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505602 BDK Inhibitor II, (S)-CPP - CAS 41998-38-3 - Calbiochem

A cell-permeable inhibitor of mitochondrial branched-chain α-ketoacid dehydrogenase complex (BCKDC) regulatory kinase BDK (IC₅₀ = 6.3 µM).

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: BCKD Kinase Inhibitor II, Branched-Chain α-Ketoacid Dehydrogenase Kinase Inhibitor II, (S)-α-Chloro-phenylpropionic acid

Primary Target: BDK
505602
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
41998-38-3C₉H₉ClO₂

Products

Catalogue NumberPackaging Qty/Pack
5.05602.0001 Glass bottle 10 mg
Description
OverviewA cell-permeable chlorophenylpropionate compound that is superior to its structural analog 4PB (Cat. No. 567616) as an inhibitor against mitochondrial branched-chain α-ketoacid dehydrogenase complex (BCKDC) regulatory kinase BDK (BCKD kinase; IC50 = 6.3 vs. 53.1 µM) due to much optimized affinity toward the BDK N-terminal allosteric site (Kd = 2.4 vs. 5.7 µM), effectively blocking BDK substrate access by preventing BDK interaction with the homo-24-meric dihydrolipoyltransferase BCKDC E2 component, while exhibiting little potency against PDK2 or BCKD phosphatase BDP even at concentrations as high as 1 mM (<10% inhibition). Shown to effectively reduce E1-α Ser293 phosphorylation with concomitant BCKDC activity upregulation in multiple tissues in mice (EDmax =160 mg/kg via i.p.) in vivo. Despite good stability and low in vivo clearance , high doses are recommended for mice treatment due to low tissue penetration efficiency.
Catalogue Number505602
Brand Family Calbiochem®
SynonymsBCKD Kinase Inhibitor II, Branched-Chain α-Ketoacid Dehydrogenase Kinase Inhibitor II, (S)-α-Chloro-phenylpropionic acid
References
ReferencesTso, S.C., et al. 2013. Proc. Natl. Acad. Sci. USA 110, 9728.
Product Information
CAS number41998-38-3
FormClear, colorless oil
Hill FormulaC₉H₉ClO₂
Chemical formulaC₉H₉ClO₂
ReversibleY
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
Biological Information
Primary TargetBDK
Purity≥98% 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
Protect from Moisture Protect from moisture
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month 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
5.05602.0001 04055977243406

Documentation

BDK Inhibitor II, (S)-CPP - CAS 41998-38-3 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

References

Reference overview
Tso, S.C., et al. 2013. Proc. Natl. Acad. Sci. USA 110, 9728.
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.

Revision07-March-2014 JSW
SynonymsBCKD Kinase Inhibitor II, Branched-Chain α-Ketoacid Dehydrogenase Kinase Inhibitor II, (S)-α-Chloro-phenylpropionic acid
DescriptionA cell-permeable chlorophenylpropionate compound that is superior to its structural analog 4PB (Cat. No. 567616) as an inhibitor against mitochondrial BCKDC (branched-chain α-ketoacid dehydrogenase complex) regulatory kinase BDK (BCKD kinase; IC50 = 6.3 vs. 53.1 µM) due to much optimized affinity toward the BDK N-terminal allosteric site (Kd = 2.4 vs. 5.7 µM) via carboxylate oxygens-mediated hydrogen bonds, as well as hydrophobic interactions mediated by the α-chlorine and the phenyl ring, effectively blocking BDK substrate access by preventing BDK interaction with the homo-24-meric dihydrolipoyltransferase BCKDC E2 component, while exhibiting little potency against PDK2 (pyruvate dehydrogenase kinase isoform 2) or BDP (BCKD phosphatase) even at concentrations as high as 1 mM (<10% inhibition). Shown to effectively reduce E1-α Ser293 phosphorylation with concomitant BCKDC activity upregulation in multiple tissues in mice (EDmax =160 mg/kg via i.p.; 60 min) in vivo, resulting in significant downregulation of serum BCAA (branched-chain amino acid) Leu/Ile and Val levels. Pharmacokinetic studies reveal good stability in vitro (half-life = 3.1 h and 6.8 h using murine liver S9 preparation or murine hepatocytes, respectively) and low clearance in vivo (CL/F = 0.113 mL/min; 40 mg/kg i.p.), however the compound does not penetrate tissues efficiently (VZ/F = 20.8 mL; 40 mg/kg i.p.) and high dosages are recommended for mice treatment.
FormClear, colorless oil
Intert gas (Yes/No) Packaged under inert gas
CAS number41998-38-3
Chemical formulaC₉H₉ClO₂
Structure formulaStructure formula
Purity≥98% by HPLC
SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
Storage Protect from moisture
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 1 month at -20°C.
Toxicity Standard Handling
ReferencesTso, S.C., et al. 2013. Proc. Natl. Acad. Sci. USA 110, 9728.