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Chemical Compound Review

AR-1I2485     cobalt(+3) cation; 3-(2-ethylhexoxy)propan...

Synonyms: AC1L4SZ9, AC1Q1T29, 84912-04-9, EINECS 284-466-2
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Disease relevance of Compound

  • A Novel Molecular Targeting Compound as K-samII/FGF-R2 Phosphorylation Inhibitor, Ki23057, for Scirrhous Gastric Cancer [1].
  • Compounds II and IV were active against all three experimental tumors; both compounds produced significant tumor regression in the human breast tumor xenograft and Compound IV caused tumor regression in the human lung tumor xenograft [2].
  • These results provide evidence that the i.v. injection of Compound 48/80 or pilocarpine causes: (a) hyperglycemia; (b) depletion of hepatic glycogen, and (c) a concomitant decrease in the number of Falck-Hillarp-positive mast cells [3].
  • The cytotoxic activities of three new synthetic catechol analogues, beta-[(p-hydroxyphenyl)amino]alanine (Compound 1), N delta-(p-hydroxyphenyl)ornithine (Compound 2), and N delta-(m-hydroxyphenyl)ornithine (Compound 3), were determined against 10 human melanoma and 5 nonmelanoma cell lines [4].
  • alpha-(N-Acetylaminomethylene)succinic acid hydrolase (Compound A hydrolase, EC 3.5.1-) and alpha-hydroxymethyl-alpha'-(N-acetylaminomethylene)succinic acid hydrolase (Compound B hydrolase, EC 3.5.1-) were purified to homogeneity from Pseudomonas MA-1 and Arthrobacter Cr-7, respectively [5].

Psychiatry related information on Compound

  • In an in vivo experiment, nociceptin significantly inhibited a light-induced (300 lux, 1 h) phase delay of locomotor activity rhythms, and this effect was inhibited by Compound B [6].
  • Complexes , also catalyzed the same reaction but required heating at 80 degrees C and longer reaction times compared with . Compound is inactive [7].
  • Also, a Compound Model is proposed, with three distinctive patterns of the parent-child relationship that impact on posttraumatic symptomatology in young children [8].

High impact information on Compound


Chemical compound and disease context of Compound

  • Two NAD+-dependent, highly specific pyridine-5-aldehyde dehydrogenases, 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic-acid (Compound 1) dehydrogenase and isopyridoxal dehydrogenase, were purified to homogeneity from Pseudomonas MA-1 and Arthrobacter Cr-7, respectively [14].
  • VP4 Protein from Human Rhinovirus 14 Is Released by Pressure and Locked in the Capsid by the Antiviral Compound WIN [15].
  • (E)-(S)-4-((S)-2-{3-[(5-methyl-isoxazole-3-carbonyl)-amino]-2-oxo-2H-pyridin-1-yl}-pent-4-ynoylamino)-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester (Compound 1) is a novel, irreversible inhibitor of human rhinovirus (HRV) 3C protease {inactivation rate constant (Kobs/[I]) of 223,000 M-1s-1} [16].
  • This compound reversed the GBL-induced DOPA synthesis (ED50 values of 5.1 mumol/kg p.o.) and inhibited the APO induced stereotypy (ED50 values of 0.6 mumol/kg p.o.). Compound 28 induced catalepsy at 10 times higher dose than that required for the antagonism of APO-induced stereotypy (ED50 value of 7.8 mumol/kg p.o.) [17].
  • Pretreatment of Compound X (a specific CCR3 antagonist), pertussis toxin, genistein, and wortmannin reduced the MAP kinase phosphorylation and cytokine production [18].

