ABSTRACT
Auxin plays a dual role in growth regulation and, depending on the tissue and concentration of the hormone, it can either promote or inhibit division and expansion processes in plants. Recent studies have revealed that, beyond transcriptional reprogramming, alternative auxin-controlled mechanisms regulate root growth. Here, we explored the impact of different concentrations of the synthetic auxin NAA that establish growth-promoting and -repressing conditions on the root tip proteome and phosphoproteome, generating a unique resource. From the phosphoproteome data, we pinpointed (novel) growth regulators, such as the RALF34-THE1 module. Our results, together with previously published studies, suggest that auxin, H+-ATPases, cell wall modifications and cell wall sensing receptor-like kinases are tightly embedded in a pathway regulating cell elongation. Furthermore, our study assigned a novel role to MKK2 as a regulator of primary root growth and a (potential) regulator of auxin biosynthesis and signalling, and suggests the importance of the MKK2 Thr31 phosphorylation site for growth regulation in the Arabidopsis root tip.
Subject(s)
Arabidopsis Proteins/genetics , Arabidopsis/genetics , Gene Expression Regulation, Plant , Peptide Hormones/genetics , Phosphoproteins/genetics , Plant Growth Regulators/pharmacology , Plant Roots/genetics , Protein Kinases/genetics , Receptors, Cell Surface/genetics , Arabidopsis/growth & development , Arabidopsis/metabolism , Arabidopsis Proteins/metabolism , Gene Expression Regulation, Developmental , Indoleacetic Acids/pharmacology , Meristem/genetics , Meristem/growth & development , Meristem/metabolism , Mitogen-Activated Protein Kinase Kinases/genetics , Mitogen-Activated Protein Kinase Kinases/metabolism , Naphthaleneacetic Acids/chemical synthesis , Naphthaleneacetic Acids/pharmacology , Peptide Hormones/metabolism , Phosphoproteins/classification , Phosphoproteins/metabolism , Phosphorylation , Plant Roots/growth & development , Plant Roots/metabolism , Protein Kinases/metabolism , Protein Processing, Post-Translational , Proteome/classification , Proteome/genetics , Proteome/metabolism , Proton-Translocating ATPases/genetics , Proton-Translocating ATPases/metabolism , Receptors, Cell Surface/metabolism , Signal TransductionABSTRACT
A series of primary ammonium monocarboxylate (PAM) salts derived from ß-alanine derivatives of pyrene and naphthalene acetic acid, along with the parent acids, were explored to probe the plausible role of orthogonal hydrogen bonding resulting from amideâ â â amide and PAM synthons on gelation. Single-crystal X-ray diffraction (SXRD) studies were performed on two parent acids and five PAM salts in the series. The data revealed that orthogonal hydrogen bonding played an important role in gelation. Structure-property correlation based on SXRD and powder X-ray diffraction data also supported the working hypothesis upon which these gelators were designed. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and cell migration assay on a highly aggressive human breast cancer cell line, MDA-MB-231, revealed that one of the PAM salts in the series, namely, PAA.B2, displayed anticancer properties, and internalization of the gelator salt in the same cell line was confirmed by cell imaging.
Subject(s)
Amides/pharmacology , Macromolecular Substances/pharmacology , Naphthaleneacetic Acids/pharmacology , Pyrenes/pharmacology , beta-Alanine/analogs & derivatives , beta-Alanine/pharmacology , Amides/chemical synthesis , Amides/chemistry , Amides/toxicity , Animals , Cell Line, Tumor , Cell Movement/drug effects , Gels , Humans , Hydrogen Bonding , Macromolecular Substances/chemical synthesis , Macromolecular Substances/chemistry , Macromolecular Substances/toxicity , Mice , Naphthaleneacetic Acids/chemical synthesis , Naphthaleneacetic Acids/chemistry , Naphthaleneacetic Acids/toxicity , Pyrenes/chemical synthesis , Pyrenes/chemistry , Pyrenes/toxicity , RAW 264.7 Cells , Viscoelastic Substances/chemical synthesis , Viscoelastic Substances/chemistry , Viscoelastic Substances/pharmacology , Viscoelastic Substances/toxicity , X-Ray Diffraction , beta-Alanine/chemical synthesis , beta-Alanine/toxicityABSTRACT
2-Acetyl-1-hydroxynaphthalene was converted into 1,4-dimethoxy-2-naphthoxyacetic acid in seven steps (methylation, Bayer-Villiger oxidation, hydrolysis, bromination, methylation, alkylation and hydrolysis). 2-Hydroxy-1,4-naphthoquinone on acetylation, aromatization, methylation and hydrolysis, respectively, also yielded the title compound.
Subject(s)
Naphthaleneacetic Acids/chemical synthesis , Naphthoquinones/chemistryABSTRACT
Analysis of the interactions between two representatives of plant hormones: synthetic (1-naphthaleneacetic acid, NAA) as well as natural (indole-3-acetic acid, IAA) and phospholipids occurring in biological membrane of both plant and animal cells was the subject of present studies. The aim of undertaken experiments was to elucidate the problem of direct influence of these plant growth regulators on phosphatidylcholines (PCs) and phosphatidylethanolamines (PEs) in monolayers at the air/water solution interface. The studied phospholipids differ not only as regards the structure of polar head-groups but also in the length of hydrophobic chains as well as their saturation degree. These differences result also in the main properties and functions of these phospholipids in biomembranes. The analysis of the results was based on the characteristics of the surface pressure (π)--area (A) isotherms registered for monolayers spread on the subphase containing plant hormone and as a reference on the surface of pure water. Moreover, as a complementary technique, Brewster angle microscopy was applied for the direct visualization of the investigated surface films. The obtained results revealed that auxins effectively influence phospholipids monolayers, regardless of the lipid structure, at the concentration of 10(-4)M. It was found that for this concentration, the influence of auxins was visibly larger in the case of PCs as compared to PEs. On the other hand, in the case of auxins solution of ≤ 10(-5)M, the observed trend was opposite. Generally, our studies showed that the natural plant hormone (IAA) interacts with the investigated lipid monolayers stronger than its synthetic derivative (NAA). The reason of these differences connects with the steric properties of both auxins; namely, the naphthalene ring of NAA molecule occupies larger space than the indole system of IAA. Therefore molecules of the latter compound penetrate easier into the region of phospholipids׳ polar head-groups. Moreover, the NH group of the indole moiety is capable of hydrogen bond formation with the acceptor groups in the polar fragment of lipid molecules. We proved also that among the investigated phospholipids, the highest susceptibility toward auxin influence show these lipids, for which during compression, surface film increases the degree of condensation.
