(Z)-4-Hydroxytamoxifen (Z-4-OHT)

(HB2508)

Product overview

  • Name
    (Z)-4-Hydroxytamoxifen (Z-4-OHT)
  • Short description
    Synthetic estrogen receptor ligand. Widely used in genome engineering (e.g. CreER/ CRISPR-Cas9).
  • Biological description

    Cell permeable, synthetic estrogen receptor ligand. Widely used in genome engineering.


    CreER system
    :

    De facto standard compound in drug-inducible manipulation of CreER recombinase. Allows external temporal control of Cre activity in vivo.


    CRISPR/Cas9 gene editing:

    Activates an inactived Cas9 nuclease (rendered inactive by insertion of a 4-OHT dependent-intein) to reduce off-target CRISPR-mediated gene editing (once bound with 4-OHT, conditionally active Cas9s modify target genomic sites with ~25-fold higher specificity than wild-type Cas9).

    Also allows tight, repeated on-off control of the nuclease activity of the ‘iCas’ Cas9 variant which shows high editing efficiency at multiple loci once bound with 4-OHT.


    4-Hydroxytamoxifen (70:30 mixture of (Z):(E) isomers) also available.

  • Alternative names
    4-HT, 4-OHT, 4-OH-TAM, OHT, TAM, 4-Hydroxytamoxifen
  • Biological action
    Activator
  • Purity
    >98%
  • Citations

Properties

  • Chemical name
    4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
  • Molecular Weight
    387.51
  • Chemical structure
    (Z)-4-Hydroxytamoxifen [68047-06-3]
  • Molecular Formula
    C26H29NO2
  • CAS Number
    68047-06-3
  • PubChem identifier
    449459
  • SMILES
    CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3
  • Source
    Synthetic
  • InChi
    InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
  • InChiKey
    TXUZVZSFRXZGTL-QPLCGJKRSA-N
  • MDL number
    MFCD00278780
  • Appearance
    White solid

Storing and Using Your Product

  • Storage instructions
    +4 °C
  • Solubility overview
    Soluble in DMSO (100 mM) and in ethanol (50 mM)
  • Handling
    This compound is light sensitive; exposure to light may affect compound performance. We therefore recommend storing the material in the dark and protecting from light. Do not store the material in solution; make up solutions and use immediately.
  • 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 (Z)-4-Hydroxytamoxifen (Z-4-OHT)

  • A chemical-inducible CRISPR-Cas9 system for rapid control of genome editing.

    Liu et al (2016) Nat Chem Biol 12(11) : 980-987.
    PubMedID: 27618190
  • Small molecule-triggered Cas9 protein with improved genome-editing specificity.

    Davis et al (2015) Nat Chem Biol 11(5) : 316-8.
    PubMedID: 25848930
  • Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator.

    Yu and Forman (2003) J Org Chem 68(24) : 9489-91.
    PubMedID: 14629178
  • A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity.

    Jordan et al (1977) J Endocrinol 75(2) : 305-16.
    PubMedID: 591813