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14533

Sigma-Aldrich

bisBenzimide H 33342 trihydrochloride

for fluorescence, ≥97.0% (HPLC)

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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:
875756-97-1
Molecular Weight:
561.93 (anhydrous basis)
Beilstein:
1234011
EC Number:
245-691-1
MDL number:
MFCD00012678
UNSPSC Code:
12161505
PubChem Substance ID:
57647173
NACRES:
NA.25

grade

for fluorescence

Quality Level

200

Assay

≥97.0% (HPLC)

fluorescence

λex 340 nm; λem 510 nm
λex 355 nm; λem 465 nm in TE buffer; DNA

storage temp.

2-8°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 H 33342 trihydrochloride can be used to study biochemicals and reagents, fluorescent probes, labels, particles and stains, luminescent compounds and detection and wavelength index. bisBenzimide H 33342 trihydrochloride, Hoechst 33342, has been used in a study to investigate the effects of inorganic and organic arsenic compounds on human T-lymphoblastoid leukemia cells. Hoechst 33342 has also been used in a study to examine the effects of 9 calcium antagonists on ABCG2/BCRP-mediated resistance and transport in HeLa and SN-38-resistant HeLa (HeLa/SN100) cells, overexpressing ABCG2/BCRP.
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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Suitable for vital DNA staining of a variety of cell types; As a probe of membrane permeability in mammalian cells

related product

Product No.
Description
Pricing

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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.

  3. What is the solubility of Product 14533, bisBenzimide H 33342 trihydrochloride?

    It is soluble in water at 50 mg/mL.  It will precipitate from phosphate buffer solutions

  4. When Product 14533, bisBenzimide H 33342 trihydrochloride, is dissolved in water, what is the pH?

    The pH of a 2% solution in water is approximately 1.9.

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M J Lydon et al.
Journal of cellular physiology, 102(2), 175-181 (1980-02-01)
A procedure has been investigated for sorting viable cells according to their DNA content. Cells are stained with the U.V. activated fluorochromes 4'6-diamidino-2-phenylindole (DAPI), Hoechst 33258 or Hoechst 33342, and sorted with a Fluorescence Activated Cell Sorter. Hoechst 33342 is
W M Grogan et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 29(6), 738-746 (1981-06-01)
The dye Hoechst 33342 and a 2-parameter cell sorter have been used to measure DNA content in viable testis cells and to sort pachytene spermatocytes and round spermatids from adult mouse testis to virtually 100% homogeneity. Early diploid spermatogenic cells
Steven S Welc et al.
Nature communications, 10(1), 2788-2788 (2019-06-28)
Many potentially therapeutic molecules have been identified for treating Duchenne muscular dystrophy. However, targeting those molecules only to sites of active pathology is an obstacle to their clinical use. Because dystrophic muscles become extensively inflamed, we tested whether expressing a therapeutic
M E Lalande et al.
Proceedings of the National Academy of Sciences of the United States of America, 78(1), 363-367 (1981-01-01)
Flow cytometric analysis of the uptake of the DNA-specific and fluorescent probe Hoechst 33342 (HO342) offers a simple and rapid method for measuring membrane transport rates in mammalian cells and identifying cellular subpopulations that differ in their membrane transport rates.
Ganna Aleshcheva et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 29(6), 2303-2314 (2015-02-15)
Real and simulated microgravity induce a variety of changes in human cells. Most importantly, changes in the cytoskeleton have been noted, and studies on microtubules have shown that they are gravisensitive. This study focuses on the effects of short-term real
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