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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

imidogen     $l^{1}-azane

Synonyms: Aminylene, Azanylene, azanediyl, nitrene, azanylidene, ...
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Disease relevance of azanylidene

  • We have developed a novel monoclonal antibody against the NH(2) terminus of the human Wnt-2 ligand that induces apoptosis in human melanoma cells overexpressing Wnt-2 [1].
  • The association between the NH(2) terminus of VEGFR-3, containing the peptide identified by phage display, and the COOH terminus of FAK was detected by in vitro and in vivo binding studies [2].
  • The monoclonal antibody 1F6 identifies a pH-dependent conformational change in the hydrophilic NH(2) terminus of NhaA Na(+)/H(+) antiporter of Escherichia coli [3].
  • Evidence is presented here that effective nucleation is possible at both ends of the collagen-like peptide (Gly-Pro-Pro)(10), using designed proteins in which this peptide is fused either NH(2)- or COOH-terminal to a nucleation domain, either T4-phage foldon or the disulfide knot of type III collagen [4].
  • All polymorphs have the trans-trans-trans conformation of the N-N-C-C-N-N backbone, but the positions of the hydrogen atoms of the NH(2) groups relative to this backbone differ between the different polymorphs through variation of the torsion angle around each NH-NH(2) bond [5].

High impact information on azanylidene

  • (2) Cavities in the interface between TBP and the minor-groove face of the AdMLP TATA box accommodate the exocyclic NH(2) groups of G in a TACA box and in a TATAAG box [6].
  • We report that the human TP73 gene generates an NH(2) terminally truncated isoform [7].
  • A peptide based on the NH(2) terminus of the C5aR and sulfated at these two tyrosines, but not its unsulfated analogue or a doubly sulfated control peptide, partially inhibited C5a association with its receptor [8].
  • An N-acetylated natural ligand of human histocompatibility leukocyte antigen (HLA)-B39. Classical major histocompatibility complex class I proteins bind peptides with a blocked NH(2) terminus in vivo [9].
  • Its product, podocin, is a new member of the stomatin family, which consists of hairpin-like integral membrane proteins with intracellular NH(2)- and COOH-termini [10].

Chemical compound and disease context of azanylidene


Biological context of azanylidene

  • Sequence-independent interactions involving the free peptidic NH(2) terminus are thought to be an essential feature of peptide binding to classical major histocompatibility complex (MHC) class I proteins [9].
  • In vitro analysis revealed that NH(2)- and COOH-terminal truncations of Op18 have opposite effects on the rates of tubulin GTP hydrolysis [12].
  • The overexpression of tagged cDNA constructs in keratinocytes revealed that the NH(2) terminus is essential for the nuclear localization, while the central domain is responsible for the interaction with EB1 and for the phenotype of transfected keratinocytes similar to terminal differentiation [13].
  • A repeated sequence motif [EEX(4)](8) at the NH(2) terminus of RAP46 or BAG-1L, a larger isoform of RAP46, is responsible for this downregulation of GR activity [14].
  • Although hVam6p exhibits homology to the Saccharomyces cerevisiae vacuolar protein sorting gene product Vam6p/Vps39p, the presence of a citron homology (CNH) domain at the NH(2) terminus is unique to the human protein [15].

Anatomical context of azanylidene

  • Ugo1p appears to contain a single transmembrane segment, with its NH(2) terminus facing the cytosol and its COOH terminus in the intermembrane space [16].
  • The recruitment of KHC to mitochondria is, in part, determined by the NH(2) terminus-splicing variant of milton [17].
  • Overexpressing the entire N2-B region or its NH(2) terminus in cardiac myocytes greatly disrupted thin filament, but not thick filament structure [18].
  • Like the NH(2) terminus of desmoplakin, that of periplakin localized to desmosomes; however, in addition, the periplakin NH(2) terminus accumulated at cell surface microvilli in association with cortical actin [19].
  • We determined the responses to thrombin, which activates intracellular signaling in endothelial cells by cleaving the NH(2) terminus of the G protein-coupled proteinase-activated receptor-1 (PAR-1) [20].

