Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity,Phytochemistry

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Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity
Phytochemistry ( IF 3.2 ) Pub Date : 2020-11-01 , DOI: 10.1016/j.phytochem.2020.112508
Mitsuru Shindo ₁ , Saki Makigawa ₂ , Kozue Kodama ₁ , Hiromi Sugiyama ₁ , Kenji Matsumoto ₁ , Takayuki Iwata ₁ , Naoya Wasano ₃ , Arihiro Kano ₁ , Miyo Terao Morita ₄ , Yoshiharu Fujii ₃

Affiliation

Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition, and revealed the structure-activity relationship in this inhibitory activity. The conformation of ku-76 is flexible owing to the open-chain structure of pentan-2,4-dienoic acid with freely rotating single bonds, and the (2Z)-alkene moiety may be isomerized by external factors. To develop more potent inhibitors and obtain insight into the target biomolecules, various analogues of ku-76, fixed through conformation and/or configuration, were synthesized and evaluated. Stereochemical fixation was effective in improving the potency of gravitropic bending inhibition. Finally, we found highly potent conformational and/or configurational analogues (ku-257, ku-294 and ku-308), that did not inhibit root growth. The inhibition of root curvature by these analogues was comparable to that of naptalam.

中文翻译：

根向地性抑制剂的设计和化学合成：ku-76的桥接类似物具有更有效的活性

此前，我们发现 (2Z,4E)-5-苯基五-2,4-二烯酸 (ku-76) 在 5 μM 浓度下是生菜胚根根向重力弯曲的选择性抑制剂，且不伴随生长抑制，并揭示了该抑制活性中的构效关系。由于戊-2,4-二烯酸具有自由旋转单键的开链结构，ku-76的构象是灵活的，并且(2Z)-烯烃部分可以通过外部因素异构化。为了开发更有效的抑制剂并深入了解目标生物分子，合成并评估了通过构象和/或构型固定的 ku-76 的各种类似物。立体化学固定可有效提高向地弯曲抑制的效力。最后，我们发现了高效的构象和/或构型类似物（ku-257、ku-294 和 ku-308），它们不会抑制根的生长。这些类似物对根部弯曲的抑制作用与抑菌灵相当。

更新日期：2020-11-01

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