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WHAT REGULATE THE GROWTH REGULATORS ?
Logos Publisher, Kiev, 1998.
ISBN 966-581-101-0Edited by B. A. Kurchii Institute if Plant Physiology and Genetics, 31/17 Vasylkivska Str.
03022 Kiev, Ukraine December, 1998202 pages, illustratedPrice: $50.00Monograph is published in Russian (30%) and in English (70%).
The papers presented in this book deal with the relationships between the structure of anychemical and its biological activity. This book in comparison to the published earlier data(Chemical structure of descriptors with an active hydrogen atom in certain bioregulators)presents the further study of the structure/activity relationships. The most important of thisis that somehow the actual molecular structure is ultimately responsible for the observedbiological effects. In our studies the common structural fragments that were called asfunctional-reactive groups (descriptors) for plant growth regulators, herbicides, pesticides,hormones and drugs were described. It is found that the presence of an active hydrogenatom or unsaturated function in the molecule is an essential factor determining biologicalactivity of any chemical. From our study it is not need to use computer aided methodsincluding molecular modelling and graphics for prediction of biological activity ofchemicals. The results obtained from the study of dependence existing between thestructure of any substance and its biological activity may be used in the designing of newcompounds including:(1) Synthetic analgesic; (2) Synthetic antioxidants; (3) Antiviral andantibacterial substances, etc. Moreover our structure/activity relationship model can beuseful to predict the toxicity of industrial and environmental chemicals.
It is proposed that in living organisms the selection of L-amino acids and D-sucrose to beused in the organic synthesises is caused by availability of an active hydrogen atom. Inthese structures a hydrogen atom is not hindered by neighbouring substituents in contrastto their parental structures, i.e., D-amino acid and L-sucrose.
In the paper "Functional-reactive groups of bioregulators" is described descriptors for suchchemicals as malondialdehyde, linolenic acid, avenin, methysazon, barbital, thyazon,lipamide, methformine, piperphos, EHT 26395, aphydan, glyftor, ethyon, dibrom, thymet,DDT, papaverin, phencapton, desopimon, salithion, ftorbenzide, sulphadimezin, ANTU,2,4-D, dual, monuron, propanidide, ruton, mephenamic acid.
In the chapter "Using of descriptors to design of novel drugs and pesticides, and to predictthe biological activity from the structure of chemicals which have not been bioassayed"such descriptors is also described for nitrogen mustard, uracil mustard, chloroxuron,diclofop, fluazifop, fluorodifen, fluoroglycofen, bifenox, picloram, ametryn, asulam,anilofos, benazolin, endothal, benztiazuron, clethodim, glyphosate, amitrol, pentachlorophenol, thiophos, azinphos, teflubenzuron, endrin, methylpotasan, pyrethrin,promecarb, diflubenzuron, bromophos-methyl, tetrasul, diphos, phosthion, acethion,dicrotophos, mevinphos, thiofanox, methomyl, phosmet, chlorfenvinphos, phorate,dichlorvos, heptachlor, chlordane, chlordecone, hexachlorocyclohexane, morphine,scopolamine, cocaine, strichnine, zongorine, lidocaine, eugenol, aspirin, disalcid,salicylamide, ibuprofen, fenoprofen, diclofenac, indomethacin, ketorolac, benorylate,propoxyohene, phenacozine, meperidine, alphaprodine, fentanyl, novocaine, tetracaine,chlorprocaine, ropivacaine, brifentanil, azacitidine, ampicillin, paracetamol, phenacetin,farcinicin, dulcin, nitrofural, furosemide, hydralazine, ethinyloestradiol, blasticidin S,melphalan, thyroliberin, metronidazole, azomycin, niridazole, pamaquine, trimethoprim,sulfalene, diiodohydroxyquin, diloxanide, melarsopol, niclosamide, levamisole, pyrantel,tetrachloroethylene, praziquantel, amantadine, trifluridine, acyclovir, pantothenic acid,cycloheximide, menthol, MPTP, kainic acid, gabaculine, sedobarbital, mephenoxalone,chlorzoxazone, cyclobenzoprine, dantrolene, diazepam, clobazepam, carbamazepine,chlorpromazine, perphenazine, meperidine, molidone, doxepin, meprobamate,phenaglycodol, cyclosporin A, batrachotoxin, gistryonikotoxin, pumiliotoxin, bufotaline,salamandrine, apamine, thyrocydin, gramicidin S, ergometrine, aflatoxin, girometrin,muscarin, amanitin, muscazone, teclophos-methyl, teboconazole, benalaxyl, blastine,butrisol, chlorothalonil, clotrimazole, naftifine, resorcinol, patulin, acrolein, cyclamates,phenelzine, aflatoxin, propylene oxide, nitrosodiethylamine, nitrosodimethylamine,aziridine, apholate, chlorobutadiene.
