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500495 RubR1 Activator, GF-15 - CAS 888042-13-5 - Calbiochem

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Synonyme: 2ʹ-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

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      Übersicht

      Replacement Information

      Key Spec Table

      CAS #Empirical Formula
      888042-13-5C₂₃H₂₁ClO₆
      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
      CAS number888042-13-5
      FormWhite solid
      Hill FormulaC₂₃H₂₁ClO₆
      Chemical formulaC₂₃H₂₁ClO₆
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality SegmentMQ100
      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
      Global Trade ITEM Number
      Bestellnummer GTIN
      500495 0

      Documentation

      RubR1 Activator, GF-15 - CAS 888042-13-5 - Calbiochem SDB

      Titel

      Sicherheitsdatenblatt (SDB) 

      Literatur

      Übersicht
      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.
      Datenblatt

      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
      CAS number888042-13-5
      Chemical formulaC₂₃H₂₁ClO₆
      Structure formulaStructure formula
      Purity≥98% by HPLC
      SolubilityDMSO (50 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
      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.