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Chemical Compound Review

CHEMBL191083     (7-dimethylaminophenothiazin- 3-ylidene)...

Synonyms: SureCN127316, CHEBI:43830, NSC3089, DNDI1417128, NSC215213, ...
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Disease relevance of methylene blue

  • Of these, MB demonstrated to be the most effective sensitizer in phosphate-buffered saline (PBS), giving > 7 log10 inactivation of the adenovirus [1].
  • DNA isolated from MB- and light-treated virions was inefficient as a template for transcription [1].
  • DNA used as a substrate was modified either by exposure to ionizing radiation or by photosensitization using visible light in the presence of methylene blue (MB) [2].
  • The suitability of MEMB agar or MSD agar for recovery of E. coli O157:H7 from heated or frozen (-20 degrees C) low- or high-fat ground beef was determined [3].
  • Cell toxicity induced by different concentrations of either MB or TB showed that 10(-5) M was the concentration at which dark damage was not observed, while an elevated photoinactivation could be detected with both thiazines [4].

Psychiatry related information on methylene blue


High impact information on methylene blue

  • The sensitivity and specificity rates for AF and MB for the diagnosis of cancer or dysplasia versus BO mucosa without dysplasia were 21%/91% and 37%/91%, respectively [6].
  • In 12 pigs, the catheter was used to inject 0.1 ml of methylene-blue (MB) dye and 8 pigs had myocardial injections of adenoviral vector (1 x 10(10) particles per site) containing the LacZ transgene [7].
  • The spectra of enzyme-sensitive sites and single-strand breaks induced by MB in vitro or by RO plus light in vivo or in vitro were examined in two yeast reporter genes: the nuclear MFA2 and the mitochondrial OLI1 [8].
  • Our 3' end labelling method is sensitive and was first developed using the well-studied inducer of oxidative DNA damage, methylene blue (MB) plus light [8].
  • Unfortunately, MB does not remain in yeast cells and yeast DNA repair mutants sensitive to active oxygen species are not sensitive to this agent, thus for in vivo experiments we turned to a polycyclic aromatic, RO 19-8022 (RO) [8].

Chemical compound and disease context of methylene blue

  • Results and discussion: Optimum lethal photosensitization (50% or more bacteria killing) of oral pathogens was achieved using halogen light illumination for 5 min and longer with 0.05% MB or exposure to light for 20 min in the presence of 0.025 and 0.01% MB [9].
  • In this study, we compared the effects of methylene blue (MB) and an L-arginine analogue on host outcome, blood pressure, lung injury, and nitric oxide (NO) production in rats following fecal peritonitis induced by cecal ligation and puncture (CLP) [10].

Biological context of methylene blue

  • However, secondary changes occur which suggest that the MB binding site is altered as a result of Ca2+ binding [11].
  • The kinetics of intracellular killing depended on both the drug concentration and the duration of exposure; over 80% of the microorganisms were inactivated within 2.5 min of incubation of the parasitized cells with 10(-4) M MB [12].
  • At the largest concentration of MB assuring no dye aggregation, nonradiative energy transfer efficiencies reach a maximum value of nearly 40% [13].
  • Pellet discs were prepared to assess the effects of compression, proportion of PVA to PCL, acetyl content of PVA, PCL hydrolysis catalyst and drug loading, using methylene blue (MB) as a model drug [14].
  • GH increased cell number as measured by methylene blue (MB) assay in cells of osteoporotic patients to 138 +/- 10% (P < 0.05, n = 7) and in normals to 138 +/- 12 (P < 0.05, n = 7) [15].

Anatomical context of methylene blue

  • Based on its preference for DNA, MB is suited for adenovirus inactivation in blood plasma [1].
  • 6. Intracellular recordings from the smooth muscle of non-perfused vessel segments demonstrated an ACh-induced hyperpolarization and decrease in membrane resistance, changes which were prevented by atropine, NOLA, MB and endothelial lysis and mimicked by SNP [16].
  • Acetylcholine (ACh)-induced relaxation of the HA was abolished by removing the endothelium or by the addition of either hemoglobin, methylene blue (MB) or Ng-mono-methyl-L-arginine [17].
  • RESULTS: Indocyanine green 0.25%, MB 0.20%, GV 0.01%, TB 0.40%, and FS 10% did not induce significant damage to corneal endothelial cells [18].
  • The uptake studies showed that the penetration kinetics of 10(-5) M MB into HeLa cells is faster than that of TB, used at the same concentration, reaching saturation (approximately 1.8 micrograms/10(6) cells) after 6 or 12 h of incubation, respectively [4].

