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Chemical Compound Review

Thionine     (7-aminophenothiazin-3- ylidene)azanium...

Synonyms: Cyanine, Katalysin, Thionin, GNF-Pf-3564, Thionine (VAN), ...
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Disease relevance of Thionine

  • No transcripts for pathogenesis-related PR-1, PR-5, or the pathogen-inducible plant defensin Pdf1.2 could be detected in uninoculated transgenic seedlings, indicating that all of the observed effects of the overexpressing lines are most likely the result of the toxicity of the THI2.1 thionin [1].
  • Graded iodination of Pyrularia thionin leads to a related loss of activity for hemolysis, phospholipase A2 activation, cytotoxicity, and lethality in mice [2].
  • The relationship of membrane potential to motility and chemotaxis of Bacillus subtilis has been tested by using the fluorescence of a cyanine dye as a probe of the potential [3].
  • This uses cytokeratin to define pixels as breast cancer (tumor mask) within the tissue array spot and then measures intensity of marker expression using a cyanine 5-conjugated antibody within the mask [4].
  • Here we have studied the protein from Azotobacter vinelandii and Klebsiella pneumoniae with Mössbauer and EPR spectroscopies, with the following results: when the MoFe protein is oxidized by addition of stoichiometric amounts (6-8 equivalents) of dissolved thionin, the well characterized P-cluster state Pox results [5].

Psychiatry related information on Thionine


High impact information on Thionine

  • We have now used the findings that the cell membrane is more highly polarized in resting than in proliferating cells and that cyanine dyes carrying a delocalized positive charge enter live cells to an extent that depends on the cell membrane potential, to develop a method of distinguishing between cycling and non-cycling cells [8].
  • A cyanine dye distinguishes between cycling and non-cycling fibroblasts [8].
  • Inhibition of cell division and growth by a redox series of cyanine dyes [9].
  • Following exposure to formyl-methionyl-leucyl-phenylalanine (FMLP), PMN from adult donors (11) showed a marked change in membrane potential (31%) as determined by fluorescence emission using the cyanine dye, 3-3-dipentyloxacarbocyanine [DiOC5(3)] [10].
  • Membrane potential measurements using the cyanine dye, Di(S)-C3-5 verified a striking hyperpolarization of IMCD cells using this protocol [11].

Chemical compound and disease context of Thionine


Biological context of Thionine


Anatomical context of Thionine

  • A similar pattern was observed when C2FCa2 cells were stained with DiOC6(3), a cyanine dye that labels endoplasmic reticulum and mitochondria (M. Terasaki, J. Song, J. R. Wong, M. J. Weiss, and L. B. Chen, Cell 38:101-108, 1984) [22].
  • Fluorescently (cyanine 5) labeled cDNA probes, made individually from mRNA samples of nine pancreatic cell lines, were each combined with fluorescently (cyanine 3) labeled universal reference mRNA [23].
  • Fluorescently (cyanine 5) labeled normal pancreas mRNA was also compared with the same universal reference mRNA reference pool [23].
  • From measurements of the interfacial tension between oil and aqueous phases, and of water permeability across liposomal membranes, Pi was concluded to relax the phospholipid bilayer structure, resulting in great reduction in the concentration of the cyanine dye necessary for induction of the leakage-type pathway [17].
  • The basic analysis has been performed in three brains, serially sectioned and stained with thionin, myelin stain, acetylcholinesterase and parvalbumin, to determine cytoarchitectonic boundaries [24].

