| Identification | Back Directory | [Name]
(S)-3'-amino Blebbistatin | [CAS]
2097141-18-7 | [Synonyms]
-amino Blebbistatin
(S)-3'-amino Blebbistatin
4H-Pyrrolo[2,3-b]quinolin-4-one, 1-(3-aminophenyl)-1,2,3,3a-tetrahydro-3a-hydroxy-6-methyl-, (3aS)- | [Molecular Formula]
C18H17N3O2 | [MOL File]
2097141-18-7.mol | [Molecular Weight]
307.35 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 20 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 12.5 mg/ml | [form ]
A crystalline solid |
| Hazard Information | Back Directory | [Description]
(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. | [storage]
Store at -20°C | [References]
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). |
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