para-Nitroblebbistatin

*para*-Nitroblebbistatin
Names
	IUPAC name (3aS)-3a-Hydroxy-6-methyl-1-(4-nitrophenyl)-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
	Other names p-Nitroblebbistatin
Identifiers
PubChem CID	102361739;
	InChI InChI=KAUXNLHXGQGFOS-GOSISDBHSA-N;
Properties
Chemical formula	C18H15N3O4
Molar mass	337.335 g·mol−1
Appearance	Yellow solid
Solubility in water	~ 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.[1] Its myosin inhibitory properties are very similar to those of blebbistatin.[2][3]

Myosin specificity

Species	Myosin type	IC₅₀
Rabbit	Skeletal muscle myosin S1	0.4 μM,[1] 0.1 μM[4]
Dictyostelium discoideum	Myosin II motor domain	2.3 μM[1]
Human	β-Cardiac myosin subfragment 1	13 μM[5]
Chicken	Heavy meromyosin fragment of skeletal muscle myosin	0.4 μM[5]

Applications

para-Nitroblebbistatin has been successfully used in fluorescent imaging experiments involving myosin IIA-GFP expressing live dendritic cells[6] and synaptophysin-pHluorin expressing live neurons.[7]

References

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 Ed. 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". 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; Varga, Máté (2016-05-31). "A highly soluble, non-phototoxic, non-fluorescent blebbistatin derivative". Scientific Reports. 6: 26141. doi:10.1038/srep26141. ISSN 2045-2322. PMC 4886532. PMID 27241904.
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. PMC 5220080. PMID 28119616.
Chabaud, Mélanie; Heuzé, Mélina L.; Bretou, Marine; Vargas, Pablo; Maiuri, Paolo; Solanes, Paola; Maurin, Mathieu; Terriac, Emmanuel; Le Berre, Maël (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. PMC 4491822. PMID 26109323.
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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[:0-1] 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 Ed. In English). 53 (31): 8211–8215. doi:10.1002/anie.201403540. ISSN 1521-3773. PMID 24954740.

[2] 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.

[3] Roman, Bart I.; Verhasselt, Sigrid; Stevens, Christian V. (2018-06-21). "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. ISSN 0022-2623. PMID 29878759.

[4] Várkuti, Boglárka H.; Képiró, Miklós; Horváth, István Ádám; Végner, László; Ráti, Szilvia; Zsigmond, Áron; Hegyi, György; Lenkei, Zsolt; Varga, Máté (2016-05-31). "A highly soluble, non-phototoxic, non-fluorescent blebbistatin derivative". Scientific Reports. 6: 26141. doi:10.1038/srep26141. ISSN 2045-2322. PMC 4886532. PMID 27241904.

[:1-5] 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. PMC 5220080. PMID 28119616.

[6] Chabaud, Mélanie; Heuzé, Mélina L.; Bretou, Marine; Vargas, Pablo; Maiuri, Paolo; Solanes, Paola; Maurin, Mathieu; Terriac, Emmanuel; Le Berre, Maël (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. PMC 4491822. PMID 26109323.

[7] 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.