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MedKoo Cat#: 463498 | Name: para-aminoBlebbistatin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

para-aminoBlebbistatin is a blebbistatin derivative, increasing water solubility, decreases the inherent fluorescence, stabilizing the molecule to circumvent its degradation by prolonged blue light exposure, and decreasing its phototoxicity while retaining the in vitro and in vivo activity of blebbistatin.

Chemical Structure

para-aminoBlebbistatin
para-aminoBlebbistatin
CAS#2097734-03-5

Theoretical Analysis

MedKoo Cat#: 463498

Name: para-aminoBlebbistatin

CAS#: 2097734-03-5

Chemical Formula: C18H17N3O2

Exact Mass: 307.1321

Molecular Weight: 307.35

Elemental Analysis: C, 70.34; H, 5.58; N, 13.67; O, 10.41

Price and Availability

Size Price Availability Quantity
1mg USD 650.00 2 Weeks
5mg USD 2,250.00 2 Weeks
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Related CAS #
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Synonym
para-aminoBlebbistatin; para aminoBlebbistatin; para-amino Blebbistatin; para-amino-Blebbistatin; (–)-4'-amino-Blebbistatin; p-amino-Blebbistatin; (S)-4'-amino-Blebbistatin;
IUPAC/Chemical Name
(S)-1-(4-aminophenyl)-3a-hydroxy-6-methyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one
InChi Key
LYWLZINJPRNWFF-GOSISDBHSA-N
InChi Code
InChI=1S/C18H17N3O2/c1-11-2-7-15-14(10-11)16(22)18(23)8-9-21(17(18)20-15)13-5-3-12(19)4-6-13/h2-7,10,23H,8-9,19H2,1H3/t18-/m1/s1
SMILES Code
O=C1[C@@]2(O)C(N(C3=CC=C(N)C=C3)CC2)=NC4=C1C=C(C)C=C4
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Para-aminoblebbistatin is a highly water soluble, non-fluorescent and photostable C15 amino-substituted derivative of blebbistatin; inhibits various (myosin II) isoforms both in vitro and in vivo.
In vitro activity:
This study reports a highly soluble (440 micromolar in aqueous buffer), non-fluorescent and photostable C15 amino-substituted derivative of blebbistatin, called para-aminoblebbistatin. Importantly, it is neither photo- nor cytotoxic, as demonstrated on HeLa cells and zebrafish embryos. Additionally, para-aminoblebbistatin bears similar myosin II inhibitory properties to blebbistatin or para-nitroblebbistatin (not to be confused with the C7 substituted nitroblebbistatin), tested on rabbit skeletal muscle myosin S1 and on M2 and HeLa cells. Due to its drastically improved solubility and photochemical feature, as well as lack of photo- or cytotoxicity, para-aminoblebbistatin may become a feasible replacement for blebbistatin, especially at applications when high concentrations of the inhibitor or blue light irradiation is required. Reference: Sci Rep. 2016 May 31;6:26141. https://pubmed.ncbi.nlm.nih.gov/27241904/
In vivo activity:
This study describes a zebrafish model in which a common MYH3 missense mutation (R672H) was introduced into the orthologous zebrafish gene smyhc1 (slow myosin heavy chain 1) (R673H). Heterozygous smyhc1R673H/+ embryos developed notochord kinks that progressed to scoliosis with vertebral fusions; motor deficits accompanied the disorganized and shortened slow-twitch skeletal muscle myofibers. Treatment of smyhc1R673H/R673H embryos with the myosin ATPase inhibitor, para-aminoblebbistatin, which decreases actin-myosin affinity, normalized the notochord phenotype. Reference: EMBO Mol Med. 2020 Nov 6;12(11):e12356. https://pubmed.ncbi.nlm.nih.gov/33016623/
Solvent mg/mL mM
Solubility
DMF 20.0 65.07
DMF:PBS (pH 7.2) (1:1) 0.5 1.63
DMSO 12.5 40.67
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 307.35 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.

