Global InformationBlebbistatin information
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| Names | |
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| IUPAC name
3a-Hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
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| Other names
(S)-Blebbistatin, (-)-Blebbistatin
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| Identifiers | |
CAS Number
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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SMILES
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| Properties | |
Chemical formula
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C18H16N2O2 |
| Molar mass | 292.338 g·mol−1 |
| Appearance | Yellow solid |
Solubility in water
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10 μM |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Blebbistatin is a myosin inhibitor mostly specific for myosin II.[1][2] It is widely used in research to inhibit heart muscle myosin, non-muscle myosin II, and skeletal muscle myosin. Blebbistatin has been especially useful in optical mapping of the heart,[3] and its recent use in cardiac muscle cell cultures has improved cell survival time.[4][5] However, its adverse characteristics e.g. its cytotoxicity and blue-light instability or low solubility in water often make its application challenging.[6][7] Recently its applicability was improved by chemical design and its derivatives overcome the limitations of blebbistatin.[2][8] E.g. para-nitroblebbistatin and para-aminoblebbistatin are photostable, and they are neither cytotoxic nor fluorescent.[7][9]
- ^ Straight AF, Cheung A, Limouze J, Chen I, Westwood NJ, Sellers JR, Mitchison TJ (March 2003). "Dissecting temporal and spatial control of cytokinesis with a myosin II Inhibitor". Science. 299 (5613): 1743–7. Bibcode:2003Sci...299.1743S. doi:10.1126/science.1081412. PMID 12637748. S2CID 38625401.
- ^ a b Roman BI, Verhasselt S, Stevens CV (June 2018). "Medicinal Chemistry and Use of Myosin II Inhibitor ( S)-Blebbistatin and Its Derivatives". Journal of Medicinal Chemistry. 61 (21): 9410–9428. doi:10.1021/acs.jmedchem.8b00503. PMID 29878759.
- ^ Swift LM, Asfour H, Posnack NG, Arutunyan A, Kay MW, Sarvazyan N (November 2012). "Properties of blebbistatin for cardiac optical mapping and other imaging applications". Pflügers Archiv. 464 (5): 503–12. doi:10.1007/s00424-012-1147-2. PMC 3586237. PMID 22990759.
- ^ Kabaeva Z, Zhao M, Michele DE (April 2008). "Blebbistatin extends culture life of adult mouse cardiac myocytes and allows efficient and stable transgene expression". American Journal of Physiology. Heart and Circulatory Physiology. 294 (4): H1667–74. doi:10.1152/ajpheart.01144.2007. PMID 18296569.
- ^ Reddy GR, West TM, Jian Z, Jaradeh M, Shi Q, Wang Y, Chen-Izu Y, Xian g YK (2018-09-21). "Illuminating cell signaling with genetically encoded FRET biosensors in adult mouse cardiomyocytes". The Journal of General Physiology. 150 (11): 1567–1582. doi:10.1085/jgp.201812119. PMC 6219686. PMID 30242036.
- ^ Kolega J (July 2004). "Phototoxicity and photoinactivation of blebbistatin in UV and visible light". Biochemical and Biophysical Research Communications. 320 (3): 1020–5. doi:10.1016/j.bbrc.2004.06.045. PMID 15240150.
- ^ a b Képiró M, Várkuti BH, Végner L, Vörös G, Hegyi G, Varga M, Málnási-Csizmadia A (July 2014). "para-Nitroblebbistatin, the non-cytotoxic and photostable myosin II inhibitor". Angewandte Chemie. 53 (31): 8211–5. doi:10.1002/anie.201403540. PMID 24954740.
- ^ Rauscher AÁ, Gyimesi M, Kovács M, Málnási-Csizmadia A (September 2018). "Targeting Myosin by Blebbistatin Derivatives: Optimization and Pharmacological Potential". Trends in Biochemical Sciences. 43 (9): 700–713. doi:10.1016/j.tibs.2018.06.006. PMID 30057142.
- ^ Várkuti BH, Képiró M, Horváth IÁ, Végner L, Ráti S, Zsigmond Á, Hegyi G, Lenkei Z, Varga M, Málnási-Csizmadia A (May 2016). "A highly soluble, non-phototoxic, non-fluorescent blebbistatin derivative". Scientific Reports. 6: 26141. Bibcode:2016NatSR...626141V. doi:10.1038/srep26141. PMC 4886532. PMID 27241904.