Subject(s)
Indoleacetic Acids/chemistry , Membrane Lipids/chemistry , Naphthaleneacetic Acids/chemistry , Naphthaleneacetic Acids/chemical synthesis , Plant Growth Regulators/chemistry , Animals , Indoleacetic Acids/chemical synthesis , Membrane Lipids/chemical synthesis , Plant Growth Regulators/chemical synthesisABSTRACT
A new "plug and play" polymeric template with the driving force of host-guest interaction between ß-CD and naphthalene-modified functional groups was designed and studied. Multiple functional groups can be loaded into the template directly and conveniently. Importantly, the "plug and play" effect of the polymeric template is reversible and the functional groups could be removed from the polymeric template conveniently by adding AD-HCl. The studies on the cell viability and phagocytosis proved that the loading and unloading process of this template could be realized in vitro.
Subject(s)
Polymers/chemistry , Polymers/chemical synthesis , Animals , COS Cells , Camptothecin/pharmacology , Cell Death/drug effects , Chlorocebus aethiops , Ethylenediamines/chemical synthesis , Ethylenediamines/chemistry , Ethylenediamines/pharmacology , HeLa Cells , Humans , Magnetic Resonance Spectroscopy , Microscopy, Confocal , Naphthaleneacetic Acids/chemical synthesis , Naphthaleneacetic Acids/chemistry , Naphthaleneacetic Acids/pharmacology , Oligopeptides/chemical synthesis , Oligopeptides/chemistry , Oligopeptides/pharmacology , Peptides/chemical synthesis , Peptides/chemistry , Peptides/pharmacology , Polymers/pharmacology , Spectrometry, Fluorescence , beta-Cyclodextrins/chemical synthesis , beta-Cyclodextrins/chemistry , beta-Cyclodextrins/pharmacologyABSTRACT
[reaction: see text] 6(A),6(D)-Bispyridinio-appended gamma-cyclodextrin effectively enhanced the excimer fluorescence of 2-naphthylacetate. This increase derived from the increase of formation of the 1:2 complex between the cation-charged gamma-cyclodextrin and 2-naphthylacetate by the electrostatic interaction between the host and the guest.
Subject(s)
Cyclodextrins/chemical synthesis , Naphthaleneacetic Acids/chemical synthesis , gamma-Cyclodextrins , Cations , Cyclodextrins/chemistry , Fluorescence , Molecular Conformation , Naphthaleneacetic Acids/chemistryABSTRACT
Eighteen esters derived from 1-naphthylacetic acid (NAA) and from hexyl isomer alcohols were synthesized and sprayed on grapevine suckers at 1, 2, 4, and 8% w/w concentrations to test their sucker control efficiency 2, 10, and 30 days and 1 year after their application. All compounds gave a prompt control of suckers. After 1 year, sucker growth was inhibited by the derivatives from primary and secondary alcohols, whereas the number of suckers was reduced only by application of naphthyl acetates of tertiary alcohols.
Subject(s)
Naphthaleneacetic Acids/pharmacology , Plant Growth Regulators/pharmacology , Rosales/drug effects , Drug Design , Esters , Molecular Structure , Naphthaleneacetic Acids/chemical synthesis , Plant Growth Regulators/chemical synthesis , Rosales/growth & development , Structure-Activity RelationshipABSTRACT
The synthesis and preliminary biological testing for in vitro cholesterol biosynthesis inhibitory activity of 2-indeneacetic acid, 2-methyl-1,2-dihydro-2-naphthoic acid, and their 5- and 7-chloro derivatives, respectively are described. These compounds were prepared as trans- and cis-analogs of the known antilipemic agent 3-methyl-4-phenyl-3-butenoic acid. Although both series of compounds showed cholesterol biosynthesis inhibitory properties, chloro substitution enhanced potency only in the cis-system. These findings are discussed in terms of a possible relationship between the cis-compounds and clofibrate-type antilipemic agents.
Subject(s)
Anticholesteremic Agents/chemical synthesis , Butyrates/chemical synthesis , Indenes/chemical synthesis , Acetates/metabolism , Animals , Butyrates/analogs & derivatives , Butyrates/pharmacology , In Vitro Techniques , Indenes/pharmacology , Liver/drug effects , Liver/metabolism , Naphthaleneacetic Acids/chemical synthesis , Naphthaleneacetic Acids/pharmacology , Rats , Sterols/biosynthesisABSTRACT
The isomeric phenylnaphthaleneacetic acids were prepared and tested for antiinflammatory activity by the anti-UV-erythema method. High potency was exhibited by 4- and 5-phenyl-1-naphthaleneacetic acid and 5- and 6-phenyl-2-naphthaleneacetic acid. The results are discussed in terms of a hypothetical receptor site.