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Hoechst 33258 analog

Cat. No. M13787
Hoechst 33258 analog Structure
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Biological Activity

Hoechst 33258 analog are part of a family of blue fluorescent dyes used to stain DNA. IC50 Value: Target: These Bis-benzimides were originally developed by Hoechst AG, which numbered all their compounds so that the dye Hoechst 33342 is the 33342nd compound made by the company. There are three related Hoechst stains: Hoechst 33258, Hoechst 33342, and Hoechst 34580. The dyes Hoechst 33258 and Hoechst 33342 are the ones most commonly used and they have similarexcitation/emission spectra. Both dyes are excited by ultraviolet light at around 350 nm, and both emit blue/cyan fluorescent light around anemission maximum at 461 nm. Unbound dye has its maximum fluorescence emission in the 510-540 nm range. Hoechst dyes are soluble in water and in organic solvents such as dimethyl formamide or dimethyl sulfoxide. Concentrations can be achieved of up to 10 mg/mL. Aqueous solutions are stable at 2-6 °C for at least six months when protected from light. For long-term storage the solutions are instead frozen at ≤-20 °C. The dyes bind to the minor groove of double-stranded DNA with a preference for sequences rich in adenine andthymine. Although the dyes can bind to all nucleic acids, AT-rich double-stranded DNA strands enhance fluorescence considerably. Hoechst dyes are cell-permeable and can bind to DNA in live or fixed cells. Therefore, these stains are often called supravital, which means that cells survive a treatment with these compounds. Cells that express specific ATP-binding cassette transporter proteins can also actively transport these stains out of their cytoplasm.

Chemical Information
Molecular Weight 510.59
CAS Number 258843-62-8
Solubility (25°C) DMSO ≥ 51 mg/mL
Storage 2-8°C, protect from light
Conversion of different model animals based on BSA (PMID: 27057123)
Species Mouse Rat Rabbit Guinea pig Hamster Dog
Weight (kg) 0.02 0.15 1.8 0.4 0.08 10
Body Surface Area (m2) 0.007 0.025 0.15 0.05 0.02 0.5
Km factor 3 6 12 8 5 20
Animal A (mg/kg) = Animal B (mg/kg) multiplied by  Animal B Km
Animal A Km

For example, to modify the dose of Compound A used for a mouse (20 mg/kg) to a dose based on the BSA for a rat, multiply 20 mg/kg by the Km factor for a mouse and then divide by the Km factor for a rat. This calculation results in a rat equivalent dose for Compound A of 10 mg/kg.

References

[1] Smita Verma, et al. Med Chem. Recent Advances in Therapeutic Applications of Bisbenzimidazoles

[2] Wenlong Wang, et al. Minerva Med. Polyphenol epigallocatechin-3-gallate inhibits hypoxia/reoxygenation-induced H9C2 cell apoptosis

[3] P E Pjura, et al. J Mol Biol. Binding of Hoechst 33258 to the minor groove of B-DNA

[4] T Hrd, et al. Photochem Photobiol. A fluorescence study of the binding of Hoechst 33258 and DAPI to halogenated DNAs

[5] M P Singh, et al. Chem Res Toxicol. Synthesis and sequence-specific DNA binding of a topoisomerase inhibitory analog of Hoechst 33258 designed for altered base and sequence recognition

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