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Chemical Compound Review

AG-F-59161     2,3,4,5-tetrachloro-6- (2,4,5,7-tetrabromo...

Synonyms: CHEMBL1205178, CTK1D6976, AC1L8TM4, T0049, 4618-23-9
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Disease relevance of Phloxine

  • Phloxine B (1 microm) stimulated wild-type CFTR and the most common cystic fibrosis mutation, DeltaF508, by increasing the open probability of phosphorylated CFTR Cl(-) channels [1].
  • A macroscopic method using the dyes Alcian blue and phloxine is described for the investigation of squamous metaplasia in the larynx [2].
  • Phloxine B phototoxicity: a mechanistic study using HaCaT keratinocytes [3].
  • Absence of mutagenicity of phloxine and phloxine B in Escherichia coli and in Salmonella typhimurium [4].
  • It was concluded that Phloxine B was teratogenic in mice at dietary levels of 3 and 5%, levels which resulted in maternal toxicity, and that a finding suggesting a teratogenic effect (split cervical arches) was also noted at the 1% dose level [5].

High impact information on Phloxine

  • Using the ATP-driven nucleotide-binding domain dimerization model of CFTR channel gating, we suggest that phloxine B, PP(i) and 2'-dATP alter channel gating by distinct mechanisms [6].
  • To identify small molecules that rescue the gating defects of G551D- and G1349D-CFTR and understand better how these agents work, we used the patch clamp technique to study the effects on G551D- and G1349D-CFTR of phloxine B, pyrophosphate (PP(i)), and 2'-deoxy ATP (2'-dATP), three agents that strongly enhance CFTR channel gating [6].
  • Based on the effects of fluorescein derivatives on transport ATPases, these data suggest that phloxine B might stimulate CFTR by binding to the ATP-binding site of the second nucleotide-binding domain (NBD2) to slow the dissociation of ATP from NBD1 [1].
  • Hematoxylin-eosin-and hematoxylin, phloxine, saffron, and alcian green-stained sections (82 cases) were examined for mitotic rate, the number of giant cells, and the pleomorphism of the stromal cells [7].
  • The Glycine Residues G551 and G1349 within the ATP-Binding Cassette Signature Motifs Play Critical Roles in the Activation and Inhibition of Cystic Fibrosis Transmembrane Conductance Regulator Channels by Phloxine B [8].

Chemical compound and disease context of Phloxine


Biological context of Phloxine

  • These phenotypes also differ in a graded fashion in the level of expression of the metallothionein gene MTII (Wh<LB<DB>vDB), the frequency of switching (Wh>LB>DB>vDB) and colouration on phloxine B-containing agar (Wh>LB>DB>vDB) [12].
  • At concentrations of more than 30 mug/ml of phloxine no further decrease in cell survival was found [13].
  • Genes induced by oxidative stress were induced by phloxine B under illumination with light and some were induced by phloxine B without light [14].
  • A Schizosaccharomyces pombe mutant deficient in Cu,Zn-superoxide dismutase (sod1 mutant) was hypersensitive to phloxine B, which is used as a food-colouring agent and also to distinguish diploid strains of Sz. pombe from haploid strains, under illumination with light [14].
  • Identification of cell type was confirmed by comparing cell counts prepared from blood smears stained with Wright's stain with wet mounts (hemacytometer preparations) stained with Phloxine B [15].

Anatomical context of Phloxine


Associations of Phloxine with other chemical compounds


Gene context of Phloxine

  • Immunohistochemical and histochemical studies were performed on sequential valve sections, including hematoxylin and eosin, hematoxylin phloxine saffron, Movat pentachrome, toluidine blue, CD31, CD34, and CD117 [25].
  • We conclude that phloxine B interacts directly with CFTR at multiple sites to modulate channel activity [1].
  • Moreover, MgATP (300 mumol/l) significantly reduced the apparent affinity for binding of phloxine B to the sulfonylurea receptor [19].
  • These sections were then stained histochemically using HPS (Hematein, Phloxine, Safran) [26].

