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.

Comenius University Faculty of Natural Sciences Department of Microbiology and Virology Mlynská dolina Ilkovičova 6 842 15 Bratislava 4 Slovak Republic

Department of Chemical Biology and Genetics Centre of the Region Haná for Biotechnological and Agricultural Research Faculty of Science Palacký University Šlechtitelů 27 CZ 783 71 Olomouc Czech Republic

Institute of Virology Biomedical Center SAS Dúbravská cesta 9 845 05 Bratislava Slovak Republic

Laboratory of Growth Regulators The Czech Academy of Sciences Institute of Experimental Botany and Palacký University Šlechtitelů 27 CZ 783 71 Olomouc Czech Republic

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$a Matušková, Vlasta $u Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic; Laboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic. Electronic address: matuskova.vlasta@gmail.com

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$a New aromatic 6-substituted 2'-deoxy-9-(β)-d-ribofuranosylpurine derivatives as potential plant growth regulators / $c V. Matušková, M. Zatloukal, J. Voller, J. Grúz, Z. Pěkná, K. Briestenská, J. Mistríková, L. Spíchal, K. Doležal, M. Strnad

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$a 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.

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$a Zatloukal, Marek $u Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic

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$a Voller, Jiří $u Laboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic

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$a Grúz, Jiří $u Laboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic

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$a Pěkná, Zuzana $u Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic

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$a Briestenská, Katarína $u Comenius University, Faculty of Natural Sciences, Department of Microbiology and Virology, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava 4, Slovak Republic; Institute of Virology, Biomedical Center SAS, Dúbravská cesta 9, 845 05 Bratislava, Slovak Republic

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$a Mistríková, Jela $u Comenius University, Faculty of Natural Sciences, Department of Microbiology and Virology, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava 4, Slovak Republic; Institute of Virology, Biomedical Center SAS, Dúbravská cesta 9, 845 05 Bratislava, Slovak Republic

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$a Spíchal, Lukáš $u Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic

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$a Doležal, Karel $u Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic; Laboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic. Electronic address: karel.dolezal@upol.cz

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