TY - JOUR
T1 - Design and chemical synthesis of root gravitropism inhibitors
T2 - Bridged analogues of ku-76 have more potent activity
AU - Shindo, Mitsuru
AU - Makigawa, Saki
AU - Kodama, Kozue
AU - Sugiyama, Hiromi
AU - Matsumoto, Kenji
AU - Iwata, Takayuki
AU - Wasano, Naoya
AU - Kano, Arihiro
AU - Morita, Miyo Terao
AU - Fujii, Yoshiharu
N1 - Publisher Copyright:
© 2020 Elsevier Ltd
PY - 2020/11
Y1 - 2020/11
N2 - 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.
AB - 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.
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U2 - 10.1016/j.phytochem.2020.112508
DO - 10.1016/j.phytochem.2020.112508
M3 - Article
C2 - 32905916
AN - SCOPUS:85090188168
SN - 0031-9422
VL - 179
JO - Phytochemistry
JF - Phytochemistry
M1 - 112508
ER -