Hoechst 33342 - CAS 23491-52-3
Molecular Formula:
C27H28N6O.3HCl
Molecular Weight:
561.93
COA:
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Application\Fluorophore:
DNA Stains
Description:
Hoechst 33258, also called Pibenzimol, an iodinated DNA-binding bibenzimidazole, is a cell dye for DNA quantitation which sensitizes DNA and cells to UVA.
Purity:
≥98% by HPLC
Appearance:
Yellow to yellow-green crystalline solid
Synonyms:
2'-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole trihydrochloride
Solubility:
Soluble to 20 mM in DMSO and to 100 mM in water.
Storage:
Store at -20°C
MSDS:
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Shelf Life:
2 years
Boiling Point:
725.9±70.0 °C
Density:
1.274±0.06 g/cm3
InChIKey:
JABNPSKWVNCGMX-UHFFFAOYSA-N
InChI:
InChI=1S/C27H28N6O/c1-3-34-21-8-4-18(5-9-21)26-28-22-10-6-19(16-24(22)30-26)27-29-23-11-7-20(17-25(23)31-27)33-14-12-32(2)13-15-33/h4-11,16-17H,3,12-15H2,1-2H3,(H,28,30)(H,29,31)
Canonical SMILES:
CCOC1=CC=C(C=C1)C2=NC3=C(N2)C=C(C=C3)C4=NC5=C(N4)C=C(C=C5)N6CCN(CC6)C
1.Cellular alteration after dilution of cryoprotective solutions used for the vitrification of in vitro-produced bovine embryos.
Kaidi S;Van Langendonckt A;Massip A;Dessy F;Donnay I Theriogenology. 1999 Aug;52(3):515-25.
Embryo quality of in vitro-produced bovine blastocysts was assessed at several steps of a vitrification procedure in which glycerol and ethylene glycol were used as cryoprotectants (3-step equilibration with cryoprotectants followed by vitrification, dilution of the cryoprotectants in 0.85 M galactose then in embryo transfer freezing medium [ETF], and finally co-culture for periods). To visualize cell membrane alterations, double staining was performed using a cell permeant fluorochrome (bisbenzimide--BIS) and a nonpermeant one (propidium iodide--PI). In Experiment 1, the effect of the vitrification procedure on the hatching rate and total cell number was assessed 72 h after treatment. Hatching rate and the number of stained nuclei were decreased in comparison with untreated embryos when blastocysts were exposed to the whole procedure with or without vitrification (respectively 42 and 53% vs 76% for hatching and 128 +/- 17 and 141 +/- 17 vs 226 +/- 13 for stained nuclei). In Experiment 2, the effect of cryoprotectants and their dilution was evaluated on membrane permeability and total cell numbers at various steps of the vitrification procedure. Blastocysts exposed only to cryoprotectant solutions and stained immediately after dilution in galactose showed no modification.
2.Establishment of a high content assay for the identification and characterisation of bioactivities in crude bacterial extracts that interfere with the eukaryotic cell cycle.
Jensen NA;Gerth K;Grotjohann T;Kapp D;Keck M;Niehaus K J Biotechnol. 2009 Mar 10;140(1-2):124-34. doi: 10.1016/j.jbiotec.2008.12.002. Epub 2008 Dec 9.
High content microscopy as a screening tool to identify bioactive agents has provided researchers with the ability to characterise biological activities at the level of single cells. Here, we describe the development and the application of a high content screening assay for the identification and characterisation of cytostatic bioactivities from Myxobacteria extracts. In an automated microscopy assay Sf9 insect cells were visualised utilising the stains bisbenzimide Hoechst 33342, calcein AM, and propidium iodide. Imaging data were processed by the ScanR Analysis-software to determine the ploidy and vitality of each cell and to quantify cell populations. More than 98% of the Sf9 cells were viable and the culture consisted of diploid ( approximately 30%), tetraploid ( approximately 60%), polyploidic (<10%) and apoptotic (<5%) cells. Treatment with the reference substances blasticidin, colchicine, paclitaxel, and cytochalasin D induced changes in ploidy and vitality, which were characteristic for the respective bioactive substance. Furthermore, crude extracts from the chivosazole producing Myxobacterium Sorangium cellulosum So ce56 induced an increase of polyploid cells and a decrease in total cell count, while a mutant producing nearly no chivosazole triggered none of these effects.
3.Migration of foreign lymphocytes from the mouse vagina into the cervicovaginal mucosa and to the iliac lymph nodes.
Ibata B;Parr EL;King NJ;Parr MB Biol Reprod. 1997 Feb;56(2):537-43.
The mode of heterosexual transmission of human immunodeficiency virus (HIV) is not yet understood. The semen of HIV-infected men contains free virus and infected cells, and it is not known which of these is more important for sexual transmission of the virus to women. Some investigators have presented in vitro studies supporting a cellular mode of transmission of HIV and have suggested that infected lymphoid cells may act as the primary source of infection. This has become known as the "Trojan Horse" hypothesis. In vivo demonstrations of such events are lacking and are not likely to be forthcoming using human subjects. To investigate the ability of normal lymphoid cells to invade the cervicovaginal mucosa in an experimental animal, we stained C3H/He (H-2Kk) mouse peritoneal lymphoid cells with bisbenzimide, a vital fluorescent DNA-binding dye, and inoculated the cells atraumatically into the vaginas of progestin-treated, BALB/c (H-2Kd) recipient mice. Donor cells were identified in recipient tissues by their bisbenzimide-fluorescent nuclei and by fluorescein staining of the membrane antigen, H-2Kk. Donor lymphoid cells were observed in histological sections of recipient cervicovaginal mucosa and also in the iliac lymph nodes of 34 of 36 recipient mice 24 h after inoculation into the vagina.
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Chemical Structure

CAS 23491-52-3 Hoechst 33342

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