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Chemical Compound Review

Orange     5-diethylamino-2-[4- (dimethylsulfamoyl)phe...

Synonyms: Orange DYE, AG-K-38768, KST-1B4366, AC1Q1SNK, CTK4H9223, ...
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Disease relevance of 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide


Psychiatry related information on 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide

  • SETTING: Alzheimer's Disease Research Center Consortium of Los Angeles and Orange Counties, California. SUBJECTS: Volunteers, recruited from the community or clinic referrals, who met clinical criteria for AD (n = 159) or VD (n = 117) or met criteria for control status without dementia (n = 134) [6].
  • Some took a psychological form (exhaustion, combat fatigue, combat stress reaction and post-traumatic stress disorder), while others were characterized by medically unexplained symptoms (soldier's heart, effort syndrome, shell shock, non-ulcer dyspepsia, effects of Agent Orange and Gulf War Syndrome) [7].
  • Two strategies for preventing the onset of alcohol abuse, and marijuana and cigarette use were tested in junior high schools in Los Angeles and Orange Counties, California. The first strategy taught skills to refuse substance use offers [8].
  • The authors believe that the mental health worker program of the Orange County, California, community mental health program is developed and stable encough that the initial steps of an economic analysis are possible [9].
  • Carcinogenicity and teratogenicity vs. psychogenicity: psychological characteristics associated with self-reported Agent Orange exposure among Vietnam combat veterans who seek treatment for substance abuse [10].

High impact information on 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide

  • CONCLUSIONS--These data suggest that lead poisoning is not a major public health problem among Orange County children and detection of infrequent cases would involve a high cost per child [3].
  • PARTICIPANTS--A total of 5115 Orange County children between 12 and 72 months of age using EPSDT services from March through December 1992 [3].
  • Dioxins and dibenzofurans in blood and adipose tissue of Agent Orange-exposed Vietnam veterans and matched controls [11].
  • The Orange (Or) gene mutation in cauliflower (Brassica oleracea var botrytis) confers the accumulation of high levels of beta-carotene in various tissues normally devoid of carotenoids [12].
  • We show that the Orange domain is an important functional domain that confers specificity among members of the Hairy/E(SPL) family [13].

Chemical compound and disease context of 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide


Biological context of 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide


Anatomical context of 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide

  • We have investigated the interactions with isolated mitochondria and intact cells of chloromethyltetramethylrosamine (CMTMRos), a probe (Mitotracker Orange) that is increasingly used to monitor the mitochondrial membrane potential (Deltapsi(m)) in situ [23].
  • Phase-dense vesicles were identified as lysosomes or other acidic vesicles by vital staining with Acridine Orange. After differential centrifugation of thyroid homogenates, calmodulin was measured by radioimmunoassay (RIA) and found in both cytosolic (89%) and membrane vesicle fractions (11%) [24].
  • Within 0-30 minutes, fluo-NT accumulated together with its receptor in Acridine Orange-positive, acidic organelles [25].
  • Heating the erythrocytes to 50 degrees C, at which temperature denaturation of spectrin and fragmentation of the erythrocytes occur, and subsequently incubating them in Acridine Orange at room temperature, caused an almost maximal rate of particle aggregation within 10-30 s, without haemolysis [26].
  • Acridine Orange, used as an in vivo indicator of acidic compartments, stained the secretory vesicles in both wild-type and mutant cells [27].

Associations of 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide with other chemical compounds

  • In this report, mass spectra generated from human serum or rat liver proteins stained with either colloidal Coomassie blue, Daiichi silver, SYPRO Orange, SYPRO Red, SYPRO Ruby, or SYPRO Tangerine are compared [28].
  • ATP-driven acidification of internal compartments of Trypanosoma cruzi epimastigotes was assayed spectrophotometrically with Acridine Orange and cells permeabilized with filipin [29].
  • Inorganic pyrophosphate promoted the acidification of an intracellular compartment in permeabilized promastigotes of Leishmania donovani, as measured by Acridine Orange uptake [30].
  • Anion-exchange chromatography on Q-Sepharose, followed by adsorption chromatography on columns of Matrex Orange A and Cibacron Blue, have been employed to purify rAFAR2 from rat liver cytosol [31].
  • These data provide little or no support for the theory that paternal exposure to Agent Orange and its dioxin contaminant is associated with adverse reproductive outcomes [32].

