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Hoechst 33342

(HB0787)
Data

Product overview

  • Name
    Hoechst 33342
  • Short description
    Blue fluorescent DNA stain. Cell permeable. Nuclear stain.
  • Biological description

    Overview

    Blue fluorescent DNA stain that is commonly used in fluorescent microscopy. It is frequently used as a nuclear stain to stain nuclei. It is excited by UV light.

    Hoechst 33342 is cell permeable and has greater cell permeability than Hoechst 33258. The stain can be used on both live and fixed cells and is often used as an alternative to DAPI.

    Hoechst 33342 binds to the AT-rich regions of the minor grove in DNA which renders it specific for nuclear chromatin. Its fluorescent intensity depends on the DNA content, chromatin structure and the position of the cell within the cell cycle.

     

    Uses and applications

    There is little fluorescent overlap with other commonly used small-molecule fluorophores / fluorescent proteins that emit in the green / red range. This makes it suitable for a wide range of applications.

    Counterstain
    Hoechst 33342 is commonly used as a counterstain in fluorescent imaging.

     

    Cell cycle studies / Apoptosis

    Hoechst 33342 can stain the condensed nuclei of apoptotic cells to allow the identification of chromatin condensation and fragmentation. It is commonly used with propidium iodide to distinguish normal/live apoptotic and dead cell populations [5]. It can additionally be used in conjunction with arcidine orange (AO) to distinguish apoptotic cells.

    Incorporation of Brdu into DNA has a quenching effect on Hoechst fluorescence. Hoechst 33342 is also used in combination with BrdU to monitor cell cycle progression.

    Stem cells

    Combination of the Hoechst 33342 stain with surface-marker phenotyping allows the characterisation of a sub-population of stem cells termed the ‘side population’ (SP).

  • Alternative names
    H33342, Bisbenzimide H 33342
  • Biological action
    Dyes & stains
  • Citations

Properties

  • Chemical name
    Bisbenzimide
  • Molecular Weight
    561.93
  • Chemical structure
    Hoechst 33342  [23491-52-3]
  • Molecular Formula
    C27H28N6O.3HCl
  • CAS Number
    23491-52-3
  • PubChem identifier
    1464
  • SMILES
    CCOC1=CC=C(C=C1)C2=NC3=C(N2)C=C(C=C3)C4=NC5=C(N4)C=C(C=C5)N6CCN(CC6)C
  • InChi
    InChI=1S/C27H28N6O/c1-3-34-21-8-4-18(5-9-21)26-28-22-10-6-19(16-24(22)30-26)27-29-23-11-7-20(17-25(23)31-27)33-14-12-32(2)13-15-33/h4-11,16-17H,3,12-15H2,1-2H3,(H,28,30)(H,29,31)
  • InChiKey
    PRDFBSVERLRRMY-UHFFFAOYSA-N
  • MDL number
    MFCD00012678

Storing and Using Your Product

  • Storage instructions
    -20°C
  • Solubility overview
    Soluble in water, and in DMSO
  • Important
    This product is for RESEARCH USE ONLY and is not intended for therapeutic or diagnostic use. Not for human or veterinary use.

References for Hoechst 33342

  • Labeling nuclear DNA with hoechst 33342.

    Chazotte B (2011) Cold Spring Harb Protoc 2011(1) : pdb.prot5557.
    PubMedID: 21205857
  • Hoechst 33342 stain and u.v. laser exposure do not induce genotoxic effects in flow-sorted boar spermatozoa.

    Parrilla I et al (2004) Reproduction 128(5) : 615-21.
    PubMedID: 15509707
  • Phototoxicity of Hoechst 33342 in time-lapse fluorescence microscopy.

    Purschke M et al (2010) Photochem Photobiol Sci 9(12) : 1634-9.
    PubMedID: 20931137
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