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530657 Myosin ATPase Activator, EMD57003 - CAS 147527-31-9 - Calbiochem

A cell-permeable, isomer of the racemate EMD-53998. Binds to the allosteric pocket of myosin motor domain and stimulates actomyosin ATPase activity (AC₅₀ = 7.0 µM for β-cardiac myosin)

Myosin ATPase Activator, EMD57003 - CAS 147527-31-9 - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: (+)-5-(1-(3,4-Dimethoxybenzoyl)-1,2,3,4-tetrahydroquinolin-6-yl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one, (+)-6-(3,6-Dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinoline, EMD-57033, Myosin Motor Activator

Primary Target: myosin
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
147527-31-9C₂₂H₂₃N₃O₄S
Description
Overview

This product has been discontinued.



A cell-permeable, bioavailable positive optical isomer of the racemate EMD-53998 that binds to the allosteric pocket of myosin motor domain (KD = 7.3 µM) and stimulates actomyosin ATPase activity (AC50 = 7.0 µM for β-cardiac myosin and 15.1 µM for skeletal muscle myosin). Exerts a positive inotropic effects on cardiac muscle and enhances diastolic performance while reducing oxygen cost of contraction in a canine canine model of tachycardia-induced heart failure. Acts as a pharmacological chaperone to protect β-cardiac myosin against heat stress and thermal denaturation and can induce refolding and reactivation of heat-inactivated myosin ATPase.
Catalogue Number530657
Brand Family Calbiochem®
Synonyms(+)-5-(1-(3,4-Dimethoxybenzoyl)-1,2,3,4-tetrahydroquinolin-6-yl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one, (+)-6-(3,6-Dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinoline, EMD-57033, Myosin Motor Activator
References
ReferencesRadke, M.B., et al. 2014. ELife 3, e01603.
Senzaki, H., et al., 2000. Circulation 101, 1040.
Gambassi, G., et al. 1993. Am. J. Physiol. 264, H728.
Solaro, R.J., et al.1993. Circ. Res.73, 981.
Product Information
CAS number147527-31-9
FormOff-white solid
Hill FormulaC₂₂H₂₃N₃O₄S
Chemical formulaC₂₂H₂₃N₃O₄S
ReversibleY
Quality LevelMQ100
Applications
Biological Information
Primary Targetmyosin
Purity≥97% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Standard Handling
Storage -20°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Packaging Information
Packaged under inert gas Packaged under inert gas
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalogue Number GTIN
530657 0

Documentation

Myosin ATPase Activator, EMD57003 - CAS 147527-31-9 - Calbiochem MSDS

Title

Safety Data Sheet (SDS) 

Myosin ATPase Activator, EMD57003 - CAS 147527-31-9 - Calbiochem Certificates of Analysis

TitleLot Number
530657

References

Reference overview
Radke, M.B., et al. 2014. ELife 3, e01603.
Senzaki, H., et al., 2000. Circulation 101, 1040.
Gambassi, G., et al. 1993. Am. J. Physiol. 264, H728.
Solaro, R.J., et al.1993. Circ. Res.73, 981.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision12-June-2014 JSW
Synonyms(+)-5-(1-(3,4-Dimethoxybenzoyl)-1,2,3,4-tetrahydroquinolin-6-yl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one, (+)-6-(3,6-Dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinoline, EMD-57033, Myosin Motor Activator
DescriptionThe cell-permeable (+) enantiomer of the racemic tetrahydroquinoline EMD-53998 is reported to enhance myosin motor function via an 1:1 allosteric interaction with motor N-terminal SH3-like βbarrel subdomain (KD = 7.3 & 23 µM, respectively, using 100 nM porcine β-cardiac myosin S1 & rabbit fast skeletal muscle heavy meromyosin/HMM), restoring the ATP-binding activity of misfolded moysin as well as enhancing both basal and actin-dependent ATPase activity of myosin preparations (AC50 in µM = 7.0/porcine β-cardiac myosin S1, 15.1/rabbit HMM, 25.8/amoeba Dictyostelium discoideum Dd myosin-2, and 35.4/Dd myosin-5b), while being ineffective toward fully denatured myosin or βbarrel subdomain-lacking Dd myosin-1B/-1C/-1D/-1E. Pro-hypertrophic effect of EMD 57033 is demonstrated in serum-free neonatal rat cardiomyocyte cultures in vitro under both normal and hyperthermia conditions (cell size enlargement by 60% at 37 °C and by 24% at 42 °C; 10 µM EMD 57033 for 24 hr) with a drastic decline in cellular atrial natriuretic peptide only under hyperthermia condition (% of 37 °C control ANP level = 47% vs. 140%, respectively, with or without 10 µM EMD 57033 for 24 h at 42 °C), while positive inotropic efficacy is reported in vivo (0.4 mg/kg/min for 20 min) in a canine model of tachycardia-induced heart failure. The (-) enantiomer EMD 57439 is a known PDE3 inhibitor with little potency toward myosin ATPase activity.
FormOff-white solid
Intert gas (Yes/No) Packaged under inert gas
CAS number147527-31-9
Chemical formulaC₂₂H₂₃N₃O₄S
Purity≥97% by HPLC
SolubilityDMSO (50 mg/ml)
Storage Protect from light
-20°C
Do Not Freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Toxicity Standard Handling
ReferencesRadke, M.B., et al. 2014. ELife 3, e01603.
Senzaki, H., et al., 2000. Circulation 101, 1040.
Gambassi, G., et al. 1993. Am. J. Physiol. 264, H728.
Solaro, R.J., et al.1993. Circ. Res.73, 981.