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Synthesis, crystal structure and biological activity of 2-Hydroxyethylammonium salt of p-Aminobenzoic Acid

Articolo
Data di Pubblicazione:
2014
Abstract:
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 and Quantum Mechanics/Molecular Mechanics (QM/MM) 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, 2-hydroxyethylamine (HEA) and IAA was performed on the model plant Arabidopsis thaliana ecotype Col 0 at five concentrations: 0.02, 0.1, 0.2, 1 and 2 mM. 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.
Tipologia CRIS:
03A-Articolo su Rivista
Keywords:
biological activity; hydrogen bonds; 2-hydroxyethylammonium p-aminobenzoate; self-assembly; TIR1 auxin receptor
Elenco autori:
CRISAN M.E.; BOUROSH P.; MAFFEI M.; FORNI A.; PIERACCINI S.; SIRONI M.; CHUMAKOV Y.M.
Autori di Ateneo:
MAFFEI Massimo Emilio
Link alla scheda completa:
https://iris.unito.it/handle/2318/147944
Link al Full Text:
https://iris.unito.it/retrieve/handle/2318/147944/24652/2014%20PLoS%20ONE%20pABA.pdf
Pubblicato in:
PLOS ONE
Journal
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