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B2261

Sigma-Aldrich

bisBenzimide H 33342 trihydrochloride

≥98% (HPLC and TLC)

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Synonym(s):
2′-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5′-bi-1H-benzimidazole trihydrochloride, HOE 33342, Hoechst 33342, bisBenzimide
Empirical Formula (Hill Notation):
C27H28N6O · 3HCl · xH2O
CAS Number:
Molecular Weight:
561.93 (anhydrous basis)
Beilstein:
1234011
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Quality Level

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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1 of 4

This Item
14533B288314530
bisBenzimide H 33258 ≥98% (HPLC and TLC)

B2883

bisBenzimide H 33258

bisBenzimide H 33258 for fluorescence, ≥98.0% (HPLC)

14530

bisBenzimide H 33258

color

yellow

color

-

color

-

color

-

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

-

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

-

form

powder

form

-

form

powder

form

powder

solubility

H2O: 20 mg/mL, phosphate buffer: precipitates

solubility

-

solubility

H2O: 10 mg/mL, water and ethanol: 10 mg/mL, phosphate buffer: precipitates

solubility

water and ethanol: 10 mg/mL, H2O: soluble, ethanol: soluble

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

200

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

B2261-500MG:4.548173947624E12
B2261-100MG:4.548173947594E12
B2261-25MG:4.548173947617E12
B2261-1G:4.5481739476E12


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Basic helix-loop-helix transcriptional factor MyoR regulates BMP-7 in acute kidney injury.
Kamiura N, et al.
American Journal of Physiology: Renal Physiology, 304, F1159-F1166 (2013)
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
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
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
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)

Articles

Cell cycle regulates vital processes like DNA repair, cancer prevention. Four stages: G1, S, G2, M. NTPs don't permeate membranes.

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