Recalculate based on batch purity %
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:
1. López-Dávila AJ, Weber N, Kraft T, Matinmehr F, Arias-Hidalgo M, Fernández J, Lomonte B, Gutiérrez JM. Cytotoxicity of snake venom Lys49 PLA2-like myotoxin on rat cardiomyocytes ex vivo does not involve a direct action on the contractile apparatus. Sci Rep. 2021 Sep 30;11(1):19452. doi: 10.1038/s41598-021-98594-5. PMID: 34593882; PMCID: PMC8484475. 2. Várkuti BH, Képiró M, Horváth IÁ, Végner L, Ráti S, Zsigmond Á, Hegyi G, Lenkei Z, Varga M, Málnási-Csizmadia A. A highly soluble, non-phototoxic, non-fluorescent blebbistatin derivative. Sci Rep. 2016 May 31;6:26141. doi: 10.1038/srep26141. PMID: 27241904; PMCID: PMC4886532. 3. Whittle J, Antunes L, Harris M, Upshaw Z, Sepich DS, Johnson AN, Mokalled M, Solnica-Krezel L, Dobbs MB, Gurnett CA. MYH3-associated distal arthrogryposis zebrafish model is normalized with para-aminoblebbistatin. EMBO Mol Med. 2020 Nov 6;12(11):e12356. doi: 10.15252/emmm.202012356. Epub 2020 Oct 5. PMID: 33016623; PMCID: PMC7645368.
In vitro protocol:
1. López-Dávila AJ, Weber N, Kraft T, Matinmehr F, Arias-Hidalgo M, Fernández J, Lomonte B, Gutiérrez JM. Cytotoxicity of snake venom Lys49 PLA2-like myotoxin on rat cardiomyocytes ex vivo does not involve a direct action on the contractile apparatus. Sci Rep. 2021 Sep 30;11(1):19452. doi: 10.1038/s41598-021-98594-5. PMID: 34593882; PMCID: PMC8484475. 2. Várkuti BH, Képiró M, Horváth IÁ, Végner L, Ráti S, Zsigmond Á, Hegyi G, Lenkei Z, Varga M, Málnási-Csizmadia A. A highly soluble, non-phototoxic, non-fluorescent blebbistatin derivative. Sci Rep. 2016 May 31;6:26141. doi: 10.1038/srep26141. PMID: 27241904; PMCID: PMC4886532.
In vivo protocol:
1. Whittle J, Antunes L, Harris M, Upshaw Z, Sepich DS, Johnson AN, Mokalled M, Solnica-Krezel L, Dobbs MB, Gurnett CA. MYH3-associated distal arthrogryposis zebrafish model is normalized with para-aminoblebbistatin. EMBO Mol Med. 2020 Nov 6;12(11):e12356. doi: 10.15252/emmm.202012356. Epub 2020 Oct 5. PMID: 33016623; PMCID: PMC7645368.
1: Martinez-Sielva A, Vicente M, Salgado-Almario J, Garcia-Blazquez A, Domingo B, Llopis J. Suppression of Contraction Raises Calcium Ion Levels in the Heart of Zebrafish Larvae. Biosensors (Basel). 2024 Apr 27;14(5):219. doi: 10.3390/bios14050219. PMID: 38785693; PMCID: PMC11118826. 2: Chung YJ, Hoare Z, Baark F, Yu CS, Guo J, Fuller W, Southworth R, Katschinski DM, Murphy MP, Eykyn TR, Shattock MJ. Elevated Na is a dynamic and reversible modulator of mitochondrial metabolism in the heart. Nat Commun. 2024 May 20;15(1):4277. doi: 10.1038/s41467-024-48474-z. PMID: 38769288; PMCID: PMC11106256. 3: López-Dávila AJ, Weber N, Kraft T, Matinmehr F, Arias-Hidalgo M, Fernández J, Lomonte B, Gutiérrez JM. Cytotoxicity of snake venom Lys49 PLA2-like myotoxin on rat cardiomyocytes ex vivo does not involve a direct action on the contractile apparatus. Sci Rep. 2021 Sep 30;11(1):19452. doi: 10.1038/s41598-021-98594-5. PMID: 34593882; PMCID: PMC8484475. 