23491-52-3

Basic information

• Product Name: Hoechst 33342
• Synonyms: 2’-(4-ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-5’-bi-1h-benzimidazole;2’-(p-ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-5’-bibenzimidazole;ho342;2'-(4-ETHOXYPHENYL)-5-(4-METHYL-1-PIPERAZINYL)-2,5-BI(1H-BENZIMIDAZOLE);2'-(4-ETHOXYPHENYL)-5-(4-METHYL-1-PIPERAZINYL)-2',5'-BI-1H-BENZIMIDAZOLE 3HCL;2'-(4-ETHOXYPHENYL)-5-(4-METHYL-1-PIPERAZINYL)-2,5'-BI-1H-BENZIMIDAZOLE, 3HCL;2'-(4-ETHOXY-PHENYL)-5-(4-METHYL-1-PIPERAZINYL)-2',5'-BI-1H-BENZIMIDAZOLE TRIHYDROCHLORIDE;2'-(4-ETHOXYPHENYL)-5-(4-METHYL-1-PIPERAZINYL)-2,5'-BI-1H-BENZIMIDAZOLE TRIHYDROCHLORIDE
• CAS NO: 23491-52-3
• Molecular Formula: C₂₇H₂₈N₆O
• Molecular Weight: 615.98
• EINECS: 245-691-1
• Mol File: 23491-52-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 725.9±70.0 °C(Predicted)
• Appearance: /
• Density: 1.274±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble20mg/mL
• PKA: 10.97±0.10(Predicted)
• BRN: 1234011
• CAS DataBase Reference: Hoechst 33342(CAS DataBase Reference)
• NIST Chemistry Reference: Hoechst 33342(23491-52-3)
• EPA Substance Registry System: Hoechst 33342(23491-52-3)

Safety Data

• Hazard Codes: Xn,C
• Statements: 22-37/38-36/37/38-20/21/22-37-35
• Safety Statements: 22-36/37-24/25-36-26-45-36/37/39
• WGK Germany: 3
• RTECS: DT4200000
• F: 3-8-10
• Hazardous Substances Data: 23491-52-3(Hazardous Substances Data)

Usage

Chemical Description

Hoechst 33342 and calcein-AM are fluorescent dyes used in biological assays.

Description

Hoechst 33342 is a fluorescent dye that is particularly useful for staining DNA, chromosomes, and nuclei. It is a yellow powder with unique chemical properties that make it an A:T-specific DNA minor groove ligand. This characteristic allows it to bind specifically to adenine and thymine bases in the DNA, making it a valuable tool for various applications in cell biology and molecular biology research.

Uses

Used in Cell Biology Research:
Hoechst 33342 is used as a vital DNA stain for a variety of cell types, allowing researchers to visualize cellular DNA and study its distribution within the cell. Its fluorescence properties make it suitable for fluorescence microscopy and flow cytometry, enabling the analysis of DNA content in living cells.
Used in DNA Content Analysis:
Hoechst 33342 is used as a probe for membrane permeability in mammalian cells, which can help in sorting living cells based on their DNA content using fluorescence-activated cell sorting (FACS). This application is particularly useful in studying cell-cycle distribution and the initial stages of apoptosis.
Used in Visualization of Chromatin Distribution:
Hoechst 33342 is employed for visualizing chromatin distribution in living cells, providing insights into the organization and structure of the cell nucleus.
Used in Detection of BrdU Incorporation:
The dye is used to detect the incorporation of bromodeoxyuridine (BrdU) into cells, which is a common method for studying DNA synthesis and cell proliferation.
Used in Visualization of Fixed Cells:
Hoechst 33342 is also used for the visualization of fixed cells by microscopy, allowing researchers to study the morphology and structure of cells in various experimental conditions.
Used in Drug Displacement Studies:
The compound has been observed to displace several known DNA intercalators, such as Adriamycin, which disrupts the DNA dye uptake. This property makes Hoechst 33342 a valuable tool for studying the interactions between different compounds and DNA.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

Upstream product

• 10031-82-0 4-ethoxybenzaldehyde 
• 23491-49-8 2-amino-4-<5'-(4''-methylpiperazin-1''-yl)benzimidazol-2'-yl>aniline 
• 109-01-3 1-methyl-piperazine 
• 1635-61-6 5-chloro-2-nitroaniline 
• 123-08-0 4-hydroxy-benzaldehyde 
• 184033-32-7 4-cyano-2-nitrotrifluoroacetanilide 
• 23623-05-4 4-<5'-(4''-methylpiperazin-1''-yl)benzimidazol-2'-yl>-2-nitroaniline 
• 6393-40-4 4-Amino 3-nitro-benzonitrile 
• 54998-08-2 4-(4-methylpiperazino)-1,2-diaminobenzene 
• 23491-48-7 5-(4-methylpiperazine-1-yl)-2-nitroaniline 

Relevant articles and documents

[125I/127I]iodoHoechst 33342: synthesis, DNA binding, and biodistribution.

An iodinated analog of the DNA-minor-groove-binding agent Hoechst 33342 has been synthesized and evaluated for DNA binding and tumor targeting. The bis-benzimidazole ring system of the title compound was constructed from the piperazinyl terminus via a Pinner-type cyclization followed by oxidative cyclization of the diamine Schiff base. To synthesize radioiodoHoechst 33342, (trimethylstannyl)Hoechst 33342 was prepared by the same strategy and subjected to mild radioiododestannylation in the presence of lactoperoxidase. After purification by HPLC, the radiochemical was separated in carrier-free form with > 85% radiochemical yield and > 99% chemical and radiochemical purity. Fluorescence spectrometric analysis of the binding of iodoHoechst 33342 to calf thymus DNA gave an equilibrium association constant (Ka) of 2.57 x 10(7) M-1 comparable to the Ka value of Hoechst 33342. Fluorescence microscopy of viable V79 cells demonstrated that the iodinated dye stained the nuclei with avidity similar to that of the noniodinated dye. The biodistribution of [125I]-iodoHoechst 33342 in LS174T tumor-bearing athymic mice 4 h postadministration showed a tumor uptake of 3-4% injected dose per gram (ID/g), tumor/blood ratio of 6-8, and tumor/ nontumor ratios above unity for most organs. A low thyroid uptake (approximately 2% ID/g) indicated that the radiochemical did not deiodinate and was stable in vivo.