14530

bisBenzimide H 33258

suitable for fluorescence, ≥98.0% (HPLC)

• Synonym(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
• Empirical Formula (Hill Notation): C₂₅H₂₄N₆O · 3HCl
• CAS Number: 23491-45-4
• Molecular Weight: 533.88
• UNSPSC Code: 12171500
• NACRES: NA.32
• PubChem Substance ID: 57647172
• EC Number: 245-690-6
• Beilstein/REAXYS Number: 4088183
• MDL number: MFCD00012679
• Assay: ≥98.0% (HPLC)
• Form: powder
• Quality level: 200

Properties

• Quality Level: 200
• assay: ≥98.0% (HPLC)
• form: powder
• solubility: 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
• suitability: suitable for fluorescence
• storage temp.: 2-8°C
• SMILES string: 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
• InChI key: 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.

Biochem/physiol Actions

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.

Other Notes

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]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves