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Hoechst 34580

Blue fluorescent dyes CAS# 23555-00-2

Hoechst 34580

Catalog No. BCC1632----Order now to get a substantial discount!

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Chemical structure

Hoechst 34580

3D structure

Chemical Properties of Hoechst 34580

Cas No. 23555-00-2 SDF Download SDF
PubChem ID 448202 Appearance Powder
Formula C27H29N7 M.Wt 451.57
Type of Compound N/A Storage Desiccate at -20°C
Synonyms HOE 34580
Solubility DMSO : ≥ 47 mg/mL (104.08 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name N,N-dimethyl-4-[6-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazol-2-yl]aniline
SMILES CN1CCN(CC1)C2=CC3=C(C=C2)N=C(N3)C4=CC5=C(C=C4)N=C(N5)C6=CC=C(C=C6)N(C)C
Standard InChIKey VMCOQLKKSNQANE-UHFFFAOYSA-N
Standard InChI InChI=1S/C27H29N7/c1-32(2)20-7-4-18(5-8-20)26-28-22-10-6-19(16-24(22)30-26)27-29-23-11-9-21(17-25(23)31-27)34-14-12-33(3)13-15-34/h4-11,16-17H,12-15H2,1-3H3,(H,28,30)(H,29,31)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Hoechst 34580

DescriptionHoechst 34580 is a cell-permeable fluorescent dye for staining DNA and nuclei.In Vitro:Hoechst 34580 prefers to locate near hydrophobic regions with binding affinity with the inhibition constant IC50 of 0.86±0.05 μM for Hoechst 34580. Hoechst 34580 is a good candidate for treating the Alzheimer’s disease by inhibiting Aβ formation. 50 μM Aβ42 solutions co-incubated with 100, 25, 12.5, 3.125, 0.78, and 0.1, 0.01 μM Hoechst 34580 at 37 °C for 70 h. Hoechst 34580 can inhibit the aggregation of Aβ42 in a dose-dependent manner. And the half-maximal concentration (IC50) is examined. The IC50 is obtained by measuring the concentration of Hoechst 34580 while maintaining the Aβ42 concentration which gave 0.86±0.05 μM for Hoechst 34580[1].

References:
[1]. Thai NQ, et al. Discovery of DNA dyes Hoechst 34580 and 33342 as good candidates for inhibiting amyloid beta formation: in silico and in vitro study. J Comput Aided Mol Des. 2016 Aug;30(8):639-50.

Hoechst 34580 Dilution Calculator

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Hoechst 34580 Molarity Calculator

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Preparing Stock Solutions of Hoechst 34580

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2145 mL 11.0725 mL 22.145 mL 44.2899 mL 55.3624 mL
5 mM 0.4429 mL 2.2145 mL 4.429 mL 8.858 mL 11.0725 mL
10 mM 0.2214 mL 1.1072 mL 2.2145 mL 4.429 mL 5.5362 mL
50 mM 0.0443 mL 0.2214 mL 0.4429 mL 0.8858 mL 1.1072 mL
100 mM 0.0221 mL 0.1107 mL 0.2214 mL 0.4429 mL 0.5536 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Hoechst 34580

Description: IC50 Value: N/A Hoechst stains are part of a family of blue fluorescent dyes used to stain DNA. 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. in vitro: N/A in vivo: N/A Clinical trial: N/A

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References on Hoechst 34580

Host-guest interaction of Hoechst 34580 and Cucurbit[7]uril.[Pubmed:21919182]

Chemphyschem. 2011 Nov 18;12(16):2933-40.

To track nuclear dynamic processes by fluorescence imaging, nuclear stains should be highly fluorescent, resistant to photobleaching, and inert to nuclear processes. The nuclear stains of the Hoechst family, such as Hoechst 34580, show bright fluorescence only on groove binding to DNA, and therefore may interfere with visualization of nuclear dynamic processes induced by other stimuli. We study host-guest interactions between Hoechst 34580 and Cucurbit[7]uril (CB7) in aqueous solutions. The formation of CB7-Hoechst 34580 inclusion complexes with stoichiometry of 2:1 in water and 1:1 in phosphate-buffered saline (PBS) solution (pH 7.0) is confirmed by (1)H NMR, absorption spectra, fluorescence spectra, MALDI-TOF MS, and molecular modeling. Compared to Hoechst 34580, the inclusion complex exhibits redshifted absorption, intensified fluorescence, improved photostability, weakened DNA binding affinity, comparable ability to penetrate cell nuclei, and better nuclear-staining capability, and thus a new avenue for the application of cucurbituril in fluorescence imaging is opened.

Discovery of DNA dyes Hoechst 34580 and 33342 as good candidates for inhibiting amyloid beta formation: in silico and in vitro study.[Pubmed:27511370]

J Comput Aided Mol Des. 2016 Aug;30(8):639-50.

Combining Lipinski's rule with the docking and steered molecular dynamics simulations and using the PubChem data base of about 1.4 million compounds, we have obtained DNA dyes Hoechst 34580 and Hoechst 33342 as top-leads for the Alzheimer's disease. The binding properties of these ligands to amyloid beta (Abeta) fibril were thoroughly studied by in silico and in vitro experiments. Hoechst 34580 and Hoechst 33342 prefer to locate near hydrophobic regions with binding affinity mainly governed by the van der Waals interaction. By the Thioflavin T assay, it was found that the inhibition constant IC50 approximately 0.86 and 0.68 muM for Hoechst 34580 and Hoechst 33342, respectively. This result qualitatively agrees with the binding free energy estimated using the molecular mechanic-Poisson Boltzmann surface area method and all-atom simulations with the AMBER-f99SB-ILDN force field and water model TIP3P. In addition, DNA dyes have the high capability to cross the blood brain barrier. Thus, both in silico and in vitro experiments have shown that Hoechst 34580 and 33342 are good candidates for treating the Alzheimer's disease by inhibiting Abeta formation.

Description

Hoechst 34580 is a cell-permeable fluorescent dye for staining DNA and nuclei.

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