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.
Highlights
The interest in carboxylate compounds in general and benzoic acid derivatives in particular continues to grow because of their chemical and biological properties
P-aminobenzoic acid has displayed biological, medicinal and industrial interest. p-aminobenzoic acid (pABA) is a compound of high biological significance, it is present in plant and animal tissues and is sometimes referred to as bacterial vitamin H1, Bx, or B10 [1]. pABA is a well-known precursor of folic acid [2], and has recently been identified as a coenzyme Q precursor [3,4], which opens new possibilities for its application in medicine
Molecular properties of HEA-pABA and pABA compared to classical auxin molecules Beside the importance of salt unit of HEA-pABA as building block for supramolecular architecture, we found a new role of this compound and its precursor on plant development as potential regulators of plant growth with an auxin-like effect
Summary
The interest in carboxylate compounds in general and benzoic acid derivatives in particular continues to grow because of their chemical and biological properties Benzoic acids and their derivatives are important structural elements for many natural products, being involved in various physiological processes in plants. Among these compounds, p-aminobenzoic acid (pABA) has displayed biological, medicinal and industrial interest. PABA is a well-known precursor of folic acid [2], and has recently been identified as a coenzyme Q precursor [3,4], which opens new possibilities for its application in medicine It is a building block used in design of drugs and frequently found as a structure moiety in drugs [5]. To the best of our knowledge, the role of folate precursor pABA as a plant growth modulator has not been investigated so far
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