A cell-permeable antagonist of calmodulin
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Isomer(s)
43152W-9 (hydrochloride)
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W-7 (hydrochloride)

Item No. 14826

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide, monohydrochloride
CAS Number
61714-27-0
Synonyms
  • NSC 683545
Molecular Formula
C16H21ClN2O2S • HCl
Formula Weight
377.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 14 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 0.3 mg/ml
λmax
224, 297 nm
SMILES
ClC1=C(C=CC=C2S(NCCCCCCN)(=O)=O)C2=CC=C1.Cl
InChi Code
InChI=1S/C16H21ClN2O2S.ClH/c17-15-9-5-8-14-13(15)7-6-10-16(14)22(20,21)19-12-4-2-1-3-11-18;/h5-10,19H,1-4,11-12,18H2;1H
InChi Key
OMMOSRLIFSCDBL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Calmodulin is a calcium-dependent protein that regulates the activity of a diverse array of enzymes, ion channels, and other proteins and thus has diverse roles in cell function.1,2 W-7 is a cell-permeable antagonist of calmodulin (Ki = 11 μM).3,4 Two molecules of W-7 bind to calcium-binding domains in each calmodulin molecule, blocking its interaction with target proteins.3 W-7 also associates, at lower affinities, with calcium-binding domains of other proteins, including troponin C and myosin light chain kinase (Ki = 70 and 300 μM, respectively).5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Benaim, G., and Villalobo, A. Phosphorylation of calmodulin. Functional implications. Eur. J. Biochem. 269(15), 3619-3631 (2002).

    2. Chin, D., and Means, A.R. Calmodulin: A prototypical calcium sensor. Trends Cell Biol. 10(8), 322-328 (2000).

    3. Osawa, M., Swindells, M.B., Tanikawa, J., et al. Solution structure of calmodulin-W-7 complex: The basis of diversity in molecular recognition. J. Mol. Biol. 276(1), 165-176 (1998).

    4. Hidaka, H., Sasaki, Y., Tanaka, T., et al. N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide, a calmodulin antagonist, inhibits cell proliferation. Proc. Natl. Acad. Sci. USA 78(7), 4354-4357 (1981).

    5. Adhikari, B.B., and Wang, K. Interplay of troponin- and myosin-based pathways of calcium activation in skeletal and cardiac muscle: The use of W7 as an inhibitor of thin filament activation. Biophys. J. 86(1), 359-370 (2004).

    6. Hoffman, R.M.B., and Sykes, B.D. Structure of the inhibitor W7 bound to the regulatory domain of cardiac troponin C. Biochemistry 48(24), 5541-5552 (2009).

    7. Zimmer, M., and Hofmann, F. Calmodulin antagonists inhibit activity of myosin light-chain kinase independent of calmodulin. Eur. J. Biochem. 142(2), 393-397 (1984).