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B2261

Sigma-Aldrich

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)
Beilstein:
1234011
MDL number:
MFCD00012678
UNSPSC Code:
12171500
PubChem Substance ID:
24891639
NACRES:
NA.47

product name

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

Quality Level

300

Assay

≥98% (HPLC and TLC)

form

powder

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

SMILES string

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

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

InChI key

FYEVKHPLBHLWHK-UHFFFAOYSA-N

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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.

Physical properties

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.

related product

Product No.
Description
Pricing

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  5. What is a typical concentration of Product B2261, bisBenzimide H 33342 trihydrochloride, for staining DNA in cells?

    200 micrograms per mL.

  6. Can solvents other than water be used to dissolve Product B2261, bisBenzimide H 33342 trihydrochloride?

    Hoechst 33342 can be dissolved in N,N-dimethylformamide (DMF).

  7. Which Hoechst dye is suitable for chromosomal analysis?

    Hoechst 33258 (Product No. B2883) is the preferred Hoechst dye for chromosomal analysis. Hoechst 33342 (Product No. B2261) is a poor fluorochrome for chromosomal analysis.

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
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
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)
P E Mozdziak et al.
Cytometry, 41(2), 89-95 (2000-09-26)
5-Bromo-2'-deoxyuridine (BrdU) is a powerful compound to study the mitotic activity of a cell. Most techniques that identify BrdU-labeled cells require conditions that kill the cells. However, the fluorescence intensity of the membrane-permeable Hoechst dyes is reduced by the incorporation
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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