Analytical, diagnostic and therapeutic context of Phloxine

  • A centrifugal counter-current chromatographic method for preparative purification of commercial tetrabromotetrachlorofluorescein and Phloxine B (D&C Red Nos. 27 and 28, respectively) was developed [27].
  • After treatment with phloxine for 2 h division of cells in normal medium was inhibited for 120 h [13].
  • Identification of the decarboxylated analog of tetrabromotetrachloro-fluorescein and its quantification in the color additives D&C Red Nos. 27 and 28 (phloxine B) using high-performance liquid chromatography [28].
  • In males, the incidence of altered foci and haemangioma in the liver was 19 and 14%, respectively, in the control groups, whereas only 2% occurred in the group given 0.4% phloxine (P < 0.05) [29].
  • To evaluate the mutagenicity of 1-carboxyl-5,7-dibromo-6-hydroxy-2,3,4-trichloroxanthone (HXCA), which is an impurity present in Food Red No. 104 (FR104, Phloxine B, the Japanese counterpart of D&C Red No. 28), HXCA was isolatedfrom FR104 using pH-zone-refining counter-current chromatography and preparative HPLC [30].


  1. Phloxine B interacts with the cystic fibrosis transmembrane conductance regulator at multiple sites to modulate channel activity. Cai, Z., Sheppard, D.N. J. Biol. Chem. (2002) [Pubmed]
  2. An alcian blue-phloxine method for the gross demonstration of squamous metaplasia in the larynx. Watt, J., Gregory, I., Stell, P.M. J. Pathol. (1975) [Pubmed]
  3. Phloxine B phototoxicity: a mechanistic study using HaCaT keratinocytes. Inbaraj, J.J., Kukielczak, B.M., Chignell, C.F. Photochem. Photobiol. (2005) [Pubmed]
  4. Absence of mutagenicity of phloxine and phloxine B in Escherichia coli and in Salmonella typhimurium. Maus, K.L., Nestmann, E.R., Kowbel, D.J. Mutat. Res. (1981) [Pubmed]
  5. A teratogenicity study of Phloxine B in ICR mice. Seno, M., Fukuda, S., Umisa, H. Food Chem. Toxicol. (1984) [Pubmed]
  6. Differential sensitivity of the cystic fibrosis (CF)-associated mutants G551D and G1349D to potentiators of the cystic fibrosis transmembrane conductance regulator (CFTR) Cl- channel. Cai, Z., Taddei, A., Sheppard, D.N. J. Biol. Chem. (2006) [Pubmed]
  7. The prognostic significance of histomorphometry and immunohistochemistry in giant cell tumors of bone. Fornasier, V.L., Protzner, K., Zhang, I., Mason, L. Hum. Pathol. (1996) [Pubmed]
  8. The Glycine Residues G551 and G1349 within the ATP-Binding Cassette Signature Motifs Play Critical Roles in the Activation and Inhibition of Cystic Fibrosis Transmembrane Conductance Regulator Channels by Phloxine B. Melin, P., Norez, C., Callebaut, I., Becq, F. J. Membr. Biol. (2006) [Pubmed]
  9. Expanding the bactericidal action of the food color additive phloxine B to gram-negative bacteria. Rasooly, R. FEMS Immunol. Med. Microbiol. (2005) [Pubmed]
  10. Studies on the toxicity of coal-tar dyes II. Examination of the biological reaction of coal-tar dyes to vital body. Tonogai, Y., Ito, Y., Iwaida, M., Tati, M., Ose, Y., Sato, T. The Journal of toxicological sciences. (1979) [Pubmed]
  11. Toxicity and residual effectiveness of insecticides on insecticide-treated spheres for controlling females of Rhagoletis pomonella (Diptera: Tephritidae). Hu, X.P., Prokopy, R.J., Clark, J.M. J. Econ. Entomol. (2000) [Pubmed]
  12. Phenotypic switching and filamentation in Candida glabrata. Lachke, S.A., Joly, S., Daniels, K., Soll, D.R. Microbiology (Reading, Engl.) (2002) [Pubmed]
  13. Mutagenesis in cultured human diploid cells. IV. Induction of 8-azaguanine resistant mutations by phloxine, a mutagenic red dye. Kuroda, Y. Mutat. Res. (1975) [Pubmed]