Associations of azanylidene with other chemical compounds

  • Here, we characterize a new member of the family, beta-netrin. beta-Netrin is homologous to the NH(2) terminus of laminin chain short arms; it contains a laminin-like domain VI and 3.5 laminin EGF repeats and a netrin C domain [21].
  • We find that the carbonyl oxygen on the backbone of the arginine finger supplied in trans by p120GAP (Arg-789) interacts with a water molecule in the active site that is forming a bridge between the NH(2) group of the Gln-61 and the gamma-phosphate of GTP [22].
  • Different HhH cassettes fused with either NH(2) terminus or COOH terminus of DNA polymerases broaden the salt concentration range of the polymerase activity significantly (up to 0.5 M NaCl or 1.8 M potassium glutamate) [23].
  • The NH(2) terminus of MKP-1 was also found to inhibit the activation of the serum response element (SRE) by preventing MAPK-mediated phosphorylation of the regulatory serine 383 residue on Elk-1 [24].
  • Intramolecular NH(2)- and COOH-terminal binding, which occurs when merlin transitions to the growth-suppressive form, also brings about a similar change in buoyant density [25].

Gene context of azanylidene

  • The Sec2p NH(2) terminus encodes an exchange factor for the Rab protein Sec4p [26].
  • Regulated overexpression of the NH(2) terminus of SNX1 containing the PX domain decreased the rate of ligand-induced epidermal growth factor receptor degradation, an effect consistent with inhibition of endogenous SNX1 function in the endosome compartment [27].
  • These findings demonstrate that ERK3 is conjugated to ubiquitin via its free NH(2) terminus [28].
  • Immunocytochemistry of expressed full-length and deletion mutants of BRCA1 showed that the NH(2) terminus of BRCA1 is important for nuclear dot formation in S-phase [29].
  • CDK2-cyclin A1/E1 and CDK1-cyclin B1 phosphorylate BARD1 on its NH(2) terminus in vivo and in vitro [30].

Analytical, diagnostic and therapeutic context of azanylidene

  • By using scanning force microscopy and fluorescence resonance energy transfer-based experiments we provide evidence for an intramolecular interaction between the NH(2) and COOH termini of CLIP-170 [31].
  • When a yeast two-hybrid assay is used, deletion analysis of the interacting domain on Vsx-1 shows that Ubc9 binds to a nuclear localization signal (NLS) at the NH(2) terminus of the homeodomain [32].
  • Complete sequence analysis revealed no other similarities with TSP1, but identified unique signal sequences, as well as metalloprotease and disintegrin-like domains in the NH(2) termini [33].
  • The epitope of mAb 1F6 was located at the NH(2) terminus of NhaA by probing proteolytic fragments in Western blot analysis and amino acid sequencing [3].
  • Competition/association assays and site-directed mutagenesis of the NH(2) terminus of p57(Kip2) identified the intermediate alpha-helix domain, located between the Cdk and the cyclin binding sites, as essential for MyoD interaction [34].


