WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H574595
CAS#: 1177356-70-5
Description: (+)-Blebbistatin is the inactive enantiomer of (–)-blebbistatin, which is a selective inhibitor of non-muscle myosin II ATPases.
Hodoodo Cat#: H574595
Name: (+)-Blebbistatin
CAS#: 1177356-70-5
Chemical Formula: C18H16N2O2
Exact Mass: 292.12
Molecular Weight: 292.340
Elemental Analysis: C, 73.95; H, 5.52; N, 9.58; O, 10.95
Synonym: (+)-Blebbistatin; (R)-Blebbistatin
IUPAC/Chemical Name: 1,2,3,3a-tetrahydro-3aR-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one
InChi Key: LZAXPYOBKSJSEX-SFHVURJKSA-N
InChi Code: InChI=1S/C18H16N2O2/c1-12-7-8-15-14(11-12)16(21)18(22)9-10-20(17(18)19-15)13-5-3-2-4-6-13/h2-8,11,22H,9-10H2,1H3/t18-/m0/s1
SMILES Code: Cc1ccc2N=C3N(CC[C@@]3(O)C(=O)c2c1)c1ccccc1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info: 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. (R)-nitro-Blebbistatin is a more stable form of (+)-blebbistatin. The addition of a nitro group stabilizes the molecule to circumvent its degradation by prolonged blue light exposure. (R)-nitro-Blebbistatin has the same stereochemistry as the inactive (+)-blebbistatin enantiomer.
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| In vivo activity: |
The following data is based on the product molecular weight 292.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Boberg L, Rahman A, Poljakovic M, Arner A. Protein kinase C activation of a blebbistatin sensitive contractile component in the wall of hypertrophying mouse urinary bladder. Neurourol Urodyn. 2015 Feb;34(2):196-202. doi: 10.1002/nau.22531. Epub 2013 Nov 26. PubMed PMID: 25794194.
2: Wang X, Chong M, Wang X, Wang H, Zhang J, Xu H, Zhang J, Liu D. Block the function of nonmuscle myosin II by blebbistatin induces zebrafish embryo cardia bifida. In Vitro Cell Dev Biol Anim. 2015 Mar;51(3):211-7. doi: 10.1007/s11626-014-9836-0. Epub 2014 Nov 18. PubMed PMID: 25403653.
3: Wilson C, Naber N, Pate E, Cooke R. The myosin inhibitor blebbistatin stabilizes the super-relaxed state in skeletal muscle. Biophys J. 2014 Oct 7;107(7):1637-46. doi: 10.1016/j.bpj.2014.07.075. PubMed PMID: 25296316; PubMed Central PMCID: PMC4190596.
4: Doller A, Badawi A, Schmid T, Brauss T, Pleli T, zu Heringdorf DM, Piiper A, Pfeilschifter J, Eberhardt W. The cytoskeletal inhibitors latrunculin A and blebbistatin exert antitumorigenic properties in human hepatocellular carcinoma cells by interfering with intracellular HuR trafficking. Exp Cell Res. 2015 Jan 1;330(1):66-80. doi: 10.1016/j.yexcr.2014.09.010. Epub 2014 Sep 21. PubMed PMID: 25240929.
5: Lv Y, Lu S, Lu T, Kou J, Yu B. Homology model of nonmuscle myosin heavy chain IIA and binding mode analysis with its inhibitor blebbistatin. J Mol Model. 2013 Apr;19(4):1801-10. doi: 10.1007/s00894-012-1750-3. Epub 2013 Jan 13. PubMed PMID: 23315199.
6: Brack KE, Narang R, Winter J, Ng GA. The mechanical uncoupler blebbistatin is associated with significant electrophysiological effects in the isolated rabbit heart. Exp Physiol. 2013 May;98(5):1009-27. doi: 10.1113/expphysiol.2012.069369. Epub 2013 Jan 4. PubMed PMID: 23291912; PubMed Central PMCID: PMC3734628.
7: Yumoto M, Watanabe M. Blebbistatin, a myosin II inhibitor, suppresses Ca(2+)-induced and "sensitized"-contraction of skinned tracheal muscles from guinea pig. J Smooth Muscle Res. 2013;49:89-98. PubMed PMID: 24662474.
8: Swift LM, Asfour H, Posnack NG, Arutunyan A, Kay MW, Sarvazyan N. Properties of blebbistatin for cardiac optical mapping and other imaging applications. Pflugers Arch. 2012 Nov;464(5):503-12. doi: 10.1007/s00424-012-1147-2. Epub 2012 Sep 19. PubMed PMID: 22990759; PubMed Central PMCID: PMC3586237.
9: Mikulich A, Kavaliauskiene S, Juzenas P. Blebbistatin, a myosin inhibitor, is phototoxic to human cancer cells under exposure to blue light. Biochim Biophys Acta. 2012 Jul;1820(7):870-7. doi: 10.1016/j.bbagen.2012.04.003. Epub 2012 Apr 10. PubMed PMID: 22507270.
