Synonym
Bisbenzimide; Bisbenzimidazole; NSC 322921; NSC322921; NSC-322921; Hoe-33258; Hoe 33258; Hoe33258; Hoechst 33258; Hoechst33258; Hoechst-33258
IUPAC/Chemical Name
4-(5-(4-methylpiperazin-1-yl)-1H,1'H-[2,5'-bibenzo[d]imidazol]-2'-yl)phenol
InChi Key
INAAIJLSXJJHOZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H24N6O/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)
SMILES Code
CN1CCN(CC1)C2=CC3=C(NC(=N3)C4=CC5=C(NC(=N5)C6=CC=C(O)C=C6)C=C4)C=C2
Appearance
To be determined
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
424.51
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Sakamoto T, Hasegawa D, Fujimoto K. Fluorine-modified bisbenzimide derivative as a molecular probe for bimodal and simultaneous detection of DNAs by (19)F NMR and fluorescence. Chem Commun (Camb). 2015 May 25;51(42):8749-52. doi: 10.1039/c5cc01995h. PubMed PMID: 25873342.
2: Sakamoto T, Hasegawa D, Fujimoto K. Simultaneous detection of single-nucleotide polymorphisms in a DNA bulge structure using a fluorine-modified bisbenzimide derivative. Analyst. 2016 Feb 21;141(4):1214-7. doi: 10.1039/c5an02389k. PubMed PMID: 26661831.
3: Kittimongkolsuk P, Tencomnao T, Santiyanont R. Semi-quantitative detection of gene expression using bisbenzimide dye. Genet Mol Res. 2011 Nov 22;10(4):3747-59. doi: 10.4238/2011.November.22.8. PubMed PMID: 22179998.
4: Tran-Nguyen LT, Schneider B. Cesium chloride-bisbenzimide gradients for separation of phytoplasma and plant DNA. Methods Mol Biol. 2013;938:381-93. doi: 10.1007/978-1-62703-089-2_32. PubMed PMID: 22987432.
5: Ikeda M, Nakagawa H, Suzuki T, Miyata N. Novel bisbenzimide-nitroxides for nuclear redox imaging in living cells. Bioorg Med Chem Lett. 2012 Mar 1;22(5):1949-52. doi: 10.1016/j.bmcl.2012.01.042. PubMed PMID: 22306124.
6: Landex NL, Kayser L. Optimization of an Acridine Orange-bisbenzimide procedure for the detection of apoptosis-associated fluorescence colour changes in etoposide-treated cell cultures. J Mol Histol. 2004 Feb;35(2):133-9. PubMed PMID: 15328917.
7: Iwashita Y, Crang AJ, Blakemore WF. Redistribution of bisbenzimide Hoechst 33342 from transplanted cells to host cells. Neuroreport. 2000 Apr 7;11(5):1013-6. PubMed PMID: 10790874.
8: Demkin VV, Edelstein MV, Zimin AL, Edelstein IA, Suvorov MM. Detection of sequence variation in PCR-amplified fragments of omp2 gene from three species of the family Chlamydiaceae using agarose gel electrophoresis containing bisbenzimide-PEG. FEMS Microbiol Lett. 2000 Mar 15;184(2):215-8. PubMed PMID: 10713423.
9: Müller M, Kruse L, Tabrett AM, Barbara DJ. Detection of a single base exchange in PCR-amplified DNA fragments using agarose gel electrophoresis containing bisbenzimide-PEG. Nucleic Acids Res. 1997 Dec 15;25(24):5125-6. PubMed PMID: 9396825; PubMed Central PMCID: PMC147133.
10: Laube U, Kiderlen AF. Detection of parasites with DNA-binding bisbenzimide H33258 in Pneumocystis carinii- and Leishmania-containing materials. Parasitol Res. 1998 Jul;84(7):559-64. PubMed PMID: 9694372.
11: Laube U, Kiderlen AF. Detection of Pneumocystis carinii with DNA-binding bisBenzimide 33258 Hoechst. J Eukaryot Microbiol. 1997 Nov-Dec;44(6):35S. PubMed PMID: 9508423.
12: Schnell SA, Wessendorf MW. Bisbenzimide: a fluorescent counterstain for tissue autoradiography. Histochem Cell Biol. 1995 Feb;103(2):111-4. PubMed PMID: 7543364.
13: Karlovsky P, de Cock AW. Buoyant density of DNA-Hoechst 33258 (bisbenzimide) complexes in CsCl gradients: Hoechst 33258 binds to single AT base pairs. Anal Biochem. 1991 Apr;194(1):192-7. PubMed PMID: 1714251.
14: Young SD, Hill RP. Radiation sensitivity of tumour cells stained in vitro or in vivo with the bisbenzimide fluorochrome Hoechst 33342. Br J Cancer. 1989 Nov;60(5):715-21. PubMed PMID: 2478182; PubMed Central PMCID: PMC2247311.
15: Bergström I, Heinänen A, Salonen K. Comparison of acridine orange, acriflavine, and bisbenzimide stains for enumeration of bacteria in clear and humic waters. Appl Environ Microbiol. 1986 Mar;51(3):664-7. PubMed PMID: 16347028; PubMed Central PMCID: PMC238937.
16: Andersen O, Rønne M. Effects of ethidium bromide and bisbenzimide (Hoechst 33258) on human lymphocyte chromosome structure. Hereditas. 1986;105(2):269-72. PubMed PMID: 2434451.
17: Bean B, Fogle TA, Gates RD. Rapid staining for the sperm penetration assay using a bisbenzimide dye. Fertil Steril. 1991 Jan;55(1):214-6. PubMed PMID: 1702740.
18: Jin R, Breslauer KJ. Characterization of the minor groove environment in a drug-DNA complex: bisbenzimide bound to the poly[d(AT)].poly[d(AT)]duplex. Proc Natl Acad Sci U S A. 1988 Dec;85(23):8939-42. PubMed PMID: 2461559; PubMed Central PMCID: PMC282622.
19: Hernández LF, Palmer JH. Fluorescent staining of primary plant cell walls using bisbenzimide (33258 Hoechst) fluorochrome. Stain Technol. 1988 May;63(3):190-2. PubMed PMID: 2459818.
20: Portugal J, Waring MJ. Assignment of DNA binding sites for 4',6-diamidine-2-phenylindole and bisbenzimide (Hoechst 33258). A comparative footprinting study. Biochim Biophys Acta. 1988 Feb 28;949(2):158-68. PubMed PMID: 2449244.
