A mitochondria-targeting thiol reactive probe
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IBTP (iodide)

Item No. 18802

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4-iodobutyl)triphenyl-phosphonium, monoiodide
CAS Number
159085-21-9
Molecular Formula
C22H23IP • I
Formula Weight
572.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 100mMEthanol: 50mM
SMILES
ICCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[I-]
InChi Code
InChI=1S/C22H23IP.HI/c23-18-10-11-19-24(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H/q+1;/p-1
InChi Key
XWDMWKLGLADJFM-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $57

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    10 mg

    $107

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    25 mg

    $252

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    Product Description

    IBTP is a lipophilic cation that is accumulated in mitochondria and forms stable thioether adducts in a thiol-specific manner.1 As a result, mitochondrial proteins that have changed thiol redox state following oxidative stress are selectively tagged with IBTP and can be separated by two-dimensional electrophoresis and isolated.1 IBTP-tagged proteins can also be evaluated by immunoblotting using an antibody directed against the triphenylphosphonium moiety of the IBTP molecule.2 IBTP has also been used as a mitochondria-targeted soft electrophile to inhibit mitochondrial oxidative phosphorylation.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lin, T.-K., Hughes, G., Muratovska, A., et al. Specific modification of mitochondrial protein thiols in response to oxidative stress: A proteomics approach. The Journal of Biological Chemisty 277(19), 17048-17056 (2002).

    2. Venkatraman, A., Landar, A., Davis, A.J., et al. Oxidative modification of hepatic mitochondria protein thiols: Effect of chronic alcohol consumption. Am. J. Physiol. Gastrointest. Liver Physiol. 286(4), G521-G527 (2004).

    3. Vayalil, P.K., Oh, J.-Y., Zhou, F., et al. A novel class of mitochondria-targeted soft electrophiles modifies mitochondrial proteins and inhibits mitochondrial metabolism in breast cancer cells through redox mechanisms. PLoS One 10(3), (2015).