Bisbenzimide

Bisbenzimide

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Names
IUPAC name 2’-(4-Ethoxyphenyl)-6-(4-methyl-1-piperazinyl)-1H,3’H-2,5’-bibenzimidazole
Other names Hoechst 33342
Identifiers
CAS Number	23491-52-3
ChemSpider	1420
Jmol 3D model	Interactive image
PubChem	1464
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) Key: PRDFBSVERLRRMY-UHFFFAOYSA-N InChI=1/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) Key: PRDFBSVERLRRMY-UHFFFAOYAR
SMILES CCOc1ccc(cc1)c2[nH]c3cc(ccc3n2)c4[nH]c5cc(ccc5n4)N6CCN(CC6)C
Properties
Chemical formula	C27H28N6O
Molar mass	452.56 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bisbenzimide is an organic compound used as a fluorescent stain for DNA in molecular biology applications. Several bisbenzimides are used and are collectively called Hoechst stains.

File:Hoechst 33342 Stain - Platynereis dumerilii larvae.jpg

Nuclei of Platynereis dumerilii larvae stained with Hoechst 33342.

Application

Bisbenzimides tend to bind to A-T rich regions of DNA and can decrease its density. Bisbenzimide mixed with DNA samples can then be used to separate DNA according to their AT percentage using a cesium chloride (CsCl) gradient centrifugation.

References

• Sigma Aldrich Product Information Page
• Fluorescence Spectra: http://www.fluorophores.tugraz.at/substance/463