Biological context of Compound

  • We used an intracellular polyglutamine protein aggregation assay based on fluorescence resonance energy transfer (FRET) to identify inhibitors of androgen receptor (AR) aggregation in three libraries of biologically active small molecules: the Annotated Compound Library, the NINDS Custom Collection and a kinase inhibitor collection [19].
  • Alternatively, the physiological substrate H2O2 brings both protons to the active site of HRP, and Compound I is subsequently formed via rearrangement of the proton from the proximal to the distal oxygen atom of the bound peroxide [20].
  • The kinetics of formation and breakdown of the putative active oxygenating intermediate in cytochrome P450, a ferryl-oxo-(pi) porphyrin cation radical (Compound I), have been analyzed in the reaction of a thermostable P450, CYP119, with meta-chloroperoxybenzoic acid (m-CPBA) [21].
  • The inhibition of microsomal G-6-P transport by compound A was associated with inhibition of the rate of glucose output from rat hepatocytes incubated in the presence of 25 nmol/l glucagon (IC50 approximately 320 nmol/l.) Compound A (1 micromol/l) also inhibited the basal rate of glucose production by rat hepatocytes by 47% [22].
  • Furthermore, Compound A and LTB4 induced chemotaxis in primary mouse keratinocytes [23].

Anatomical context of Compound

  • From stopped flow data, the oxidation was concluded to occur by way of two-electron transfer and the rate constant for the reaction of thyroid peroxidase Compound I with thyroglobulin was estimated to be 1.0 X 10(7) M-1 s-1 [24].
  • Cultured rat embryonic skin fibroblasts phagocytosed rat mast cell granules added to the medium or released from co-cultured mast cells by rabbit anti-rat IgE or Compound 48/80 [25].
  • Using a fluorogenic peptide containing an amyloid precursor protein gamma-secretase cleavage site and Compound E, a specific gamma-secretase inhibitor, we found high levels of gamma-secretase activity in renal brush border membrane vesicles [26].
  • Rat eosinophils have been showed to respond chemotactically to the supernatant from mast cells which have been disrupted by freezing and thawing and from mast cells which have been specifically degranulated by Compound 48/80 or by antigen challenge or sensitised cells [27].
  • CPPD crystals also activated the ERK1 and ERK2 forms of MAP kinase (wortmannin insensitive), PKC (Compound 3 sensitive) and protein kinase B (wortmannin sensitive) in neutrophils [28].

Associations of Compound with other chemical compounds

  • In the reaction between equimolar amounts of horseradish peroxidase and chlorite, the native enzyme is oxidized directly to Compound II (Hewson, W.D., and Hager, L.P. (1979) J. Biol. Chem. 254, 3175-3181) [29].
  • Formation of the ferryl (FeIV=O) porphyrin radical cation known as Compound I in the reaction of horseradish peroxidase (HRP) with H2O2 is catalyzed by His-42, a residue that facilitates the binding of H2O2 to the iron and subsequent rupture of the dioxygen bond [30].
  • The highly pH-dependent chemistry of Compound II can be readily demonstrated by the reduction of Compound I, with ferrocyanide at acidic, neutral, and alkaline pH values [29].
  • Resonance Raman spectra of ferrous and ferric cytochrome c peroxidase and Compound ES and their pH dependences were investigated in resonance with Soret band [31].
  • Spectral simulation based on Gaussian analyses and visible bands indicate that H2O2- and TBHP-induced intermediates' spectra of the wild type are close to that of Compound I of horseradish peroxidase, whereas TBHP- and CHP-induced intermediates' spectra of the mutants are close to that of Compound II of horseradish peroxidase [32].

Gene context of Compound

  • In contrast, LPO Compound II is unstable and decays within seconds to ground state, suggesting that SCN- may serve as a substrate for Compound II [33].
  • MPO and EPO Compound II is relatively stable and decays gradually within minutes to ground state upon H2O2 exhaustion [33].
  • We previously found that 2-(2-mercaptoethanol)-3-methyl-1,4-napthoquinone or Compound 5 (Cpd 5), is a Cdc25A protein phosphatase inhibitor and causes prolonged, strong ERK phosphorylation which is triggered by epidermal growth factor receptor (EGFR) activation [34].
  • Preincubation with alphaCGRP(8-37) (10(-7) -10(-5) M) and a novel nonpeptide CGRP antagonist "Compound 1" (WO98/11128) (10(-7)-10(-5) M) caused a dose-dependent rightward shift of the concentration-response curves for alphaCGRP with pA(2) values of 7.0 and 7.1, respectively [35].
  • This was accomplished by treating mice genetically deficient in either LXRalpha or LXRbeta with an agonist with equal potency for both isoforms (Compound B) or a synthetic agonist selective for LXRalpha (Compound A) [36].

