2097141-18-7

(S)-3’-amino Blebbistatin is a more stable and less phototoxic form of (–)-blebbistatin , which is a selective cell-permeable inhibitor of non-muscle myosin II ATPases.^1,2 (–)-Blebbistatin rapidly and reversibly inhibits Mg-ATPase activity and in vitro motility of non-muscle myosin IIA and IIB for several species (IC₅₀s = 0.5-5 μM), while poorly inhibiting smooth muscle myosin (IC₅₀ = 80 μM).³ Through these effects, it blocks apoptosis-related bleb formation, directed cell migration, and cytokinesis in vertebrate cells. However, prolonged exposure to blue light (450-490 nm) results in degradation of blebbistatin to an inactive product via cytotoxic intermediates, which may be problematic for its use in fluorescent live cell imaging applications.^4,5 The addition of a 3’-amino group decreases the inherent fluorescence while retaining the activity of (–)-blebbistatin.⁶ (S)-3'-amino Blebbistatin has the same stereochemistry as the active (–)-blebbistatin enantiomer.

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1. Straight, A.F., Cheung, A., Limouze, J., et al. Dissecting temporal and spatial control of cytokinesis with a myosin II inhibitor Science 299(5613),1743-1747(2003).
2. Kovács, M., Tóth, J., Hetényi, C., et al. Mechanism of blebbistatin inhibition of myosin II J. Biol. Chem. 279(34),35557-35563(2004).
3. Limouze, J., Straight, A.F., Mitchison, T., et al. Specificity of blebbistatin, an inhibitor of myosin II J. Muscle Res. Cell Motil. 25(4-5),337-341(2004).
4. Kolega, J. Phototoxicity and photoinactivation of blebbistatin in UV and visible light Biochem. Biophys. Res. Commun. 320(3),1020-1025(2004).
5. Sakamoto, T., Limouze, J., Combs, C.A., et al. Blebbistatin, a myosin II inhibitor, is photoinactivated by blue light Biochemistry 44(2),584-588(2005).
6. Verhasselt, S., Roman, B.I., De Wever, O., et al. Discovery of (S)-3'-hydroxyblebbistatin and (S)-3'-aminoblebbistatin: Polar myosin II inhibitors with superior research tool properties Org. Biomol. Chem. 15(9),2104-2118(2017).