  1. An anti-Wnt-2 monoclonal antibody induces apoptosis in malignant melanoma cells and inhibits tumor growth. You, L., He, B., Xu, Z., Uematsu, K., Mazieres, J., Fujii, N., Mikami, I., Reguart, N., McIntosh, J.K., Kashani-Sabet, M., McCormick, F., Jablons, D.M. Cancer Res. (2004) [Pubmed]
  2. Vascular endothelial growth factor receptor-3 and focal adhesion kinase bind and suppress apoptosis in breast cancer cells. Garces, C.A., Kurenova, E.V., Golubovskaya, V.M., Cance, W.G. Cancer Res. (2006) [Pubmed]
  3. The monoclonal antibody 1F6 identifies a pH-dependent conformational change in the hydrophilic NH(2) terminus of NhaA Na(+)/H(+) antiporter of Escherichia coli. Venturi, M., Rimon, A., Gerchman, Y., Hunte, C., Padan, E., Michel, H. J. Biol. Chem. (2000) [Pubmed]
  4. Collagen triple helix formation can be nucleated at either end. Frank, S., Boudko, S., Mizuno, K., Schulthess, T., Engel, J., Bächinger, H.P. J. Biol. Chem. (2003) [Pubmed]
  5. Abundant polymorphism in a system with multiple hydrogen-bonding opportunities: oxalyl dihydrazide. Ahn, S., Guo, F., Kariuki, B.M., Harris, K.D. J. Am. Chem. Soc. (2006) [Pubmed]
  6. TATA element recognition by the TATA box-binding protein has been conserved throughout evolution. Patikoglou, G.A., Kim, J.L., Sun, L., Yang, S.H., Kodadek, T., Burley, S.K. Genes Dev. (1999) [Pubmed]
  7. DeltaNp73, a dominant-negative inhibitor of wild-type p53 and TAp73, is up-regulated in human tumors. Zaika, A.I., Slade, N., Erster, S.H., Sansome, C., Joseph, T.W., Pearl, M., Chalas, E., Moll, U.M. J. Exp. Med. (2002) [Pubmed]
  8. Sulfated tyrosines contribute to the formation of the C5a docking site of the human C5a anaphylatoxin receptor. Farzan, M., Schnitzler, C.E., Vasilieva, N., Leung, D., Kuhn, J., Gerard, C., Gerard, N.P., Choe, H. J. Exp. Med. (2001) [Pubmed]
  9. An N-acetylated natural ligand of human histocompatibility leukocyte antigen (HLA)-B39. Classical major histocompatibility complex class I proteins bind peptides with a blocked NH(2) terminus in vivo. Yagüe, J., Alvarez, I., Rognan, D., Ramos, M., Vázquez, J., de Castro, J.A. J. Exp. Med. (2000) [Pubmed]
  10. Podocin, a raft-associated component of the glomerular slit diaphragm, interacts with CD2AP and nephrin. Schwarz, K., Simons, M., Reiser, J., Saleem, M.A., Faul, C., Kriz, W., Shaw, A.S., Holzman, L.B., Mundel, P. J. Clin. Invest. (2001) [Pubmed]
  11. Effect of biomaterial surface properties on fibronectin-alpha5beta1 integrin interaction and cellular attachment. Lee, M.H., Ducheyne, P., Lynch, L., Boettiger, D., Composto, R.J. Biomaterials (2006) [Pubmed]
  12. Op18/stathmin mediates multiple region-specific tubulin and microtubule-regulating activities. Larsson, N., Segerman, B., Howell, B., Fridell, K., Cassimeris, L., Gullberg, M. J. Cell Biol. (1999) [Pubmed]
  13. Ubinuclein, a novel nuclear protein interacting with cellular and viral transcription factors. Aho, S., Buisson, M., Pajunen, T., Ryoo, Y.W., Giot, J.F., Gruffat, H., Sergeant, A., Uitto, J. J. Cell Biol. (2000) [Pubmed]
  14. A nuclear action of the eukaryotic cochaperone RAP46 in downregulation of glucocorticoid receptor activity. Schneikert, J., Hübner, S., Martin, E., Cato, A.C. J. Cell Biol. (1999) [Pubmed]
  15. Human Vam6p promotes lysosome clustering and fusion in vivo. Caplan, S., Hartnell, L.M., Aguilar, R.C., Naslavsky, N., Bonifacino, J.S. J. Cell Biol. (2001) [Pubmed]
  16. UGO1 encodes an outer membrane protein required for mitochondrial fusion. Sesaki, H., Jensen, R.E. J. Cell Biol. (2001) [Pubmed]
