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23491-45-4 molecular structure
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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 and InChIs

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

Cite this record

CBID:130847 http://www.chembase.cn/molecule-130847.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
23491-45-4
EC Number
245-690-6
MDL Number
MFCD00012679
Beilstein Number
4088183
PubChem SID
24891565
24891414
24895727
24848715
162225125
PubChem CID
16211278

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 16211278 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.88762  H Acceptors
H Donor LogD (pH = 5.5) -1.6212612 
LogD (pH = 7.4) 2.4976797  Log P 3.318285 
Molar Refractivity 140.6014 cm3 Polarizability 50.867336 Å3
Polar Surface Area 75.49 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
ethanol: soluble expand Show data source
H2O: soluble expand Show data source
H2O: soluble10 mg/mL expand Show data source
phosphate buffer: precipitates expand Show data source
water and ethanol: soluble10 mg/mL expand Show data source
Apperance
powder expand Show data source
Fluorescence
λex 338 nm; λem 505 nm (pH 7.0) expand Show data source
λex 355 nm; λem 465 nm in TE buffer; DNA expand Show data source
RTECS
SM1140500 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/38 expand Show data source
Safety Statements
23-24/25 expand Show data source
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
≥98% (HPLC and TLC) expand Show data source
≥98.0% (HPLC) expand Show data source
Grade
for fluorescence expand Show data source
Suitability
passes application test for fluorescence expand Show data source
suitable for cell culture expand Show data source
Quality Level
GMP expand Show data source
Empirical Formula (Hill Notation)
C25H24N6O · 3HCl expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B1155 external link
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 external link
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 external link
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 external link
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 external link
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

REFERENCES

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