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Chemical Compound Review

Bipyridyl     2-pyridin-2-ylpyridine

Synonyms: dipyridyl, Bipyridine, Umdipyridyl, Bipy, 2,2-Bipyridine, ...
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Disease relevance of 2,2'-BIPYRIDINE


High impact information on 2,2'-BIPYRIDINE

  • The injury was prevented by catalase which removes H2O2 and by cell-permeable, metal-chelating agents such as desferrioxamine or bipyridine [6].
  • Pulse label and chase experiments revealed that coprecipitated procollagen was detectable as long as procollagen was present in the endoplasmic reticulum of alpha,alpha'-dipyridyl-treated cells [7].
  • When cells were heat shocked, or when stable triple-helix formation was inhibited by treatment with alpha,alpha'-dipyridyl, coprecipitation of procollagen with HSP47 was increased [7].
  • Fur recently was found to regulate hmp in Salmonella typhimurium, and in Escherichia coli, the iron-chelating agent 2,2'-dipyridyl induces hmp expression [8].
  • In addition, we demonstrate that the binding of DtxR to a diphtheria tox promoter/operator probe requires the addition of Mn2+ to the reaction mixture; however, binding may be blocked by addition of the chelator 2,2'-dipyridyl, anti-DtxR antiserum, and excess unlabeled probe to the reaction mixture [9].

Chemical compound and disease context of 2,2'-BIPYRIDINE


Biological context of 2,2'-BIPYRIDINE


Anatomical context of 2,2'-BIPYRIDINE

  • Although the bipyridine agent amrinone is reported to have a positive inotropic effect on the left ventricle, the effect of this drug on right ventricular contractility in the clinical setting is unknown [20].
  • When unhydroxylated collagen produced by normal control and OI fibroblasts incubated with alpha,alpha'-dipyridyl was examined, mutant OI molecules melted at a lower temperature than control [21].
  • The reactions of the hemoprotein with hydroperoxides are inhibited by alpha,alpha'-dipyridyl and aniline, with which pea microsomes form binding spectra [22].
  • Preexposure of mouse inflammatory peritoneal macrophages to either DHP (0.5 to 2.5 mM) or 2,2'-dipyridyl (0.1 to 0.3 mM) for 24 h produced a dose-related suppression of their response to activation by lipid A to mediate tumor cytotoxicity of L1210 mouse leukemia targets [23].
  • The cytotoxic effects of 2,2'-dipyridyl on several leukemia cell lines have been reported, and a potent teratogenic effect of 2,2'-dipyridyl has been observed in rats [24].

Associations of 2,2'-BIPYRIDINE with other chemical compounds


Gene context of 2,2'-BIPYRIDINE

  • The tyrosine phosphatase inhibitor, potassium bisperoxo (bipyridine) oxovanadate V, normalizes the growth rate of PRL-3 expressing cells to that of parental HEK293 cells in a concentration-dependent manner [30].
  • To determine whether the aerobic and anaerobic respiratory pathways of Escherichia coli are regulated in response to iron availability, strains containing lacZ reporter fusions to the cydAB, cyoABCDE, narGHJI, dmsABC and frdABCD operons were grown in medium limited for iron by use of the chelator, 2,2'-dipyridyl [31].
  • To determine if these post-translational modifications contribute to the functional integrity of human protein S (HPS), recombinant human protein S lacking Hya and Hyn (rHPSdesHya/Hyn) was purified from the medium of human kidney 293 cells that were transfected with HPS cDNA and grown in the presence of the hydroxylase inhibitor 2,2'-dipyridyl [32].
  • We examined the effects of the inhibitors of C1q or collagen biosynthesis, 2,2'-dipyridyl (DP), and 3,4-dehydro-DL-proline (DHP) on murine macrophage (M phi) FcR subclass-mediated antibody-dependent cellular cytotoxicity (ADCC) and phagocytosis of sheep erythrocyte targets [33].
  • The SP-D translation product migrated faster than the major cellular form of SP-D but approximately 1 kDa slower than cellular SP-D synthesized in the presence of 2,2'-dipyridyl plus tunicamycin [34].

