Influence of derivatives of 2-((6-r-quinolin-4-yl)thio)acetic acid on rhizogenesis of Paulownia clones

  • M. Zavhorodnii Khortytsia National Academy
  • N. Derevianko Khortytsia National Academy
  • T. Shkopynska Medical Professional College Zaporozhye State Medical University
  • M. Kornet Zaporizhzhya National University
  • O. Brazhko Zaporizhzhya National University
Keywords: hybrid molecules; quinoline derivatives; stimulation of rhizogenesis; bioavailability factors; lipophilicity; toxicity; progressive motility; microclonal propagation of plants.

Abstract

In recent years, the demand for effective and low-toxic stimulators of rhizogenesis, which are used in microclonal propagation of plants, has been increasing in Ukraine. One of the promising directions in the search for effective compounds is molecular modeling based on known natural and synthetic compounds. The development of new highly effective and low-toxic biologically active compounds is largely based on derivatives of nitrogen-containing heterocycles, and quinoline occupies a significant place among them. Modern methods of chemometric analysis make it possible to find certain regularities in the "chemical structure – biological activity" and to select the most promising compounds for experimental research. The values of lipophilicity log P for neutral forms and the value of the distribution coefficient log D at pH = 7 were obtained by quantum chemical calculation. The values of log P and log D of the studied compounds are in the most favourable interval for overcoming the biological membranes of the cells of the root system, depending on the pH of the environment. According to Lipinski’s "rule of five", all studied compounds can show high biological activity. The toxicity of compounds of 2-((6-R-quinolin-4-yl)thio)acetic acid derivatives was evaluated by computer programs and experimentally. Among the derivatives of 2-((6-R-quinolin-4-yl)thio)acetic acid, the most toxic compounds were those that did not have alkoxy substituents in the 6th position of the quinoline ring. Sodium salts are more toxic than the corresponding acids. This is due to an increase in the bioavailability of ionized compounds. Derivatives of 2-((6-R-quinolin-4-yl)thio)acetic acid (sodium salt of 2-((quinolin-4-yl)thio)acetic acid (QAC-5) showed the greatest toxic effect on the model of the study of progressive sperm motility) and 2-((quinolin-4-yl)thio)acetic acid (QAC-1), which will reduce this indicator by 15–20% compared to intact. The toxicity assessment of the studied compounds made it possible to determine a number of factors of the structure of molecules which affect the level of toxic action of 2-((6-R-quinolin-4-yl)thio)acetic acid derivatives and the directions of creation of non-toxic growth stimulants in this series. The impact on rhizogenesis during microclonal reproduction in vitro in explants Paulownia clone 112 and further adaptation of microplants in vivo hybrid molecules of quinoline and acetic acid, which are analogues of known growth stimulants, was studied. A number of factors influencing the level of influence on rhizogenesis of the action of derivatives of 2-((6-R-quinolin-4- yl)thio)acetic acid and directions of creation of highly active substances in this series was defined. The studied compounds showed a high stimulating effect on rhizogenesis in vitro in Paulownia explants. It was established that the sodium salt of 2-((quinolin-4-yl)thio)acetic acid was the greatest stimulator of rhizogenesis compared to the corresponding original acid. The presence of alkoxy groups in the 6th position and methyl in the 2nd position of the quinoline ring of 2-((6-R-quinolin-4-yl)thio)acetic acid reduced the activity of the compounds. The selection of new effective, low-toxic, less expensive substances was carried out for further testing as potential stimulators of rhizogenesis for microclonal propagation of plants.

References

Amer, A., & Omar, H. (2019). In-vitro propagation of the multipurpose Egyptian medicinal plant Pimpinella anisum. Egyptian Pharmaceutical Journal, 18(3), 254–262.
Anjos, J. D., Stefanello, C. A., Vieira, L. D., Polesi, L. G., Guerra, M. P., & Fraga, H. P. D. (2021). The cytokinin 6-benzylaminopurine improves the formation and development of Dryadella zebrina (Orchidaceae) in vitro shoots. Brazilian Journal of Botany, 44(4), 811–819.
Aremu, A. O., Dolezal, K., & Van Staden, J. (2015). New cytokinin-like compounds as a tool to improve rooting and establishment of micropropagated plantlets. Acta Horticulturae, 6th International Symposium on Production and Establishment of Micropropagated Plants, Sanremo, Italy, 497–503.
Arteta, T. A., Hameg, R., Landin, M., Gallego, P. P., & Barreal, M. E. (2018). Neural networks models as decision-making tool for in vitro proliferation of hardy kiwi. European Journal of Horticultural Science, 83(4), 259–265.
