WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H525741
CAS#: 6266-66-6
Description: PEO-IAA is a novel potent auxin antagonist.
Hodoodo Cat#: H525741
Name: PEO-IAA
CAS#: 6266-66-6
Chemical Formula: C18H15NO3
Exact Mass: 293.11
Molecular Weight: 293.322
Elemental Analysis: C, 73.71; H, 5.15; N, 4.78; O, 16.36
Synonym: PEO-IAA
IUPAC/Chemical Name: 2-(1H-Indol-3-yl)-4-oxo-4-phenylbutanoic acid
InChi Key: SJVMWLJNHPHNPT-UHFFFAOYSA-N
InChi Code: InChI=1S/C18H15NO3/c20-17(12-6-2-1-3-7-12)10-14(18(21)22)15-11-19-16-9-5-4-8-13(15)16/h1-9,11,14,19H,10H2,(H,21,22)
SMILES Code: O=C(O)C(C1=CNC2=C1C=CC=C2)CC(C3=CC=CC=C3)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.03.00
More Info:
| Biological target: | PEO-IAA is an indole-3-acetic acid (IAA) antagonist. PEO-IAA is an auxin antagonist that binds to transport inhibitor response 1/auxin signaling F-box proteins (TIR1/AFBs). |
| In vitro activity: | The involvement of auxin signaling in the regulation of chromatin accessibility was analyzed. This study verified the involvement of TIR1/AFBs-mediated auxin signaling in the regulation of chromatin accessibility by using PEO-IAA and a cultured cell line of A. thaliana, MM2d. The results of the comet assay revealed that PEO-IAA treatment caused a ~1.6-fold increase in DSBs accumulation (Fig. 2A,B). In addition, PEO-IAA treatment increased the chromatin sensitivity to MNase as shown by the faster digestion of PEO-IAA-treated chromatin (Fig. 2C). The results of ATAC-seq, which reveals accessible chromatin regions by using the action of Tn5 transposase that causes DNA cleavage and simultaneous insertion of sequencing adapters into open chromatin regions30, confirmed that PEO-IAA treatment indeed increased chromatin accessibility, especially in the gene body region (Fig. 2D,E). Although the possible involvement of another auxin signaling pathway cannot be excluded, these results suggested that auxin acts in the regulation of chromatin accessibility through the TIR1/AFBs-mediated auxin signaling pathway. It was presumed that the regulation of genes related to chromatin accessibility would be downstream of the TIR1/AFBs pathway. To identify such genes, this study analyzed gene expression in MM2d cells treated with PEO-IAA by RNA-seq. It was found that PEO-IAA treatment significantly altered the expression of 3833 genes (p |
| In vivo activity: | This study investigated the pathways regulated by 26SP using a 26SP subunit mutant, rpt5a, which is hypersensitive to high-B stress. Five-day-old seedlings pre-incubated vertically on normal MGRL medium were transferred to fresh medium containing indicated concentrations of B, indole-3-acetic acid (IAA), α-(phenyl ethyl-2-one)-indole-3-acetic acid (PEO-IAA) (Hayashi et al., 2012), and trans-zeatin (tZ). The negative effect of PEO-IAA on root growth under the normal B condition was comparable between the wild type and the rpt5a mutants. However, the effect of PEO-IAA under the high-B condition differed between the wild type and the rpt5a mutants. In rpt5a-4 and rpt5a-6, 1.25 μM PEO-IAA treatment alleviated the inhibitory effect of high-B stress on root growth (Figure 5B). In addition, the negative effect of higher concentrations of PEO-IAA on root growth was less than that in the wild type under the high-B condition (Figure 5B). The present results suggested that the enhancement in auxin responses through the TIR1/AFB-dependent auxin signaling pathway is a critical cause of the severe inhibition of root growth in the rpt5a mutant under high-B stress. Combined with the observed improvement of RAM morphology in the rpt5a mutant under high-B stress by PEO-IAA treatment, which stabilizes AUX/IAA proteins (Figure 5), it is considered that 26SP functions to fine-tune the homoeostasis of AUX/IAA proteins to maintain the auxin responses required for RAM maintenance at the appropriate level under the high-B condition. Front Plant Sci. 2019; 10: 590.Published online 2019 May 14. doi: 10.3389/fpls.2019.00590 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6530338/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 40.0 | 136.40 |
