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Chemical Compound Review

CHEBI:52293     4-methylbenzenesulfonate; 1-methyl-4-[(Z)...

Synonyms: AC1O5PIK, FT-0687512, ST51006864, 17237_FLUKA, 390062_SIAL, ...
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Disease relevance of thiazole orange


High impact information on thiazole orange


Biological context of thiazole orange

  • After biotinylation, the percentage of biotin-negative, thiazole-orange-positive platelets increased gradually from 0.72% at 30 minutes to 5.44% at 24 hours [9].
  • The thiazole orange dyes provide the most sensitive detection with limiting sensitivities of 2-4 amol of DNA base pairs per band, and detection of the 603-bp fragment was successful, injecting from phi X174/HaeIII samples containing only 1-2 fg of this fragment per microliter [10].
  • The thiazole orange is able to intercalate and fluoresce when the conjugate binds, at concentrations where little fluorescence is observed from either the conjugate alone or the conjugate mixed with DNA lacking the zinc finger target sequence [11].
  • This study investigates the effect of Epo therapy on platelet reactivity, peripheral platelet counts and thiazole orange-positive (TO+) platelets in extremely low birth weight (ELBW) infants [12].
  • Thiazole orange is also shown to oxidize the 5'-G of remote GG sequences, depending on the details of the intervening DNA sequence [11].

Anatomical context of thiazole orange


Associations of thiazole orange with other chemical compounds

  • Fluorescence of the cyanine dye Thiazole Orange (TO) is quenched by intramolecular twisting in the excited state [18].
  • The 96-well format assay (512 hairpins) can be conducted at a minimal cost (presently ca. $100 for hairpin deoxyoligonucleotides/assay with ethiduim bromide or less with thiazole orange), with a rapid readout using a fluorescent plate reader (15 min), and is adaptable to automation (Tecan Genesis Workstation 100 robotic system) [19].
  • Cells were stained with the fluorescent dyes Thiazole Orange for RNA and Hoechst 33342 for DNA and analyzed by flow cytometry and fluorescence microscopy [20].
  • Reticulocyte counting by flow cytometry with thiazole orange was compared to manual or automated counting of new methylene blue stained blood smears [15].
  • The phifl value (0.17) of thiazole orange, 1-(N,N'-trimethylaminopropyl)-4-[3-methyl-2,3-dihydro-(benzo-1,3-thiazole)-2-methylidene]-quinolinium iodide (TO-Pro 1) in the presence of the oligonucleotide duplex (TO-Pro 1: dA15.d5'[CACT15CAC3'] (1:1)) is much less than that for some of the hybrids of the conjugates [21].

Gene context of thiazole orange

  • First, two subsequent amplification reactions utilizing exo- Klenow polymerase were performed under direct observation using the fluorescent dye thiazole orange [22].
  • During EPO-treatment, the percentage of thiazole orange-positive (TO+) platelets increased significantly to 17.2 +/- 1.6% (mean +/- 1 SE; n = 3) on day 5 compared to a pre-treatment level of 8.5 +/- 0.9% (p = 0.029) [23].
  • Two-color multiplex fluorescence detection of HLA-H genotypes was accomplished by prelabeling the standard pBR322 MspI DNA ladder with a red emitting bis-intercalation dye (butyl TOTIN) and on-column labeling of the HLA-H DNA with thiazole orange [24].
  • A single zinc finger derived from the DNA-binding domain of the glucocorticoid receptor (GR) has been tethered to the intercalating fluorophore thiazole orange, and the DNA recognition characteristics of the conjugate have been examined [11].
  • On the contrary, when the thiazole orange is tethered to the oligo-alpha-thymidylate or oligo-beta-thymidylate, no significant stabilization of the duplexes formed with poly r(A) can be observed [25].