Analytical, diagnostic and therapeutic context of 2,2'-BIPYRIDINE

  • In the case of the bipyridine tripeptides, the titration stoichiometry and mass spectra indicate that the metal ions form interstrand cross-links between two oligopeptides, creating duplex structures linked exclusively by metal ions [35].
  • Self-assembled M(6)L(4)-type coordination nanocage with 2,2'-bipyridine ancillary ligands. Facile crystallization and X-ray analysis of shape-selective enclathration of neutral guests in the cage [36].
  • The two-dimensional ordering of a number of 2,2'-bipyridine derivatives at the liquid/solid interface has been investigated by scanning tunneling microscopy [37].
  • Topical application of NG-methyl-L-arginine and 2,2'-dipyridyl were used to examine the respective roles of nitric oxide and reactive oxygen species in solar-simulated ultraviolet radiation-induced immunosuppression in humans in vivo [38].
  • Liposomes ( approximately 100-nm diameter) containing Ru(bpy)32+ (bpy = 2,2'-bipyridine) were prepared as an electrogenerated chemiluminescent (ECL) tag for a sandwich-type immunoassay of human C-reactive protein (CRP) [39].


  1. Evaluation of a new bipyridine inotropic agent--milrinone--in patients with severe congestive heart failure. Baim, D.S., McDowell, A.V., Cherniles, J., Monrad, E.S., Parker, J.A., Edelson, J., Braunwald, E., Grossman, W. N. Engl. J. Med. (1983) [Pubmed]
  2. Use of site-directed mutagenesis to identify an upstream regulatory sequence of sodA gene of Escherichia coli K-12. Naik, S.M., Hassan, H.M. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  3. Effects of milrinone on left ventricular performance and myocardial contractility in patients with severe heart failure. Sonnenblick, E.H., Grose, R., Strain, J., Zelcer, A.A., LeJemtel, T.H. Circulation (1986) [Pubmed]
  4. Developmental changes in the cardiac effects of amrinone in the dog. Binah, O., Legato, M.J., Danilo, P., Rosen, M.R. Circ. Res. (1983) [Pubmed]
  5. Cloning and sequence analysis of an EnvCD homologue in Pseudomonas aeruginosa: regulation by iron and possible involvement in the secretion of the siderophore pyoverdine. Poole, K., Heinrichs, D.E., Neshat, S. Mol. Microbiol. (1993) [Pubmed]
  6. Nitroxide stable radicals protect beating cardiomyocytes against oxidative damage. Samuni, A., Winkelsberg, D., Pinson, A., Hahn, S.M., Mitchell, J.B., Russo, A. J. Clin. Invest. (1991) [Pubmed]
  7. Involvement of the stress protein HSP47 in procollagen processing in the endoplasmic reticulum. Nakai, A., Satoh, M., Hirayoshi, K., Nagata, K. J. Cell Biol. (1992) [Pubmed]
  8. Direct inhibition by nitric oxide of the transcriptional ferric uptake regulation protein via nitrosylation of the iron. D'Autreaux, B., Touati, D., Bersch, B., Latour, J.M., Michaud-Soret, I. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  9. Specific binding of the diphtheria tox regulatory element DtxR to the tox operator requires divalent heavy metal ions and a 9-base-pair interrupted palindromic sequence. Tao, X., Boyd, J., Murphy, J.R. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  10. Improvement in indexes of diastolic performance in patients with congestive heart failure treated with milrinone. Monrad, E.S., McKay, R.G., Baim, D.S., Colucci, W.S., Fifer, M.A., Heller, G.V., Royal, H.D., Grossman, W. Circulation (1984) [Pubmed]