Associations of Thionine with other chemical compounds

  • We evaluated 10 rhodamine and cyanine dyes as carcinoma-specific mitochondrial photosensitizers in vitro [25].
  • Cellular responses to Pyrularia thionin are mediated by Ca2+ influx and phospholipase A2 activation and are inhibited by thionin tyrosine iodination [2].
  • This question can be tested by binding proflavin and thionin to haptoglobin because these dyes are known to interact specifically with serine proteases at the peptide binding site [26].
  • This suggests that binding of the J-aggregates onto the template CMA is sterically controlled by the asymmetric environment of glucose residues (of CMA) so that more twisting power is exerted with increasing DS (of CMA), rendering the cyanine dye/CMA complex a more rigid (a high fluorescence intensity) super-helix [27].
  • The PVN of 5 PWS patients (2 males and 3 females), varying in age between 22-64 yr, and 27 controls (14 males and 13 females) without any primary neurological or psychiatric diseases was morphometrically investigated after conventional staining with thionine and immunocytochemical staining for OXT and vasopressin (AVP) [28].

Gene context of Thionine

  • On alternating days, the bFGF and FGFR-1 antisense-targeted tumors received injections of cyanine fluorochrome-conjugated antibodies to a human melanoma and mouse blood vessel marker [29].
  • Pituitaries from 7 suicide victims and 11 cardiac deaths were sectioned into 10-microns slides, stained with thionin and processed for in situ hybridization using a riboprobe complementary to human POMC mRNA [30].
  • The PLA2 inhibitor aristolochic acid (10 microM) blocked IL-1 beta-induced IL-6 release and the release of IL-6 caused by Pyrularia pubera thionin (5 micrograms/ml), a stimulator of PLA2 activity [31].
  • Interestingly, the ratio of p75(NTR) expressing neurons to the total number of neurons as staining with thionin was significantly higher in the CA1 and CA2 subfields of AD hippocampus than in controls [32].
  • A cyanine dye, dis-C3- (5) was used to determine the effects of IFN on the membrane potential in cancer cells [33].

Analytical, diagnostic and therapeutic context of Thionine

  • We delineated this endocytic pathway in transfected cells by confocal microscopy using cyanine 3-SP and NK1-R antibodies [34].
  • Anaerobic oxidative titration of reduced FdIII with thionin indicated that each FdIII monomer exchanges two electrons [35].
  • Double-label immunofluorescence with the laser scanning confocal microscope using cyanine dyes [36].
  • We have undertaken the structural dissection of a highly knotted, cysteine-rich plant thionin, with the aim of defining a minimal, synthetically accessible, structure that preserves the bioactive properties of the parent peptide [37].
  • A mechanism involving steric interactions between the polymerase, cyanine-labeled sites on template and extending chains and the modified dUTP substrate is proposed to explain the inverse correlation between the labeling efficiency and the yield of DNA probe synthesis by PCR [38].