Analytical, diagnostic and therapeutic context of Compound


  1. A Novel Molecular Targeting Compound as K-samII/FGF-R2 Phosphorylation Inhibitor, Ki23057, for Scirrhous Gastric Cancer. Nakamura, K., Yashiro, M., Matsuoka, T., Tendo, M., Shimizu, T., Miwa, A., Hirakawa, K. Gastroenterology (2006) [Pubmed]
  2. Activity of bis-carbamoyloxymethyl derivatives of pyrroles and pyrrolizines against human tumor xenografts in nude mice. Anderson, W.K. Cancer Res. (1982) [Pubmed]
  3. Mast cell degranulation, hepatic glycogen depletion, and hyperglycemia in Compound 48/80 or pilocarpine-treated rats. Dimlich, R.V., Townsend, S.F., Reilly, F.D. Hepatology (1982) [Pubmed]
  4. Structure-activity relationships defining the cytotoxicity of catechol analogues against human malignant melanoma. Kern, D.H., Shoemaker, R.H., Hildebrand-Zanki, S.U., Driscoll, J.S. Cancer Res. (1988) [Pubmed]
  5. Enzymes of vitamin B6 degradation. Purification and properties of two N-acetylamidohydrolases. Huynh, M.S., Snell, E.E. J. Biol. Chem. (1985) [Pubmed]
  6. Role of nociceptin and opioid receptor like 1 on entrainment function in the rat suprachiasmatic nucleus. Sugino, T., Shimazoe, T., Ikeda, M., Watanabe, S. Neuroscience (2006) [Pubmed]
  7. Dioxomolybdenum(vi) complexes as catalysts for the hydrosilylation of aldehydes and ketones. Reis, P.M., Romão, C.C., Royo, B. Dalton transactions (Cambridge, England : 2003) (2006) [Pubmed]
  8. A relational perspective on PTSD in early childhood. Scheering, M.S., Zeanah, C.H. Journal of traumatic stress. (2001) [Pubmed]
  9. Mice mutant for Egfr and Shp2 have defective cardiac semilunar valvulogenesis. Chen, B., Bronson, R.T., Klaman, L.D., Hampton, T.G., Wang, J.F., Green, P.J., Magnuson, T., Douglas, P.S., Morgan, J.P., Neel, B.G. Nat. Genet. (2000) [Pubmed]
  10. Formation and toxicity of anesthetic degradation products. Anders, M.W. Annu. Rev. Pharmacol. Toxicol. (2005) [Pubmed]
  11. The late phase of the immediate wheal and flare skin reaction. Its dependence upon IgE antibodies. Solley, G.O., Gleich, G.J., Jordon, R.E., Schroeter, A.L. J. Clin. Invest. (1976) [Pubmed]
  12. Isolation of histamine-containing cells from canine fundic mucosa. Soll, A.H., Lewin, K., Beaven, M.A. Gastroenterology (1979) [Pubmed]
  13. A fully dissociated compound of plant origin for inflammatory gene repression. De Bosscher, K., Vanden Berghe, W., Beck, I.M., Van Molle, W., Hennuyer, N., Hapgood, J., Libert, C., Staels, B., Louw, A., Haegeman, G. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  14. Enzymes of vitamin B6 degradation. Purification and properties of isopyridoxal dehydrogenase and 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic-acid dehydrogenase. Lee, Y.C., Nelson, M.J., Snell, E.E. J. Biol. Chem. (1986) [Pubmed]
  15. VP4 Protein from Human Rhinovirus 14 Is Released by Pressure and Locked in the Capsid by the Antiviral Compound WIN. Gonçalves, R.B., Mendes, Y.S., Soares, M.R., Katpally, U., Smith, T.J., Silva, J.L., Oliveira, A.C. J. Mol. Biol. (2007) [Pubmed]