Gene context of 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide

  • In contrast, only the bHLH domain was required for the heterodimerization with Hey2, whereas only the Orange domain mediated the interaction between Helt and Hes5 [33].
  • The ability of Hes1 to interact with Ptf1-p48 resides within a fragment comprised of the bHLH, Orange and C-terminal domains, and does not require the N-terminal or WRPW elements [34].
  • While the overall structure with the bHLH domain, Orange domain, and WRPW motif is similar, the last motif is changed to KPYRPWG in Hey1/2 and absent in HeyL [35].
  • We report a novel missense change in BRCA1, 2640 C-->T (R841W), found in 3 cases from a subject group of 305 breast and 79 ovarian cancer cases from Orange County, CA [36].
  • In the current study, DNA resequencing/haplotyping was conducted on 136 DRD4 alleles obtained from autism probands, collected from the same geographic population as the prior ADHD probands (Orange County, CA) [37].

Analytical, diagnostic and therapeutic context of 5-diethylamino-2-[4-(dimethylsulfamoyl)phenyl]diazenyl-N-(2-pyridin-1-ylethyl)benzenesulfonamide

  • Two containing D&C Orange No. 17 were directly mutagenic [38].
  • The protein, purified by affinity chromatography with Amicon Matrex Gel Orange A, had enzyme activity characteristic of aldose reductase (alditol:NADPH+ oxidoreductase, EC [39].
  • Isoelectric focusing on a Sephadex G-15 support bed or ampholyte displacement chromatography of Orange A bound material demonstrated inhibitory activity at pH 3.5-4.5 and 6.5-7 [40].
  • The Chlase1 cDNA from Valencia Orange (Citrus sinensis cv. Valencia) was obtained by RT-PCR using degenerate primers based on the amino acid sequence of the previously purified protein [41].
  • Two suitable DNA binding dyes, SYTOX Orange and TO-PRO-3, were selected and tested for the real-time PCR processes [42].


