B2883

bisBenzimide H 33258

≥98% (HPLC and TLC)

Synonym(s):
2′-(4-Hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5′-bi(1H-benzimidazole) trihydrochloride, BXI-72, BBIH, 2-[2-(4-Hydroxyphenyl)-6-benzimidazoyl]-6-(1-methyl-4-piperazyl)benzimidazole trihydrochloride, Hoechst 33258, HOE 33258, NSC334072
Empirical Formula (Hill Notation):
C25H24N6O · 3HCl
CAS Number:
Molecular Weight:
533.88
Beilstein/REAXYS Number:
4088183
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47
Pricing and availability is not currently available.

Quality Level

assay

≥98% (HPLC and TLC)

form

powder

application(s)

hematology: suitable
histology: suitable

mp

280 °C

solubility

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

suitability

passes application test for fluorescence

Featured Industry

Diagnostic Assay Manufacturing

storage temp.

−20°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

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Application

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 has been used for nuclear staining in cells.

Packaging

25 mg in poly bottle
1 g in glass bottle
100, 500 mg in glass bottle

Biochem/physiol Actions

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Spontaneous and continuous cyclooxygenase-2-dependent prostaglandin E2 production by stromal cells in the murine small intestine lamina propria: directing the tone of the intestinal immune response.
Newberry RD, et al.
Journal of Immunology, 166, 4465-4472 (2001)
Susanna Fiorelli et al.
Cells, 8(4) (2019-04-19)
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...
Claudine Kieda et al.
Journal of molecular medicine (Berlin, Germany), 91(7), 883-899 (2013-03-09)
Tumor hypoxia is a characteristic of cancer cell growth and invasion, promoting angiogenesis, which facilitates metastasis. Oxygen delivery remains impaired because tumor vessels are anarchic and leaky, contributing to tumor cell dissemination. Counteracting hypoxia by normalizing tumor vessels in order...
Cell alignment induced by anisotropic electrospun fibrous scaffolds alone has limited effect on cardiomyocyte maturation.
Han J, et al.
Stem Cell Research, 16, 740-750 (2016)

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