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505763 ProRS Inhibitor, Halofuginone - CAS 64924-67-0 - Calbiochem

A cell-permeable racemic mixture of Halofuginone that inhibits of prolyl-tRNA synthetase.

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

Synonyms: prolyl-tRNA synthetase Inhibitor, STENOROL, HF, Hydrobromide, trans-(±)-7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone hydrobromide

Primary Target: prolyl-tRNA synthetase
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
64924-67-0C₁₆H₁₇BrClN₃O₃•HBr

Products

Catalogue NumberPackaging Qty/Pack
5.05763.0001 Glass bottle 10 mg
Description
OverviewA cell-permeable racemic mixture of Halofuginone whose D-(+)/(2R, 3S) enantiomer serves as the active inhibitor against ProRS-mediated aminoacylation by simultaneously preventing ProRS-catalyzed Pro-AMP formation and the subsequent Pro transfer from Pro-AMP to tRNAPro. Proline, but not other NEAA, is able to reverse the inhibitory effect of HF in in vitro rabbit reticulocyte lysate translations (1 µM HF; 1 mM Pro) and prevent HF-induced cellular AAR pathway activation (100 nM HF/2 mM Pro/MEF; 10 nM HF/1 mM Pro/Murine CD4+ CD25- T cells). Shown to inhibit bFGF-induced neovascularization in a murine corneal angiogenesis model (5 mg/kg/d via food intake) and significantly reduce the severity of MOG33-55-induced EAE in mice (2 µg/mouse/d i.p.) in vivo. Unlike AA-AMP mimetics, HF does not compete against ATP for ProRS binding.
Catalogue Number505763
Brand Family Calbiochem®
Synonymsprolyl-tRNA synthetase Inhibitor, STENOROL, HF, Hydrobromide, trans-(±)-7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone hydrobromide
References
ReferencesZhou, H., et al. 2013, Nature 494, 121.
Keller, T.L., et al. 2012, Nat. Chem. Biol. 12, 311.
Sundrud, M.S., et al. 2009, Science 324, 1334.
Elkin, M., et al. 2000, FASEB J. 14, 2477.
Elkin, M., et al. 1999, Clin. Cancer Res. 5, 1982.
Product Information
CAS number64924-67-0
FormWhite powder
Hill FormulaC₁₆H₁₇BrClN₃O₃•HBr
Chemical formulaC₁₆H₁₇BrClN₃O₃•HBr
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
Biological Information
Primary Targetprolyl-tRNA synthetase
Primary Target IC<sub>50</sub>18 nM
Purity≥98% by HPLC
Physicochemical Information
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
Storage and Shipping Information
Ship Code Shipped at Ambient Temperature or with Blue Ice or with Dry Ice
Toxicity Standard Handling
Storage +2°C to +8°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 3 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
5.05763.0001 04055977243536

Documentation

ProRS Inhibitor, Halofuginone - CAS 64924-67-0 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

References

Reference overview
Zhou, H., et al. 2013, Nature 494, 121.
Keller, T.L., et al. 2012, Nat. Chem. Biol. 12, 311.
Sundrud, M.S., et al. 2009, Science 324, 1334.
Elkin, M., et al. 2000, FASEB J. 14, 2477.
Elkin, M., et al. 1999, Clin. Cancer Res. 5, 1982.
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.

Revision28-March-2014 JSW
Synonymsprolyl-tRNA synthetase Inhibitor, STENOROL, HF, Hydrobromide, trans-(±)-7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone hydrobromide
DescriptionA cell-permeable racemic mixture of Halofuginone, a halogenated derivative of the Dichroa febriguga alkaloid Febrifugine, whose D-(+)/(2R, 3S) enantiomer serves as the active inhibitor against ProRS- (prolyl-tRNA synthetase) mediated aminoacylation by simultaneously targeting/blocking ProRS Proline-binding pocket with its hydroxypiperidine and tRNA 3′ end adenosine-binding site with its halogenated 4-quinazolinone, preventing not only ProRS-catalyzed prolyl adenylation (Pro-AMP formation), but also the subsequent Pro transfer from Pro-AMP to tRNAPro. Consistently, only proline, but not other NEAA, is able to reverse the inhibitory effect of HF in in vitro rabbit reticulocyte lysate translations (1 µM HF; 1 mM Pro) and prevent HF-induced cellular AAR (amino acid response) pathway activation (100 nM HF/2 mM Pro/MEF; 10 nM HF/1 mM Pro/Murine CD4+ CD25- T cells). Shown to inhibit bFGF-induced neovascularization in a murine corneal angiogenesis model (5 mg/kg/day via food intake) and significantly reduce the severity of myelin antigen MOG33-55-induced autoimmune EAE/encephalomyelitis in mice (2 µg/mouse/day i.p.) in vivo. Unlike AA-AMP mimetics, HF does not compete against ATP for ProRS binding. ATP, in its ProRS bound state, actually helps stabilize HF via hydrogen bond interactions.
FormWhite powder
Intert gas (Yes/No) Packaged under inert gas
CAS number64924-67-0
Chemical formulaC₁₆H₁₇BrClN₃O₃•HBr
Structure formulaStructure formula
Purity≥98% by HPLC
SolubilityDMSO (100 mg/ml)
Storage Protect from light
+2°C to +8°C
Do Not Freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Toxicity Standard Handling
ReferencesZhou, H., et al. 2013, Nature 494, 121.
Keller, T.L., et al. 2012, Nat. Chem. Biol. 12, 311.
Sundrud, M.S., et al. 2009, Science 324, 1334.
Elkin, M., et al. 2000, FASEB J. 14, 2477.
Elkin, M., et al. 1999, Clin. Cancer Res. 5, 1982.