Hoechst 33258 - CAS 23491-45-4
Molecular Formula:
C25H24N6O·3HCl
Molecular Weight:
533.9
COA:
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Application\Fluorophore:
DNA Stains
Description:
Hoechst 33258 is a cell-permeable, benzimidazole DNA dye with preference for adenine and thymine-rich sequences. It emits blue fluorescence (excitation 352 nm/emission maximum 461 nm) when bound to DNA in either live or fixed cells.
Purity:
≥95%
Appearance:
Yellow Solid
Synonyms:
Pibenzimol Hydrochloride; HOE 33258; 4-[6-(4-methyl-1-piperazinyl)[2,6'-bi-1H-benzimidazol]-2'-yl]-phenol trihydrochloride
Solubility:
Soluble to 20 mM in DMSO and to 100 mM in water.
Storage:
Store at -20°C
MSDS:
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Excitation:
352 nm
Emission:
461 nm
InChIKey:
SMNPLAKEGAEPJD-UHFFFAOYSA-N
InChI:
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
Canonical SMILES:
CN1CCN(CC1)C2=CC3=C(C=C2)N=C(N3)C4=CC5=C(C=C4)NC(=C6C=CC(=O)C=C6)N5.Cl.Cl.Cl
1.Recognition of RNA duplex by a neomycin-Hoechst 33258 conjugate.
Willis B1, Arya DP2. Bioorg Med Chem. 2014 Apr 1;22(7):2327-32. doi: 10.1016/j.bmc.2014.02.003. Epub 2014 Feb 18.
DNA minor groove binding drugs such as Hoechst 33258 have been shown to bind to a number of RNA structures. Similarly, RNA binding ligands such as neomycin have been shown by us to bind to a number of A-form DNA structures. A neomycin-Hoechst 33258 conjugate was recently shown to bind B-DNA, where Hoechst exhibits high affinity for the minor groove of A/T tract DNA and neomycin docks into the major groove. Further studies now indicate that the Hoechst moiety of the conjugate can be driven to bind RNA duplex as a consequence of neomycin binding in the RNA major groove. This is the first example of Hoechst 33258 binding to RNA duplex not containing bulges or loop motifs.
2.Minor-groove binding drugs: where is the second Hoechst 33258 molecule?
Fornander LH1, Wu L, Billeter M, Lincoln P, Nordén B. J Phys Chem B. 2013 May 16;117(19):5820-30. doi: 10.1021/jp400418w. Epub 2013 May 6.
Hoechst 33258 binds with high affinity into the minor groove of AT-rich sequences of double-helical DNA. Despite extensive studies of this and analogous DNA binding molecules, there still remains uncertainty concerning the interactions when multiple ligand molecules are accommodated within close distance. Albeit not of direct concern for most biomedical applications, which are at low drug concentrations, interaction studies for higher drug binding are important as they can give fundamental insight into binding mechanisms and specificity, including drug self-stacking interactions that can provide base-sequence specificity. Using circular dichroism (CD), isothermal titration calorimetry (ITC), and proton nuclear magnetic resonance ((1)H NMR), we examine the binding of Hoechst 33258 to three oligonucleotide duplexes containing AT regions of different lengths: [d(CGCGAATTCGCG)]2 (A2T2), [d(CGCAAATTTGCG)]2 (A3T3), and [d(CGAAAATTTTCG)]2 (A4T4).
3.Fluorine-modified bisbenzimide derivative as a molecular probe for bimodal and simultaneous detection of DNAs by (19)F NMR and fluorescence.
Sakamoto T1, Hasegawa D, Fujimoto K. Chem Commun (Camb). 2015 May 25;51(42):8749-52. doi: 10.1039/c5cc01995h.
3,5-Bis(trifluoromethyl)benzene modified bisbenzimide H 33258 was synthesized as a (19)F magnetic resonance-based DNA detection probe. The chemical shift and fluorescence of the probe were significantly changed by the addition of hairpin DNAs having an AATT sequence. The probe enables (19)F NMR/fluorescence bimodal detection of the model DNA double strands simultaneously.
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