  1. Agent Orange and birth defects (continued). Constable, J.D., Hatch, M.C. N. Engl. J. Med. (1984) [Pubmed]
  2. Thoracic soft-tissue sarcoma in Vietnam veterans exposed to Agent Orange. Sarma, P.R., Jacobs, J. N. Engl. J. Med. (1982) [Pubmed]
  3. Lead poisoning among low-income children in Orange County, California. A need for regionally differentiated policy. Gellert, G.A., Wagner, G.A., Maxwell, R.M., Moore, D., Foster, L. JAMA (1993) [Pubmed]
  4. Agent Orange and spontaneous abortions. Cook, R.R. JAMA (1980) [Pubmed]
  5. Purification and amino acid analysis of two human glioma-derived monocyte chemoattractants. Yoshimura, T., Robinson, E.A., Tanaka, S., Appella, E., Kuratsu, J., Leonard, E.J. J. Exp. Med. (1989) [Pubmed]
  6. Gender comparisons of cognitive performances among vascular dementia, Alzheimer disease, and older adults without dementia. Buckwalter, J.G., Rizzo, A.A., McCleary, R., Shankle, R., Dick, M., Henderson, V.W. Arch. Neurol. (1996) [Pubmed]
  7. Historical approaches to post-combat disorders. Jones, E. Philos. Trans. R. Soc. Lond., B, Biol. Sci. (2006) [Pubmed]
  8. Preventing alcohol, marijuana, and cigarette use among adolescents: peer pressure resistance training versus establishing conservative norms. Hansen, W.B., Graham, J.W. Preventive medicine. (1991) [Pubmed]
  9. Economic viability of the mental health worker. Madenlian, R., Pattison, E.M., Saxon, S. Hospital & community psychiatry. (1980) [Pubmed]
  10. Carcinogenicity and teratogenicity vs. psychogenicity: psychological characteristics associated with self-reported Agent Orange exposure among Vietnam combat veterans who seek treatment for substance abuse. Robinowitz, R., Roberts, W.R., Dolan, M.P., Patterson, E.T., Charles, H.L., Atkins, H.G., Penk, W.E. Journal of clinical psychology. (1989) [Pubmed]
  11. Dioxins and dibenzofurans in blood and adipose tissue of Agent Orange-exposed Vietnam veterans and matched controls. Kahn, P.C., Gochfeld, M., Nygren, M., Hansson, M., Rappe, C., Velez, H., Ghent-Guenther, T., Wilson, W.P. JAMA (1988) [Pubmed]
  12. The Cauliflower Or Gene Encodes a DnaJ Cysteine-Rich Domain-Containing Protein That Mediates High Levels of {beta}-Carotene Accumulation. Lu, S., Van Eck, J., Zhou, X., Lopez, A.B., O'halloran, D.M., Cosman, K.M., Conlin, B.J., Paolillo, D.J., Garvin, D.F., Vrebalov, J., Kochian, L.V., Küpper, H., Earle, E.D., Cao, J., Li, L. Plant Cell (2006) [Pubmed]
  13. Specificity for the hairy/enhancer of split basic helix-loop-helix (bHLH) proteins maps outside the bHLH domain and suggests two separable modes of transcriptional repression. Dawson, S.R., Turner, D.L., Weintraub, H., Parkhurst, S.M. Mol. Cell. Biol. (1995) [Pubmed]
  14. Analysis of glycosaminoglycans in urine by using acridine orange fluorescence. Diakun, G.P., Edwards, H.E., Allen, J.C., Phillips, G.O. Biochem. J. (1978) [Pubmed]
  15. Analysis of tear protein patterns of dry-eye patients using fluorescent staining dyes and two-dimensional quantification algorithms. Grus, F.H., Sabuncuo, P., Augustin, A.J. Electrophoresis (2001) [Pubmed]
  16. Tandem dye-ligand chromatography and biospecific elution applied to the purification of glucose-6-phosphate dehydrogenase from Leuconostoc mesenteroides. Hey, Y., Dean, P.D. Biochem. J. (1983) [Pubmed]
  17. Long-term follow-up of short intensive multiagent chemotherapy without high-dose methotrexate ('Orange') in children with advanced non-lymphoblastic non-Hodgkin's lymphoma: a children's cancer group report. Cairo, M.S., Krailo, M.D., Morse, M., Hutchinson, R.J., Harris, R.E., Kjeldsberg, C.R., Kadin, M.E., Radel, E., Steinherz, L.J., Morris, E., Finlay, J.L., Meadows, A.T. Leukemia (2002) [Pubmed]
  18. Spontaneous abortion, sex ratio, and paternal occupational exposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin. Schnorr, T.M., Lawson, C.C., Whelan, E.A., Dankovic, D.A., Deddens, J.A., Piacitelli, L.A., Reefhuis, J., Sweeney, M.H., Connally, L.B., Fingerhut, M.A. Environ. Health Perspect. (2001) [Pubmed]
  19. Apoptosis and accidental cell death in cultured human keratinocytes after thermal injury. Matylevitch, N.P., Schuschereba, S.T., Mata, J.R., Gilligan, G.R., Lawlor, D.F., Goodwin, C.W., Bowman, P.D. Am. J. Pathol. (1998) [Pubmed]
  20. Changes in yolk platelet pH during Xenopus laevis development correlate with yolk utilization. A quantitative confocal microscopy study. Fagotto, F., Maxfield, F.R. J. Cell. Sci. (1994) [Pubmed]
  21. Vitamin E deficiency impairs the modifications of mitochondrial membrane potential and mass in rat splenocytes stimulated to proliferate. Pieri, C., Moroni, F., Recchioni, R. Free Radic. Biol. Med. (1993) [Pubmed]