Analytical, diagnostic and therapeutic context of thiazole orange


  1. Thiazole orange-positive platelets in a dog with idiopathic thrombocytopenic purpura. Hanahachi, A., Kano, R., Watari, T., Hasegawa, A. Vet. Rec. (2002) [Pubmed]
  2. Utility of flow cytometric reticulocyte quantification as a predictor of engraftment in autologous bone marrow transplantation. Davis, B.H., Bigelow, N., Ball, E.D., Mills, L., Cornwell, G.G. Am. J. Hematol. (1989) [Pubmed]
  3. Platelet kinetics. Dale, G.L. Curr. Opin. Hematol. (1997) [Pubmed]
  4. The "stomatin" gene and protein in overhydrated hereditary stomatocytosis. Fricke, B., Argent, A.C., Chetty, M.C., Pizzey, A.R., Turner, E.J., Ho, M.M., Iolascon, A., von Düring, M., Stewart, G.W. Blood (2003) [Pubmed]
  5. Surface expression and functional characterization of alpha-granule factor V in human platelets: effects of ionophore A23187, thrombin, collagen, and convulxin. Alberio, L., Safa, O., Clemetson, K.J., Esmon, C.T., Dale, G.L. Blood (2000) [Pubmed]
  6. Relative reactivity of platelets from thrombopoietin- and interleukin-6-treated dogs. Peng, J., Friese, P., Wolf, R.F., Harrison, P., Downs, T., Lok, S., Dale, G.L., Burstein, S.A. Blood (1996) [Pubmed]
  7. Immunophenotypic analysis of reticulocytes in paroxysmal nocturnal hemoglobinuria. Ware, R.E., Rosse, W.F., Hall, S.E. Blood (1995) [Pubmed]
  8. Markedly high population of affected reticulocytes negative for decay-accelerating factor and CD59 in paroxysmal nocturnal hemoglobinuria. Iwamoto, N., Kawaguchi, T., Nagakura, S., Hidaka, M., Horikawa, K., Kagimoto, T., Takatsuki, K., Nakakuma, H. Blood (1995) [Pubmed]
  9. Demonstration that thiazole-orange-positive platelets in the dog are less than 24 hours old. Dale, G.L., Friese, P., Hynes, L.A., Burstein, S.A. Blood (1995) [Pubmed]
  10. High-sensitivity capillary electrophoresis of double-stranded DNA fragments using monomeric and dimeric fluorescent intercalating dyes. Zhu, H., Clark, S.M., Benson, S.C., Rye, H.S., Glazer, A.N., Mathies, R.A. Anal. Chem. (1994) [Pubmed]
  11. Fluorescent and photochemical properties of a single zinc finger conjugated to a fluorescent DNA-binding probe. Thompson, M., Woodbury, N.W. Biochemistry (2000) [Pubmed]
  12. Changes in thrombopoiesis and platelet reactivity in extremely low birth weight infants undergoing erythropoietin therapy for treatment of anaemia of prematurity. Haiden, N., Cardona, F., Schwindt, J., Berger, A., Kuhle, S., Homoncik, M., Jilma-Stohlawetz, P., Pollak, A., Jilma, B. Thromb. Haemost. (2005) [Pubmed]
  13. Flow cytometric analysis of thiazole orange uptake by platelets: a diagnostic aid in the evaluation of thrombocytopenic disorders. Kienast, J., Schmitz, G. Blood (1990) [Pubmed]
  14. Thiazole orange, a DNA-binding photosensitizer with flexible structure, can inactivate pathogens in red blood cell suspensions while maintaining red cell storage properties. Skripchenko, A., Wagner, S.J., Thompson-Montgomery, D., Awatefe, H. Transfusion (2006) [Pubmed]
  15. Reticulocyte quantification by flow cytometry, image analysis, and manual counting. Schimenti, K.J., Lacerna, K., Wamble, A., Maston, L., Iaffaldano, C., Straight, M., Rabinovitch, A., Lazarus, H.M., Jacobberger, J.W. Cytometry. (1992) [Pubmed]
  16. Laser scanning confocal microscopy and factor analysis of biomedical image sequences (FAMIS) to detect and characterise HPV DNA sequences by FISH in HeLa cells. Kahn, E., Lizard, G., Frouin, F., Roignot, P., Chardonnet, Y., Di Paola, R. Cytometry. (1997) [Pubmed]
  17. A flow cytometric technique using thiazole orange to detect platelet engraftment following pediatric stem-cell transplants. Figuerres, E., Olszewski, M., Kletzel, M. Cytotherapy. (2001) [Pubmed]
  18. Large dynamic Stokes shift of DNA intercalation dye Thiazole Orange has contribution from a high-frequency mode. Karunakaran, V., Pérez Lustres, J.L., Zhao, L., Ernsting, N.P., Seitz, O. J. Am. Chem. Soc. (2006) [Pubmed]
  19. A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity. Boger, D.L., Fink, B.E., Brunette, S.R., Tse, W.C., Hedrick, M.P. J. Am. Chem. Soc. (2001) [Pubmed]
  20. Human cytogenetic biomonitoring using flow-cytometric analysis of micronuclei in transferrin-positive immature peripheral blood reticulocytes. Abramsson-Zetterberg, L., Zetterberg, G., Bergqvist, M., Grawé, J. Environ. Mol. Mutagen. (2000) [Pubmed]
  21. Fluorescent properties of oligonucleotide-conjugated thiazole orange probes. Privat, E., Melvin, T., Mérola, F., Schweizer, G., Prodhomme, S., Asseline, U., Vigny, P. Photochem. Photobiol. (2002) [Pubmed]
  22. Modelling viral evolution in vitro using exo- Klenow polymerase: continuous selection of strand displacement amplified DNA that binds an oligodeoxynucleotide to form a triple-helix. Walter, N.G. J. Mol. Biol. (1995) [Pubmed]
  23. Erythropoietin potentiates thrombus development in a canine arterio-venous shunt model. Wolf, R.F., Gilmore, L.S., Friese, P., Downs, T., Burstein, S.A., Dale, G.L. Thromb. Haemost. (1997) [Pubmed]
  24. High-speed DNA genotyping using microfabricated capillary array electrophoresis chips. Woolley, A.T., Sensabaugh, G.F., Mathies, R.A. Anal. Chem. (1997) [Pubmed]
  25. Synthesis and binding properties of oligo-2'-deoxyribonucleotides covalently linked to a thiazole orange derivative. Privat, E., Asseline, U. Bioconjug. Chem. (2001) [Pubmed]
  26. Preconcentration and separation of double-stranded DNA fragments by electrophoresis in plastic microfluidic devices. Wainright, A., Nguyen, U.T., Bjornson, T., Boone, T.D. Electrophoresis (2003) [Pubmed]
  27. Relationship between size and thiazole orange fluorescence of platelets in patients undergoing high-dose chemotherapy. Balduini, C.L., Noris, P., Spedini, P., Belletti, S., Zambelli, A., Da Prada, G.A. Br. J. Haematol. (1999) [Pubmed]
  28. Analysis of double-stranded DNA by capillary electrophoresis with laser-induced fluorescence detection using the monomeric dye SYBR green I. Skeidsvoll, J., Ueland, P.M. Anal. Biochem. (1995) [Pubmed]
  29. Synthesis and fluorescence studies of thiazole orange tethered onto oligonucleotide: development of a self-contained DNA biosensor on a fiber optic surface. Wang, X., Krull, U.J. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
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