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500495 | RubR1 Activator, GF-15 - Calbiochem

500495
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical Formula
      C₂₃H₂₁ClO₆

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      5.00495.0001
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          Glass bottle 25 mg
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          Description
          OverviewA cell-permeable 2'-benzyloxy griseofulvin derivative that displays enhanced mammalian cancer-selective toxicity (IC50 ≤2, ≤4, ≤12, and ≥30 µM against panels of leukemia, myeloma, solid tumors, and non-malignant cell lines, respectively), but little antifungal activity, by activating spindle-assembly-checkpoint without affecting microtubule kinetochore attachment. Cancer cells are reported to undergo multipolar (MP) mitosis with normal or supernumerary centrosomes in the presence of GF-15, resulting in subsequent apoptotic cell death. Shown to retard HT29 colon cancer & OPM2 myeloma tumor expansion in mice (20 mg/kg/day i.p.) in vivo. GF-15 half-life is expected to be least 48 h in cultures.

          Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.
          Catalogue Number500495
          Brand Family Calbiochem®
          Synonyms2ʹ-Benzyloxy-2ʹ-demethoxygriseofulvin, (2S,6ʹR)-(7-Chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1ʹ-(2ʹ-benzyloxy-6ʹ-methylcyclohex-2ʹ-en-4ʹ-one), (2S,5ʹR)-3ʹ-benzyloxy-7-chloro-4,6-dimethoxy-5ʹ-methyl-spiro(benzofuran-2,4ʹ-cyclohex-2-ene)-1ʹ,3-dione, (1ʹS,6ʹR)-2ʹ-(benzyloxy)-7-chloro-4,6-dimethoxy-6ʹ-methyl-3H-spiro(benzofuran-2,1ʹ-cyclohex[2]ene)-3,4ʹ-dione, Supernumerary Centrosomes Clustering Inhibitor
          References
          ReferencesRaab, M.S., et al. 2012. Cancer Res. 72, 5374.
          Ronnest, M.H., et al. 2009. J. Med. Chem. 52, 3342.
          Crosse, R., et al. 1964. J. Gen. Microbiol. 34, 51.
          Product Information
          FormWhite solid
          Hill FormulaC₂₃H₂₁ClO₆
          Chemical formulaC₂₃H₂₁ClO₆
          ReversibleY
          Structure formula Image
          Applications
          Biological Information
          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 +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

          SDS

          Title

          Safety Data Sheet (SDS) 

          References

          Reference overview
          Raab, M.S., et al. 2012. Cancer Res. 72, 5374.
          Ronnest, M.H., et al. 2009. J. Med. Chem. 52, 3342.
          Crosse, R., et al. 1964. J. Gen. Microbiol. 34, 51.
          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.

          Revision23-May-2013 JSW
          Synonyms2ʹ-Benzyloxy-2ʹ-demethoxygriseofulvin, (2S,6ʹR)-(7-Chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1ʹ-(2ʹ-benzyloxy-6ʹ-methylcyclohex-2ʹ-en-4ʹ-one), (2S,5ʹR)-3ʹ-benzyloxy-7-chloro-4,6-dimethoxy-5ʹ-methyl-spiro(benzofuran-2,4ʹ-cyclohex-2-ene)-1ʹ,3-dione, (1ʹS,6ʹR)-2ʹ-(benzyloxy)-7-chloro-4,6-dimethoxy-6ʹ-methyl-3H-spiro(benzofuran-2,1ʹ-cyclohex[2]ene)-3,4ʹ-dione, Supernumerary Centrosomes Clustering Inhibitor
          DescriptionA cell-permeable 2′-benzyloxy griseofulvin derivative that displays enhanced mammalian cancer-selective toxicity (IC50 ≤2, ≤4, ≤12, and ≥30 µM against panels of leukemia, myeloma, solid tumors, and non-malignant cell lines, respectively), but little antifungal activity, by activating spindle-assembly-checkpoint (Pos. vs. Neg. RubR1 staining of metaphase PC-3 kinetophores with or without 24 h 0.75 µM GF-15 treatment) without affecting microtubule kinetochore attachment (Neg. Mad2 staining of metaphase PC-3 kinetophores with or without GF-15). Cancer cells are reported to undergo multipolar (MP) mitosis with normal or supernumerary centrosomes (Aberrant vs. declustered, respectively) in the presence of GF-15 (%Declustered / %Aberrant MP mitotic cells among all anaphase cells = 5.6/<0.5, 10/3.9, 16/18, 28/30, respectively, in PC-3 cultures treated with 0, 0.375, 0.75, or 1.5 µM GF-15 for 24 h), resulting in subsequent apoptotic cell death. Shown to retard OPM2 myeloma- and HT29 colon cancer-derived tumor expansion in mice (by 49% and 56%, respectively at the end of 2-wk treatment; 10 i.p. dosages at 20 mg/kg/day in 2 weeks) in vivo. Based on stability data obtained with its p-iodobenzyl analogue, GF-15 half-life is expected to be least 48 h in cultures.
          FormWhite solid
          Intert gas (Yes/No) Packaged under inert gas
          Chemical formulaC₂₃H₂₁ClO₆
          Structure formula
          Purity≥98% by HPLC
          SolubilityDMSO (50 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
          ReferencesRaab, M.S., et al. 2012. Cancer Res. 72, 5374.
          Ronnest, M.H., et al. 2009. J. Med. Chem. 52, 3342.
          Crosse, R., et al. 1964. J. Gen. Microbiol. 34, 51.