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Chemical Compound Review

AC1O54Y4     N'-amino-N-imino- methanimidamide

Synonyms: N'-amino-N-iminomethanimidamide
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Disease relevance of Formazan


Psychiatry related information on Formazan

  • In XTT assay, the production of formazan increases with reaction time over a protracted period of time, we assessed the possibility of performing assays with fewer cells than MTT was used [6].

High impact information on Formazan

  • METHODS: Effects were assayed by a formazan-based colorimetric assay, [(3)H]thymidine incorporation, fluorescent nuclear staining, annexin V binding, DNA fragmentation assay, and immunoblotting of cytoplasmic and membrane fractions for PKC isozymes [7].
  • The stimulatory state of Kupffer cells based on the ability to produce superoxide anions estimated by formazan deposition after liver perfusion with nitro blue tetrazolium and phorbol myristate acetate was increased between 24 and 72 hours after operation [8].
  • Incubation of rings with nitro blue tetrazolium (NBT) resulted in blue formazan staining of the adventitia, and lucigenin chemiluminescence was significantly greater when detected from the adventitial compared with the intimal aspect of the artery [9].
  • By means of a formazan dye-based spectrophotometric assay of cell viability and light microscopy, manumycin was shown to decrease the number of viable cells in all six of the cell lines though to a lesser degree in DRO and C643 cells than in ARO, Hth-74, KAT-4, and KAT-18 cells [10].
  • AS cyclin D1 significantly inhibited cell proliferation by both [3H]thymidine incorporation in six SCC cell lines (P = 0.01-0.001) and the conversion of tetrazolium salt to formazan in four SCC cell lines (P = 0.01-0.004) [11].

Chemical compound and disease context of Formazan

  • Toxicity is assessed by an objective, automated method based on the reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide to an insoluble purple formazan by the mitochondria of viable cells and correlates with that based on trypan blue exclusion [12].
  • The rate of appearance of red-colored formazan indicating reduction of 2,3,5,-triphenyltetrazolium chloride by Mycoplasma pneumoniae was dependent on the inoculum size [13].
  • Conclusions: Formation of formazan from TTC can depend on both the staining method and the metabolic burden of the brain tissue causing uncertainties in the volume of ischemia-induced brain injury measured by TTC staining [14].
  • A study was performed on 74 medicolegal autopsy cases for the purpose of comparing the reliability of four different techniques (haematoxylin-eosin stain, acridine orange method, formazan test and K/Na ratio) used for the postmortem diagnosis of myocardial infarction [15].
  • These results suggest that alterations in cell cycle phase redistribution of MCF-7 human breast cancer, by ursolic acid, may significantly influence MTT reduction to formazan [16].

Biological context of Formazan


Anatomical context of Formazan

  • NBT was reduced to formazan in 71% of monocytes exposed to promastigotes [22].
  • In rat hepatocytes in primary culture incubated with nitro blue tetrazolium, formazan content was increased by addition of t-butyl hydroperoxide, a potent oxidant, in a dose-related manner, but not by addition of valinomycin, which kills hepatocytes through mitochondrial damage [23].
  • The protection against SZ and ROI was associated with preserved mitochondrial activity, as determined by the ability of the islet cells to convert the tetrazolium salt 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide into its formazan [24].
  • Activated peritoneal macrophages exhibiting phagocytosing capacity produced an electron-dense precipitate of formazan in contact sites of macrophage plasmalemma and phagocytosed yeast cells [25].
  • Endothelial cell viability was determined by measuring cellular reduction of 3-[4,5-dimethylthiazol-2-yl]-2,3-diphenyltetrazolium bromide to a purple formazan dye [26].