  1. Overexpression of an endogenous thionin enhances resistance of Arabidopsis against Fusarium oxysporum. Epple, P., Apel, K., Bohlmann, H. Plant Cell (1997) [Pubmed]
  2. Cellular responses to Pyrularia thionin are mediated by Ca2+ influx and phospholipase A2 activation and are inhibited by thionin tyrosine iodination. Evans, J., Wang, Y.D., Shaw, K.P., Vernon, L.P. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  3. Sensory electrophysiology of bacteria: relationship of the membrane potential to motility and chemotaxis in Bacillus subtilis. Miller, J.B., Koshland, D.E. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  4. Using a xenograft model of human breast cancer metastasis to find genes associated with clinically aggressive disease. Kluger, H.M., Chelouche Lev, D., Kluger, Y., McCarthy, M.M., Kiriakova, G., Camp, R.L., Rimm, D.L., Price, J.E. Cancer Res. (2005) [Pubmed]
  5. Mössbauer studies of solid thionin-oxidized MoFe protein of nitrogenase. Lindahl, P.A., Papaefthymiou, V., Orme-Johnson, W.H., Münck, E. J. Biol. Chem. (1988) [Pubmed]
  6. Subfield- and layer-specific changes in parvalbumin, calretinin and calbindin-D28K immunoreactivity in the entorhinal cortex in Alzheimer's disease. Mikkonen, M., Alafuzoff, I., Tapiola, T., Soininen, H., Miettinen, R. Neuroscience (1999) [Pubmed]
  7. Band broadening caused by the multiple labeling of proteins in micellar electrokinetic chromatography with diode laser-induced fluorescence detection. Jing, P., Kaneta, T., Imasaka, T. Journal of chromatography. A. (2002) [Pubmed]
  8. A cyanine dye distinguishes between cycling and non-cycling fibroblasts. Cohen, R.L., Muirhead, K.A., Gill, J.E., Waggoner, A.S., Horan, P.K. Nature (1981) [Pubmed]
  9. Inhibition of cell division and growth by a redox series of cyanine dyes. Zigman, S., Gilman, P. Science (1980) [Pubmed]
  10. Defective membrane potential changes in neutrophils from human neonates. Sacchi, F., Hill, H.R. J. Exp. Med. (1984) [Pubmed]
  11. Atrial natriuretic peptides inhibit conductive sodium uptake by rabbit inner medullary collecting duct cells. Zeidel, M.L., Kikeri, D., Silva, P., Burrowes, M., Brenner, B.M. J. Clin. Invest. (1988) [Pubmed]
  12. Identification of dye-sensitive strains of Brucella melitensis. Corbel, M.J. J. Clin. Microbiol. (1991) [Pubmed]
  13. Electricity generation in microbial fuel cells using neutral red as an electronophore. Park, D.H., Zeikus, J.G. Appl. Environ. Microbiol. (2000) [Pubmed]
  14. Protective effect of organic cation transport inhibitors on cis-diamminedichloroplatinum-induced nephrotoxicity. Bird, J.E., Walser, M.M., Quebbemann, A.J. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  15. Cyanine dye as monitor of membrane potentials in Escherichia coli cells and membrane vesicles. Letellier, L., Shechter, E. Eur. J. Biochem. (1979) [Pubmed]
  16. Platonin, a cyanine photosensitizing dye, causes attenuation of circulatory shock, hypercoagulable state, and tissue ischemia during heat stroke. Lee, J.J., Lin, M.T., Wang, N.L., Lin, C.L., Chang, C.K. Shock (2005) [Pubmed]
  17. Formation of a leakage-type ion pathway in lipid bilayer membranes by divalent cationic cyanine dyes in cooperation with inorganic phosphate. Role of the cyanine dye in uncoupling of oxidative phosphorylation. Takeguchi, N., Saitoh, T., Morii, M., Yoshikawa, K., Terada, H. J. Biol. Chem. (1985) [Pubmed]
  18. Optical probe responses on sarcoplasmic reticulum. Oxacarbocyanines. Russell, J.T., Beeler, T., Martonosi, A. J. Biol. Chem. (1979) [Pubmed]
  19. Direct observation of endocytosis of gastrin releasing peptide and its receptor. Grady, E.F., Slice, L.W., Brant, W.O., Walsh, J.H., Payan, D.G., Bunnett, N.W. J. Biol. Chem. (1995) [Pubmed]
  20. Interaction of certain cationic dyes with the respiratory chain of rat liver mitochondria. Conover, T.E., Schneider, R.F. J. Biol. Chem. (1981) [Pubmed]
