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Chemical Structure| 168649-23-8 Chemical Structure| 168649-23-8

Structure of 5-Ph-IAA
CAS No.: 168649-23-8

Chemical Structure| 168649-23-8

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5-Ph-IAA is a derivative of IAA, combining with the OsTIR1 (F74G) mutant to establish the auxin-induced degron 2 system (AID2), effectively degrading mAID fusion proteins, commonly used in tumor research.

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Product Citations

Product Citations

Frankel, Elisa B ; Tiroumalechetty, Araven ; Su, Zhaoqian ; Henry, Parise S ; Mueller, Brian D ; Jorgensen, Erik M , et al.

Abstract: Neurexin cell-adhesion molecules regulate synapse development and function by recruiting synaptic components. Here, we uncover a mechanism for presynaptic assembly that precedes neurexin recruitment, mediated by interactions between cytosolic proteins and membrane phospholipids. Developmental imaging in C. elegans reveals that the intracellular active zone protein SYD-1 accumulates at nascent presynapses prior to its binding partner neurexin. Combining molecular dynamics simulations to model intrinsic interactions between SYD-1 and lipid bilayers with biochemical and in vivo validation of these predictions, we find that PIP2-interacting residues in the SYD-1 C2 domain are required for active zone assembly. Genetic perturbation of a PIP2-generating enzyme disrupts synaptic SYD-1 accumulation, while the PIP2-interacting domain of mammalian RIM1 can compensate for the SYD-1 C2 domain, suggesting functional homology between these proteins. Finally, we propose that the evolutionarily conserved g-neurexin isoform represents a minimal neurexin sequence that stabilizes nascent presynaptic assemblies, potentially a core function of this isoform.

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Product Details of 5-Ph-IAA

CAS No. :168649-23-8
Formula : C16H13NO2
M.W : 251.28
SMILES Code : O=C(O)CC1=CNC2=C1C=C(C3=CC=CC=C3)C=C2
MDL No. :MFCD21897325
InChI Key :ACCCWYHBDGKDKN-UHFFFAOYSA-N
Pubchem ID :15207491

Safety of 5-Ph-IAA

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Isoform Comparison

Biological Activity

Description
5-Ph-IAA is an IAA derivative. As a ligand, 5-Ph-IAA forms the auxin-inducible degron 2 (AID2) system in conjunction with an OsTIR1 (F74G) mutant. AID2 facilitates the quick and effective depletion of mAID-fused proteins for investigating protein function in live cells, resulting in tumor suppression [1].

In Vitro:

Cell Line
Concentration Treated Time Description References
yeast cells 1 μM 60 min Assess degradation efficiency of AID*-tagged proteins, ∼88% of proteins were significantly reduced in OsTIR1+ background J Cell Biol. 2025 Feb 3;224(2):e202409007
Mouse hippocampal neurons 200 nM 60 min Test the degradation effect of AID2 system in neurons, showing rapid degradation Nat Commun. 2020 Nov 11;11(1):5701
HCT116 cells 1 µM 4 h Test the degradation effect of 5-Ph-IAA on the reporter gene, showing no leaky degradation and high efficiency Nat Commun. 2020 Nov 11;11(1):5701

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mouse Transgenic mice (pMK411#16, #19, TG-CAG-AID-mCherry, Rosa-CAG-TIR1(F74G), AID-DCP2) Intraperitoneal injection 5 mg/kg (adult mice) or 1 mg/kg (embryos) Single injection, observation time from 1 hour to 72 hours To validate the ability of the AID2 system to rapidly degrade target proteins in vivo and its reversibility. Results showed that AID-tagged proteins were significantly degraded within 6 hours post-injection and recovered within 72 hours. Dev Growth Differ. 2024 Sep;66(7):384-393
Caenorhabditis elegans C. elegans strain expressing AtTIR1(F79G)::mRuby and AID*::GFP NGM plate 5 µM 4 hours To evaluate the degradation efficacy of 5-Ph-IAA in C. elegans, results showed that 5 μM 5-Ph-IAA effectively induced the degradation of the AID*::GFP reporter protein. Genetics. 2022 Feb 4;220(2):iyab218
Nude mice Xenograft tumour model Intraperitoneal injection 1-10 mg/kg Daily for one week Test the inhibitory effect of 5-Ph-IAA on tumour growth, showing significant suppression Nat Commun. 2020 Nov 11;11(1):5701

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.98mL

0.80mL

0.40mL

19.90mL

3.98mL

1.99mL

39.80mL

7.96mL

3.98mL

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
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. 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

References

 

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