  16. In vitro antiviral activity and single-dose pharmacokinetics in humans of a novel, orally bioavailable inhibitor of human rhinovirus 3C protease. Patick, A.K., Brothers, M.A., Maldonado, F., Binford, S., Maldonado, O., Fuhrman, S., Petersen, A., Smith, G.J., Zalman, L.S., Burns-Naas, L.A., Tran, J.Q. Antimicrob. Agents Chemother. (2005) [Pubmed]
  17. Novel antipsychotic agents with dopamine autoreceptor agonist properties: synthesis and pharmacology of 7-[4-(4-phenyl-1-piperazinyl)butoxy]-3,4-dihydro-2(1H)-quinolinone derivatives. Oshiro, Y., Sato, S., Kurahashi, N., Tanaka, T., Kikuchi, T., Tottori, K., Uwahodo, Y., Nishi, T. J. Med. Chem. (1998) [Pubmed]
  18. The role of mitogen-activated protein kinases in eotaxin-induced cytokine production from bronchial epithelial cells. Cui, C.H., Adachi, T., Oyamada, H., Kamada, Y., Kuwasaki, T., Yamada, Y., Saito, N., Kayaba, H., Chihara, J. Am. J. Respir. Cell Mol. Biol. (2002) [Pubmed]
  19. Biologically active molecules that reduce polyglutamine aggregation and toxicity. Desai, U.A., Pallos, J., Ma, A.A., Stockwell, B.R., Thompson, L.M., Marsh, J.L., Diamond, M.I. Hum. Mol. Genet. (2006) [Pubmed]
  20. Formation and decay of hydroperoxo-ferric heme complex in horseradish peroxidase studied by cryoradiolysis. Denisov, I.G., Makris, T.M., Sligar, S.G. J. Biol. Chem. (2002) [Pubmed]
  21. Kinetic characterization of compound I formation in the thermostable cytochrome P450 CYP119. Kellner, D.G., Hung, S.C., Weiss, K.E., Sligar, S.G. J. Biol. Chem. (2002) [Pubmed]
  22. Plasma glucose levels are reduced in rats and mice treated with an inhibitor of glucose-6-phosphate translocase. Parker, J.C., VanVolkenburg, M.A., Levy, C.B., Martin, W.H., Burk, S.H., Kwon, Y., Giragossian, C., Gant, T.G., Carpino, P.A., McPherson, R.K., Vestergaard, P., Treadway, J.L. Diabetes (1998) [Pubmed]
  23. Characterization of a mouse second leukotriene B4 receptor, mBLT2: BLT2-dependent ERK activation and cell migration of primary mouse keratinocytes. Iizuka, Y., Yokomizo, T., Terawaki, K., Komine, M., Tamaki, K., Shimizu, T. J. Biol. Chem. (2005) [Pubmed]
  24. Iodination and oxidation of thyroglobulin catalyzed by thyroid peroxidase. Nakamura, M., Yamazaki, I., Nakagawa, H., Ohtaki, S., Ui, N. J. Biol. Chem. (1984) [Pubmed]
  25. Phagocytosis of mast cell granules by cultured fibroblasts. Subba Rao, P.V., Friedman, M.M., Atkins, F.M., Metcalfe, D.D. J. Immunol. (1983) [Pubmed]
  26. Linking receptor-mediated endocytosis and cell signaling: evidence for regulated intramembrane proteolysis of megalin in proximal tubule. Zou, Z., Chung, B., Nguyen, T., Mentone, S., Thomson, B., Biemesderfer, D. J. Biol. Chem. (2004) [Pubmed]
  27. An eosinophilotactic factor derived from rat mast cells. Mann, P.R., Cruickshank, C.N. J. Pathol. (1975) [Pubmed]
  28. Activation of S6 kinase in human neutrophils by calcium pyrophosphate dihydrate crystals: protein kinase C-dependent and phosphatidylinositol-3-kinase-independent pathways. Tudan, C., Jackson, J.K., Charlton, L., Pelech, S.L., Sahl, B., Burt, H.M. Biochem. J. (1998) [Pubmed]
  29. Oxidation of horseradish peroxidase compound II to compound I. Hewson, W.D., Hager, L.P. J. Biol. Chem. (1979) [Pubmed]