The free radical mechanism of action (with ethylene formation) of acetylcholine and someacetylcholine congeners are presented in schemes. Also free radical mechanisms ofaction are presented for D-tubucurarine, edrophonium, neostigmine, pyridostigmine,spermidine, putrescine, cadaverine, dopamine, physostigmine, pilocarpine, arecoline, 5-hydroxytryptamine, GABA, volatile anaesthetics (ethylene, diethyl ether, halothane,chloroform, fluoroxene, ethylene oxide, nitrous oxide, vinyl ether, enflurane), midazolam,etomidate, ketamine, cAMP, cGMP, estradiol, L-histamine, nizatidine, vitamin U,famotodine, serotonin, pheniramine, burimamide, fentanyl, nicotine, lobelin, muscarin,local anaesthetics (chlorprocaine, pramoxine, lidocaine), antineoplastic drugs(chlorambucil, chlortrianisene, misoindazole, mititane, aminoglutethimide), nitric oxide, etc.
It is proposed hypothetical free radical pathways for mode of action of narcotic substancesand prevention of narcotic dependence in animals by antioxidative substances.
Also the dependence between the chemical structure of such substances as arecoline,adrenocorticotropic hormone, alpha-amanitin, antagonists, aminoglutethimide, alpha-tocopherol, abscisic acid, apamin, anatoxin, antineoplastic drugs, ampicillin, aflatoxins,bufotaline, burimamide, beta2 adrenergic receptor, batrachotoxin, bufataline, chliroxuron,cAMP, cholesterol, cadaverine, chloroform, cyclosporins, chlorprocaine, cocaine,chlorambucil, chlortrianisene, atecholamines, D-tubucurarine, dopamine, DMT, 2,4-D ,diethyl ether, estradiol, edrophonium, ethylene oxide, etomidate, ethylene, ergometrine,enflurane, famotodine, fluoroxene, fentanyl, gramicidin S, GABA, gramicidin S,glucocorticoid receptors, girometrin, Glyphosate, halothane, 5-hydroxytryptamine, HIV,harmaline, insecticides, ketamine, lobelin, local anaesthetics, lidocaine, L-histamine, L-amino acids, heroin, LSD, misoindazole, meprobamate, morphine, methiparathion,mititane, midazolam, muscarin, muscazone, microcystins, mescaline, menthol,nitrozodimethylamine, nodularin, nitrous oxide, nitric oxide, nicotine, nizatidine, neurotoxinfrom poison of cobra, neostigmine, narcotic substances, 31-norlanosterol, neuropeptides, opioids, putrescine, pumiliotoxins, physostigmine, pyridostigmine, pilocarpine,pheniramine, phenacetin, pramoxine, picloram, pregnenolone, phosphatidylinositol,prostaglandins, spermidine, serotonin, scopolamine, strichnine, saxitoxin, salamandrine,toxicity, toxins, testosterone, thyrocydin, thiophos, thiofanox, TMA, volatile anaesthetics,vinyl ether, vitamin U, vitamin A, vitamin B and their biological activity is described.
Possible mechanisms of regulation of transcription by growth substances and the model ofDNA storage in chromosome are proposed. The central idea of this model is that DNAhaving snaky structure is placed between two layers of nucleosomes.