  14. Pro-oxidant action of phloxine B on fission yeast Schizosaccharomyces pombe. Mutoh, N., Kawabata, M., Nakagawa, C.W., Kitajima, S. Yeast (2005) [Pubmed]
  15. A new method for the identification and enumeration of chicken heterophils and eosinophils. Ferris, M., Bacha, W.J. Avian Dis. (1984) [Pubmed]
  16. Potent stimulation and inhibition of the CFTR Cl(-) current by phloxine B. Bachmann, A., Russ, U., Waldegger, S., Quast, U. Br. J. Pharmacol. (2000) [Pubmed]
  17. High-resolution MR imaging of the cadaveric human spinal cord: normal anatomy. Solsberg, M.D., Lemaire, C., Resch, L., Potts, D.G. AJNR. American journal of neuroradiology. (1990) [Pubmed]
  18. Three types of cytoplasmic granules in cardiac muscle cells of cynomolgus monkeys (Macaca fascicularis). Jasty, V., Jamison, J.R., Hartnagel, R.E. Vet. Pathol. (1984) [Pubmed]
  19. Interaction of fluorescein derivatives with sulfonylurea binding in insulin-secreting cells. Schwanstecher, M., Bachmann, C., Löser, S., Panten, U. Pharmacology (1995) [Pubmed]
  20. Fluorescence and confocal laser scanning microscopy imaging of elastic fibers in hematoxylin-eosin stained sections. de Carvalho, H.F., Taboga, S.R. Histochem. Cell Biol. (1996) [Pubmed]
  21. Rapid quantification of hexachlorobenzene in the color additives D&C Red Nos. 27 and 28 (phloxine B) using solid-phase microextraction and gas chromatography-mass spectrometry. Andrzejewski, D., Weisz, A. Journal of chromatography. A. (1999) [Pubmed]
  22. Method for determination of xanthene dyes in guava fruits and its application in a field dissipation study. Alcantara-Licudine, J.P., Bui, N.L., Li, Q.X., McQuate, G.T., Peck, S.L. Journal of AOAC International. (2000) [Pubmed]
  23. The composition of Erythrosins, Fluorescein, Phloxine and Rose Bengal: a study using thin-layer chromatography and solvent extraction. Marshall, P.N. Histochem. J. (1976) [Pubmed]
  24. Relationship between interphase AgNOR distribution and nucleolar size in cancer cells. Derenzini, M., Farabegoli, F., Trerè, D. Histochem. J. (1992) [Pubmed]
  25. CD117-positive cells and mast cells in adult human cardiac valves--observations and implications for the creation of bioengineered grafts. Veinot, J.P., Prichett-Pejic, W., Song, J., Waghray, G., Parks, W., Mesana, T.G., Ruel, M. Cardiovascular pathology : the official journal of the Society for Cardiovascular Pathology. (2006) [Pubmed]
  26. Morphometric study of the upper intercostal nerves: practical application for neurotizations in traumatic brachial plexus palsies. Asfazadourian, H., Tramond, B., Dauge, M.C., Oberlin, C. Chirurgie de la main. (1999) [Pubmed]
  27. Preparative purification of tetrabromotetrachlorofluorescein and phloxine B by centrifugal counter-current chromatography. Weisz, A., Langowski, A.J., Meyers, M.B., Thieken, M.A., Ito, Y. J. Chromatogr. (1991) [Pubmed]
  28. Identification of the decarboxylated analog of tetrabromotetrachloro-fluorescein and its quantification in the color additives D&C Red Nos. 27 and 28 (phloxine B) using high-performance liquid chromatography. Weisz, A., Wright, P.R., Andrzejewski, D., Meyers, M.B., Glaze, K., Mazzola, E.J. Journal of chromatography. A. (2006) [Pubmed]
  29. Tumorigenicity study of phloxine (FR 104) in B6C3F1 mice. Ito, A., Fujimoto, N., Okamoto, T., Ando, Y., Watanabe, H. Food Chem. Toxicol. (1994) [Pubmed]
  30. Lack of mutagenicity of a red food colour impurity (1-carboxyl-5,7-dibromo-6-hydroxy-2,3,4-trichloroxanthone) in phloxine B. Aoki, H., Ogawa, Y., Yukawa, C., Nakamura, M., Nakazawa, H. Food additives and contaminants. (2002) [Pubmed]
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