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Chemical Structure| 6266-66-6 Chemical Structure| 6266-66-6

Structure of PEO-IAA
CAS No.: 6266-66-6

Chemical Structure| 6266-66-6

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PEO-IAA is a selective indole-3-acetic acid (IAA) antagonist that binds to the auxin transport protein TIR1, blocking the auxin signaling pathway. This makes PEO-IAA significant for applications in plant growth regulation and auxin-related research.

Synonyms: 2-(1H-Indol-3-yl)-4-oxo-4-phenyl-butyric acid

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Product Details of PEO-IAA

CAS No. :6266-66-6
Formula : C18H15NO3
M.W : 293.32
SMILES Code : O=C(O)C(C1=CNC2=C1C=CC=C2)CC(C3=CC=CC=C3)=O
Synonyms :
2-(1H-Indol-3-yl)-4-oxo-4-phenyl-butyric acid
MDL No. :MFCD00170195

Safety of PEO-IAA

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Single-celled conchocelis 30 µM PEO-IAA + 5, 10, 20 µM IAA 2 weeks IAA treatment reversed the inhibitory effects of PEO-IAA on branch formation Cells. 2022 Aug 26;11(17):2652
Wild-type Arabidopsis thaliana seedlings 10 µM 4 hours To investigate the effect of PEO-IAA on the inhibition of root cell elongation under B deficiency, results showed that PEO-IAA completely mitigated the inhibition of root cell elongation caused by B deficiency. J Exp Bot. 2015 Jul;66(13):3831-40
Cannabis sativa L. cultivar 'Tatanka Pure CBD' 1 µM 4 weeks To investigate the effect of PEO-IAA on gene expression and cannabinoid content. Results showed that although some changes in RGE profiles could be observed, no differences were statistically significant compared to the control. However, the cultivar ‘Tatanka Pure CBD’ showed a statistically significant increase (at a statistical significance level α= 0.05) in the concentration of the cannabinoid CBDA. Plants (Basel). 2023 Apr 15;12(8):1664
Cannabis sativa L. cultivar 'USO-31' 1 µM 4 weeks To investigate the effect of PEO-IAA on gene expression and cannabinoid content. Results showed that although some changes in RGE (relative gene expression) profiles could be observed, no differences were statistically significant compared to the control. Plants (Basel). 2023 Apr 15;12(8):1664
MM2d cells 10 µM 6 hours or 2 days PEO-IAA treatment increased chromatin accessibility, as confirmed by ATAC-seq analysis, especially in the gene body region. Sci Rep. 2018 May 17;8(1):7773
Single-celled conchocelis 10, 20, 30, 40, 50 µM 7 days PEO-IAA repressed the regeneration and polarized tip growth of the apical stem cell in a concentration-dependent manner Cells. 2022 Aug 26;11(17):2652
Catharanthus roseus cell suspension culture 50, 100, 200 µM 96 hours To evaluate the effect of PEO-IAA as an elicitor on the production of monoterpenoid indole alkaloids (MIAs). Results showed that 100 µM PEO-IAA produced the highest concentration of vindoline (2.58 µg/mg DW) in nodal culture, while in cell suspension culture, the effect of PEO-IAA concentration on vindoline production was not significant. Front Plant Sci. 2023 Dec 20;14:1286584

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Arabidopsis thaliana Rpt5a mutant Medium treatment 1.25 µM and 5 µM 4 days PEO-IAA treatment alleviated the inhibitory effect of high-B stress on root growth in the rpt5a mutant and restored the morphology of the root apical meristem. Front Plant Sci. 2019 May 14;10:590
Arabidopsis thaliana Root apical meristem of Arabidopsis seedlings Liquid medium treatment 10 µM 2 days PEO-IAA treatment increased chromatin accessibility, as evidenced by increased distance between 180-bp repeats and the closest chromocenter, and increased number of 45S rDNA signals separated from 180-bp repeat signals. Sci Rep. 2018 May 17;8(1):7773
Cotton (Gossypium hirsutum) Cotton seedlings Spray 10 mM PEO-IAA solution Sprayed once before inoculation and twice after inoculation Application of external PEO-IAA (an auxin antagonist) had a contrary trend with IAA application. TRV:STTM393 and TRV:00 plants with pre-applied exogenous PEO-IAA showed significantly reduced susceptibility to V. dahliae infection compared to the mock treatment, while TRV:OEmiR393 and TRV:GhTIR1 plants exhibited similar symptoms with PEO-IAA. Front Plant Sci. 2022 May 3;13:888703
Arabidopsis thaliana Wild-type and mutants (ein2-1, eir1-4, aux1-22) Added to the media before solidification 10 μM Single treatment, lasting 4 hours To study the effect of PEO-IAA on root cell elongation under B deficiency, results showed that PEO-IAA completely restored root cell elongation under B deficiency. J Exp Bot. 2015 Jul;66(13):3831-40
Arabidopsis thaliana Arabidopsis root infection model Medium treatment 300 μM 2 days Inhibition of miRNA172 promoter activity New Phytol. 2018 Jan;217(2):813-827

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.41mL

0.68mL

0.34mL

17.05mL

3.41mL

1.70mL

34.09mL

6.82mL

3.41mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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