Awada, R., Verdier, D., Froger, S., Brulard, E., Maraschin, S. D., Etienne, H., & Breton, D. (2020). An innovative automated active compound screening system allows high-throughput optimization of somatic embryogenesis in Coffea arabica. Scientific Reports, 10(1), 810.
Bergmann, B. A., & Whetten, R. (1998). In vitro rooting and early greenhouse growth of micropropagated Paulownia elongata shoots. New Forests, 15, 127–138.
Bogdan, A. M., Brazhko, O. A., & Labenska, I. B. (2019). Acute toxicity and hypoglycemic activity of 7-chloro-4-thio-substituted quinoline. Bulletin of Zaporizhzhia National University, Biological Sciences, 1, 23–30 (in Ukrainian).
Brazhko, O. A., Omelyanchik, L. O., Zavgorodniy, M. P., & Martynovsky, M. P. (2013). Chemistry and biological activity of 2(4)-thioquinolines and 9-thioacridines. Zaporizhzhia National University, Zaporizhzhya (in Ukrainian).
Brazhko, O. A., Gencheva, V. I., Kornet, M. M., & Zavgorodniy, M. P. (2020). Modern aspects of drugs creation based on QuS-program development. Lambert Academic Publishing, Republic of Moldova.
Brazhko, O. A., Zavgorodniy, M. P., Kornet, M. M., Lagron, A. V., Dobrodub, I. V. (2018). Synthesis and biological activity of derivatives (2-methyl(phenyl)-6-r-quinolin-4-yl-sulphanyl)carboxylic acid. Science Review. 7(7), 8–10.
Brazhko, O. A., Kornet, M. M., & Zavgorodniy, M. P. (2011). Pat. 97937 Ukraine, IPC С07D 215/36, С07D 219/04, С07D 221/06, С07D 221/16, С07D 319/14. No. 2011 11474; stated. 28.09.2011; published March 26, 2012 Bull. No. 6.10.
Chalageri, G., Dhananjaya, S. P., Raghavendra, P., Kumar, L. M. S., Babu, U. V., & Varma, S. R. (2019). Substituting plant vegetative parts with callus cell extracts: Сase study with Woodfordia fruticosa Kurz. – A potent ingredient in skin care formulations. South African Journal of Botany, 123, 351–360.
Derevianko, N. P, Brazhko, O. A, Zavgorodniy, M. P, & Vasilieva, T. M. (2016). Efficiency and safety of new plant growth stimulants based on heterocarboxylic acid derivatives. Agroecological Journal, 3, 100–104 (in Ukrainian).
Dhooghe, E., Lootens, P., Van Poucke, C., De Keyser, E., & Van Huylenbroeck, J. (2021). Antitranspirants putrescine and abscisic acid improve acclimatization of micropropagated spathiphyllum 'lima' Regel. Propagation of Ornamental Plants, 21(3), 67–77.
Fokina, A. V., Satarova, T. M., Smetanin, V. T., & Kucenko, N. I. (2018). Optimization of microclonal propagation in vitro of oregano (Origanum vulgare). Biosystems Diversity, 26(2), 98–102.
Grishchenko, O. V., Subbotin, E. P., Gafitskaya, I. V., Vereshchagina, Y. V., Burkovskaya, E. V., Khrolenko, Y. A., & Kulchin, Y. N. (2022). Growth of micropropagated Solanum tuberosum L. plantlets under artificial solar spectrum and different mono- and polychromatic LED lights. Horticultural Plant Journal, 8(2), 205–214.
Ilczuk, A., Jagiello-Kubiec, K., & Jacygrad, E. (2013). The effect of carbon source in culture medium on micropropagation of common ninebark (Physocarpus opulifolius (L.) Maxim.) 'Diable D'or'. Acta Scientiarum Polonorum-Hortorum Cultus, 12(3), 23–33.
Ivashchuk, O. A., Batlutskaya, I. V., Maslova, E. V., Shcherbinina, N. V., Shamraev, A. A., & Gaidai, P. A. (2018). Approaches to conservation of biodiversity of rare and endangered medicinal plants on the basis of microclonal multiplication with optimization of parameters by methods of neural network modeling. Research Journal of Pharmaceutical Biological and Chemical Sciences, 9(5), 2347–2356.
Ivashuk, O. A., Batlutskaya, I., Shcherbinina, N. V., Maslova, E. V., & Degtyareva, K. A. (2017). Approaches to the construction of simulation model of the process optimization of rare plants microclonal propagation. International Journal of Advanced Biotechnology and Research, 8(4), 2187–2192.