GENERAL CONCLUSIONS
1. The primary role of described Descriptors in the designing of novel bioregulators is to detect leads without performing experiments.
2. Using of Descriptors having active hydrogen at nitrogen atoms (-NH-) can be preferable in the designing of novel bioregulators with desirable prompt biologicaleffects. In order to achieve prolonged and more strong biological effects using ofDescriptors having active hydrogen at carbon atoms (>CH-) could be more suitable.
3. Chemicals having non-aromatic non-substituted cyclic structures possess strong 4. Substances bearing flanking substitutes such as -COOH, -OH, -COR and -COOR possess strong biological activity for plants and microbes whereas their toxicity formammals is moderate or slight.
5. Chemicals having Descriptors which are formed by P and S atoms possess as very strong toxicity as biological activity.
6. Chemicals having Descriptors which are not formed by P and S atoms possess very/or strong biological activity, their toxicity is only moderate.
7. Only substituents which have small sizes in alpha-position to active hydrogen atoms are suitable for their introduction to basic formulae to receive the bioregulators withpotent strong biological activity.
8. Bridgehead olefins which can form long-lived bridged free radicals in vivo possess 9. In order to design potent bioregulators with strong biological effects it is need to introduce to their formulae cis isomers.
10. Selection of Descriptors and flanking groups is the main condition that must be carry out in the designing of novel bioregulators.
11. Chemicals whose the free radicals are stabilised by resonance possess strong toxicity 12. Conjugation of chemicals having NH2-groups as flanking substitutes with cellular biopolymers can be the main cause of their low toxicity.
13. Chemicals having lipophylic CH3-groups as flanking substitutes possess strong toxicity 14. Chemicals having the oxygen in the ring of the molecule possess strong biological 15. Substances that can form in vivo more than one free radical center simultaneously possess strong biological (analgesic) activity.
16. Factors which stabilise free radicals increase biological activity of bioregulators.
This book is intended for anyone who studies structure/activity relationships to improvedesigning process of novel bioregulators. Also, it will be of interest to biochemistry,agronomy, pharmacology, and to agricultural and medicinal chemists, pharmaceuticalchemists, and molecular biologists. It is an original new approach in the molecularmechanisms of biological action of diverse chemical and physical factors. It can also serveas an instruction to design of novel pesticides and drugs.
CONTENTS
Preface, p. 7.
1. What Regulate the Growth Regulators ?, pp.8-10.
2. The Mechanisms of Action of Growth Regulators, pp.11-12.
3. Possible Alternative Way of Ethylene Formation from Quaternary Ammonium Salts, 4. Possible Reactions of Ethylene Oxidation and Formation of its Free Radicals, pp.25-33.
5. Decreasing of Endogenous Content of Abscisic Acid in the Winter Rye Seedlings Influenced by Some Natural and Synthetic Bioregulators, pp.34-37.
6. On the Possible Antioxidative Mode of Action of Plant Stress Growth Regulator Abscisic 7. The Membrane Aspects of the Mode of Action of Nonprotein Bioregulators, pp.42-69.
8. Functional-reactive Groups of Bioregulators, pp.70-80.
9. The Summarising Model of Action of Growth Retardants on Crops to Prevent Lodging, 10. On the Possible Antioxidative Mode of Action of Stress Proteins, p.82 (In English).
11. Preference in the Metabolism of D- or L- Chiral Molecules is Caused by the Selection of Chemical Reactions with the low Energy Activation, pp.83-86.
12. Chemical Structure of Descriptors with an Active Hydrogen Atom in Certain Bioregulators, pp.87-95 (In English). 13. Using of Descriptors to Design of Novel Drugs and Pesticides, and to Predict the Biological Activity from the Structure of Chemicals which have not been Bioassayed,pp.96-175 (In English). 14. Lipids as Possible Source of Stress Ethylene Formation and its Mode of Action, 15. Theoretical Investigation of Relationships Between the Chemical Structure of Some Blue-Green Algae Metabolites and their Biological Activity, pp.178-185 (In English). Conclusions and Perspectives, pp.186-202.
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