Associations of Formazan with other chemical compounds

  • Furthermore, the following studies showed that inhibition of Ia by NO was not due to macrophage death: trypan blue exclusion, macrophage adhesion, conversion of the tetrazolium dye (MTT) to its formazan by a functioning electron transport system, and phagocytosis of IgG opsonized SRBCs [27].
  • Treatment of frozen sections to demonstrate succinate dehydrogenase showed early changes in the character of formazan, suggesting the possibility of a transient alteration in the hydrogen transport system [28].
  • No production of formazan occurred, when non-opsonized latex particles were ingested by macrophages [25].
  • When a liver perfusion with nitro blue tetrazolium (NBT) and phorbol myristate acetate (PMA) was performed in carbon tetrachloride (CCl4)-intoxicated rats, formazan deposition was remarkable in macrophages in the necrotic areas of the liver, its intensity varying with the extent of injury [29].
  • When peroxisomal membranes were assayed under native conditions using NADH or NADPH as inducer, two different O2(-).-dependent Formazan Blue bands were detected [30].

Gene context of Formazan

  • Differential 'medium conditioning' led to a difference in formazan production per cell between IFN and control cells and this was the major basis of the observed discrepancy [31].
  • RESULTS: Leptin stimulated proliferation of serum-deprived fetal rat islet cells, as indicated by increased formation of formazan dye from a tetrazolium salt WST-1 [32].
  • In addition, a new staining procedure is described that allows the visualization of GPT activity on gels by the deposition of formazan [33].
  • The presence of formazan deposits within Purkinje cells was verified by colocalization with calbindin D-28k immunoreactivity [34].
  • Two cell populations of almost equal size could be discerned in heterozygotes for G6PD deficiency, one completely negative, the other with a variable amount of formazan per cell [35].

Analytical, diagnostic and therapeutic context of Formazan

  • The same culture dishes were assessed by image analysis and by formazan colorimetry for purposes of comparing multiple methods of measuring growth as well as growth inhibition [36].
  • This highly quantitative in vitro colorimetric bioassay is based upon the reduction of a tetrazolium salt, 3-[4,5-dimethyl-thiazol-2-yl]2,5-diphenyl tetrazolium bromide (MTT), to its formazan by lactogen-activated Nb2 cells [37].
  • Cell number was determined by mitochondrial formazan production; apoptosis was measured by Tdt-mediated dUTP nick end labeling reaction and DNA fragmentation-based enzyme-linked immunosorbent assay [38].
  • When the same compounds (0.1 microgram) were administered to mice which had been pretreated i.p. with thioglycollate 6 days prior to the experiment, PMA, PDB, 4-O-Me-PMA, mezerein and A23187 all caused an increase in the number of formazan-positive PECs 2 h after treatment [39].
  • Enumeration of respiring Pseudomonas spp. in milk within 6 hours by fluorescence in situ hybridization following formazan reduction [40].


