New aromatic 6-substituted 2′-deoxy-9-(β)-D-ribofuranosylpurine derivatives as potential plant growth regulators

0522677 - ÚEB 2020 RIV GB eng J - Journal Article
Matušková, Vlasta - Zatloukal, M. - Voller, Jiří - Grúz, Jiří - Pěkná, Z. - Briestenská, K. - Mistríková, J. - Spíchal, L. - Doležal, Karel - Strnad, Miroslav
New aromatic 6-substituted 2′-deoxy-9-(β)-D-ribofuranosylpurine derivatives as potential plant growth regulators.
Bioorganic & Medicinal Chemistry. Roč. 28, č. 2 (2020), č. článku 115230. ISSN 0968-0896. E-ISSN 1464-3391
R&D Projects: GA MŠMT(CZ) EF16_019/0000827
Institutional support: RVO:61389030
Keywords : 2′-Deoxyribosides * Antioxidative capacity * Antiviral testing * Aromatic cytokinins * Plant growth regulator * Purine derivatives
OECD category: Biochemistry and molecular biology
Impact factor: 3.641, year: 2020
Method of publishing: Open access
https://www.sciencedirect.com/science/article/pii/S0968089619317304

Cytokinins are naturally occurring substances that act as plant growth regulators promoting plant growth and development, including shoot initiation and branching, and also affecting apical dominance and leaf senescence. Aromatic cytokinin 6-benzylaminopurine (BAP) has been widely used in micropropagation systems and biotechnology. However, its 9-glucoside (BAP9G) accumulates in explants, causing root inhibition and growth heterogenity. To overcome BAP disadvantages, a series of ring-substituted 2′-deoxy-9-(β)-D-ribofuranosylpurine derivatives was prepared and examined in different classical cytokinin bioassays. Amaranthus, senescence and tobacco callus bioassays were employed to provide details of cytokinin activity of 2′-deoxy-9-(β)-D-ribosides compared to their respective free bases and ribosides. The prepared derivatives were also tested for their recognition by cytokinin receptors of Arabidopsis thaliana AHK3 and CRE1/AHK4. The ability of aromatic N6-substituted adenine-2′-deoxy-9-(β)-D-ribosides to promote plant growth and delay senescence was increased considerably and, in contrast to BAP, no loss of cytokinin activity at higher concentrations was observed. The presence of a 2′-deoxyribosyl moiety at the N9-position led to an increase in cytokinin activities in comparison to the free bases and ribosides. The antioxidant capacity, cytotoxicity and effect on the MHV-68 gammaherpesvirus strain were also examined.
Permanent Link: http://hdl.handle.net/11104/0307127