The following data is based on the product molecular weight 293.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Sakamoto T, Sotta N, Suzuki T, Fujiwara T, Matsunaga S. The 26S Proteasome Is Required for the Maintenance of Root Apical Meristem by Modulating Auxin and Cytokinin Responses Under High-Boron Stress. Front Plant Sci. 2019 May 14;10:590. doi: 10.3389/fpls.2019.00590. PMID: 31156663; PMCID: PMC6530338. 2. Hasegawa J, Sakamoto T, Fujimoto S, Yamashita T, Suzuki T, Matsunaga S. Auxin decreases chromatin accessibility through the TIR1/AFBs auxin signaling pathway in proliferative cells. Sci Rep. 2018 May 17;8(1):7773. doi: 10.1038/s41598-018-25963-y. PMID: 29773913; PMCID: PMC5958073. |
| In vitro protocol: | 1.Hasegawa J, Sakamoto T, Fujimoto S, Yamashita T, Suzuki T, Matsunaga S. Auxin decreases chromatin accessibility through the TIR1/AFBs auxin signaling pathway in proliferative cells. Sci Rep. 2018 May 17;8(1):7773. doi: 10.1038/s41598-018-25963-y. PMID: 29773913; PMCID: PMC5958073. |
| In vivo protocol: | 1. Sakamoto T, Sotta N, Suzuki T, Fujiwara T, Matsunaga S. The 26S Proteasome Is Required for the Maintenance of Root Apical Meristem by Modulating Auxin and Cytokinin Responses Under High-Boron Stress. Front Plant Sci. 2019 May 14;10:590. doi: 10.3389/fpls.2019.00590. PMID: 31156663; PMCID: PMC6530338. |
1: Takato S, Kakei Y, Mitsui M, Ishida Y, Suzuki M, Yamazaki C, Hayashi KI, Ishii T, Nakamura A, Soeno K, Shimada Y. Auxin signaling through SCF(TIR1/AFBs) mediates feedback regulation of IAA biosynthesis. Biosci Biotechnol Biochem. 2017 Apr 13:1-7. doi: 10.1080/09168451.2017.1313694. [Epub ahead of print] PubMed PMID: 28406060.
2: Tamaki H, Reguera M, Abdel-Tawab YM, Takebayashi Y, Kasahara H, Blumwald E. Targeting Hormone-Related Pathways to Improve Grain Yield in Rice: A Chemical Approach. PLoS One. 2015 Jun 22;10(6):e0131213. doi: 10.1371/journal.pone.0131213. eCollection 2015. PubMed PMID: 26098557; PubMed Central PMCID: PMC4476611.
3: Camacho-Cristóbal JJ, Martín-Rejano EM, Herrera-Rodríguez MB, Navarro-Gochicoa MT, Rexach J, González-Fontes A. Boron deficiency inhibits root cell elongation via an ethylene/auxin/ROS-dependent pathway in Arabidopsis seedlings. J Exp Bot. 2015 Jul;66(13):3831-40. doi: 10.1093/jxb/erv186. Epub 2015 Apr 28. PubMed PMID: 25922480; PubMed Central PMCID: PMC4473985.
4: Yoshimoto K, Noutoshi Y, Hayashi K, Shirasu K, Takahashi T, Motose H. A chemical biology approach reveals an opposite action between thermospermine and auxin in xylem development in Arabidopsis thaliana. Plant Cell Physiol. 2012 Apr;53(4):635-45. doi: 10.1093/pcp/pcs017. Epub 2012 Feb 17. PubMed PMID: 22345435.
5: Takanashi K, Sugiyama A, Yazaki K. Involvement of auxin distribution in root nodule development of Lotus japonicus. Planta. 2011 Jul;234(1):73-81. doi: 10.1007/s00425-011-1385-0. Epub 2011 Mar 3. PubMed PMID: 21369920.
6: Ishida T, Adachi S, Yoshimura M, Shimizu K, Umeda M, Sugimoto K. Auxin modulates the transition from the mitotic cycle to the endocycle in Arabidopsis. Development. 2010 Jan;137(1):63-71. doi: 10.1242/dev.035840. PubMed PMID: 20023161.
7: Nishimura T, Nakano H, Hayashi K, Niwa C, Koshiba T. Differential downward stream of auxin synthesized at the tip has a key role in gravitropic curvature via TIR1/AFBs-mediated auxin signaling pathways. Plant Cell Physiol. 2009 Nov;50(11):1874-85. doi: 10.1093/pcp/pcp129. Epub 2009 Nov 6. PubMed PMID: 19897572.