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  2. Respiratory burst activity of intestinal macrophages in normal and inflammatory bowel disease. Mahida, Y.R., Wu, K.C., Jewell, D.P. Gut (1989) [Pubmed]
  3. Formazan cells in protein and protein-calorie malnutrition. Felsenfeld, O., Gyr, K. Am. J. Clin. Nutr. (1977) [Pubmed]
  4. Superoxide dismutase ameliorates neuronal death from hypoxia in culture. Rosenbaum, D.M., Kalberg, J., Kessler, J.A. Stroke (1994) [Pubmed]
  5. Quantitative reduction of 2,3,4-triphenyl tetrazolium chloride by hamster trachea organ cultures: effects of Mycoplasma pneumoniae cells and membranes. Gabridge, M.G., Polisky, R.B. Infect. Immun. (1976) [Pubmed]
  6. High-sensitivity antitumor drug sensitivity testing. Kondo, T., Wada, K., Kawashima, M., Sato, Y., Yamauchi, M. Oncology (1994) [Pubmed]
  7. Distinct protein kinase C isozymes signal mitogenesis and apoptosis in human colon cancer cells. Weller, S.G., Klein, I.K., Penington, R.C., Karnes, W.E. Gastroenterology (1999) [Pubmed]
  8. Provocation of massive hepatic necrosis by endotoxin after partial hepatectomy in rats. Mochida, S., Ogata, I., Hirata, K., Ohta, Y., Yamada, S., Fujiwara, K. Gastroenterology (1990) [Pubmed]
  9. Superoxide anion from the adventitia of the rat thoracic aorta inactivates nitric oxide. Wang, H.D., Pagano, P.J., Du, Y., Cayatte, A.J., Quinn, M.T., Brecher, P., Cohen, R.A. Circ. Res. (1998) [Pubmed]
  10. Manumycin enhances the cytotoxic effect of paclitaxel on anaplastic thyroid carcinoma cells. Yeung, S.C., Xu, G., Pan, J., Christgen, M., Bamiagis, A. Cancer Res. (2000) [Pubmed]
  11. Antisense cyclin D1 induces apoptosis and tumor shrinkage in human squamous carcinomas. Sauter, E.R., Nesbit, M., Litwin, S., Klein-Szanto, A.J., Cheffetz, S., Herlyn, M. Cancer Res. (1999) [Pubmed]
  12. Drug metabolite toxicity assessed in human lymphocytes with a purified, reconstituted cytochrome P-450 system. Leeder, J.S., Cannon, M., Nakhooda, A., Spielberg, S.P. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  13. Estimation of Mycoplasma pneumoniae inoculum size by rate of tetrazolium reduction. Bredt, W. J. Clin. Microbiol. (1976) [Pubmed]
  14. Use of TTC staining for the evaluation of tissue injury in the early phases of reperfusion after focal cerebral ischemia in rats. Benedek, A., M??ricz, K., Jur??nyi, Z., Gigler, G., L??vay, G., H??rsing, L.G., M??tyus, P., Sz??n??si, G., Albert, M. Brain Res. (2006) [Pubmed]
  15. Comparison of different techniques for the postmortem diagnosis of myocardial infarction. Lachica, E., Villanueva, E., Luna, A. Forensic Sci. Int. (1988) [Pubmed]
  16. MCF-7 cell cycle arrested at G1 through ursolic acid, and increased reduction of tetrazolium salts. Es-Saady, D., Simon, A., Jayat-Vignoles, C., Chulia, A.J., Delage, C. Anticancer Res. (1996) [Pubmed]
  17. Extensive oxidative DNA damage in hepatocytes of transgenic mice with chronic active hepatitis destined to develop hepatocellular carcinoma. Hagen, T.M., Huang, S., Curnutte, J., Fowler, P., Martinez, V., Wehr, C.M., Ames, B.N., Chisari, F.V. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  18. Molecular chemotherapy combined with radiation therapy enhances killing of cholangiocarcinoma cells in vitro and in vivo. Pederson, L.C., Buchsbaum, D.J., Vickers, S.M., Kancharla, S.R., Mayo, M.S., Curiel, D.T., Stackhouse, M.A. Cancer Res. (1997) [Pubmed]
  19. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Scudiero, D.A., Shoemaker, R.H., Paull, K.D., Monks, A., Tierney, S., Nofziger, T.H., Currens, M.J., Seniff, D., Boyd, M.R. Cancer Res. (1988) [Pubmed]
  20. Effect of chronic ethanol ingestion on fatty acid oxidation by hepatic mitochondria. Cederbaum, A.I., Lieber, C.S., Beattie, D.S., Rubin, E. J. Biol. Chem. (1975) [Pubmed]
