Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity.
Compositae
Gravitropism
Inhibitor
Lactuca sativa
Organic synthesis
Structure modification
Journal
Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434
Informations de publication
Date de publication:
Nov 2020
Nov 2020
Historique:
received:
01
04
2020
revised:
22
08
2020
accepted:
25
08
2020
pubmed:
10
9
2020
medline:
11
11
2020
entrez:
9
9
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32905916
pii: S0031-9422(20)30353-8
doi: 10.1016/j.phytochem.2020.112508
pii:
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
112508Informations de copyright
Copyright © 2020 Elsevier Ltd. All rights reserved.