528124 | Piperlongumine - CAS 20069-09-4 - Calbiochem

528124
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₁₇H₁₉NO₅ 20069-09-4

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      528124-25MG
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          Glass bottle 25 mg
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          Description
          OverviewA cell-permeable, orally bioavailable natural product isolated from the plant species, Piper longum L, which selectively induces cell death in cancer cells that express both wild-type and mutant p53, dose-dependently from 1–15 µM, but not in primary normal cells and non-transformed immortalized cells. It significantly enhances wild-type p53 and PUMA expression, and inhibits the expression of several pro-survival proteins, including BCL2, surviving, and XIAP, in various types of cancer cells, but not in normal cells. It elicits ROS and apoptosis in several human cancer cells (EJ, MDA-MB-231, U2OS and MDA-MB-435), possibly through interaction with oxidative stress responders such as GSTP1 and CBR1, and can be reversed by NAC (3 mM) in EJ cells. Additionally, it exhibits anti-tumour effects and inhibits the formation of blood vessels in xenograft-tumour mice without obvious toxicity, and inhibits tumor growth and their associated metastases in a MMTV-PyVT breast cancer transgenic mouse model ( 2.4 mg/kg, daily for two weeks, i.p.), which is more effective than paclitaxel.
          Catalogue Number528124
          Brand Family Calbiochem®
          Synonyms(E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one, Piplartine
          References
          ReferencesRaj, L., et al. 2011. Nature 475, 231.
          Product Information
          CAS number20069-09-4
          FormOff-white solid
          Hill FormulaC₁₇H₁₉NO₅
          Chemical formulaC₁₇H₁₉NO₅
          Structure formula ImageStructure formula Image
          Applications
          Biological Information
          Purity≥97% by HPLC
          Physicochemical Information
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          Safety Information
          Product Usage Statements
          Storage and Shipping Information
          Ship Code Shipped with Blue Ice or with Dry Ice
          Toxicity Regulatory Review
          Storage -20°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 3 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) 

          Certificates of Analysis

          TitleLot Number
          528124

          References

          Reference overview
          Raj, L., et al. 2011. Nature 475, 231.
          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.

          Revision15-June-2012 JSW
          Synonyms(E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one, Piplartine
          DescriptionA cell-permeable, orally bioavailable natural product isolated from the plant species, Piper longum L, which selectively induces cell death in cancer cells that express both wild-type and mutant p53, dose-dependently from 1–15 µM, but not in primary normal cells and non-transformed immortalized cells. It significantly enhances wild-type p53 and PUMA expression, and inhibits the expression of several pro-survival proteins, including BCL2, surviving, and XIAP, in various types of cancer cells, but not in normal cells. It elicits ROS and apoptosis in several human cancer cells (EJ, MDA-MB-231, U2OS and MDA-MB-435), possibly through interaction with oxidative stress responders such as GSTP1 and CBR1, and can be reversed by NAC (3 mM) in EJ cells. Additionally, it exhibits anti-tumour effects and inhibits the formation of blood vessels in xenograft-tumour mice without obvious toxicity, and inhibits tumor growth and their associated metastases in a MMTV-PyVT breast cancer transgenic mouse model ( 2.4 mg/kg, daily for two weeks, i.p.), which is more effective than paclitaxel.
          FormOff-white solid
          Intert gas (Yes/No) Packaged under inert gas
          CAS number20069-09-4
          Chemical formulaC₁₇H₁₉NO₅
          Structure formulaStructure formula
          Purity≥97% by HPLC
          SolubilityDMSO
          Storage -20°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 3 months at -20°C.
          Toxicity Regulatory Review
          ReferencesRaj, L., et al. 2011. Nature 475, 231.