  11. Ferrous ion autoxidation and its chelation in iron-loaded human liver HepG2 cells. Huang, X., Dai, J., Fournier, J., Ali, A.M., Zhang, Q., Frenkel, K. Free Radic. Biol. Med. (2002) [Pubmed]
  12. Elimination of retroviral infectivity by N-ethylmaleimide with preservation of functional envelope glycoproteins. Morcock, D.R., Thomas, J.A., Gagliardi, T.D., Gorelick, R.J., Roser, J.D., Chertova, E.N., Bess, J.W., Ott, D.E., Sattentau, Q.J., Frank, I., Pope, M., Lifson, J.D., Henderson, L.E., Crise, B.J. J. Virol. (2005) [Pubmed]
  13. Inactivation of Aeromonas hydrophila by Fe(II)-related-radical generation in oxidizing groundwaters. Kersters, I., Verstraete, W. Appl. Environ. Microbiol. (1996) [Pubmed]
  14. Hydroxamate-mediated transport of iron controlled by ColV plasmids. Stuart, S.J., Greenwood, K.T., Luke, R.K. J. Bacteriol. (1980) [Pubmed]
  15. Reduced secretion of structurally abnormal type I procollagen in a form of osteogenesis imperfecta. Barsh, G.S., Byers, P.H. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  16. Evidence that an iron chelator regulates collagen synthesis by decreasing the stability of procollagen mRNA. Ikeda, H., Wu, G.Y., Wu, C.H. Hepatology (1992) [Pubmed]
  17. Labeling of cysteine 231 in acetylcholinesterase from Torpedo nobiliana by the active-site directed reagent, 1-bromo-2-[14C] pinacolone. Effects of 2,2'-dipyridyl disulfide and other sulfhydryl reagents. Salih, E., Howard, S., Chishti, S.B., Cohen, S.G., Liu, W.S., Cohen, J.B. J. Biol. Chem. (1993) [Pubmed]
  18. NapF is a cytoplasmic iron-sulfur protein required for Fe-S cluster assembly in the periplasmic nitrate reductase. Olmo-Mira, M.F., Gavira, M., Richardson, D.J., Castillo, F., Moreno-Vivián, C., Roldán, M.D. J. Biol. Chem. (2004) [Pubmed]
  19. Post-translational modifications of the core-specific lectin. Relationship to assembly, ligand binding, and secretion. Colley, K.J., Baenziger, J.U. J. Biol. Chem. (1987) [Pubmed]
  20. Effect of amrinone on right ventricular function: predominance of afterload reduction. Konstam, M.A., Cohen, S.R., Salem, D.N., Das, D., Aronovitz, M.J., Brockway, B.A. Circulation (1986) [Pubmed]
  21. Decreased thermal denaturation temperature of osteogenesis imperfecta mutant collagen is independent of post-translational overmodifications of lysine and hydroxylysine. Rao, V.H., Steinmann, B., de Wet, W., Hollister, D.W. J. Biol. Chem. (1989) [Pubmed]
  22. The carbon monoxide-binding hemoprotein reducible by hydrogen peroxide in microsomal fractions of pea seeds. Ishimaru, A., Yamazaki, I. J. Biol. Chem. (1977) [Pubmed]
  23. Inhibitors of C1q biosynthesis suppress activation of murine macrophages for both antibody-independent and antibody-dependent tumor cytotoxicity. Leu, R.W., Zhou, A.Q., Shannon, B.J., Herriott, M.J. J. Immunol. (1990) [Pubmed]
  24. Toxicity of dipyridyl compounds and related compounds. Li, S., Crooks, P.A., Wei, X., de Leon, J. Crit. Rev. Toxicol. (2004) [Pubmed]
  25. Ferritin and superoxide-dependent lipid peroxidation. Thomas, C.E., Morehouse, L.A., Aust, S.D. J. Biol. Chem. (1985) [Pubmed]
