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Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid

p-Aminobenzoic acid (pABA) plays important roles in a wide variety of metabolic processes. Herein we report the synthesis, theoretical calculations, crystallographic investigation, and in vitro determination of the biological activity and phytotoxicity of the pABA salt, 2-hydroxyethylammonium p-amin...

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Autores principales: Crisan, Manuela E., Bourosh, Paulina, Maffei, Massimo E., Forni, Alessandra, Pieraccini, Stefano, Sironi, Maurizio, Chumakov, Yurii M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4108362/
https://www.ncbi.nlm.nih.gov/pubmed/25054237
http://dx.doi.org/10.1371/journal.pone.0101892
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author Crisan, Manuela E.
Bourosh, Paulina
Maffei, Massimo E.
Forni, Alessandra
Pieraccini, Stefano
Sironi, Maurizio
Chumakov, Yurii M.
author_facet Crisan, Manuela E.
Bourosh, Paulina
Maffei, Massimo E.
Forni, Alessandra
Pieraccini, Stefano
Sironi, Maurizio
Chumakov, Yurii M.
author_sort Crisan, Manuela E.
collection PubMed
description p-Aminobenzoic acid (pABA) plays important roles in a wide variety of metabolic processes. Herein we report the synthesis, theoretical calculations, crystallographic investigation, and in vitro determination of the biological activity and phytotoxicity of the pABA salt, 2-hydroxyethylammonium p-aminobenzoate (HEA-pABA). The ability of neutral and anionic forms of pABA to interact with TIR1 pocket was investigated by calculation of molecular electrostatic potential maps on the accessible surface area, docking experiments, Molecular Dynamics and Quantum Mechanics/Molecular Mechanics calculations. The docking study of the folate precursor pABA, its anionic form and natural auxin (indole-3-acetic acid, IAA) with the auxin receptor TIR1 revealed a similar binding mode in the active site. The phytotoxic evaluation of HEA-pABA, pABA and 2-hydroxyethylamine (HEA) was performed on the model plant Arabidopsis thaliana ecotype Col 0 at five different concentrations. HEA-pABA and pABA acted as potential auxin-like regulators of root development in Arabidopsis thaliana (0.1 and 0.2 mM) and displayed an agravitropic root response at high concentration (2 mM). This study suggests that HEA-pABA and pABA might be considered as potential new regulators of plant growth.
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spelling pubmed-41083622014-07-24 Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid Crisan, Manuela E. Bourosh, Paulina Maffei, Massimo E. Forni, Alessandra Pieraccini, Stefano Sironi, Maurizio Chumakov, Yurii M. PLoS One Research Article p-Aminobenzoic acid (pABA) plays important roles in a wide variety of metabolic processes. Herein we report the synthesis, theoretical calculations, crystallographic investigation, and in vitro determination of the biological activity and phytotoxicity of the pABA salt, 2-hydroxyethylammonium p-aminobenzoate (HEA-pABA). The ability of neutral and anionic forms of pABA to interact with TIR1 pocket was investigated by calculation of molecular electrostatic potential maps on the accessible surface area, docking experiments, Molecular Dynamics and Quantum Mechanics/Molecular Mechanics calculations. The docking study of the folate precursor pABA, its anionic form and natural auxin (indole-3-acetic acid, IAA) with the auxin receptor TIR1 revealed a similar binding mode in the active site. The phytotoxic evaluation of HEA-pABA, pABA and 2-hydroxyethylamine (HEA) was performed on the model plant Arabidopsis thaliana ecotype Col 0 at five different concentrations. HEA-pABA and pABA acted as potential auxin-like regulators of root development in Arabidopsis thaliana (0.1 and 0.2 mM) and displayed an agravitropic root response at high concentration (2 mM). This study suggests that HEA-pABA and pABA might be considered as potential new regulators of plant growth. Public Library of Science 2014-07-23 /pmc/articles/PMC4108362/ /pubmed/25054237 http://dx.doi.org/10.1371/journal.pone.0101892 Text en © 2014 Crisan et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Crisan, Manuela E.
Bourosh, Paulina
Maffei, Massimo E.
Forni, Alessandra
Pieraccini, Stefano
Sironi, Maurizio
Chumakov, Yurii M.
Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid
title Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid
title_full Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid
title_fullStr Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid
title_full_unstemmed Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid
title_short Synthesis, Crystal Structure and Biological Activity of 2-Hydroxyethylammonium Salt of p-Aminobenzoic Acid
title_sort synthesis, crystal structure and biological activity of 2-hydroxyethylammonium salt of p-aminobenzoic acid
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4108362/
https://www.ncbi.nlm.nih.gov/pubmed/25054237
http://dx.doi.org/10.1371/journal.pone.0101892
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