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bisBenzimide H 33258_Molecular_structure_CAS_23491-45-4)
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bisBenzimide H 33258

Catalog No. 14530 Name Sigma Aldrich
CAS Number 23491-45-4 Website http://www.sigmaaldrich.com
M. F. C27H33Cl3N6O2 Telephone 1-800-521-8956
M. W. 579.94892 Fax
Purity ≥98.0% (HPLC) Email
Storage Chembase ID: 130847

SYNONYMS

Title
赫斯特荧光染料 33258
IUPAC name
4-{6-[6-(4-methylpiperazin-1-yl)-1,4-dihydroquinazolin-2-yl]-1,4-dihydroquinazolin-2-yl}phenol hydrate trihydrochloride
IUPAC Traditional name
4-{6-[6-(4-methylpiperazin-1-yl)-1,4-dihydroquinazolin-2-yl]-1,4-dihydroquinazolin-2-yl}phenol hydrate trihydrochloride
Synonyms
2′-(4-Hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5′-bi(1H-benzimidazole) trihydrochloride
Hoechst 33258
烟酸己可碱 三盐酸盐
2-[2-(4-Hydroxyphenyl)-6-benzimidazoyl]-6-(1-methyl-4-piperazyl)benzimidazole trihydrochloride
BBIH
HOE 33258
甲嗪双苯咪酚 三盐酸盐

DATABASE IDS

Beilstein Number 4088183
CAS Number 23491-45-4
EC Number 245-690-6
PubChem SID 24848715
MDL Number MFCD00012679

PROPERTIES

Empirical Formula (Hill Notation) C25H24N6O · 3HCl
Grade for fluorescence
Purity ≥98.0% (HPLC)
Fluorescence λex 338 nm; λem 505 nm (pH 7.0)
Fluorescence λex 355 nm; λem 465 nm in TE buffer; DNA
Solubility water and ethanol: soluble10 mg/mL
Solubility H2O: soluble
Solubility ethanol: soluble
GHS Pictograms GHS07
GHS Signal Word Warning
GHS Hazard statements H302-H315-H319
European Hazard Symbols Harmful Harmful (Xn)
MSDS Link Download
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
GHS Precautionary statements P305 + P351 + P338
Risk Statements 22-36/38
RTECS SM1140500
Safety Statements 26-36
Storage Temperature 2-8°C
German water hazard class 3

DETAILS

Description (English)
Biochem/physiol Actions
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 cells12; simple two-step fluorimetric assay of DNA in isolated nuclei, cell extracts, or crude homogenates using Hoechst 3325813
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 apoptosis8,9, sorting living cells based on DNA content, and acting as a probe for DNA-Drug interactions3. 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
Useful for staining DNA, chromosomes and nuclei. May be used for fluorescence microscopy or flow cytometry.Excitation max. = 346 nmEmission max. = 460 nm
Description (简体中文)
Biochem/physiol Actions
膜渗透性 DNA 荧光染色剂,具有低细胞毒性,可插入 DNA 的 A-T 区。
Other Notes
Useful reagent for cytogenetic studies; for the fluorescent staining of DNA in cells12; simple two-step fluorimetric assay of DNA in isolated nuclei, cell extracts, or crude homogenates using Hoechst 3325813
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 apoptosis8,9, sorting living cells based on DNA content, and acting as a probe for DNA-Drug interactions3. 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
用于 DNA、染色体及细胞核的染色。可用于荧光显微术或流式细胞术。 最大激发波长 = 346nm 最大发射波长 = 460nm

REFERENCES