Kalinin, F. L. (1984). Biologically active substances in crop production. Naukova Dumka, Kyiv.
Kornet, M. M., Brazhko, О. А., Zavhorodniy, M. P., Tkach, V. V., Kruglyak, O. S., & de Oliveira, S. C. (2021). Electrochemical determination of antioxidant activity of new 4-thiosubstituted quinoline derivatives with potential radioprotecting properties. Biointerface Research in Applied Chemistry, 11(2), 9148–9156.
Kornet, M. M., Dudareva, G. F., Gencheva, V. I., Klimova, O. O., Peretiatko, V. V., & Brazhko, O. A. (2020). Growth-regulatory activity of 2-methyl-4-thioquinoline derivatives. Ukrainian Journal of Ecology, 10(2), 279–283.
Kornet, M. M. (2012). Biological activity of S-(quinolin-4-yl)-L-cysteine derivatives and their structural analogues. Institut of Bioorganic Chemistry and Petrochemistry, Kiev (in Ukrainian).
Kulak, V., Longboat, S., Brunet, N. D., Shukla, M., & Saxena, P. (2022). In vitro technology in plant conservation: Relevance to biocultural diversity. Plants, 11(4), 503.
Maistrenko, G. G., & Krasnoborov, I. M. (2009). Microclonal propagation and biological features of Scrophularia umbrosa Dumort. cultured in vitro. Contemporary Problems of Ecology, 2(6), 501–505.
Martin, T. M. (2016). Toxicity Estimation Software Tool (TEST). Environmental Protection Agency, Washington.
Matskevich, V. V., Podgaetsky, A. A., & Filipova, L. M. (2019). Microclonal propagation of certain plant species (technology protocols). Scientific and practical manual. BNAU, Bila Tserkva.
Metelytsia, L., Hodyna, D., Dobrodub, I., Semenyuta, I., Zavhorodnii, M., Blagodatny, V., & Brazhko, O. (2020). Design of (quinolin-4-ylthio)carboxylic acids as new Escherichia coli DNA gyrase B inhibitors: Machine learning studies, molecular docking, synthesis and biological testing. Computational Biology and Chemistry, 85, 107224.
Mikhovich, Z. E., & Teteryuk, L. V. (2020). In vitro culture of the Ural endemic Gypsophila uralensis Less. (Caryophyllaceae). Turczaninowia, 23(3), 29–35.
Misyri, V., Tsekouras, V., Iliopoulos, V., Mavrikou, S., Evergetis, E., Moschopoulou, G., & Haroutounian, S. A. (2021). Farm or lab? Chamazulene content of Artemisia arborescens (Vill.) L. essential oil and callus volatile metabolites isolate. Industrial Crops and Products, 160, 113114.
Omelyanchyk, L., Brazhko, O., Labenska, I., Zavgorodniy, M., & Petrusha, Y., (2018). Biological activity and physicochemical properties N-acid derivatives S-(2-methylquinolin-4-yl)-L-cysteine. Zaporizhzhia National University, Zaporizhzhya.
Orlikowska, T., Zawadzka, M., Zenkteler, E., & Sobiczewski, P. (2012). Influence of the biocides PPM (TM) and Vitrofural on bacteria isolated from contaminated plant tissue cultures and on plant microshoots grown on various media. Journal of Horticultural Science and Biotechnology, 87(3), 223–230.
Pereira, V. J., Asmar, S. A., Biase, N. G., Luz, J. M. Q., & de Melo, B. (2018). Statistics applied to plant micropropagation: A critical review of inadequate use. Bioscience Journal, 34(5), 1308–1318.
Rodrigues, V., Kumar, A., Gokul, S., Verma, R. S., Rahman, L. U., & Sundaresan, V. (2020). Micropropagation, encapsulation, and conservation of Decalepis salicifolia, a vanillin isomer containing medicinal and aromatic plant. In Vitro Cellular and Developmental Biology-Plant, 56(4), 526–537.
Yakovleva-Nosar, S. O., Derevyanko, N. P., Yevlash, A. S., Brazhko, O. A., Zavhorodnii, M. P., Tkach, V. V., & Yagodynets, P. I. (2022). A search of the efficient s-hetarylsuccinate landscape design plant growth stimulators. Biointerface Research in Applied Chemistry, 12(1), 465–469.
Stefanov, O. V. (Ed.). (2001). Preclinical study of drugs (methodological recommendation). Avitsena, Kyiv (in Ukrainian).
Tiuzikov, I. A. (2013). Metabolic syndrome and male infertility (literature review). Andrology and Genital Surgery, 2, 5–10 (in Russian).
