A phenylic substituted indole and ligand used for bump and hole
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5-Ph-IAA

Item No. 38161

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-phenyl-1H-indole-3-acetic acid
CAS Number
168649-23-8
Molecular Formula
C16H13NO2
Formula Weight
251.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 0.2 mg/ml
λmax
253 nm
SMILES
O=C(CC1=CNC2=CC=C(C3=CC=CC=C3)C=C21)O
InChi Code
InChI=1S/C16H13NO2/c18-16(19)9-13-10-17-15-7-6-12(8-14(13)15)11-4-2-1-3-5-11/h1-8,10,17H,9H2,(H,18,19)
InChi Key
ACCCWYHBDGKDKN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $74

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    10 mg

    $132

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    25 mg

    $293

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    50 mg

    $512

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    Cayman Chemical
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    Product Description

    5-Ph-IAA is a phenylic substituted indole and ligand used for bump and hole, a technique used to study single protein isoforms when familial homology would interfere with other isoform-selective approaches.1,2 It activates a bump-and-hole-modified protein, transport inhibitor response 1 (TIR1), which forms a PROTAC-associated complex that targets and degrades sister chromatid cohesion 1 (RAD21) and induces cell cycle arrest at the G2 or M phase in Arabidopsis when used at a concentration of 1 µM.2 Intraperitoneal administration of 5-Ph-IAA (1, 3, or 10 mg/kg per day) reduces tumor growth via the same process by targeting and degrading bromodomain-containing protein 4 (BRD4) in an HCT116 colorectal cancer xenograft mouse model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Islam, K. The bump-and-hole tactic: Expanding the scope of chemical genetics. Cell Chem. Biol. 25(10), 1171-1184 (2018).

    2. Yesbolatova, A., Saito, Y., Kitamoto, N., et al. The auxin-inducible degron 2 technology provides sharp degradation control in yeast, mammalian cells, and mice. Nat. Commun. 11(1), 5701 (2020).