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Merck

B2261

bisBenzimide H 33342 trihydrochloride

≥98% purity (HPLC and TLC), powder

Synonym(s):

2′-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5′-bi-1H-benzimidazole trihydrochloride, HOE 33342, Hoechst 33342, bisBenzimide

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About This Item

Empirical Formula (Hill Notation):
C27H28N6O · 3HCl · xH2O
CAS Number:
875756-97-1
Molecular Weight:
561.93 (anhydrous basis)
NACRES:
NA.47
PubChem Substance ID:
24891639
UNSPSC Code:
12171500
MDL number:
MFCD00012678
Beilstein/REAXYS Number:
1234011

Key Documents

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Product Name

bisBenzimide H 33342 trihydrochloride, ≥98% (HPLC and TLC)

InChI

1S/C29H32N6O.3ClH/c1-3-36-25-8-4-20(5-9-25)28-30-18-22-16-21(6-10-26(22)32-28)29-31-19-23-17-24(7-11-27(23)33-29)35-14-12-34(2)13-15-35;;;/h4-11,16-17H,3,12-15,18-19H2,1-2H3,(H,30,32)(H,31,33);3*1H

SMILES string

Cl[H].Cl[H].Cl[H].CCOc1ccc(cc1)C2=NCc3cc(ccc3N2)C4=NCc5cc(ccc5N4)N6CCN(C)CC6

InChI key

FYEVKHPLBHLWHK-UHFFFAOYSA-N

assay

≥98% (HPLC and TLC)

form

powder

technique(s)

titration: suitable

color

yellow

pH

1.7 (20 °C)

solubility

H2O: 20 mg/mL
phosphate buffer: precipitates

suitability

suitable for fluorescence

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

Quality Level

300

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Application

Bisbenzimide Hoechst 33342 is a specific stain for AT-rich regions of double-stranded DNA and has been shown to displace several known DNA intercalators. This fluorescent dye has been used in sorting living cells based on DNA content, used in flow cytometry for the determination of DNA content, and for the visualization of chromatin distribution in living cells. It has been used to detect BrdU incorporation into cells and in studying the initial stages apoptosis and cellcycle distribution., Chromosomes that are dividing or replicating will not stain with this dye.
Useful for staining DNA, chromosomes and nuclei. May be used for fluorescence microscopy or flow cytometry.
Excitation max. = 346 nm
Emission max. = 460 nm

Biochem/physiol Actions

Membrane-permeable, fluorescent DNA stains with low cytotoxicity that intercalate in A-T regions of DNA.

General description

Fluorescent properties of bisBenzimide H 33342:
Free dye: Excitation maximum = 340 nm, Emission maximum = 510 nm (5 mM HEPES, 10 mM NaCl, pH 7.0) DNA complex: Excitation maximum = 355 nm, Emission maximum = 465 nm (5 mM HEPES, 10 mM NaCl, pH 7.0)

Preparation Note

This product is soluble in water (50 mg/ml), yielding a clear solution. The pH of a 2% solution is 1.9. It has been observed that this material will precipitate from phosphate buffer solutions.
Aqueous solutions are stable for 1 month if kept in the dark at 2-8 °C.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
079M4107V
13181137
029M4103V
088M4061V
13180314

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The transforming activity of Wnt effectors correlates with their ability to induce the accumulation of mammary progenitor cells.
Liu BY, et al.
Proceedings of the National Academy of Sciences of the USA, 101, 4158-4163 (2004)
F Belloc et al.
Cytometry, 17(1), 59-65 (1994-09-01)
A flow cytometric method to detect apoptotic cells is described. This method is based on the detection of differences in chromatin condensation with Hoechst 33342 as a probe and the detection of dead cells with propidium iodide as a probe
M G Ormerod et al.
Cytometry, 14(6), 595-602 (1993-01-01)
We have recently developed a method for the separation and quantification of viable apoptotic cells without the need for permeabilisation or fixation of the cells. The method is based on the observation that apoptotic rat thymocytes fluoresce more brightly than
M Gregoire et al.
Experimental cell research, 152(1), 38-46 (1984-05-01)
Chromatin distribution was visualized in living cells with the selective DNA fluorochrome Hoechst 33342. This dye was shown to be non-toxic on the rat kangaroo PTO cell line by measuring the labelled cell growth rate. The aim of this work
D J Arndt-Jovin et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 25(7), 585-589 (1977-07-01)
The methods for measuring the deoxyribonucleic acid content of individual mammalian cells and sorting them on the basis of this parameter have until now required fixation or other treatment which renders the cells nonviable. Using a class of bis-benzimidazole dyes
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