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...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Manuela E Crisan, Paulina Bourosh, Massimo E Maffei, Alessandra Forni, Stefano Pieraccini, Maurizio Sironi, Yurii M Chumakov
Formato:	article
Lenguaje:	EN
Publicado:	Public Library of Science (PLoS) 2014
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/e0c14f27305649449fc93285225ed69c
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:e0c14f27305649449fc93285225ed69c
record_format	dspace
spelling	oai:doaj.org-article:e0c14f27305649449fc93285225ed69c2021-11-25T06:07:30ZSynthesis, crystal structure and biological activity of 2-hydroxyethylammonium salt of p-aminobenzoic acid.1932-620310.1371/journal.pone.0101892https://doaj.org/article/e0c14f27305649449fc93285225ed69c2014-01-01T00:00:00Zhttps://www.ncbi.nlm.nih.gov/pmc/articles/pmid/25054237/pdf/?tool=EBIhttps://doaj.org/toc/1932-6203p-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.Manuela E CrisanPaulina BouroshMassimo E MaffeiAlessandra ForniStefano PieracciniMaurizio SironiYurii M ChumakovPublic Library of Science (PLoS)articleMedicineRScienceQENPLoS ONE, Vol 9, Iss 7, p e101892 (2014)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Manuela E Crisan Paulina Bourosh Massimo E Maffei Alessandra Forni Stefano Pieraccini Maurizio Sironi Yurii M Chumakov Synthesis, crystal structure and biological activity of 2-hydroxyethylammonium salt of p-aminobenzoic acid.
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.
format	article
author	Manuela E Crisan Paulina Bourosh Massimo E Maffei Alessandra Forni Stefano Pieraccini Maurizio Sironi Yurii M Chumakov
author_facet	Manuela E Crisan Paulina Bourosh Massimo E Maffei Alessandra Forni Stefano Pieraccini Maurizio Sironi Yurii M Chumakov
author_sort	Manuela E Crisan
title	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_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_sort	synthesis, crystal structure and biological activity of 2-hydroxyethylammonium salt of p-aminobenzoic acid.
publisher	Public Library of Science (PLoS)
publishDate	2014
url	https://doaj.org/article/e0c14f27305649449fc93285225ed69c
work_keys_str_mv	AT manuelaecrisan synthesiscrystalstructureandbiologicalactivityof2hydroxyethylammoniumsaltofpaminobenzoicacid AT paulinabourosh synthesiscrystalstructureandbiologicalactivityof2hydroxyethylammoniumsaltofpaminobenzoicacid AT massimoemaffei synthesiscrystalstructureandbiologicalactivityof2hydroxyethylammoniumsaltofpaminobenzoicacid AT alessandraforni synthesiscrystalstructureandbiologicalactivityof2hydroxyethylammoniumsaltofpaminobenzoicacid AT stefanopieraccini synthesiscrystalstructureandbiologicalactivityof2hydroxyethylammoniumsaltofpaminobenzoicacid AT mauriziosironi synthesiscrystalstructureandbiologicalactivityof2hydroxyethylammoniumsaltofpaminobenzoicacid AT yuriimchumakov synthesiscrystalstructureandbiologicalactivityof2hydroxyethylammoniumsaltofpaminobenzoicacid
_version_	1718414194956566528

Synthesis, crystal structure and biological activity of 2-hydroxyethylammonium salt of p-aminobenzoic acid.

Ejemplares similares