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<p>Cytokinins (CKs) are important group of phytohormones that influence a vast number of processes throughout all stages of plant ontogenesis. Components of the CK signaling chain mainly act as negative regulators of plant adaptation to unfavorable environmental conditions. The fine tuning of the CK signaling, a targeted and careful decrease in CK activity in definite plant organs and tissues, can increase the survival and productivity of agricultural plants affected by stress factors. One of the promising options to achieve this goal is the use of anticytokinins (antiCKs) with pronounced receptor specificity. To date, many synthetic analogs of natural CKs are known; however, there is little progress in the development of CK antagonists. In this work, a large series of <i>N</i><sup>6</sup>-substituted adenosine derivatives were synthesized and studied as potential antiCKs for individual CK receptors from <i>Arabidopsis thaliana</i>. To dissect the dependence of CK antagonist activity on the structure of the adenosine derivatives, we studied effects of modifications of the sugar moiety at the <i>N</i>9 position, as well as different substituents at the <i>N</i><sup>6</sup> position of the purine heterocycle. The cognate nucleobases for all tested nucleoside derivatives were also assessed for both CK agonist and antagonist activity. As a result, new receptor-specific antiCKs were found both among nucleoside derivatives and nucleobases. The activity of such compounds was shown to strictly depend on the structure of the <i>N</i><sup>6</sup>-substituent. In several cases, the presence of the intact β-D-ribofuranose residue at <i>N</i>9 of purine heterocycle was critical for the manifestation of the antiCK properties, since cognate nucleobases exhibited not antagonist, but definite CK agonist activity. Most if not all, newly found antiCKs acted non-competitively at the receptor level by yet unknown molecular mechanism. Some of these regulators exhibited dual activities, usually acting as antiCKs with AHK2 and AHK4, but as CK agonists with AHK3 receptors. Such new class of cytokinin-related regulators with opposite activities depending on the receptor opens large prospects for their practical application in biotechnology and agriculture.</p>

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Distinct N6-Substituted Adenosine Derivatives Exhibit Receptor-Specific Anticytokinin Action by Unknown Non-competitive Mechanism

  • 期刊论文

  • 发表日期：

    2025年4月17日

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  • Anastasia A. Zenchenko,
  • Ekaterina M. Savelieva,
  • Julia D. Semenova,
  • Mikhail S. Drenichev,
  • Pavel N. Solyev,
  • Dmitry V. Arkhipov,
  • Georgy A. Romanov,
  • Vladimir E. Oslovsky

摘要

Cytokinins (CKs) are important group of phytohormones that influence a vast number of processes throughout all stages of plant ontogenesis. Components of the CK signaling chain mainly act as negative regulators of plant adaptation to unfavorable environmental conditions. The fine tuning of the CK signaling, a targeted and careful decrease in CK activity in definite plant organs and tissues, can increase the survival and productivity of agricultural plants affected by stress factors. One of the promising options to achieve this goal is the use of anticytokinins (antiCKs) with pronounced receptor specificity. To date, many synthetic analogs of natural CKs are known; however, there is little progress in the development of CK antagonists. In this work, a large series of N6-substituted adenosine derivatives were synthesized and studied as potential antiCKs for individual CK receptors from Arabidopsis thaliana. To dissect the dependence of CK antagonist activity on the structure of the adenosine derivatives, we studied effects of modifications of the sugar moiety at the N9 position, as well as different substituents at the N6 position of the purine heterocycle. The cognate nucleobases for all tested nucleoside derivatives were also assessed for both CK agonist and antagonist activity. As a result, new receptor-specific antiCKs were found both among nucleoside derivatives and nucleobases. The activity of such compounds was shown to strictly depend on the structure of the N6-substituent. In several cases, the presence of the intact β-D-ribofuranose residue at N9 of purine heterocycle was critical for the manifestation of the antiCK properties, since cognate nucleobases exhibited not antagonist, but definite CK agonist activity. Most if not all, newly found antiCKs acted non-competitively at the receptor level by yet unknown molecular mechanism. Some of these regulators exhibited dual activities, usually acting as antiCKs with AHK2 and AHK4, but as CK agonists with AHK3 receptors. Such new class of cytokinin-related regulators with opposite activities depending on the receptor opens large prospects for their practical application in biotechnology and agriculture.