Hoechst 33258 UltraPure - ≥99%(HPLC) , CAS No.23491-45-4

CAS: 23491-45-4 Cat. No.: H266330 Molecular Weight: 533.90 Beilstein Registry Number: 4088183 EC Number: 245-690-6 PubChem CID: 31953

GRADE & PURITY ≥99%(HPLC)

Synonyms

HOE 33258 | HOECHST 33258 | BBIH | BXI-72 | NSC334072 | 2′-(4-Hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5′-bi(1H-benzimidazole) | 2-[2-(4-Hydroxyphenyl)-6-benzimidazoyl]-6-(1-methyl-4-piperazyl)benzimidazole

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Hoechst 33258 is a nuclear staining reagent that can penetrate cell membranes and stain DNA. It releases strong blue fluorescence after intercalating double-stranded DNA. Hoechst 33258 is often used for cell apoptosis detection. After staining, observe with a fluorescence microscope or detect with a flow cytometer. The excitation and emission wavelengths of Hoechst 33258-DNA are 352 nm and 461 nm, respectively.

Instructions

1. For fixed cells or tissues

1) For cell or tissue samples, after fixation, wash them appropriately to remove fixative. Then, if immunofluorescence staining is required, perform immunofluorescence staining first, and then follow the subsequent steps for Hoechst 33258 staining after the staining is completed. If no other staining is required, the subsequent Hoechst 33258 staining is directly performed.

2) For adherent cells or tissue sections, add a small amount of Hoechst 33258 staining solution to cover the sample. For suspended cells, add at least 3 times the volume of the sample to be stained with staining solution and mix well. Leave at room temperature for 3-5 minutes.

3) Aspirate the Hoechst 33258 staining solution, wash 2-3 times with TBST, PBS or saline, 3-5 minutes each time.

4) Observe directly under a fluorescence microscope or after mounting the slide. When observing cell apoptosis, the nucleus of apoptotic cells will be densely stained, or fragmented and densely stained.

2. For living cells or tissues

5) Add an appropriate amount of Hoechst 33258 staining solution, which must fully cover the sample to be stained. Usually, 1ml staining solution is needed for one well of a six-well plate, and 100 microliters of staining solution is required for one well of a 96-well plate.

6) Incubate for 20-30 minutes at a temperature suitable for cell culture. Discard the staining solution, wash 2-3 times with PBS or culture solution to perform fluorescence detection.

Storage conditions: Store at -20°C and protected from light, valid for one year.

Precautions

1) Hoechst 33258 is irritating to the human body, please pay attention to proper protection.

2) Fluorescent dyes have the problem of quenching. It is recommended to complete the test on the same day after dyeing.

3) To slow down fluorescence quenching, anti-fluorescence quenching mounting solution can be used.

4) For your safety and health, please wear lab coats and disposable gloves for operation.

Specifications

Synonyms

HOE 33258 | HOECHST 33258 | BBIH | BXI-72 | NSC334072 | 2′-(4-Hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2, 5′-bi(1H-benzimidazole) | 2-[2-(4-Hydroxyphenyl)-6-benzimidazoyl]-6-(1-methyl-4-piperazyl)benzimidazole

Specifications & Purity

≥99%(HPLC)

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%(HPLC)

Names and Identifiers

• Pubchem Sid: 504753482
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504753482
• Canonical Smiles: CN1CCN(CC1)C2=CC3=C(C=C2)N=C(N3)C4=CC5=C(C=C4)N=C(N5)C6=CC=C(C=C6)O.Cl.Cl.Cl
• IUPAC Name: 4-[6-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazol-2-yl]phenol;trihydrochloride
• InChIKey: SMNPLAKEGAEPJD-UHFFFAOYSA-N
• INCHI: 1S/C25H24N6O.3ClH/c1-30-10-12-31(13-11-30)18-5-9-21-23(15-18)29-25(27-21)17-4-8-20-22(14-17)28-24(26-20)16-2-6-19(32)7-3-16;;;/h2-9,14-15,32H,10-13H2,1H3,(H,26,28)(H,27,29);3*1H
• Isomeric SMILES: CN1CCN(CC1)C2=CC3=C(C=C2)N=C(N3)C4=CC5=C(C=C4)N=C(N5)C6=CC=C(C=C6)O.Cl.Cl.Cl
• WGK Germany: 3
• RTECS: SM1140500
• PubChem CID: 31953
• Molecular Weight: 533.90
• Beilstein: 4088183

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzimidazoles
      • Subclass Phenylbenzimidazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzimidazoles
• Subclass: Phenylbenzimidazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylbenzimidazoles
• Alternative Parents: N-arylpiperazines Phenylimidazoles Dialkylarylamines N-methylpiperazines 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Heteroaromatic compounds Trialkylamines Azacyclic compounds Organooxygen compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylbenzimidazole - N-arylpiperazine - 2-phenylimidazole - Dialkylarylamine - Tertiary aliphatic/aromatic amine - 1-hydroxy-2-unsubstituted benzenoid - Phenol - N-alkylpiperazine - N-methylpiperazine - Monocyclic benzene moiety - 1,4-diazinane - Benzenoid - Piperazine - Azole - Heteroaromatic compound - Imidazole - Tertiary aliphatic amine - Tertiary amine - Azacycle - Hydrochloride - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylbenzimidazoles. These are compounds containing a phenylbenzimidazole skeleton, which consists of a benzimidazole moiety where its imidazole ring is attached to a phenyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TOP1 Tclin DNA topoisomerase I (7553 Activities)

Discover Target: TOP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

Discover Target: TOP2A

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DU-145 (51482 Activities)

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MCF7 (126967 Activities)

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A549 (127892 Activities)

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KG-1 (867 Activities)

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HeLa (62764 Activities)

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Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Shigella flexneri (1836 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Acinetobacter baumannii (41033 Activities)

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Citrobacter freundii (1864 Activities)

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Escherichia coli (133304 Activities)

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Enterococcus faecium (13803 Activities)

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Enterococcus faecalis (29875 Activities)

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Calf thymus DNA (4845 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light & Heat sensitive
• Melt Point(°C): 314°C
• Molecular Weight: 533.900 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 532.131 Da
• Monoisotopic Mass: 532.131 Da
• Topological Polar Surface Area: 84.100 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 634.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 4

XLogP3

References

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