Tung, H. T., Bao, H. G., Cuong, D. M., Ngan, H. T. M., Hien, V. T., Luan, V. Q., & Nhut, D. T. (2021). Silver nanoparticles as the sterilant in large-scale micropropagation of chrysanthemum. In Vitro Cellular and Developmental Biology-Plant, 57(6), 897–906.
Yegizbayeva, T. K., Yausheva, T. V., Oleichenko, S. N., & Licea-Moreno, R. J. (2020). Influence of nutrition compositions on microclonal propagation different genotypes of the walnut Juglans regia L. Bulletin of the National Academy of Sciences of the Republic of Kazakhstan, 1, 105–112.
Zakharova, O., Kolesnikova, E., Kolesnikov, E., Yevtushenko, N., Morkovin, V., & Gusev, A. (2020). CuO nanoparticles effects on poplar(x)aspen hybrid clones at various stages of microclonal propagation. International Forestry Forum on Forest Ecosystems as Global Resource of the Biosphere – Calls, Threats, Solutions (Forestry), 595(1), 012001.
Ziauka, J., Kuusiene, S., & Silininkas, M. (2013). Fast growing aspens in the development of a plant micropropagation system based on plant-produced ethylene action. Biomass and Bioenergy, 53, 20–28.
Abu-Hashem, A. A., Abdelgawad, A. A. M., Hussein, H. A. R., & Gouda, M. A. (2022). Synthetic and reactions routes to tetrahydrothieno 3,2-b quinoline derivatives (part IV). Mini-Reviews in Organic Chemistry, 19(1), 74–91.
Hassan, M. M., & Alzandi, A. R. A. (2020). Synthesis, structure elucidation and plants growth promoting effects of novel quinolinyl chalcones. Arabian Journal of Chemistry, 13(7), 6184–6190.
Koprulu, T. K., Okten, S., Atalay, V. E., Tekin, S., & Cakmak, O. (2021). Biological activity and molecular docking studies of some new quinolines as potent anticancer agents. Medical Oncology, 38(7), 84.
Lenin, S., Sujatha, R., & Shanmugasundaram, P. (2022). Pharmacological properties and bioavailability studies of 3-methyl quinoline. International Journal of Life Science and Pharma Research, 12(1), L100–L104.
Lu, W., Chen, J. C., Shi, J. Z., Xu, L., Yang, S. L., & Gao, B. H. (2021). A novel quinoline-based turn-on fluorescent probe for the highly selective detection of Al (III) and its bioimaging in living cells, plants tissues and zebrafish. Journal of Biological Inorganic Chemistry, 26(1), 57–66.
Namitha, R., Priyadarshini, G. S., & Selvi, G. (2021). Pharmacological studies on novel triazino quinolines. Advances in Pharmacology and Pharmacy, 9(4), 81–86.
Salem, M. A., Abu-Hashem, A. A., Abdelgawad, A. A. M., & Gouda, M. A. (2021). Synthesis and reactivity of thieno 2,3-b quinoline derivatives (Part II). Journal of Heterocyclic Chemistry, 58(9), 1705–1740.
Singh, K., Sharma, R., & Sahare, H. (2022). Implications of synthetic chemicals and natural plant extracts in improving vase life of flowers. Scientia Horticulturae, 302, 111133.
Vostrikova, T. V., Kalaev, V. N., Medvedeva, S. M., Novichikhina, N. P., & Shikhaliev, K. S. (2020). Synthesized organic compounds as growth stimulators for woody plants. Periodico Tche Quimica, 17(35), 327–337.
Vostrikova, T. V., Kalaev, V. N., Potapov, A. Y., Manakhelokhe, G. M., & Shikhaliev, K. S. (2021). Use of new compounds of the quinoline series as growth and yield stimulants of agricultural crop. Periodico Tche Quimica, 18(38), 123–136.
Yepes, A. F., Quintero-Saumeth, J., & Cardona-Galeano, W. (2021). Biologically active quinoline-hydrazone conjugates as potential Trypanosoma cruzi DHFR-TS inhibitors: Docking, molecular dynamics, MM/PBSA and drug-likeness studies. ChemistrySelect, 6(12), 2928–2938.
Published
2022-07-11
How to Cite
Zavhorodnii, M., Derevianko, N., Shkopynska, T., Kornet, M., & Brazhko, O. (2022). Influence of derivatives of 2-((6-r-quinolin-4-yl)thio)acetic acid on rhizogenesis of Paulownia clones . Regulatory Mechanisms in Biosystems, 13(3), 213-218. Retrieved from https://medicine.dp.ua/index.php/med/article/view/814