14530

bisBenzimide H 33258

for fluorescence, ≥98.0% (HPLC)

• Synonyme(s) : 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
• Formule empirique (notation de Hill): C₂₅H₂₄N₆O · 3HCl
• Numéro CAS: 23491-45-4
• Poids moléculaire : 533.88
• Beilstein: 4088183
• Numéro CE : 245-690-6
• Numéro MDL: MFCD00012679
• Code UNSPSC : 12171500
• ID de substance PubChem : 57647172
• Nomenclature NACRES : NA.32

Propriétés

• Qualité: for fluorescence
• Niveau de qualité: 200
• Essai: ≥98.0% (HPLC)
• Forme: powder
• Solubilité: water and ethanol: 10 mg/mL; H₂O: soluble; ethanol: soluble
• Fluorescence: λ_ex 338 nm; λ_em 505 nm (pH 7.0); λ_ex 355 nm; λ_em 465 nm in TE buffer; DNA
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: OWRSPPSBNWJJAR-UHFFFAOYSA-N

Description

Application

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 [1][2] with a high binding constant, making it a useful stain for DNA, chromosomes, and nuclei [3][4]. 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)[5]. Furthermore, the solution ionic strength and pH has been shown to be independent of the Stokes′ shift of bisBenzimide H 33258 [3]. The properties of this dye make it useful in several applications such as detecting mycoplasma contamination in tissue culture [6][7], indicating early onset of apoptosis[8][9], sorting living cells based on DNA content, and acting as a probe for DNA-Drug interactions[3]. 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.[10] 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) .[11] 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

bisBenzimide H 33258 is useful for staining DNA, chromosomes, and nuclei. May be used for fluorescence microscopy or flow cytometry.

Actions biochimiques/physiologiques

bisBenzimide H 33258 is a potent and selective Bcl-XL inhibitor.

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.

Autres remarques

Useful reagent for cytogenetic studies; for the fluorescent staining of DNA in cells[12]; simple two-step fluorimetric assay of DNA in isolated nuclei, cell extracts, or crude homogenates using Hoechst 33258[13]

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves