344270 Forskolin, Coleus forskohlii - CAS 66575-29-9 - Calbiochem

344270
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Empirical FormulaCAS #
C₂₂H₃₄O₇66575-29-9

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344270-10MGCN
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      Description
      OverviewThe major cell-permeable diterpene isolated from the Indian plant Coleus forskohlii. At low doses, it acts as a positive inotropic agent. At higher doses, it serves as a hypotensive and vasodilatory agent due to its actions as a smooth muscle relaxant. No major side effects are observed at effective doses. Forskolins pharmacological activities are due to its activation of adenylate cyclase (EC50 = 4 µM), resulting in increased cAMP levels. The exact mechanism of forskolins positive inotropic effect is unknown but may be related to a cAMP-dependent increase in Na+ permeability that results in indirect augmentation of Ca2+ release. Inhibits MAP kinase in rat renal mesangial cells (IC50 = 25 µM). Also acts as a Hh pathway antagonist. Shown to inhibit apoptosis in cerebellar granule cells and to induce apoptosis in resting human B lymphocytes.
      Catalogue Number344270
      Brand Family Calbiochem®
      Synonyms7β-Acetoxy-8,13-epoxy-1α,6β,9α-trihydroxy-labd-14-en-11-one, Colforsin
      References
      ReferencesD'Orazio, J.A., et al. 2006. Nature 443, 340.
      Noveen, A., et al. 1996. Biochem. Biophys. Res. Commun. 219, 180.
      Galli, C., et al. 1995. J. Neurosci. 15, 1172.
      Li, X., et al. 1995. Am. J. Physiol. 269, C986.
      Lomo, J., et al. 1995. J. Immunol. 154, 1634.
      Uneyama, H., et al. 1993. J. Biol. Chem. 268, 168.
      Laurenza, A., et al. 1989. Trends Pharmacol. Sci. 10, 442.
      Adashi, E.Y., and Resnick, C.E. 1986. J. Cell. Biochem. 31, 217.
      Seamon, K.B., and Daly, J.W. 1986. Adv. Cyclic Nucleotide Protein Phosphorylation Res. 20, 1.
      Huang, R., et al. 1982. Cyclic Nucleotide Res. 8, 385.
      Metzger, H., and Lindner, E. 1981. IRCS Med. Sci. Biochem. Cardiovasc. System Pharmacol. 9, 99.
      Product Information
      CAS number66575-29-9
      ATP CompetitiveN
      FormWhite to off-white crystalline solid
      Hill FormulaC₂₂H₃₄O₇
      Chemical formulaC₂₂H₃₄O₇
      ReversibleN
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetAdenylate cyclase
      Primary Target IC<sub>50</sub>25 µM inhibiting MAP kinase in rat renal mesangial cells; EC50 = 4 µM for activation of adenylate cyclase
      Purity≥99% by HPLC
      Physicochemical Information
      Cell permeableY
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      RTECSQL6150000
      Safety Information
      R PhraseR: 21

      Harmful in contact with skin.
      S PhraseS: 36

      Wear suitable protective clothing.
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Ambient Temperature Only
      Toxicity Harmful
      Storage +15°C to +30°C
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, store in the refrigerator (4°C). DMSO stock solutions are stable for up to 4 months at 4°C.
      Packaging Information
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      Forskolin, Coleus forskohlii - CAS 66575-29-9 - Calbiochem Certificates of Analysis

      TitleLot Number
      344270

      References

      Reference overview
      D'Orazio, J.A., et al. 2006. Nature 443, 340.
      Noveen, A., et al. 1996. Biochem. Biophys. Res. Commun. 219, 180.
      Galli, C., et al. 1995. J. Neurosci. 15, 1172.
      Li, X., et al. 1995. Am. J. Physiol. 269, C986.
      Lomo, J., et al. 1995. J. Immunol. 154, 1634.
      Uneyama, H., et al. 1993. J. Biol. Chem. 268, 168.
      Laurenza, A., et al. 1989. Trends Pharmacol. Sci. 10, 442.
      Adashi, E.Y., and Resnick, C.E. 1986. J. Cell. Biochem. 31, 217.
      Seamon, K.B., and Daly, J.W. 1986. Adv. Cyclic Nucleotide Protein Phosphorylation Res. 20, 1.
      Huang, R., et al. 1982. Cyclic Nucleotide Res. 8, 385.
      Metzger, H., and Lindner, E. 1981. IRCS Med. Sci. Biochem. Cardiovasc. System Pharmacol. 9, 99.

