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Key Documents

14530

Sigma-Aldrich

bisBenzimide H 33258

for fluorescence, ≥98.0% (HPLC)

Sinonimo/i:

2′-(4-Hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5′-bi(1H-benzimidazole) trihydrochloride, 2-[2-(4-Hydroxyphenyl)-6-benzimidazoyl]-6-(1-methyl-4-piperazyl)benzimidazole trihydrochloride, BBIH, BXI-72, HOE 33258, Hoechst 33258, NSC334072

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About This Item

Formula empirica (notazione di Hill):
C25H24N6O · 3HCl
Numero CAS:
Peso molecolare:
533.88
Beilstein:
4088183
Numero CE:
Numero MDL:
Codice UNSPSC:
12171500
ID PubChem:
NACRES:
NA.32

Grado

for fluorescence

Livello qualitativo

Saggio

≥98.0% (HPLC)

Forma fisica

powder

Solubilità

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

Fluorescenza

λex 338 nm; λem 505 nm (pH 7.0)
λex 355 nm; λem 465 nm in TE buffer; DNA

Temperatura di conservazione

2-8°C

Stringa SMILE

Cl[H].Cl[H].Cl[H].[H]O[H].CN1CCN(CC1)c2ccc3NC(=NCc3c2)c4ccc5NC(=NCc5c4)c6ccc(O)cc6

InChI

1S/C27H28N6O.3ClH.H2O/c1-32-10-12-33(13-11-32)22-5-9-25-21(15-22)17-29-27(31-25)19-4-8-24-20(14-19)16-28-26(30-24)18-2-6-23(34)7-3-18;;;;/h2-9,14-15,34H,10-13,16-17H2,1H3,(H,28,30)(H,29,31);3*1H;1H2
OWRSPPSBNWJJAR-UHFFFAOYSA-N

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Applicazioni

A bibenzimidazole dye that has been utilized as a fluorescent stain. It is membrane-permeable and selectively binds to adenine-thymine regions in the minor groove of B-form DNA with a high binding constant, making it a useful stain for DNA, chromosomes, and nuclei . It has been shown that the fluorescence is relatively insensitive to the presence of various solution reagents (i.e., BSA, RNA, Tris, sucrose, TEA/EDTA, Triton X-100, and SDS). Furthermore, the solution ionic strength and pH has been shown to be independent of the Stokes′ shift of bisBenzimide H 33258 . The properties of this dye make it useful in several applications such as detecting mycoplasma contamination in tissue culture , indicating early onset of apoptosis, sorting living cells based on DNA content, and acting as a probe for DNA-Drug interactions. Utilized in the design and development of a fluorimetric assay to quantitate cell numbers in microtiter plates. The methodology of the assay is based on Hoechst 33258 binding to DNA and is sensitive for a thousand cells. One application of this is assay is the normalization of ELISA data. The illumination of Hoechst 33253 coupled with Merocyanine 540 can be utilized as an effective method to eradicate bacterial infections (i.e., A. laidlawii contaminated corneal endothelial cell cultures) . BisBenzimide H 33258 is commonly used in many established staining protocols (David M. Terrian, Cancer Cell Signaling – Methods and Protocols,
Springer, Volume 218 ).
bisBenzimide H 33258 is useful for staining DNA, chromosomes and nuclei. bisBenzimide H 33258 may be used for fluorescence microscopy or flow cytometry.
Excitation max. = 346 nm
Emission max. = 460 nm

Azioni biochim/fisiol

bisBenzimide H 33258 is a potent and selective Bcl-XL inhibitor. bisBenzimide H 33258 is a membrane-permeable, fluorescent DNA stain with low cytotoxicity that intercalate in A-T regions of DNA.

Altre note

Useful reagent for cytogenetic studies; for the fluorescent staining of DNA in cells; simple two-step fluorimetric assay of DNA in isolated nuclei, cell extracts, or crude homogenates using Hoechst 33258

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


Certificati d'analisi (COA)

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Y J Kim et al.
Analytical biochemistry, 174(1), 168-176 (1988-10-01)
A simple two-step fluorometric assay of DNA in cartilage explants, utilizing the bisbenzimidazole dye Hoechst 33258, is described. Cartilage explants were prepared for assay by digestion with papain. Aliquots of the digest were mixed with dye solution, and the fluorescence
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)
K H Elstein et al.
Experimental cell research, 211(2), 322-331 (1994-04-01)
We compared cellular flow cytometric methods employing carboxyfluorescein (CF), Höechst 33342, and Höechst 33258 with a nuclear method in their ability to discriminate apoptotic subpopulations in rat thymocyte cultures exposed to dexamethasone or tributyltin. In the nuclear technique, apoptotic cells
E Papadimitriou et al.
Journal of immunological methods, 162(1), 41-45 (1993-06-04)
A sensitive fluorimetric assay based on DNA binding of the fluorescent dye Hoechst 33258 was developed to quantitate cell numbers in microtiter plates. The cells were fixed and incubated with the dye solution. The bound dye was extracted with ethanol
Fluorometric properties of the bibenzimidazole derivative Hoechst 33258, a fluorescent probe specific for AT concentration in chromosomal DNA.
B Weisblum et al.
Chromosoma, 46(3), 255-260 (1974-01-01)

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