(HB2508) Product overview
Name (Z)-4-Hydroxytamoxifen (Z-4-OHT)
Description Synthetic estrogen receptor ligand. Widely used in genome engineering (e.g. CreER/ CRISPR-Cas9).
Alternative names 4-HT, 4-OHT, 4-OH-TAM, OHT, TAM, 4-Hydroxytamoxifen Biological Data
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
May also be used for TRAPing / in the TRAP / TRAP2 system (Targeted recombination in active populations).
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. Solubility & Handling
Storage instructions -20°C
Solubility overview Soluble in DMSO (100 mM) and in ethanol (50 mM)
Storage of solid
This compound is light sensitive; exposure to light may affect compound performance. You should therefore store the material in the dark and protect from light.
Storage of solutions
Do not store the material in solution; make up solutions and use immediately:
The compound has been shown to isomerise rapidly in solution in most solvents (particulaly solvents with a low dielectric contstant). You should therefore make up and use solutions immediately.
The isomerisation process can be precluded by storage of the compound at -25°C in the dark as a THF solution containing ca. 0.025% BHT. (Katzenellenbogen et al (1982) J. Org. Chem. 47 2387.)
Important This product is for RESEARCH USE ONLY and is not intended for therapeutic or diagnostic use. Not for human or veterinary use. Chemical Data
Chemical name 4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
Molecular Formula C 26H 29NO 2
PubChem identifier 449459
InChiKey TXUZVZSFRXZGTL-QPLCGJKRSA-N References for (Z)-4-Hydroxytamoxifen (Z-4-OHT)
References are publications that support the biological activity of the product
A chemical-inducible CRISPR-Cas9 system for rapid control of genome editing. Liu et al (2016) Nat Chem Biol 12(11) : 980-987. Small molecule-triggered Cas9 protein with improved genome-editing specificity. Davis et al (2015) Nat Chem Biol 11(5) : 316-8. Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator. Yu and Forman (2003) J Org Chem 68(24) : 9489-91. A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. Jordan et al (1977) J Endocrinol 75(2) : 305-16.
These publications cite the use of (Z)-4-Hydroxytamoxifen (Z-4-OHT) purchased from Hello Bio:
SCN2A contributes to oligodendroglia excitability and development in the mammalian brain Gould and Kim (2021) Cell Rep. (10) : 36 A machine-vision approach for automated pain measurement at millisecond timescales Jones et al. (2020) bioRxiv preprint : 1-19