Chemistry:Para-Aminoblebbistatin
From HandWiki
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| IUPAC name
(3aS)-3a-Hydroxy-6-methyl-1-(4-aminophenyl)-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
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Other names
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C18H17N3O2 | |
| Molar mass | 307.353 g·mol−1 |
| Appearance | Yellow solid |
| ~ 400 μM | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
para-Aminoblebbistatin is a water-soluble, non-fluorescent, photostable myosin II inhibitor, developed from blebbistatin.[1] Among the several blebbistatin derivatives it is one of the most promising for research applications.[2][3] Furthermore, it has a favourable overall profile considering inhibitory properties and ADME calculations.[4]
Myosin specificity
| Species | Myosin type | IC50 |
|---|---|---|
| Rabbit | Skeletal muscle myosin S1 | 1.3 μM,[1] 9.22 μM,[4] 0.98 μM[5] |
| Dictyostelium discoideum | Myosin II motor domain | 6.6 μM,[1] 8.5 μM[5] |
| Human | slow-twitch skeletal muscle fibre (force) | 10 μM[6] |
| Pig (left ventricle) | cardiac myosin | 5.3 μM[5] |
| Chicken (gizzard) | smooth muscle myosin S1 | 13 μM[5] |
| Human (expressed in Sf9 cells) | non-muscle myosin 2A / B / C motor domains | 9 / 20 / 7.2 μM[5] |
| Drosophila melanogaster | bodywall muscle fiber | 8.5 μM[5] |
References
- ↑ 1.0 1.1 1.2 "A highly soluble, non-phototoxic, non-fluorescent blebbistatin derivative". Scientific Reports 6: 26141. May 2016. doi:10.1038/srep26141. PMID 27241904. Bibcode: 2016NatSR...626141V.
- ↑ "Medicinal Chemistry and Use of Myosin II Inhibitor ( S)-Blebbistatin and Its Derivatives". Journal of Medicinal Chemistry 61 (21): 9410–9428. November 2018. doi:10.1021/acs.jmedchem.8b00503. PMID 29878759.
- ↑ "Targeting Myosin by Blebbistatin Derivatives: Optimization and Pharmacological Potential". Trends in Biochemical Sciences 43 (9): 700–713. September 2018. doi:10.1016/j.tibs.2018.06.006. PMID 30057142.
- ↑ 4.0 4.1 "Recovering Actives in Multi-Antitarget and Target Design of Analogs of the Myosin II Inhibitor Blebbistatin". Frontiers in Chemistry 6: 179. 2018. doi:10.3389/fchem.2018.00179. PMID 29881723. Bibcode: 2018FrCh....6..179R.
- ↑ 5.0 5.1 5.2 5.3 5.4 5.5 in press: "Improved inhibitory and ADMET properties of blebbistatin derivatives indicate that blebbistatin scaffold is ideal for drug development targeting myosin-2". Journal of Pharmacology and Experimental Therapeutics. 2020.
- ↑ "Cycling Cross-Bridges Contribute to Thin Filament Activation in Human Slow-Twitch Fibers". Frontiers in Physiology 11: 144. 2020-03-24. doi:10.3389/fphys.2020.00144. PMID 32265723.
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