4-{6-[6-(4-methylpiperazin-1-yl)-1,4-dihydroquinazolin-2-yl]-1,4-dihydroquinazolin-2-yl}phenol hydrate trihydrochloride

• ChemBase ID: 130847
• Molecular Formular: C27H33Cl3N6O2
• Molecular Mass: 579.94892
• Monoisotopic Mass: 578.17305737
• SMILES: CN1CCN(CC1)c1ccc2c(c1)CN=C(N2)c1ccc2c(c1)CN=C(N2)c1ccc(cc1)O.O.Cl.Cl.Cl
• Canonical SMILES: CN1CCN(CC1)c1ccc2c(c1)CN=C(N2)c1ccc2c(c1)CN=C(N2)c1ccc(cc1)O.O.Cl.Cl.Cl
• InChI: 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
• InChIKey: OWRSPPSBNWJJAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• 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; 2-[2-(4-Hydroxyphenyl)-6-benzimidazoyl]-6-(1-methyl-4-piperazyl)benzimidazole trihydrochloride; Bisbenzimide H 33258; Hoechst Stain solution; BBIH; HOE 33258; Hoechst 33258; bisBenzimide H 33258; 烟酸己可碱 三盐酸盐; 甲嗪双苯咪酚 三盐酸盐; 赫斯特荧光染料 33258

Database IDs

• CAS Number: 23491-45-4
• EC Number: 245-690-6
• MDL Number: MFCD00012679
• Beilstein Number: 4088183
• PubChem SID: 162225125; 24891565; 24895727; 24848715; 24891414
• PubChem CID: 16211278

CALCULATED PROPERTIES

• Acid pKa: 8.88762
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.6212612
• LogD (pH = 7.4): 2.4976797
• Log P: 3.318285
• Molar Refractivity: 140.6014 cm^3
• Polarizability: 50.867336 Å^3
• Polar Surface Area: 75.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; H2O: soluble; H2O: soluble10 mg/mL; phosphate buffer: precipitates; water and ethanol: soluble10 mg/mL
• Apperance: powder
• Fluorescence: λex 338 nm; λem 505 nm (pH 7.0); λex 355 nm; λem 465 nm in TE buffer; DNA

Safety Information

• RTECS: SM1140500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/38
• Safety Statements: 23-24/25; 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (HPLC and TLC); ≥98.0% (HPLC)
• Grade: for fluorescence
• Suitability: passes application test for fluorescence; suitable for cell culture
• Quality Level: GMP
• Empirical Formula (Hill Notation): C25H24N6O · 3HCl

DETAILS

Sigma Aldrich - B1155

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。
Application
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

Sigma Aldrich - 14530

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

Sigma Aldrich - H6024

Components
Contains 0.5μg/ml Hoechst bisbenzimide 33258 fluorochrome stain and thimerosal.
Application
A fluorescent DNA stain qualified for use in Mycoplama staining.

Sigma Aldrich - B2883

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。
Application
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

Sigma Aldrich - 33266

Biochem/physiol Actions
Membrane-permeable, fluorescent DNA stain with low cytotoxicity that intercalate in A-T regions of DNA.
Application
Useful for staining DNA, chromosomes and nuclei. May be used for fluorescence microscopy or flow cytometry.Excitation max. = 346 nmEmission max. = 460 nm