  22. Orange juice substantially reduces the bioavailability of the beta-adrenergic-blocking agent celiprolol. Lilja, J.J., Juntti-Patinen, L., Neuvonen, P.J. Clin. Pharmacol. Ther. (2004) [Pubmed]
  23. Chloromethyltetramethylrosamine (Mitotracker Orange) induces the mitochondrial permeability transition and inhibits respiratory complex I. Implications for the mechanism of cytochrome c release. Scorrano, L., Petronilli, V., Colonna, R., Di Lisa, F., Bernardi, P. J. Biol. Chem. (1999) [Pubmed]
  24. Association of calmodulin with lysosomes. Nielsen, T.B., Field, J.B., Dedman, J.R. J. Cell. Sci. (1987) [Pubmed]
  25. Ligand-induced internalization of neurotensin in transfected COS-7 cells: differential intracellular trafficking of ligand and receptor. Vandenbulcke, F., Nouel, D., Vincent, J.P., Mazella, J., Beaudet, A. J. Cell. Sci. (2000) [Pubmed]
  26. The mobility of intramembrane particles in non-haemolysed human erythrocytes. Factors affecting acridine-orange-induced particle aggregation. Lelkes, G., Fodor, I., Lelkes, G., Hollán, S.R. J. Cell. Sci. (1986) [Pubmed]
  27. The secretory vesicle in living Paramecium is acidic. Busch, G.R., Satir, B.H. J. Cell. Sci. (1989) [Pubmed]
  28. Mass spectrometry compatibility of two-dimensional gel protein stains. Lauber, W.M., Carroll, J.A., Dufield, D.R., Kiesel, J.R., Radabaugh, M.R., Malone, J.P. Electrophoresis (2001) [Pubmed]
  29. Two types of H+-ATPase are involved in the acidification of internal compartments in Trypanosoma cruzi. Scott, D.A., Docampo, R. Biochem. J. (1998) [Pubmed]
  30. Presence of a vacuolar H+-pyrophosphatase in promastigotes of Leishmania donovani and its localization to a different compartment from the vacuolar H+-ATPase. Rodrigues, C.O., Scott, D.A., Docampo, R. Biochem. J. (1999) [Pubmed]
  31. Purification from rat liver of a novel constitutively expressed member of the aldo-keto reductase 7 family that is widely distributed in extrahepatic tissues. Kelly, V.P., Ireland, L.S., Ellis, E.M., Hayes, J.D. Biochem. J. (2000) [Pubmed]
  32. Paternal serum dioxin and reproductive outcomes among veterans of Operation Ranch Hand. Wolfe, W.H., Michalek, J.E., Miner, J.C., Rahe, A.J., Moore, C.A., Needham, L.L., Patterson, D.G. Epidemiology (Cambridge, Mass.) (1995) [Pubmed]
  33. Helt, a novel basic-helix-loop-helix transcriptional repressor expressed in the developing central nervous system. Nakatani, T., Mizuhara, E., Minaki, Y., Sakamoto, Y., Ono, Y. J. Biol. Chem. (2004) [Pubmed]
  34. Interactions between hairy/enhancer of split-related proteins and the pancreatic transcription factor Ptf1-p48 modulate function of the PTF1 transcriptional complex. Ghosh, B., Leach, S.D. Biochem. J. (2006) [Pubmed]
  35. Characterization of the human and mouse HEY1, HEY2, and HEYL genes: cloning, mapping, and mutation screening of a new bHLH gene family. Steidl, C., Leimeister, C., Klamt, B., Maier, M., Nanda, I., Dixon, M., Clarke, R., Schmid, M., Gessler, M. Genomics (2000) [Pubmed]
  36. BRCA1 R841W: a strong candidate for a common mutation with moderate phenotype. Barker, D.F., Almeida, E.R., Casey, G., Fain, P.R., Liao, S.Y., Masunaka, I., Noble, B., Kurosaki, T., Anton-Culver, H. Genet. Epidemiol. (1996) [Pubmed]
  37. Sequence variants of the DRD4 gene in autism: further evidence that rare DRD4 7R haplotypes are ADHD specific. Grady, D.L., Harxhi, A., Smith, M., Flodman, P., Spence, M.A., Swanson, J.M., Moyzis, R.K. Am. J. Med. Genet. B Neuropsychiatr. Genet. (2005) [Pubmed]
  38. Mutagenicity of some lipsticks and their dyes. Green, M.R., Pastewka, J.V. J. Natl. Cancer Inst. (1980) [Pubmed]
  39. Characterization and purification of a mammalian osmoregulatory protein, aldose reductase, induced in renal medullary cells by high extracellular NaCl. Bedford, J.J., Bagnasco, S.M., Kador, P.F., Harris, H.W., Burg, M.B. J. Biol. Chem. (1987) [Pubmed]
  40. Identification of proteins in pooled human follicular fluid which suppress follicular response to gonadotropins. diZerega, G.S., Marrs, R.P., Roche, P.C., Campeau, J.D., Kling, O.R. J. Clin. Endocrinol. Metab. (1983) [Pubmed]
  41. Chlorophyll breakdown by chlorophyllase: isolation and functional expression of the Chlase1 gene from ethylene-treated Citrus fruit and its regulation during development. Jacob-Wilk, D., Holland, D., Goldschmidt, E.E., Riov, J., Eyal, Y. Plant J. (1999) [Pubmed]
  42. Towards a portable microchip system with integrated thermal control and polymer waveguides for real-time PCR. Wang, Z., Sekulovic, A., Kutter, J.P., Bang, D.D., Wolff, A. Electrophoresis (2006) [Pubmed]
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