Associations of methylene blue with other chemical compounds

  • In contrast to MB, photodynamic treatment with RB, UP or AIPcS4 did not lead to DNA damage [1].
  • 4. Application of NOLA or MB in perfused vessels significantly increased constriction frequency, further indicating perfusion-associated release of EDNO [16].
  • In addition to determining localization of the photosensitizer within biofilms using confocal laser scanning microscopy (CLSM), we compared the bacterial killing efficacy of erythrosine with that of two well-characterized photosensitizers, methylene blue (MB) and photofrin [19].
  • 3. Perfusion of arteries with N omega-nitro-L-arginine methyl ester (L-NAME, 10 microM) or methylene blue (MeB, 0.5 microM) had no effect on PP or NA release in unstimulated arteries [20].
  • After a brief survey of gel filtration chromatography (GFC) and the self-association equilibrium, it is shown that GFC is a unique tool for investigating the self-association of many substances, such as surfactants, chlorpromazine hydrochloride (CPZ), Methylene Blue (MB) and a sulfobetaine derivative (CHAPS) of cholic acid [21].

Gene context of methylene blue

  • In two phase II clinical trials on methylene blue (MB) antimalarial therapy in rural Burkina Faso, paediatric and adult participants were tested for G6PD deficiency [22].
  • These results suggest that, compared with heat treatment and MB phototreatment, virucidal DMMB treatment preserves not only the oxidative state of hemoglobin but also the antioxidant systems against superoxide and hydrogen peroxide, although the reduced GR activity may limit the quenching capacity of antioxidants in DMMB-treated SFH [23].
  • Under conditions that inactivated VSV by 5.69 log10 (1.37 J/cm2 irradiation and 24 microM MB) there was little effect of MB phototreatment on SOD, CAT, GPX and GSH activities [23].
  • Significantly (P < or = 0.05) lower recovery of heat-stressed cells was observed on MSMA than on TSA, MEMB agar, or MSD agar [3].
  • Neither AMT nor RB binds to poly G, although MB has some affinity for this polymer [24].

Analytical, diagnostic and therapeutic context of methylene blue

  • AF endoscopy was followed by high resolution video endoscopy (VE) plus tissue staining with 0.5% MB [6].
  • Methylene blue (MB), riboflavin (RB) and psoralen sensitizers (4' aminomethyl-4,5',8-trimethylpsoralen [AMT] and derivatives) are under study as sensitizers of viral inactivation of blood products such as plasma proteins, platelets and red cells, all of which lack genomic nucleic acid [24].
  • Fifteen minutes later, fiberoptic bronchoscopy was performed via the bronchial lumen of the DLT to determine whether MB had seeped past the bronchial cuff [25].
  • The reduction of MetHb to functional hemoglobins was also carried out with intravenous injections of methylene blue (MB) [26].
  • In addition, each sample was analyzed with direct microscopic method (DMSCC), using 3 different stainings for each sample: methylene blue (MB), May-Grünwald-Giemsa (MGG) and Pyronin Y-methyl green (PGM) [27].


