Bisbenzimide

Bisbenzimide
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
3D model (Jmol)	Interactive image
ChemSpider	1420
ECHA InfoCard	100.041.523
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
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.

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

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