      Brochure

      Title
      Activators and Inhibitors of Adenylate Cyclase Technical Bulletin

      Citations

      Title
    • Ryan W Carlin, et al. (2006) PVD9902, a porcine vas deferens epithelial cell line that exhibits neurotransmitter-stimulated anion secretion and expresses numerous HCO3- transporters. American Journal of Physiology Cell Physiology 290, C1560-C1571.
    • Iwona Bogacka, et al. (2005) Structural and functional consequences of mitochondrial biogenesis in human adipocytes in vitro. Journal of Clinical Endocrinology and Metabolism in press,.
    • Michael J. Cross, et al. (2002) The Shb Adaptor Protein Binds to Tyrosine 766 in the FGFR-1 and Regulates the Ras/MEK/MAPK Pathway via FRS2 Phosphorylation in Endothelial Cells. Molecular Biology of the Cell 13, 2881-2893.
    • 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.

      Revision20-November-2008 JSW
      Synonyms7β-Acetoxy-8,13-epoxy-1α,6β,9α-trihydroxy-labd-14-en-11-one, Colforsin
      DescriptionA cardioactive diterpene isolated from the Indian plant Coleus forskolii. At low doses, acts as a positive inotropic agent in dogs, cats, spontaneously hypertensive and normal rats, and isolated guinea pig heart. At higher doses, acts as a hypotensive and vasodilatory agent due to its action as a smooth muscle relaxant. No major side effects are observed at effective doses. Rapid and reversible activator of adenylate cyclase (EC50 = 4 µM) in membranes and intact cells. Does not affect the activity of guanylate cyclase or cyclic nucleotide phophodiesterases. The exact mechanism of forskolin's positive inotropic effect is unknown but may be related to a cAMP-dependent increase in Na+ permeability, which results in indirect augmentation of Ca2+ release. Inhibits MAP kinase in rat renal mesangial cells (IC50 = 25 µM). Also acts as a Hh pathway antagonist. Shown to inhibit apoptosis in cerebellar granule cells and to induce apoptosis in resting human B-lymphocytes.
      FormWhite to off-white crystalline solid
      CAS number66575-29-9
      RTECSQL6150000
      Chemical formulaC₂₂H₃₄O₇
      Structure formulaStructure formula
      Purity≥99% by HPLC
      SolubilityDMSO (5 mg/ml). Ethanol is reported to inhibit forskolin-mediated activation of adenylate cyclase. DMSO is the recommended solvent; at ≤5% DMSO final concentration, little inhibition of the adenylate cyclase activation will occur.
      Storage +15°C to +30°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, store in the refrigerator (4°C). DMSO stock solutions are stable for up to 4 months at 4°C.
      Toxicity Harmful
      Merck USA index14, 2476
      ReferencesD'Orazio, J.A., et al. 2006. Nature 443, 340.
      Noveen, A., et al. 1996. Biochem. Biophys. Res. Commun. 219, 180.
      Galli, C., et al. 1995. J. Neurosci. 15, 1172.
      Li, X., et al. 1995. Am. J. Physiol. 269, C986.
      Lomo, J., et al. 1995. J. Immunol. 154, 1634.
      Uneyama, H., et al. 1993. J. Biol. Chem. 268, 168.
      Laurenza, A., et al. 1989. Trends Pharmacol. Sci. 10, 442.
      Adashi, E.Y., and Resnick, C.E. 1986. J. Cell. Biochem. 31, 217.
      Seamon, K.B., and Daly, J.W. 1986. Adv. Cyclic Nucleotide Protein Phosphorylation Res. 20, 1.
      Huang, R., et al. 1982. Cyclic Nucleotide Res. 8, 385.
      Metzger, H., and Lindner, E. 1981. IRCS Med. Sci. Biochem. Cardiovasc. System Pharmacol. 9, 99.
      Citation
    • Ryan W Carlin, et al. (2006) PVD9902, a porcine vas deferens epithelial cell line that exhibits neurotransmitter-stimulated anion secretion and expresses numerous HCO3- transporters. American Journal of Physiology Cell Physiology 290, C1560-C1571.
    • Iwona Bogacka, et al. (2005) Structural and functional consequences of mitochondrial biogenesis in human adipocytes in vitro. Journal of Clinical Endocrinology and Metabolism in press,.
    • Michael J. Cross, et al. (2002) The Shb Adaptor Protein Binds to Tyrosine 766 in the FGFR-1 and Regulates the Ras/MEK/MAPK Pathway via FRS2 Phosphorylation in Endothelial Cells. Molecular Biology of the Cell 13, 2881-2893.