Sebastian, Dörmann, Peter, Jaillais, Yvon, Johnen, Philipp, Russinova, Eugenia, Gizeli, Electra, Schaaf, Gabriel, Moschou, Panagiotis Nikolaou, Liu, Chen, Mentzelopoulou, Andriani, Papagavriil, Fotini, Ramachandran, Prashanth, Perraki, Artemis, Claus, Lucas, Barg, Sebastian, Dörmann, Peter, Jaillais, Yvon, Johnen, Philipp, Russinova, Eugenia, Gizeli, Electra, Schaaf, Gabriel, and Moschou, Panagiotis Nikolaou

Abstract

Protein function can be modulated by phase transitions in their material properties, which can range from liquid- to solid-like; yet, the mechanisms that drive these transitions and whether they are important for physiology are still unknown. In the model plant Arabidopsis, we show that developmental robustness is reinforced by phase transitions of the plasma membrane-bound lipid-binding protein SEC14-like. Using imaging, genetics, and in vitro reconstitution experiments, we show that SEC14-like undergoes liquid-like phase separation in the root stem cells. Outside the stem cell niche, SEC14-like associates with the caspase-like protease separase and conserved microtubule motors at unique polar plasma membrane interfaces. In these interfaces, SEC14-like undergoes processing by separase, which promotes its liquid-to-solid transition. This transition is important for root development, as lines expressing an uncleavable SEC14-like variant or mutants of separase and associated microtubule motors show similar developmental phenotypes. Furthermore, the processed and solidified but not the liquid form of SEC14-like interacts with and regulates the polarity of the auxin efflux carrier PINFORMED2. This work demonstrates that robust development can involve liquid-to-solid transitions mediated by proteolysis at unique plasma membrane interfaces.

Published
2023
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19. Adaptor protein complex interaction map in Arabidopsis identifies P34 as a common stability regulator

Author

Wang, Peng, Siao, Wei, Zhao, Xiuyang, Arora, Deepanksha, Wang, Ren, Eeckhout, Dominique, Van Leene, Jelle, Kumar, Rahul, Houbaert, Anaxi, De Winne, Nancy, Mylle, Evelien, Vandorpe, Michael, Korver, Ruud A., Testerink, Christa, Gevaert, Kris, Vanneste, Steffen, De Jaeger, Geert, Van Damme, Daniël, Russinova, Eugenia, Wang, Peng, Siao, Wei, Zhao, Xiuyang, Arora, Deepanksha, Wang, Ren, Eeckhout, Dominique, Van Leene, Jelle, Kumar, Rahul, Houbaert, Anaxi, De Winne, Nancy, Mylle, Evelien, Vandorpe, Michael, Korver, Ruud A., Testerink, Christa, Gevaert, Kris, Vanneste, Steffen, De Jaeger, Geert, Van Damme, Daniël, and Russinova, Eugenia

Abstract

Adaptor protein (AP) complexes are evolutionarily conserved vesicle transport regulators that recruit coat proteins, membrane cargoes and coated vesicle accessory proteins. As in plants endocytic and post-Golgi trafficking intersect at the trans-Golgi network, unique mechanisms for sorting cargoes of overlapping vesicular routes are anticipated. The plant AP complexes are part of the sorting machinery, but despite some functional information, their cargoes, accessory proteins and regulation remain largely unknown. Here, by means of various proteomics approaches, we generated the overall interactome of the five AP and the TPLATE complexes in Arabidopsis thaliana. The interactome converged on a number of hub proteins, including the thus far unknown adaptin binding-like protein, designated P34. P34 interacted with the clathrin-associated AP complexes, controlled their stability and, subsequently, influenced clathrin-mediated endocytosis and various post-Golgi trafficking routes. Altogether, the AP interactome network offers substantial resources for further discoveries of unknown endomembrane trafficking regulators in plant cells.

Published
2023

20. Danger-associated peptide signaling in Arabidopsis requires clathrin

Author

Ortiz-Morea, Fausto Andres, Savatin, Daniel V., Dejonghe, Wim, Kumar, Rahul, Luo, Yu, Adamowski, Maciej, Van den Begin, Jos, Dressano, Keini, de Oliveira, Guilherme Pereira, Zhao, Xiuyang, Lu, Qing, Madder, Annemieke, Friml, Jiří, de Moura, Daniel Scherer, and Russinova, Eugenia

Published
2016

23. Cell type–specific attenuation of brassinosteroid signaling precedes stomatal asymmetric cell division.

Author

Eun-­Ji Kim, Cheng Zhang, Boyu Guo, Eekhout, Thomas, Houbaert, Anaxi, Wendrich, Jos R., Vandamme, Niels, Tiwari, Manish, Simon-­-­Vezo, Claire, Vanhoutte, Isabelle, Saeys, Yvan, Kun Wang, Yuxian Zhu, De Rybel, Bert, and Russinova, Eugenia

Subjects
CELL division, STOMATA, SCAFFOLD proteins, ARABIDOPSIS thaliana, CELL communication
Abstract

