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Sigma-Aldrich

Hoechst 33258 solution

1 mg/mL in H2O, ≥98.0% (HPLC)

Synonym(s):

bisBenzimide H 33258 solution

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About This Item

Empirical Formula (Hill Notation):
C25H24N6O · 3HCl
CAS Number:
23491-45-4
Molecular Weight:
533.88
UNSPSC Code:
12171500
PubChem Substance ID:
329770334
NACRES:
NA.32

Assay

≥98.0% (HPLC)

form

liquid

concentration

1 mg/mL in H2O

solubility

DMF: soluble
H2O: soluble

fluorescence

λex 355 nm; λem 465 nm in TE buffer; DNA

storage temp.

2-8°C

SMILES string

Cl.Cl.Cl.CN1CCN(CC1)c2ccc3[nH]c(nc3c2)-c4ccc5nc([nH]c5c4)-c6ccc(O)cc6

InChI

1S/C25H24N6O.3ClH/c1-30-10-12-31(13-11-30)18-5-9-21-23(15-18)29-25(27-21)17-4-8-20-22(14-17)28-24(26-20)16-2-6-19(32)7-3-16;;;/h2-9,14-15,32H,10-13H2,1H3,(H,26,28)(H,27,29);3*1H

InChI key

SMNPLAKEGAEPJD-UHFFFAOYSA-N

General description

Hoechst 33258, also known as bisbenzimide, is a fluorescent blue dye. It is categorized as a chromosomal stain that binds to the minor groove of the DNA double helix recognizing a run of four A-T base pairs.

Application

Hoechst 33258 is used to estimate DNA concentration in samples by fluorometry which is better than spectrophotometry, allowing the determination of nanogram quantities of DNA. Also, Hoechst 33258 is suitable to detect mycoplasma contamination in cell cultures due to its high fluorescence ability.

Storage Class Code

10 - Combustible liquids

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Natalia Busto et al.
The journal of physical chemistry. B, 119(13), 4575-4581 (2015-03-12)
The functionality of the bisbenzimide Hoechst 33258 in solution has been largely exploited in the quantification of DNA. Understanding of its behavior is essential to promote its widespread application and learning of biological processes. A detailed study of the dimerization
Cornelia Fritsch et al.
PLoS genetics, 15(7), e1008269-e1008269 (2019-07-13)
Development of eye tissue is initiated by a conserved set of transcription factors termed retinal determination network (RDN). In the fruit fly Drosophila melanogaster, the zinc-finger transcription factor Glass acts directly downstream of the RDN to control identity of photoreceptor
Yulia Kraus et al.
Developmental biology, 468(1-2), 59-79 (2020-09-26)
The cnidarian "planula" larva shows radial symmetry around a polarized, oral-aboral, body axis and comprises two epithelia cell layers, ectodermal and endodermal. This simple body plan is set up during gastrulation, a process which proceeds by a variety of modes
In situ detection of mycoplasma contamination in cell cultures by fluorescent Hoechst 33258 stain.
T R Chen
Experimental cell research, 104(2), 255-262 (1977-02-01)
A Fede et al.
Structure (London, England : 1993), 1(3), 177-186 (1993-11-15)
The chromosomal stain, Hoechst 33258, binds to the minor groove of the DNA double helix and specifically recognizes a run of four A-T base pairs. Extensive biochemical and biophysical studies have been aimed at understanding the binding of the dye
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