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Merck

B2883

bisBenzimide H 33258

≥98% (HPLC and TLC)

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

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About This Item

Empirical Formula (Hill Notation):
C25H24N6O · 3HCl
CAS Number:
23491-45-4
Molecular Weight:
533.88
UNSPSC Code:
12171500
NACRES:
NA.47
PubChem Substance ID:
24891414
EC Number:
245-690-6
Beilstein/REAXYS Number:
4088183
MDL number:
MFCD00012679

Key Documents

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InChI key

OWRSPPSBNWJJAR-UHFFFAOYSA-N

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

SMILES string

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

assay

≥98% (HPLC and TLC)

form

powder

mp

280 °C

solubility

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

suitability

passes application test for fluorescence

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

Quality Level

200

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Related Categories

Application

bisBenzimide H 33258 has been used for nuclear staining in cells.
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.

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

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.

B2883-500MG-PW: + B2883-VAR: + B2883-500MG: + B2883-1G: + B2883-BULK: + B2883-100MG: + B2883-25MG-PW: + B2883-25MG: + B2883-1G-PW: + B2883-100MG-PW: + 2540002:

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Certificates of Analysis (COA)

Lot/Batch Number
0000486015
0000486015
0000401273
0000401276
0000401274

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Reactive oxygen species (ROS) induce nuclear factor erythroid 2-related factor 2 (Nrf2) activation as an adaptive defense mechanism, determining the synthesis of antioxidant molecules, including heme-oxygenase-1 (HO-1). HO-1 protects cells against oxidative injury, degrading free heme and inhibiting ROS production.
Florian Ehrlich et al.
Scientific reports, 9(1), 10924-10924 (2019-07-31)
Keratins are the main cytoskeletal proteins of epithelial cells and changes in the expression of keratins have contributed to the evolutionary adaptation of epithelia to different environments. Keratin K24 was proposed to be a differentiation marker of epidermal keratinocytes but
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We explored the clinical and pathological impact of epidermal growth factor receptor (EGFR) extracellular domain missense mutations. Retrospective assessment of 260 de novo glioblastoma patients revealed a significant reduction in overall survival of patients having tumors with EGFR mutations at
Cell alignment induced by anisotropic electrospun fibrous scaffolds alone has limited effect on cardiomyocyte maturation.
Han J, et al.
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