  1. Photodynamic treatment of adenoviral vectors with visible light: an easy and convenient method for viral inactivation. Schagen, F.H., Moor, A.C., Cheong, S.C., Cramer, S.J., van Ormondt, H., van der Eb, A.J., Dubbelman, T.M., Hoeben, R.C. Gene Ther. (1999) [Pubmed]
  2. Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Boiteux, S., Gajewski, E., Laval, J., Dizdaroglu, M. Biochemistry (1992) [Pubmed]
  3. Suitability of selective plating media for recovering heat- or freeze-stressed Escherichia coli O157:H7 from tryptic soy broth and ground beef. Rocelle, M., Clavero, S., Beuchat, L.R. Appl. Environ. Microbiol. (1995) [Pubmed]
  4. Uptake and photoeffectiveness of two thiazines in HeLa cells. Cañete, M., Villanueva, A., Juarranz, A. Anticancer Drug Des. (1993) [Pubmed]
  5. Methylene Blue--a therapeutic dye for all seasons? Wainwright, M., Crossley, K.B. Journal of chemotherapy (Florence, Italy) (2002) [Pubmed]
  6. Biopsy surveillance is still necessary in patients with Barrett's oesophagus despite new endoscopic imaging techniques. Egger, K., Werner, M., Meining, A., Ott, R., Allescher, H.D., Höfler, H., Classen, M., Rösch, T. Gut (2003) [Pubmed]
  7. Electromagnetic guidance for catheter-based transendocardial injection: a platform for intramyocardial angiogenesis therapy. Results in normal and ischemic porcine models. Kornowski, R., Leon, M.B., Fuchs, S., Vodovotz, Y., Flynn, M.A., Gordon, D.A., Pierre, A., Kovesdi, I., Keiser, J.A., Epstein, S.E. J. Am. Coll. Cardiol. (2000) [Pubmed]
  8. Spontaneous and photosensitiser-induced DNA single-strand breaks and formamidopyrimidine-DNA glycosylase sensitive sites at nucleotide resolutionin the nuclear and mitochondrial DNA of Saccharomyces cerevisiae. Meniel, V., Waters, R. Nucleic Acids Res. (1999) [Pubmed]
  9. Lethal photosensitization of oral pathogens via red-filtered halogen lamp. Krespi, Y., Slatkine, M., Marchenko, M., Protic, J. Oral diseases. (2005) [Pubmed]
  10. Methylene blue--a promising treatment modality in sepsis induced by bowel perforation. Galili, Y., Kluger, Y., Mianski, Z., Iaina, A., Wollman, Y., Marmur, S., Soffer, D., Chernikovsky, T., Klausner, J.P., Robau, M.Y. European surgical research. Europäische chirurgische Forschung. Recherches chirurgicales européennes. (1997) [Pubmed]
  11. Ion-induced DNA structure change in nucleosomes. Hogan, M.E., Hayes, B., Wang, N.C., Austin, R.H. Biochemistry (1986) [Pubmed]
  12. Intracellular parasite killing induced by electron carriers. II. Correlation between parasite killing and the induction of oxidative events in macrophages. Mauel, J., Schnyder, J., Baggiolini, M. Mol. Biochem. Parasitol. (1984) [Pubmed]
  13. Energy transfer among dyes on particulate solids. Rodríguez, H.B., Iriel, A., San Román, E. Photochem. Photobiol. (2006) [Pubmed]
  14. Compressed poly(vinyl alcohol)-polycaprolactone admixture as a model to evaluate erodible implants for sustained drug delivery. Wang, P.Y. J. Biomed. Mater. Res. (1989) [Pubmed]
  15. Human marrow stromal osteoblast-like cells do not show reduced responsiveness to in vitro stimulation with growth hormone in patients with postmenopausal osteoporosis. Kassem, M., Brixen, K., Mosekilde, L., Eriksen, E.F. Calcif. Tissue Int. (1994) [Pubmed]
  16. Endothelium-dependent modulation of pacemaking in lymphatic vessels of the guinea-pig mesentery. von der Weid, P.Y., Crowe, M.J., Van Helden, D.F. J. Physiol. (Lond.) (1996) [Pubmed]
  17. Role of endothelium in responses of isolated hepatic vessels to vasoactive agents. Joshi, S.N., Lonigro, A.J., Secrest, R.J., Chapnick, B.M. J. Pharmacol. Exp. Ther. (1991) [Pubmed]
  18. Comparison of dyes for cataract surgery. Part 1: cytotoxicity to corneal endothelial cells in a rabbit model. Chang, Y.S., Tseng, S.Y., Tseng, S.H., Chen, Y.T., Hsiao, J.H. Journal of cataract and refractive surgery. (2005) [Pubmed]
  19. Erythrosine is a potential photosensitizer for the photodynamic therapy of oral plaque biofilms. Wood, S., Metcalf, D., Devine, D., Robinson, C. J. Antimicrob. Chemother. (2006) [Pubmed]
  20. Modulation by the endothelium of sympathetic vasoconstriction in an in vitro preparation of the rat tail artery. Thorin, E., Atkinson, J. Br. J. Pharmacol. (1994) [Pubmed]
  21. Gel filtration chromatographic study on the self-association of surfactants and related compounds. Funasaki, N. Advances in colloid and interface science. (1993) [Pubmed]
  22. Diagnosis of red cell G6PD deficiency in rural Burkina Faso: comparison of a rapid fluorescent enzyme test on filter paper with polymerase chain reaction based genotyping. Meissner, P.E., Coulibaly, B., Mandi, G., Mansmann, U., Witte, S., Schiek, W., Müller, O., Heiner Schirmer, R., Mockenhaupt, F.P., Bienzle, U. Br. J. Haematol. (2005) [Pubmed]
  23. Comparison of the effects of different antiviral treatments on the antioxidant systems of stroma-free hemoglobin. Hirayama, J., Abe, H., Kamo, N., Ikebuchi, K., Ikeda, H. Photochem. Photobiol. (2001) [Pubmed]
  24. Binding affinities of commonly employed sensitizers of viral inactivation. Dardare, N., Platz, M.S. Photochem. Photobiol. (2002) [Pubmed]
  25. A comparison of the reliability of two techniques of left double-lumen tube bronchial cuff inflation in producing water-tight seal of the left mainstem bronchus. Hannallah, M.S., Gharagozloo, F., Gomes, M.N., Chase, G.A. Anesth. Analg. (1998) [Pubmed]
  26. Noninvasive in vivo monitoring of methemoglobin formation and reduction with broadband diffuse optical spectroscopy. Lee, J., El-Abaddi, N., Duke, A., Cerussi, A.E., Brenner, M., Tromberg, B.J. J. Appl. Physiol. (2006) [Pubmed]
  27. Fossomatic cell-counting on ewe milk: comparison with direct microscopy and study of variation factors. Gonzalo, C., Martínez, J.R., Carrledo, J.A., San Primitivo, F. J. Dairy Sci. (2003) [Pubmed]
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