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Hoechst 33342 trihydrochloride (CAS 23491-52-3)

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Alternate Names:
Bisbenzimide
Application:
Hoechst 33342 trihydrochloride is an A:T-specific DNA minor groove ligand used for visualizing cellular DNA
CAS Number:
23491-52-3
Purity:
≥95%
Molecular Weight:
561.93
Molecular Formula:
C27H28N6O•3HCl
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Hoechst 33342 trihydrochloride is a fluorochrome widely used to visualize cellular DNA, providing valuable insights into its structure and function. This A:T-specific DNA minor groove ligand serves multiple purposes in research. It facilitates the identification and quantification of cellular components like proteins and lipids. Moreover, it finds utility in drug delivery applications, enabling targeted delivery to specific cells or tissues. Excitation of the dye occurs at approximately 350 nm, with an emission maximum around 461 nm. Compared to other Hoechst dyes, Hoechst-33342 possesses enhanced lipophilicity due to an additional ethyl group. It displaces several known DNA intercalators and can disrupt DNA dye uptake in conjunction with Adriamycin (sc-200923). This compound is utilized for various purposes, including sorting living cells based on DNA content using FACS, visualizing chromatin distribution in live cells, detecting BrdU incorporation, and examining fixed cells under microscopy. Additionally, it plays a role in studying early apoptosis stages and cell-cycle distribution. Notably, Hoechst-33342 exhibits diverse effects on different cell types. It induces cell differentiation, binds reversibly to Friend erythroleukemia cells, inhibits Topo I (topoisomerase I), induces apoptosis in HL-60 cells, regulates Ca2+ efflux, and influences cell differentiation in junctional sarcoplasmic reticulum cells. Hoechst 33342 trihydrochloride interacts with DNA through non-covalent binding, forming a fluorescent complex. The dye specifically binds to the minor groove of double-stranded DNA, causing fluorescence quenching upon binding. Although it can bind to both single- and double-stranded DNA, its affinity is higher for the latter. While Hoechst 33342 can also bind to RNA, its binding affinity for RNA is lower compared to DNA.


Hoechst 33342 trihydrochloride (CAS 23491-52-3) References

  1. Hoechst 33342-induced apoptosis is associated with decreased immunoreactive topoisomerase I and topoisomerase I-DNA complex formation.  |  Zhang, X. and Kiechle, F. 2001. Ann Clin Lab Sci. 31: 187-98. PMID: 11337909
  2. Binding characteristics of Hoechst 33258 with calf thymus DNA, poly[d(A-T)], and d(CCGGAATTCCGG): multiple stoichiometries and determination of tight binding with a wide spectrum of site affinities.  |  Loontiens, FG., et al. 1990. Biochemistry. 29: 9029-39. PMID: 1702995
  3. Specific staining of DNA with the fluorescent antibiotics, mithramycin, chromomycin, and olivomycin.  |  Crissman, HA. and Tobey, RA. 1990. Methods Cell Biol. 33: 97-103. PMID: 1707496
  4. Differentiation of EC cells in vitro by the fluorescent dye Hoechst 33342.  |  Steuer, B., et al. 1990. Exp Cell Res. 186: 149-57. PMID: 2298232
  5. A new method for rapid and sensitive detection of bromodeoxyuridine in DNA-replicating cells.  |  Crissman, HA. and Steinkamp, JA. 1987. Exp Cell Res. 173: 256-61. PMID: 2960553
  6. Vital DNA staining and cell sorting by flow microfluorometry.  |  Lydon, MJ., et al. 1980. J Cell Physiol. 102: 175-81. PMID: 6154714
  7. Visualization of chromatin distribution in living PTO cells by Hoechst 33342 fluorescent staining.  |  Gregoire, M., et al. 1984. Exp Cell Res. 152: 38-46. PMID: 6201374
  8. Hoechst 33342 dye uptake as a probe of membrane permeability changes in mammalian cells.  |  Lalande, ME., et al. 1981. Proc Natl Acad Sci U S A. 78: 363-7. PMID: 6941251
  9. Analysis and sorting of living cells according to deoxyribonucleic acid content.  |  Arndt-Jovin, DJ. and Jovin, TM. 1977. J Histochem Cytochem. 25: 585-9. PMID: 70450
  10. Transcriptional regulation of differentiation, selective toxicity and ATGCAAAT binding of bisbenzimidazole derivatives in human melanoma cells.  |  Wong, SS., et al. 1994. Biochem Pharmacol. 47: 827-37. PMID: 7510966
  11. A flow cytometric method using Hoechst 33342 and propidium iodide for simultaneous cell cycle analysis and apoptosis determination in unfixed cells.  |  Belloc, F., et al. 1994. Cytometry. 17: 59-65. PMID: 7528124
  12. Increased membrane permeability of apoptotic thymocytes: a flow cytometric study.  |  Ormerod, MG., et al. 1993. Cytometry. 14: 595-602. PMID: 8404365
  13. Spectral studies on 33258 Hoechst and related bisbenzimidazole dyes useful for fluorescent detection of deoxyribonucleic acid synthesis.  |  Latt, SA. and Stetten, G. 1976. J Histochem Cytochem. 24: 24-33. PMID: 943439

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Hoechst 33342 trihydrochloride, 100 mg

sc-200908
100 mg
$139.00