  30. Rescue of His-42 --> Ala horseradish peroxidase by a Phe-41 --> His mutation. Engineering of a surrogate catalytic histidine. Savenkova, M.I., Newmyer, S.L., Montellano, P.R. J. Biol. Chem. (1996) [Pubmed]
  31. Resonance Raman study on cytochrome c peroxidase and its intermediate. Presence of the Fe(IV) = O bond in compound ES and heme-linked ionization. Hashimoto, S., Teraoka, J., Inubushi, T., Yonetani, T., Kitagawa, T. J. Biol. Chem. (1986) [Pubmed]
  32. Glu318 and Thr319 mutations of cytochrome P450 1A2 remarkably enhance homolytic O-O cleavage of alkyl hydroperoxides. An optical absorption spectral study. Shimizu, T., Murakami, Y., Hatano, M. J. Biol. Chem. (1994) [Pubmed]
  33. Thiocyanate modulates the catalytic activity of mammalian peroxidases. Tahboub, Y.R., Galijasevic, S., Diamond, M.P., Abu-Soud, H.M. J. Biol. Chem. (2005) [Pubmed]
  34. Cdc25A and ERK interaction: EGFR-independent ERK activation by a protein phosphatase Cdc25A inhibitor, compound 5. Wang, Z., Zhang, B., Wang, M., Carr, B.I. J. Cell. Physiol. (2005) [Pubmed]
  35. Investigation of CGRP receptors and peptide pharmacology in human coronary arteries. Characterization with a nonpeptide antagonist. Hasbak, P., Saetrum Opgaard, O., Eskesen, K., Schifter, S., Arendrup, H., Longmore, J., Edvinsson, L. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  36. Different roles of liver X receptor alpha and beta in lipid metabolism: effects of an alpha-selective and a dual agonist in mice deficient in each subtype. Lund, E.G., Peterson, L.B., Adams, A.D., Lam, M.H., Burton, C.A., Chin, J., Guo, Q., Huang, S., Latham, M., Lopez, J.C., Menke, J.G., Milot, D.P., Mitnaul, L.J., Rex-Rabe, S.E., Rosa, R.L., Tian, J.Y., Wright, S.D., Sparrow, C.P. Biochem. Pharmacol. (2006) [Pubmed]
  37. Sulfonamide anilides, a novel class of histone deacetylase inhibitors, are antiproliferative against human tumors. Fournel, M., Trachy-Bourget, M.C., Yan, P.T., Kalita, A., Bonfils, C., Beaulieu, C., Frechette, S., Leit, S., Abou-Khalil, E., Woo, S.H., Delorme, D., MacLeod, A.R., Besterman, J.M., Li, Z. Cancer Res. (2002) [Pubmed]
  38. Reduced affinity for Isoniazid in the S315T mutant of Mycobacterium tuberculosis KatG is a key factor in antibiotic resistance. Yu, S., Girotto, S., Lee, C., Magliozzo, R.S. J. Biol. Chem. (2003) [Pubmed]
  39. A Cdc25A antagonizing K vitamin inhibits hepatocyte DNA synthesis in vitro and in vivo. Carr, B.I., Wang, Z., Wang, M., Kar, S., Wilcox, C.S., Rosi, K., Southwick, E., Lazo, J.S. J. Mol. Biol. (2003) [Pubmed]
  40. High-resolution crystal structures and spectroscopy of native and compound I cytochrome c peroxidase. Bonagura, C.A., Bhaskar, B., Shimizu, H., Li, H., Sundaramoorthy, M., McRee, D.E., Goodin, D.B., Poulos, T.L. Biochemistry (2003) [Pubmed]
  41. Involvement of the alpha subunit of farnesyl-protein transferase in substrate recognition. Pellicena, P., Scholten, J.D., Zimmerman, K., Creswell, M., Huang, C.C., Miller, W.T. Biochemistry (1996) [Pubmed]
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