Chemistry:Para-Nitroblebbistatin
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| Names | |
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| IUPAC name
(3aS)-3a-Hydroxy-6-methyl-1-(4-nitrophenyl)-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
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| Other names
p-Nitroblebbistatin
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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| Properties | |
| C18H15N3O4 | |
| Molar mass | 337.335 g·mol−1 |
| Appearance | Yellow solid |
| ~ 5 μM | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
para-Nitroblebbistatin is a non-phototoxic, photostable myosin inhibitor with low fluorescence.[2] Its myosin inhibitory properties are very similar to those of blebbistatin.[citation needed][3][4]
Myosin specificity
| Species | Myosin type | IC50 |
|---|---|---|
| Rabbit | Skeletal muscle myosin S1 | 0.4 μM,[2] 0.1 μM[5][6] |
| Dictyostelium discoideum | Myosin II motor domain | 2.3 μM,[2] 9 μM[6] |
| Human | β-Cardiac myosin subfragment 1 | 13 μM[7] |
| Chicken | Heavy meromyosin fragment of skeletal muscle myosin | 0.4 μM[7] |
| Pig (left ventricle) | cardiac myosin | 3.9 μM[6] |
| Chicken (gizzard) | smooth muscle myosin S1 | 5.6 μM[6] |
| Human (expressed in Sf9 cells) | non-muscle myosin 2A / B / C motor domains | 18 / 14 / 5 μM[6] |
Applications
para-Nitroblebbistatin has been successfully used in fluorescent imaging experiments involving myosin IIA-GFP expressing live dendritic cells[8] and synaptophysin-pHluorin expressing live neurons.[9]
References
- ↑ "para-Nitroblebbistatin | Targetmol". https://www.targetmol.com/compound/para-Nitroblebbistatin.
- ↑ 2.0 2.1 2.2 Képiró, Miklós; Várkuti, Boglárka H.; Végner, László; Vörös, Gergely; Hegyi, György; Varga, Máté; Málnási-Csizmadia, András (2014-07-28). "para-Nitroblebbistatin, the non-cytotoxic and photostable myosin II inhibitor". Angewandte Chemie International Edition in English 53 (31): 8211–8215. doi:10.1002/anie.201403540. ISSN 1521-3773. PMID 24954740.
- ↑ Rauscher, Anna Á.; Gyimesi, Máté; Kovács, Mihály; Málnási-Csizmadia, András (July 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. ISSN 0968-0004. PMID 30057142.
- ↑ Roman, Bart I.; Verhasselt, Sigrid; Stevens, Christian V. (2018-06-21). "Medicinal Chemistry and Use of Myosin II Inhibitor (S)-Blebbistatin and Its Derivatives" (in en). Journal of Medicinal Chemistry 61 (21): 9410–9428. doi:10.1021/acs.jmedchem.8b00503. ISSN 0022-2623. PMID 29878759.
- ↑ Várkuti, Boglárka H.; Képiró, Miklós; Horváth, István Ádám; Végner, László; Ráti, Szilvia; Zsigmond, Áron; Hegyi, György; Lenkei, Zsolt et al. (2016-05-31). "A highly soluble, non-phototoxic, non-fluorescent blebbistatin derivative". Scientific Reports 6: 26141. doi:10.1038/srep26141. ISSN 2045-2322. PMID 27241904. Bibcode: 2016NatSR...626141V.
- ↑ 6.0 6.1 6.2 6.3 6.4 in press: Gyimesi et al Improved inhibitory and ADMET properties of blebbistatin derivatives indicate that blebbistatin scaffold is ideal for drug development targeting myosin-2 in Journal of Pharmacology and Experimental Therapies (2020)
- ↑ 7.0 7.1 Tang, Wanjian; Blair, Cheavar A.; Walton, Shane D.; Málnási-Csizmadia, András; Campbell, Kenneth S.; Yengo, Christopher M. (2016). "Modulating Beta-Cardiac Myosin Function at the Molecular and Tissue Levels". Frontiers in Physiology 7: 659. doi:10.3389/fphys.2016.00659. ISSN 1664-042X. PMID 28119616.
- ↑ Chabaud, Mélanie; Heuzé, Mélina L.; Bretou, Marine; Vargas, Pablo; Maiuri, Paolo; Solanes, Paola; Maurin, Mathieu; Terriac, Emmanuel et al. (2015-06-25). "Cell migration and antigen capture are antagonistic processes coupled by myosin II in dendritic cells". Nature Communications 6: 7526. doi:10.1038/ncomms8526. ISSN 2041-1723. PMID 26109323. Bibcode: 2015NatCo...6.7526C.
- ↑ Soykan, Tolga; Kaempf, Natalie; Sakaba, Takeshi; Vollweiter, Dennis; Goerdeler, Felix; Puchkov, Dmytro; Kononenko, Natalia L.; Haucke, Volker (2017). "Synaptic Vesicle Endocytosis Occurs on Multiple Timescales and Is Mediated by Formin-Dependent Actin Assembly". Neuron 93 (4): 854–866.e4. doi:10.1016/j.neuron.2017.02.011. PMID 28231467.
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