ABSTRACT
We studied the effect of benzylamine, benzyl alcohol, and their derivatives (constituting a new group of synthetic analogues of natural auxins) on rooting of leaf and stem cuttings, rhizogenesis and growth of barley plantlets and tomato seedlings, and tomato plant productivity. These compounds promoted rooting of leaf and stem bean cuttings, increased rhizogenic activity, and stimulated the development of root systems in barley and tomato seeds. The activity of the compounds studied was similar to that of standard substances (3-indoleacetic acid potassium salt and 2-naphthylacetic acid). The benzyl group attached to the oxygen or nitrogen atom was shown to be the smallest molecular structure which provided auxin activity of the compounds. Derivatives of benzyl alcohol containing the quaternary ammonium fragment possessed auxin and anti-gibberellin (retardant) properties. They were selected by chemical synthesis of low-molecular-weight bioregulators with desired properties (a combination of chemical fragments with complementary physiological activity in the molecule). Auxin and anti-gibberellin (retardant) activities produced a synergistic effect. Germination of seeds treated with these compounds was accompanied by a more significant increase in the weight and length of roots (compared to standard auxins). The rate of seedling establishment reached 100%. The development of fruits and accumulation of reserve nutrient substances were synchronized and accelerated after spraying vegetating plants with solutions of studied compounds. The synergistic effect underlay a significant increase in the amount and quality of the crop (e.g., tomatoes).
Subject(s)
Benzene Derivatives/pharmacology , Indoleacetic Acids/pharmacology , Plants/drug effects , Benzene Derivatives/chemistry , Indoleacetic Acids/chemistry , Plant DevelopmentABSTRACT
The importance of six theoretically calculated molecular parameters in the antigibberellin (retardant) activity of quaternary ammonium salts is studied using regression analysis. A bioassay system based on cell culture of fungus Gibberella fujikuroi is used to determine the activity. In the case of N,N,N-trimethyl-N-(2-hydroxyethyl)ammonium chloride (choline) and N,N,N-triethyl-N-(2-hydroxyethyl)ammonium chloride (N,N,N-triethylcholine) derivatives with linear structure, the polarizability, proton acceptor activity, and lipophilicity of these compounds exert the largest effect on the antigibberellin activity. The antigibberellin activity of more sterically hindered N,N-dialkylpiperidinium salts was mainly defined by the steric parameter, while the polarizability, proton acceptor activity, and (through them) lipophilicity exert a lesser effect. Other parameters are of minor importance for the three groups of compounds studied. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 6; see also http://www.maik.ru.
Subject(s)
Gibberella/drug effects , Gibberellins/antagonists & inhibitors , Quaternary Ammonium Compounds/chemistry , Magnetic Resonance Spectroscopy , Models, Molecular , Quaternary Ammonium Compounds/pharmacology , Regression Analysis , Structure-Activity RelationshipSubject(s)
Gibberellins/antagonists & inhibitors , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/pharmacology , Gibberella/drug effects , Gibberella/growth & development , Gibberella/metabolism , Gibberellins/metabolism , Quantitative Structure-Activity Relationship , Quaternary Ammonium Compounds/chemical synthesis , Salts/chemical synthesis , Salts/chemistry , Salts/pharmacologySubject(s)
Drug Design , Hormones/metabolism , Indoleacetic Acids/chemistry , Plant Physiological Phenomena , Agriculture/methods , Crops, Agricultural/metabolism , Gibberellins/chemistry , Histidine/chemistry , Models, Chemical , Peptides/chemistry , Plant Roots/drug effects , Plant Roots/physiology , Salts/chemistryABSTRACT
The effect of exchange of 15-hydroxyl for fluor on biological activity of PGF2 alpha and PGE2 on isolated smooth muscles of different organs has been studied. The exchange leads to significant increase in contractile (100-fold) and relaxation (1000-fold) activity of PGF2 alpha on smooth respiratory muscles. At the same time, the effect of 15-fluor-15-deoxyprostaglandin F2 alpha on smooth muscles of intestinal and vascular tracts did not differ from that of PGF2 alpha. Similar modification of PGE2 led to the decrease (10-fold) both in contractile and relaxation activity on all studied types of smooth muscles. The data obtained have been discussed within the boundaries of prostanoid receptor classification (Kennedy, 1982). Fluor derivative of PGF2 alpha may be used for pharmacological differentiation of EP-receptors.
Subject(s)
Dinoprost/analogs & derivatives , Dinoprostone/analogs & derivatives , Muscle, Smooth/drug effects , Animals , Cricetinae , Dinoprost/pharmacology , Dinoprostone/pharmacology , Dose-Response Relationship, Drug , Guinea Pigs , In Vitro Techniques , Male , Mesocricetus , Muscle Contraction/drug effects , Rats , Structure-Activity RelationshipABSTRACT
In a search for stable thromboxanomimetics the action of 11-fluoro-11-deoxyprostaglandin F2 alpha (11-fluoro-PGF2 alpha) on the aggregatory properties of platelets and the tone of the vascular, respiratory and gastrointestinal smooth muscles was studied. It was found that 11-fluoro-PGF2 alpha, in contrast to PGF2 alpha, induces platelet aggregation and exhibits a high activity with respect to smooth muscles sensitive to thromboxane A2 alpha (TXA2) and a low activity for smooth muscles sensitive to PGF2 alpha 9-11-epoxyimino-PGH2 (a specific antagonist of TXA2 receptors) competitively blocked the action of 11-fluoro-PGF2 alpha on vascular smooth muscles. Thus, 11-fluoro-PGF2 exhibits properties of a thromboxanomimetic that makes it possible to propose it for modelling TXA2-induced biological effects.
