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

CAS: 23491-45-4 Cat. No.: H266330 Peso molecular: 533.90 Beilstein Registry Number: 4088183 Número EC: 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

Descripción general

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

Sinónimos

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

Especificaciones y pureza

≥99%(HPLC)

Condiciones de almacenamiento de almacenamiento

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

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥99%(HPLC)

Nombres e identificadores

• Pubchem Sid: 504753482
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504753482
• Sonrisas canónicas: 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
• Isómeros 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 Alemania: 3
• RTECS: SM1140500
• PubChem CID: 31953
• Peso molecular: 533.90
• Beilstein: 4088183

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

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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Objetivos asociados (no humanos)

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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Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Light & Heat sensitive
• Punto de fusión (°C): 314°C
• Peso molecular: 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

Referencias

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20. Yanghui Chen, Yuan Li, Junliang Luo, Zixin Li, Yu Huang, Jia Cai, Dongneng Jiang, Defeng Zhang, Jichang Jian, Jun Qiang, Bei Wang.  (2024)  A novel study of brain microvascular endothelial cells induced by astrocyte conditioned medium for constructing blood brain barrier model in vitro: A promising tool for meningitis of teleost.  FISH & SHELLFISH IMMUNOLOGY,      [PMID:38266792] [10.1016/j.fsi.2024.109401]

21. Ouyang Boshu, Shan Caihua, Shen Shun, Dai Xinnan, Chen Qingwang, Su Xiaomin, Cao Yongbin, Qin Xifeng, He Ying, Wang Siyu, Xu Ruizhe, Hu Ruining, Shi Leming, Lu Tun, Yang Wuli, Peng Shaojun, Zhang Jun, Wang Jianxin, Li Dongsheng, Pang Zhiqing.  (2024)  AI-powered omics-based drug pair discovery for pyroptosis therapy targeting triple-negative breast cancer.  Nature Communications,  15  (1): (1-20).  [PMID:39215014] [10.1038/s41467-024-51980-9]

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