In Arabidopsis thaliana, brassinosteroid (BR) signaling and stomatal development are connected through the SHAGGY/GSK3-like kinase BR INSENSITIVE2 (BIN2). BIN2 is a key negative regulator of BR signaling but it plays a dual role in stomatal development. BIN2 promotes or restricts stomatal asymmetric cell division (ACD) depending on its subcellular localization, which is regulated by the stomatal lineage-specific scaffold protein POLAR. BRs inactivate BIN2, but how they govern stomatal development remains unclear. Mapping the single-cell transcriptome of stomatal lineages after triggering BR signaling with either exogenous BRs or the specific BIN2 inhibitor, bikinin, revealed that the two modes of BR signaling activation generate spatiotemporally distinct transcriptional responses. We established that BIN2 is always sensitive to the inhibitor but, when in a complex with POLAR and its closest homolog POLAR-LIKE1, it becomes protected from BR-mediated inactivation. Subsequently, BR signaling in ACD precursors is attenuated, while it remains active in epidermal cells devoid of scaffolds and undergoing differentiation. Our study demonstrates how scaffold proteins contribute to cellular signal specificity of hormonal responses in plants. [ABSTRACT FROM AUTHOR]

Published
2023
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24. BRASSINOSTEROID INSENSITIVE1 internalization can occur independent of ligand binding

Author

Neubus Claus, Lucas Alves, primary, Liu, Derui, additional, Hohmann, Ulrich, additional, Vukašinović, Nemanja, additional, Pleskot, Roman, additional, Liu, Jing, additional, Schiffner, Alexei, additional, Jaillais, Yvon, additional, Wu, Guang, additional, Wolf, Sebastian, additional, Van Damme, Daniël, additional, Hothorn, Michael, additional, and Russinova, Eugenia, additional

Published
2023
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32. Tripartite hormonal regulation of plasma membrane H+-ATPase activity

Author

0000-0003-0956-6310, 0000-0002-0569-1977, 0000-0002-5886-9425, Miao, Rui, Russinova, Eugenia, Rodríguez, Pedro L., 0000-0003-0956-6310, 0000-0002-0569-1977, 0000-0002-5886-9425, Miao, Rui, Russinova, Eugenia, and Rodríguez, Pedro L.

Abstract

The enzyme activity of the plasma membrane (PM) proton pump, well known as arabidopsis PM H+-ATPase (AHA) in the model plant arabidopsis (Arabidopsis thaliana), is controlled by phosphorylation. Three different classes of phytohormones, brassinosteroids (BRs), abscisic acid (ABA), and auxin regulate plant growth and responses to environmental stimuli, at least in part by modulating the activity of the pump through phosphorylation of the penultimate Thr residue in its carboxyl terminus. Here, we review the current knowledge regarding this tripartite hormonal AHA regulation and highlight mechanisms of activation and deactivation, as well as the significance of hormonal crosstalk. Understanding the complexity of PM H+-ATPase regulation in plants might provide new strategies for sustainable agriculture.

Published
2022

34. Tackling Drought Stress: RECEPTOR-LIKE KINASES Present New Approaches

Author

Marshall, Alex, Aalen, Reidunn B., Audenaert, Dominique, Beeckman, Tom, Broadley, Martin R., Butenko, Melinka A., Caño-Delgado, Ana I., de Vries, Sacco, Dresselhaus, Thomas, Felix, Georg, Graham, Neil S., Foulkes, John, Granier, Christine, Greb, Thomas, Grossniklaus, Ueli, Hammond, John P., Heidstra, Renze, Hodgman, Charlie, Hothorn, Michael, Inzé, Dirk, Østergaard, Lars, Russinova, Eugenia, Simon, Rüdiger, Skirycz, Aleksandra, Stahl, Yvonne, Zipfel, Cyril, and De Smet, Ive

Published
2012

37. Proteome-wide cellular thermal shift assay reveals unexpected cross-talk between brassinosteroid and auxin signaling

Author

Lu, Qing, primary, Zhang, Yonghong, additional, Hellner, Joakim, additional, Giannini, Caterina, additional, Xu, Xiangyu, additional, Pauwels, Jarne, additional, Ma, Qian, additional, Dejonghe, Wim, additional, Han, Huibin, additional, Van de Cotte, Brigitte, additional, Impens, Francis, additional, Gevaert, Kris, additional, De Smet, Ive, additional, Friml, Jiří, additional, Molina, Daniel Martinez, additional, and Russinova, Eugenia, additional

Published
2022
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41. Update on Receptors and Signaling

Author

Cheung, Alice Y, Qu, Li-Jia, Russinova, Eugenia, Zhao, Yunde, Zipfel, Cyril, and University of Zurich

Subjects
0106 biological sciences, Physiology, Pathogen-Associated Molecular Pattern Molecules, Receptors, Cell Surface, Plant Science, 580 Plants (Botany), Plants, Biology, 01 natural sciences, Plant science, Sense and respond, 10126 Department of Plant and Microbial Biology, Sense (molecular biology), Genetics, Plant Immunity, Editorial - Focus Issue, 10211 Zurich-Basel Plant Science Center, Peptides, Receptor, Neuroscience, Signal Transduction, 010606 plant biology & botany
Abstract

The ability of cells to sense and respond to endogenous cues as well as cues from neighboring cells and tissues underlies the life and death of cells, their growth and proliferation, differentiation into tissues, and ultimately development into morphologically diverse organisms. Being able to sense

Published
2020

49. ROPGAP-dependent interaction between brassinosteroid and ROP2-GTPase signaling controls pavement cell shape in Arabidopsis

Author

Zhang, Cheng, primary, Lauster, Theresa, additional, Tang, Wenxin, additional, Houbaert, Anaxi, additional, Zhu, Shanshuo, additional, Eeckhout, Dominique, additional, De Smet, Ive, additional, De Jaeger, Geert, additional, Jacobs, Thomas B., additional, Xu, Tongda, additional, Müller, Sabine, additional, and Russinova, Eugenia, additional

Published
2022
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