  21. Amplified quenching of a conjugated polyelectrolyte by cyanine dyes. Tan, C., Atas, E., Müller, J.G., Pinto, M.R., Kleiman, V.D., Schanze, K.S. J. Am. Chem. Soc. (2004) [Pubmed]
  22. Expression of avian Ca2+-ATPase in cultured mouse myogenic cells. Karin, N.J., Kaprielian, Z., Fambrough, D.M. Mol. Cell. Biol. (1989) [Pubmed]
  23. Identification of differentially expressed genes in pancreatic cancer cells using cDNA microarray. Han, H., Bearss, D.J., Browne, L.W., Calaluce, R., Nagle, R.B., Von Hoff, D.D. Cancer Res. (2002) [Pubmed]
  24. The parahippocampal gyrus in the baboon: anatomical, cytoarchitectonic and magnetic resonance imaging (MRI) studies. Blaizot, X., Martinez-Marcos, A., Arroyo-Jimenez Md, M.d.e.l. .M., Marcos, P., Artacho-Pérula, E., Muñoz, M., Chavoix, C., Insausti, R. Cereb. Cortex (2004) [Pubmed]
  25. Intramitochondrial dyes allow selective in vitro photolysis of carcinoma cells. Oseroff, A.R., Ohuoha, D., Ara, G., McAuliffe, D., Foley, J., Cincotta, L. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  26. Hemoglobin binding site and its relationship to the serine protease-like active site of haptoglobin. Arcoleo, J.P., Greer, J. J. Biol. Chem. (1982) [Pubmed]
  27. Super-helix formation induced by cyanine J-aggregates onto random-coil carboxymethyl amylose as template. Kim, O.K., Je, J., Jernigan, G., Buckley, L., Whitten, D. J. Am. Chem. Soc. (2006) [Pubmed]
  28. Alterations in the hypothalamic paraventricular nucleus and its oxytocin neurons (putative satiety cells) in Prader-Willi syndrome: a study of five cases. Swaab, D.F., Purba, J.S., Hofman, M.A. J. Clin. Endocrinol. Metab. (1995) [Pubmed]
  29. Noninvasive dynamic fluorescence imaging of human melanomas reveals that targeted inhibition of bFGF or FGFR-1 in melanoma cells blocks tumor growth by apoptosis. Valesky, M., Spang, A.J., Fisher, G.W., Farkas, D.L., Becker, D. Mol. Med. (2002) [Pubmed]
  30. Localization and quantification of pro-opiomelanocortin mRNA and glucocorticoid receptor mRNA in pituitaries of suicide victims. López, J.F., Palkovits, M., Arató, M., Mansour, A., Akil, H., Watson, S.J. Neuroendocrinology (1992) [Pubmed]
  31. Induction of interleukin-6 release by interleukin-1 in rat anterior pituitary cells in vitro: evidence for an eicosanoid-dependent mechanism. Spangelo, B.L., Jarvis, W.D., Judd, A.M., MacLeod, R.M. Endocrinology (1991) [Pubmed]
  32. Increased p75(NTR) expression in hippocampal neurons containing hyperphosphorylated tau in Alzheimer patients. Hu, X.Y., Zhang, H.Y., Qin, S., Xu, H., Swaab, D.F., Zhou, J.N. Exp. Neurol. (2002) [Pubmed]
  33. Interferon-gamma activates the voltage-gated calcium channel in RPMI 4788 cells. Iwagaki, H., Fuchimoto, S., Miyake, M., Aoki, H., Orita, K. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  34. Delineation of the endocytic pathway of substance P and its seven-transmembrane domain NK1 receptor. Grady, E.F., Garland, A.M., Gamp, P.D., Lovett, M., Payan, D.G., Bunnett, N.W. Mol. Biol. Cell (1995) [Pubmed]
  35. Purification and characterization of a novel dimeric ferredoxin (FdIII) from Rhodobacter capsulatus. Jouanneau, Y., Meyer, C., Gaillard, J., Forest, E., Gagnon, J. J. Biol. Chem. (1993) [Pubmed]
  36. Double-label immunofluorescence with the laser scanning confocal microscope using cyanine dyes. Sargent, P.B. Neuroimage (1994) [Pubmed]
  37. Structural dissection of a highly knotted peptide reveals minimal motif with antimicrobial activity. Vila-Perelló, M., Sánchez-Vallet, A., García-Olmedo, F., Molina, A., Andreu, D. J. Biol. Chem. (2005) [Pubmed]
  38. Directly labeled DNA probes using fluorescent nucleotides with different length linkers. Zhu, Z., Chao, J., Yu, H., Waggoner, A.S. Nucleic Acids Res. (1994) [Pubmed]
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