4: Nishimura Y, Shi S, Li Q, Bershadsky AD, Viasnoff V. Crosstalk between myosin II and formin functions in the regulation of force generation and actomyosin dynamics in stress fibers. Cells Dev. 2021 Dec;168:203736. doi: 10.1016/j.cdev.2021.203736. Epub 2021 Aug 26. PMID: 34455135. 5: Gyimesi M, Rauscher AÁ, Suthar SK, Hamow KÁ, Oravecz K, Lőrincz I, Borhegyi Z, Déri MT, Kiss ÁF, Monostory K, Szabó PT, Nag S, Tomasic I, Krans J, Tierney PJ, Kovács M, Kornya L, Málnási-Csizmadia A. Improved Inhibitory and Absorption, Distribution, Metabolism, Excretion, and Toxicology (ADMET) Properties of Blebbistatin Derivatives Indicate That Blebbistatin Scaffold Is Ideal for drug Development Targeting Myosin-2. J Pharmacol Exp Ther. 2021 Mar;376(3):358-373. doi: 10.1124/jpet.120.000167. Epub 2021 Jan 19. PMID: 33468641. 6: Ušaj M, Moretto L, Vemula V, Salhotra A, Månsson A. Single molecule turnover of fluorescent ATP by myosin and actomyosin unveil elusive enzymatic mechanisms. Commun Biol. 2021 Jan 13;4(1):64. doi: 10.1038/s42003-020-01574-0. PMID: 33441912; PMCID: PMC7806905. 7: Lopez Davila AJ, Zhu L, Fritz L, Kraft T, Chalovich JM. The Positively Charged C-Terminal Region of Human Skeletal Troponin T Retards Activation and Decreases Calcium Sensitivity. Biochemistry. 2020 Nov 3;59(43):4189-4201. doi: 10.1021/acs.biochem.0c00499. Epub 2020 Oct 19. PMID: 33074652. 8: Whittle J, Antunes L, Harris M, Upshaw Z, Sepich DS, Johnson AN, Mokalled M, Solnica-Krezel L, Dobbs MB, Gurnett CA. MYH3-associated distal arthrogryposis zebrafish model is normalized with para-aminoblebbistatin. EMBO Mol Med. 2020 Nov 6;12(11):e12356. doi: 10.15252/emmm.202012356. Epub 2020 Oct 5. PMID: 33016623; PMCID: PMC7645368. 9: Pénzes M, Túrós D, Máthé D, Szigeti K, Hegedűs N, Rauscher AÁ, Tóth P, Ivic I, Padmanabhan P, Pál G, Dobolyi Á, Gyimesi M, Málnási-Csizmadia A. Direct myosin-2 inhibition enhances cerebral perfusion resulting in functional improvement after ischemic stroke. Theranostics. 2020 Apr 6;10(12):5341-5356. doi: 10.7150/thno.42077. PMID: 32373216; PMCID: PMC7196296. 10: López-Dávila AJ, Chalovich JM, Zittrich S, Piep B, Matinmehr F, Málnási- Csizmadia A, Rauscher AÁ, Kraft T, Brenner B, Stehle R. Cycling Cross-Bridges Contribute to Thin Filament Activation in Human Slow-Twitch Fibers. Front Physiol. 2020 Mar 24;11:144. doi: 10.3389/fphys.2020.00144. PMID: 32265723; PMCID: PMC7105683. 11: Várkuti BH, Képiró M, Horváth IÁ, Végner L, Ráti S, Zsigmond Á, Hegyi G, Lenkei Z, Varga M, Málnási-Csizmadia A. A highly soluble, non-phototoxic, non- fluorescent blebbistatin derivative. Sci Rep. 2016 May 31;6:26141. doi: 10.1038/srep26141. PMID: 27241904; PMCID: PMC4886532.

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