  26. Folding of carboxyl domain and assembly of procollagen I. Doege, K.J., Fessler, J.H. J. Biol. Chem. (1986) [Pubmed]
  27. Structural and catalytic properties of copper in lysyl oxidase. Gacheru, S.N., Trackman, P.C., Shah, M.A., O'Gara, C.Y., Spacciapoli, P., Greenaway, F.T., Kagan, H.M. J. Biol. Chem. (1990) [Pubmed]
  28. A luminescence sensor of inositol 1,4,5-triphosphate and its model compound by ruthenium-templated assembly of a bis(Zn2+-cyclen) complex having a 2,2'-bipyridyl linker (cyclen = 1,4,7,10-tetraazacyclododecane). Aoki, S., Zulkefeli, M., Shiro, M., Kohsako, M., Takeda, K., Kimura, E. J. Am. Chem. Soc. (2005) [Pubmed]
  29. Photoinduced energy- and electron-transfer processes within dynamic self-assembled donor-acceptor arrays. Kercher, M., König, B., Zieg, H., De Cola, L. J. Am. Chem. Soc. (2002) [Pubmed]
  30. Role of PRL-3, a human muscle-specific tyrosine phosphatase, in angiotensin-II signaling. Matter, W.F., Estridge, T., Zhang, C., Belagaje, R., Stancato, L., Dixon, J., Johnson, B., Bloem, L., Pickard, T., Donaghue, M., Acton, S., Jeyaseelan, R., Kadambi, V., Vlahos, C.J. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  31. The effect of iron limitation on expression of the aerobic and anaerobic electron transport pathway genes in Escherichia coli. Cotter, P.A., Darie, S., Gunsalus, R.P. FEMS Microbiol. Lett. (1992) [Pubmed]
  32. beta-Hydroxyaspartic acid and beta-hydroxyasparagine residues in recombinant human protein S are not required for anticoagulant cofactor activity or for binding to C4b-binding protein. Nelson, R.M., VanDusen, W.J., Friedman, P.A., Long, G.L. J. Biol. Chem. (1991) [Pubmed]
  33. Effects of inhibitors of C1q biosynthesis on macrophage Fc receptor subclass-mediated antibody-dependent cellular cytotoxicity and phagocytosis. Mocharla, R., Mocharla, H., Leu, R.W. Cell. Immunol. (1987) [Pubmed]
  34. Primary translation products of pulmonary surfactant protein D. Crouch, E., Rust, K., Persson, A., Mariencheck, W., Moxley, M., Longmore, W. Am. J. Physiol. (1991) [Pubmed]
  35. Artificial oligopeptide scaffolds for stoichiometric metal binding. Gilmartin, B.P., Ohr, K., McLaughlin, R.L., Koerner, R., Williams, M.E. J. Am. Chem. Soc. (2005) [Pubmed]
  36. Self-assembled M(6)L(4)-type coordination nanocage with 2,2'-bipyridine ancillary ligands. Facile crystallization and X-ray analysis of shape-selective enclathration of neutral guests in the cage. Kusukawa, T., Fujita, M. J. Am. Chem. Soc. (2002) [Pubmed]
  37. Metal ion complexation: a route to 2 D templates? De Feyter, S., Abdel-Mottaleb, M.M., Schuurmans, N., Verkuijl, B.J., van Esch, J.H., Feringa, B.L., De Schryver, F.C. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  38. Nitric oxide appears to be a mediator of solar-simulated ultraviolet radiation-induced immunosuppression in humans. Kuchel, J.M., Barnetson, R.S., Halliday, G.M. J. Invest. Dermatol. (2003) [Pubmed]
  39. Electrogenerated chemiluminescence. 83. Immunoassay of human C-reactive protein by using Ru(bpy)3(2+)-encapsulated liposomes as labels. Zhan, W., Bard, A.J. Anal. Chem. (2007) [Pubmed]
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