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

530985
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Empirical FormulaCAS #
C₂₃H₂₁ClN₂O₃ 1443437-74-8

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      Glass bottle 10 mg
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      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

      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 +2°C to +8°C
      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.
      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.