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New aromatic 6-substituted 2'-deoxy-9-(β)-d-ribofuranosylpurine derivatives as potential plant growth regulators.
Bioorganic & Medicinal Chemistry ( IF 3.3 ) Pub Date : 2019-11-29 , DOI: 10.1016/j.bmc.2019.115230
Vlasta Matušková 1 , Marek Zatloukal 2 , Jiří Voller 3 , Jiří Grúz 3 , Zuzana Pěkná 2 , Katarína Briestenská 4 , Jela Mistríková 4 , Lukáš Spíchal 2 , Karel Doležal 1 , Miroslav Strnad 3
Affiliation  

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.

中文翻译:

新的芳香6-取代的2'-脱氧-9-(β)-d-呋喃核糖基嘌呤衍生物作为潜在的植物生长调节剂。

细胞分裂素是天然存在的物质,可充当植物生长调节剂,促进植物的生长和发育,包括芽的萌芽和分支,还影响根部的优势和叶片的衰老。芳香族细胞分裂素6-苄基氨基嘌呤(BAP)已被广泛用于微繁系统和生物技术中。但是,其9-葡萄糖苷(BAP9G)积累在外植体中,引起根抑制和生长异质性。为了克服BAP的缺点,制备了一系列环取代的2'-脱氧-9-(β)-d-呋喃呋喃糖基嘌呤衍生物,并在不同的经典细胞分裂素生物测定法中进行了研究。使用mar菜,衰老和烟草愈伤组织生物测定法来提供2'-脱氧-9-(β)-d-核糖苷与其各自的游离碱和核糖苷相比的细胞分裂素活性的详细信息。还测试了所制备的衍生物被拟南芥AHK3和CRE1 / AHK4的细胞分裂素受体识别的能力。芳香N6取代的腺嘌呤2'-脱氧9-(β)-d-核糖苷促进植物生长和延缓衰老的能力显着提高,并且与BAP相比,在较高浓度下未观察到细胞分裂素活性的损失。与游离碱和核糖苷相比,在N9位上2'-脱氧核糖基部分的存在导致细胞分裂素活性的增加。还检查了抗病毒能力,细胞毒性以及对MHV-68γ疱疹病毒株的影响。促进植物生长和延缓衰老的-deoxy-9-(β)-d-核糖苷显着增加,与BAP相比,在较高浓度下未观察到细胞分裂素活性的损失。与游离碱和核苷相比,在N9位上2'-脱氧核糖基部分的存在导致细胞分裂素活性的增加。还检查了抗病毒能力,细胞毒性以及对MHV-68γ疱疹病毒株的影响。促进植物生长和延缓衰老的-deoxy-9-(β)-d-核糖苷显着增加,与BAP相比,在较高浓度下未观察到细胞分裂素活性的损失。与游离碱和核糖苷相比,在N9位上2'-脱氧核糖基部分的存在导致细胞分裂素活性的增加。还检查了抗病毒能力,细胞毒性以及对MHV-68γ疱疹病毒株的影响。
更新日期:2019-11-30
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