PEO-IAA | CAS#6266-66-6 | Auxin antagonist

MedKoo Cat#: 525741 | Name: PEO-IAA

Description:

WARNING: This product is for research use only, not for human or veterinary use.

PEO-IAA is a novel potent auxin antagonist.

Chemical Structure

PEO-IAA

CAS#6266-66-6

Theoretical Analysis

MedKoo Cat#: 525741

Name: PEO-IAA

CAS#: 6266-66-6

Chemical Formula: C18H15NO3

Exact Mass: 293.1052

Molecular Weight: 293.32

Elemental Analysis: C, 73.71; H, 5.15; N, 4.78; O, 16.36

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Size	Price	Availability
50mg	USD 90.00	Ready to ship
100mg	USD 150.00	Ready to ship
200mg	USD 250.00	Ready to ship
500mg	USD 550.00	Ready to ship
1g	USD 950.00	Ready to ship
2g	USD 1,650.00	Ready to ship
5g	USD 3,650.00	Ready to ship

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Synonym

PEO-IAA; PEOIAA; 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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A8T09K14

QC Data

View QC data: current batch, Lot#A8T09K14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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 < 0.01): 1222 of them were down-regulated (PEO-IAA/DMSO ≤0.67-fold) and 1434 were up-regulated (Supplementary Fig. S1, Dataset S1) Consistent with this, the PEO-IAA treatment also decreased the level of histone H4 protein. The PEO-IAA treatment increased the distance between the 180-bp repeats and the closest chromocenter (Fig. 4A,B). Similarly, the number of 45S rDNA signals separated from the 180-bp repeat signals was increased after 10 μM PEO-IAA treatment (Fig. 4C,D). These results indicated that chromatin accessibility is increased by the inhibition of the TIR1/AFBs pathway in root meristematic cells of A. thaliana seedlings. Sci Rep. 2018; 8: 7773.Published online 2018 May 17. doi: 10.1038/s41598-018-25963-y https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5958073/

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	mg/mL	mM
Solubility
	DMSO	40.0	136.40

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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: Ahmed J, Sajjad Y, Gatasheh MK, Ibrahim KE, Huzafa M, Khan SA, Situ C, Abbasi AM, Hassan A. Genome-wide identification of NAC transcription factors and regulation of monoterpenoid indole alkaloid biosynthesis in Catharanthus roseus. Front Plant Sci. 2023 Dec 20;14:1286584. doi: 10.3389/fpls.2023.1286584. PMID: 38223288; PMCID: PMC10785006. 2: Šenkyřík JB, Křivánková T, Kaczorová D, Štefelová N. Investigation of the Effect of the Auxin Antagonist PEO-IAA on Cannabinoid Gene Expression and Content in Cannabis sativa L. Plants under In Vitro Conditions. Plants (Basel). 2023 Apr 15;12(8):1664. doi: 10.3390/plants12081664. PMID: 37111886; PMCID: PMC10142887. 3: Taya K, Takeuchi S, Takahashi M, Hayashi KI, Mikami K. Auxin Regulates Apical Stem Cell Regeneration and Tip Growth in the Marine Red Alga Neopyropia yezoensis. Cells. 2022 Aug 26;11(17):2652. doi: 10.3390/cells11172652. PMID: 36078060; PMCID: PMC9454478. 4: Shi G, Wang S, Wang P, Zhan J, Tang Y, Zhao G, Li F, Ge X, Wu J. Cotton miR393-TIR1 Module Regulates Plant Defense Against Verticillium dahliae via Auxin Perception and Signaling. Front Plant Sci. 2022 May 3;13:888703. doi: 10.3389/fpls.2022.888703. PMID: 35592575; PMCID: PMC9111529. 5: 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. 6: 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. 7: Kimura T, Haga K, Shimizu-Mitao Y, Takebayashi Y, Kasahara H, Hayashi KI, Kakimoto T, Sakai T. Asymmetric Auxin Distribution is Not Required to Establish Root Phototropism in Arabidopsis. Plant Cell Physiol. 2018 Apr 1;59(4):823-835. doi: 10.1093/pcp/pcy018. Erratum in: Plant Cell Physiol. 2018 Apr 1;59(4):876. doi: 10.1093/pcp/pcy075. PMID: 29401292. 8: Díaz-Manzano FE, Cabrera J, Ripoll JJ, Del Olmo I, Andrés MF, Silva AC, Barcala M, Sánchez M, Ruíz-Ferrer V, de Almeida-Engler J, Yanofsky MF, Piñeiro M, Jarillo JA, Fenoll C, Escobar C. A role for the gene regulatory module microRNA172/TARGET OF EARLY ACTIVATION TAGGED 1/FLOWERING LOCUS T (miRNA172/TOE1/FT) in the feeding sites induced by Meloidogyne javanica in Arabidopsis thaliana. New Phytol. 2018 Jan;217(2):813-827. doi: 10.1111/nph.14839. Epub 2017 Nov 3. PMID: 29105090; PMCID: PMC5922426. 9: Dahlke RI, Fraas S, Ullrich KK, Heinemann K, Romeiks M, Rickmeyer T, Klebe G, Palme K, Lüthen H, Steffens B. Protoplast Swelling and Hypocotyl Growth Depend on Different Auxin Signaling Pathways. Plant Physiol. 2017 Oct;175(2):982-994. doi: 10.1104/pp.17.00733. Epub 2017 Aug 31. PMID: 28860155; PMCID: PMC5619902. 10: 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 SCFTIR1/AFBs mediates feedback regulation of IAA biosynthesis. Biosci Biotechnol Biochem. 2017 Jul;81(7):1320-1326. doi: 10.1080/09168451.2017.1313694. Epub 2017 Apr 13. Erratum in: Biosci Biotechnol Biochem. 2021 May 25;85(6):1562. doi: 10.1093/bbb/zbab052. PMID: 28406060. 11: 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. PMID: 26098557; PMCID: PMC4476611. 12: 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. PMID: 25922480; PMCID: PMC4473985. 13: 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. PMID: 22345435. 14: 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. PMID: 21369920. 15: 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. PMID: 20023161. 16: 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. PMID: 19897572.