10: Brines L, Such-Miquel L, Gallego D, Trapero I, Del Canto I, Zarzoso M, Soler C, Pelechano F, Cánoves J, Alberola A, Such L, Chorro FJ. Modifications of mechanoelectric feedback induced by 2,3-butanedione monoxime and Blebbistatin in Langendorff-perfused rabbit hearts. Acta Physiol (Oxf). 2012 Sep;206(1):29-41. doi: 10.1111/j.1748-1716.2012.02441.x. Epub 2012 May 16. PubMed PMID: 22497862.
11: Matsui Y, Nakayama Y, Okamoto M, Fukumoto Y, Yamaguchi N. Enrichment of cell populations in metaphase, anaphase, and telophase by synchronization using nocodazole and blebbistatin: a novel method suitable for examining dynamic changes in proteins during mitotic progression. Eur J Cell Biol. 2012 May;91(5):413-9. doi: 10.1016/j.ejcb.2011.12.008. Epub 2012 Feb 25. PubMed PMID: 22365812.
12: Lou Q, Li W, Efimov IR. The role of dynamic instability and wavelength in arrhythmia maintenance as revealed by panoramic imaging with blebbistatin vs. 2,3-butanedione monoxime. Am J Physiol Heart Circ Physiol. 2012 Jan 1;302(1):H262-9. doi: 10.1152/ajpheart.00711.2011. Epub 2011 Oct 28. PubMed PMID: 22037192; PubMed Central PMCID: PMC3334231.
13: Lang E, Qadri SM, Zelenak C, Gu S, Rotte A, Draeger A, Lang F. Inhibition of suicidal erythrocyte death by blebbistatin. Am J Physiol Cell Physiol. 2011 Aug;301(2):C490-8. doi: 10.1152/ajpcell.00043.2011. Epub 2011 May 18. PubMed PMID: 21593446.
14: Lawson CP, Slawin AM, Westwood NJ. Application of the copper catalysed N-arylation of amidines in the synthesis of analogues of the chemical tool, blebbistatin. Chem Commun (Camb). 2011 Jan 21;47(3):1057-9. doi: 10.1039/c0cc03624b. Epub 2010 Nov 15. PubMed PMID: 21079840.
15: Huang J, Zhang J, Pathak A, Li J, Stouffer GA. Perivascular delivery of blebbistatin reduces neointimal hyperplasia after carotid injury in the mouse. J Pharmacol Exp Ther. 2011 Jan;336(1):116-26. doi: 10.1124/jpet.110.174615. Epub 2010 Oct 18. PubMed PMID: 20956482; PubMed Central PMCID: PMC3014304.
16: Minozzo FC, Rassier DE. Effects of blebbistatin and Ca2+ concentration on force produced during stretch of skeletal muscle fibers. Am J Physiol Cell Physiol. 2010 Nov;299(5):C1127-35. doi: 10.1152/ajpcell.00073.2010. Epub 2010 Aug 18. PubMed PMID: 20720178.
17: Zhang X, Kuppam DS, Melman A, DiSanto ME. In vitro and in vivo relaxation of urinary bladder smooth muscle by the selective myosin II inhibitor, blebbistatin. BJU Int. 2011 Jan;107(2):310-7. doi: 10.1111/j.1464-410X.2010.09366.x. PubMed PMID: 20482706.
18: Takács B, Billington N, Gyimesi M, Kintses B, Málnási-Csizmadia A, Knight PJ, Kovács M. Myosin complexed with ADP and blebbistatin reversibly adopts a conformation resembling the start point of the working stroke. Proc Natl Acad Sci U S A. 2010 Apr 13;107(15):6799-804. doi: 10.1073/pnas.0907585107. Epub 2010 Mar 29. PubMed PMID: 20351242; PubMed Central PMCID: PMC2872372.
19: Jou CJ, Spitzer KW, Tristani-Firouzi M. Blebbistatin effectively uncouples the excitation-contraction process in zebrafish embryonic heart. Cell Physiol Biochem. 2010;25(4-5):419-24. doi: 10.1159/000303046. Epub 2010 Mar 23. PubMed PMID: 20332622; PubMed Central PMCID: PMC3025892.
20: Watanabe M, Yumoto M, Tanaka H, Wang HH, Katayama T, Yoshiyama S, Black J, Thatcher SE, Kohama K. Blebbistatin, a myosin II inhibitor, suppresses contraction and disrupts contractile filaments organization of skinned taenia cecum from guinea pig. Am J Physiol Cell Physiol. 2010 May;298(5):C1118-26. doi: 10.1152/ajpcell.00269.2009. Epub 2010 Feb 17. PubMed PMID: 20164381.
