title: Synthesis, crystal structure and biological activity of 2-hydroxyethylammonium salt of p-aminobenzoic acid.
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, 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.
authors: Department of Organic Chemistry, Institute of Chemistry Timisoara of Romanian Academy, Timisoara, Romania.
authors: Manuela E
authors: ME
authors: Crisan
authors: Laboratory of Physical Methods of Solid State Investigation "T. Malinowski", Institute of Applied Physics, Academy of Sciences of Moldova, Chisinau, Republic of Moldova.
authors: Paulina
authors: P
authors: Bourosh
authors: Department of Life Sciences and Systems Biology, Plant Physiology Unit, Innovation Centre, University of Turin, Torino, Italy.
authors: Massimo E
authors: ME
authors: Maffei
authors: ISTM-CNR, Institute of Molecular Sciences and Technologies of CNR and INSTM UdR, Milano, Italy.
authors: Alessandra
authors: A
authors: Forni
authors: ISTM-CNR, Institute of Molecular Sciences and Technologies of CNR and INSTM UdR, Milano, Italy; Department of Chemistry and INSTM UdR, University of Milan, Milano, Italy.
authors: Stefano
authors: S
authors: Pieraccini
authors: ISTM-CNR, Institute of Molecular Sciences and Technologies of CNR and INSTM UdR, Milano, Italy; Department of Chemistry and INSTM UdR, University of Milan, Milano, Italy.
authors: Maurizio
authors: M
authors: Sironi
authors: Laboratory of Physical Methods of Solid State Investigation "T. Malinowski", Institute of Applied Physics, Academy of Sciences of Moldova, Chisinau, Republic of Moldova.
authors: Yurii M
authors: YM
authors: Chumakov
mesh_terms: D010129:4-Aminobenzoic Acid / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D017360:Arabidopsis / Q000187:drug effects / Q000254:growth & development; D018360:Crystallography, X-Ray; D005492:Folic Acid / Q000737:chemistry / Q000378:metabolism; D006860:Hydrogen Bonding; D007210:Indoleacetic Acids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D062105:Molecular Docking Simulation; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D010937:Plant Growth Regulators / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011956:Receptors, Cell Surface / Q000737:chemistry / Q000378:metabolism; D017550:Spectroscopy, Fourier Transform Infrared; D055672:Static Electricity
chemical_list: D007210:Indoleacetic Acids; D010937:Plant Growth Regulators; D000644:Quaternary Ammonium Compounds; D011956:Receptors, Cell Surface; C030737:indoleacetic acid; D005492:Folic Acid; D010129:4-Aminobenzoic Acid