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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)

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Synonyme: (+)-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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      Übersicht

      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
      Bestellnummer GTIN
      530657 0

      Documentation

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

      Titel

      Sicherheitsdatenblatt (SDB) 

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

      TitelChargennummer
      530657

      Literatur

      Übersicht
      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.
      Datenblatt

      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.