  21. Oxidative killing of the intraerythrocytic malaria parasite Plasmodium yoelii by activated macrophages. Ockenhouse, C.F., Shear, H.L. J. Immunol. (1984) [Pubmed]
  22. Differential survival of Leishmania donovani amastigotes in human monocytes. Pearson, R.D., Harcus, J.L., Roberts, D., Donowitz, G.R. J. Immunol. (1983) [Pubmed]
  23. In situ detection of oxidative stress in rat hepatocytes. Mochida, S., Masaki, N., Ohta, Y., Matsui, A., Ogata, I., Fujiwara, K. J. Pathol. (1992) [Pubmed]
  24. Metabolic activation of islet cells improves resistance against oxygen radicals or streptozocin, but not nitric oxide. Burkart, V., Brenner, H.H., Hartmann, B., Kolb, H. J. Clin. Endocrinol. Metab. (1996) [Pubmed]
  25. Visualization of reactive oxygen species formation by phagocytizing macrophages. Peskin, A.V., Khramtsov, A.V., Morozov, I.A., Zemskov, V.M., Zbarsky, I.B. Exp. Cell Res. (1984) [Pubmed]
  26. Improvement of endothelial cell viability at 4 degrees C by addition of lazaroid U74500A to preservation solutions. Killinger, W.A., Dorofi, D.B., Keagy, B.A., Johnson, G. Transplantation (1992) [Pubmed]
  27. Inhibition of macrophage Ia expression by nitric oxide. Sicher, S.C., Vazquez, M.A., Lu, C.Y. J. Immunol. (1994) [Pubmed]
  28. Exeriences with isoprenaline induced myocardial necrosis in the rat. Woolf, N., Davies, M.J., Shaw, M.J., Trickey, R.J. J. Pathol. (1976) [Pubmed]
  29. In situ evaluation of the stimulatory state of hepatic macrophages based on their ability to produce superoxide anions in rats. Mochida, S., Ogata, I., Ohta, Y., Yamada, S., Fujiwara, K. J. Pathol. (1989) [Pubmed]
  30. Characterization of membrane polypeptides from pea leaf peroxisomes involved in superoxide radical generation. López-Huertas, E., Corpas, F.J., Sandalio, L.M., Del Río, L.A. Biochem. J. (1999) [Pubmed]
  31. The MTT assay underestimates the growth inhibitory effects of interferons. Jabbar, S.A., Twentyman, P.R., Watson, J.V. Br. J. Cancer (1989) [Pubmed]
  32. Fetal pancreatic islets express functional leptin receptors and leptin stimulates proliferation of fetal islet cells. Islam, M.S., Sjöholm, A., Emilsson, V. Int. J. Obes. Relat. Metab. Disord. (2000) [Pubmed]
  33. Chromosomal location of soluble glutamic-pyruvic transaminase-1 (Gpt-1) in the mouse. Eicher, E.M., Womack, J.E. Biochem. Genet. (1977) [Pubmed]
  34. NADPH-diaphorase histochemistry in the postnatal mouse cerebellum suggests specific developmental functions for nitric oxide. Brüning, G. J. Neurosci. Res. (1993) [Pubmed]
  35. A sensitive cytochemical staining method for glucose-6-phosphate dehydrogenase activity in individual erythrocytes. II. Further improvements of the staining procedure and some observations with glucose-6-phosphate dehydrogenase deficiency. Van Noorden, C.J., Vogels, I.M. Br. J. Haematol. (1985) [Pubmed]
  36. Morphometric and colorimetric analyses of human tumor cell line growth and drug sensitivity in soft agar culture. Alley, M.C., Pacula-Cox, C.M., Hursey, M.L., Rubinstein, L.R., Boyd, M.R. Cancer Res. (1991) [Pubmed]
  37. The measurement of growth hormone bioactivity in patient serum using an eluted stain assay. Dattani, M.T., Hindmarsh, P.C., Pringle, P.J., Brook, C.G., Marshall, N.J. J. Clin. Endocrinol. Metab. (1995) [Pubmed]
  38. Growth factor effects on apoptosis of rat gastric enterochromaffin-like cells. Mahr, S., Neumayer, N., Kolb, H.J., Schepp, W., Classen, M., Prinz, C. Endocrinology (1998) [Pubmed]
  39. Tumor promoters differ in their ability to stimulate superoxide anion radical production by murine peritoneal exudate cells following in vivo administration. Witz, G., Czerniecki, B.J. Carcinogenesis (1989) [Pubmed]
  40. Enumeration of respiring Pseudomonas spp. in milk within 6 hours by fluorescence in situ hybridization following formazan reduction. Kitaguchi, A., Yamaguchi, N., Nasu, M. Appl. Environ. Microbiol. (2005) [Pubmed]
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