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530985 MICAL-2 Inhibitor II, CCG-203971 - CAS 1443437-74-8 - Calbiochem

A cell-permeable, restricted form of CCG-1423 with enhanced potency (IC₅₀ = 4.2 µM vs 16.6 µM for PC-3 cell migration), but reduced off-target toxicity.

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

Synonyms: N-(4-Chlorophenyl)-1-(3-(furan-2-yl)benzoyl)piperidine-3-carboxamide, CCG 203971, MLK1 Nuclear Translocation Inhibitor II

Primary Target: MICAL-2
530985
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
1443437-74-8C₂₃H₂₁ClN₂O₃

Products

Catalogue NumberPackaging Qty/Pack
5309850001 Glass bottle 10 mg
Description
OverviewA cell-permeable, bioavailable, conformationally restricted form of CCG-1423 (Cat. No. 555558) that exhibits enhanced potency (IC50 = 4.2 µM vs 16.6 µM for PC-3 cell migration), but reduced off-target toxicity (IC50 > 100 µM in PC3 cells). Selectively represses sclerodermal fibroblasts proliferation without affecting normal cells (~30 µM). Shown to be more effective in reducing MRTF/SRF-regulated gene transcriptional signaling than Y-27632 (Cat. No. 688000). Suppresses Rho/MRTF/SRF-regulated fibrotic gene expression in primary dermal fibroblasts derived from systemic sclerosis patients in a dose-dependent manner and reverses myofibroblast phenotype in TGFβ-stimulated normal dermal fibroblasts. Blocks MRTF nuclear localization by interfering with the microtubule associated monooxygenase, calponin and LIM domain containing 2 (MICAL-2), mediated regulation of intranuclear actin polymerization. Although exhibits a short in-vivo half-life (~25 min), at higher dosage effectively prevents bleomycin-induced fibrosis in C57BL/6J mice (100 mg/kg, i.p., b.i.d.).

Please note that the molecular weight for this compound is batch-specific due to variable water content.
Catalogue Number530985
Brand Family Calbiochem®
SynonymsN-(4-Chlorophenyl)-1-(3-(furan-2-yl)benzoyl)piperidine-3-carboxamide, CCG 203971, MLK1 Nuclear Translocation Inhibitor II
References
ReferencesHaak, A.J., et al. 2014. J. Pharmacol. Exp. Ther. 349, 480.
Johnson, L.A., et al. 2014. Inflamm. Bowel Dis. 20, 154.
Bell, J.L., et al. 2013. Bioorg. Med. Chem. Lett. 23, 3826.
Product Information
CAS number1443437-74-8
FormOff-white powder
Hill FormulaC₂₃H₂₁ClN₂O₃
Chemical formulaC₂₃H₂₁ClN₂O₃
ReversibleY
Quality LevelMQ100
Applications
Biological Information
Primary TargetMICAL-2
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 +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 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
5309850001 04055977242461

Documentation

MICAL-2 Inhibitor II, CCG-203971 - CAS 1443437-74-8 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

References

Reference overview
Haak, A.J., et al. 2014. J. Pharmacol. Exp. Ther. 349, 480.
Johnson, L.A., et al. 2014. Inflamm. Bowel Dis. 20, 154.
Bell, J.L., et al. 2013. Bioorg. Med. Chem. Lett. 23, 3826.
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.

Revision29-August-2014 JSw
SynonymsN-(4-Chlorophenyl)-1-(3-(furan-2-yl)benzoyl)piperidine-3-carboxamide, CCG 203971, MLK1 Nuclear Translocation Inhibitor II
DescriptionA cell-permeable nipecotic bis(amide), chemically modified from CCG-1423 (Cat. No. 555558) for reduced toxicity (non-toxic up to 100 µM in PC-3 cultures and 100 mg/kg/d in mice via i.p.), that effectively downregulates SRF/MLK1 (MRTF-A) target genes mRNA level in primary dermal fibroblast cultures from SSc (systemic sclerosis) patients (IC50 ≤30 µM post 24 h incubation) as well as in LPA-stimulated NIH 3T3 fibroblasts (IC50 = 1 - 3 µM; drug added 23 h prior to 1 h 10 µM LPA stimulation). Likewise, 3-day 10 µM CCG-203971 treatment is shown to reduce cellular α-SMA (α smooth muscle actin) protein and proliferation of SSc dermal fibroblasts to the same level as seen in dermal fibroblasts from healthy donors as well as to prevent 10 ng/mL TGFβ-induced α-SMA upregulation in normal dermal fibroblasts. When administered via intraperitoneal injection (100 mg/50 µL DMSO/kg/12 h), CCG-203971 is reported to be efficacious in preventing bleomycin-(100 µg/µL/1 cm2 skin/animal/day s.c.) induced skin fibrosis in mice (skin thickness = 1.9- vs. 3.5-fold of control, with or without drug treatment at the end of 2-wk induction period) in vivo.
FormOff-white powder
Intert gas (Yes/No) Packaged under inert gas
CAS number1443437-74-8
Chemical formulaC₂₃H₂₁ClN₂O₃
Purity≥97% 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 6 months at -20°C.
Toxicity Standard Handling
ReferencesHaak, A.J., et al. 2014. J. Pharmacol. Exp. Ther. 349, 480.
Johnson, L.A., et al. 2014. Inflamm. Bowel Dis. 20, 154.
Bell, J.L., et al. 2013. Bioorg. Med. Chem. Lett. 23, 3826.