  17. Axonal transport of mitochondria requires milton to recruit kinesin heavy chain and is light chain independent. Glater, E.E., Megeath, L.J., Stowers, R.S., Schwarz, T.L. J. Cell Biol. (2006) [Pubmed]
  18. I-band titin in cardiac muscle is a three-element molecular spring and is critical for maintaining thin filament structure. Linke, W.A., Rudy, D.E., Centner, T., Gautel, M., Witt, C., Labeit, S., Gregorio, C.C. J. Cell Biol. (1999) [Pubmed]
  19. Subcellular distribution of envoplakin and periplakin: insights into their role as precursors of the epidermal cornified envelope. DiColandrea, T., Karashima, T., Määttä, A., Watt, F.M. J. Cell Biol. (2000) [Pubmed]
  20. G protein-coupled receptor kinase-5 regulates thrombin-activated signaling in endothelial cells. Tiruppathi, C., Yan, W., Sandoval, R., Naqvi, T., Pronin, A.N., Benovic, J.L., Malik, A.B. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  21. A novel member of the netrin family, beta-netrin, shares homology with the beta chain of laminin: identification, expression, and functional characterization. Koch, M., Murrell, J.R., Hunter, D.D., Olson, P.F., Jin, W., Keene, D.R., Brunken, W.J., Burgeson, R.E. J. Cell Biol. (2000) [Pubmed]
  22. The arginine finger of RasGAP helps Gln-61 align the nucleophilic water in GAP-stimulated hydrolysis of GTP. Resat, H., Straatsma, T.P., Dixon, D.A., Miller, J.H. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  23. Helix-hairpin-helix motifs confer salt resistance and processivity on chimeric DNA polymerases. Pavlov, A.R., Belova, G.I., Kozyavkin, S.A., Slesarev, A.I. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  24. The noncatalytic amino terminus of mitogen-activated protein kinase phosphatase 1 directs nuclear targeting and serum response element transcriptional regulation. Wu, J.J., Zhang, L., Bennett, A.M. Mol. Cell. Biol. (2005) [Pubmed]
  25. Activation of the tumor suppressor merlin modulates its interaction with lipid rafts. Stickney, J.T., Bacon, W.C., Rojas, M., Ratner, N., Ip, W. Cancer Res. (2004) [Pubmed]
  26. The role of the COOH terminus of Sec2p in the transport of post-Golgi vesicles. Elkind, N.B., Walch-Solimena, C., Novick, P.J. J. Cell Biol. (2000) [Pubmed]
  27. Endosomal localization and function of sorting nexin 1. Zhong, Q., Lazar, C.S., Tronchère, H., Sato, T., Meerloo, T., Yeo, M., Songyang, Z., Emr, S.D., Gill, G.N. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  28. N-Terminal ubiquitination of extracellular signal-regulated kinase 3 and p21 directs their degradation by the proteasome. Coulombe, P., Rodier, G., Bonneil, E., Thibault, P., Meloche, S. Mol. Cell. Biol. (2004) [Pubmed]
  29. The BRCA1 and BARD1 association with the RNA polymerase II holoenzyme. Chiba, N., Parvin, J.D. Cancer Res. (2002) [Pubmed]
  30. Down-regulation of BRCA1-BARD1 ubiquitin ligase by CDK2. Hayami, R., Sato, K., Wu, W., Nishikawa, T., Hiroi, J., Ohtani-Kaneko, R., Fukuda, M., Ohta, T. Cancer Res. (2005) [Pubmed]
  31. Conformational changes in CLIP-170 regulate its binding to microtubules and dynactin localization. Lansbergen, G., Komarova, Y., Modesti, M., Wyman, C., Hoogenraad, C.C., Goodson, H.V., Lemaitre, R.P., Drechsel, D.N., van Munster, E., Gadella, T.W., Grosveld, F., Galjart, N., Borisy, G.G., Akhmanova, A. J. Cell Biol. (2004) [Pubmed]
  32. Ubc9 interacts with a nuclear localization signal and mediates nuclear localization of the paired-like homeobox protein Vsx-1 independent of SUMO-1 modification. Kurtzman, A.L., Schechter, N. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  33. METH-1, a human ortholog of ADAMTS-1, and METH-2 are members of a new family of proteins with angio-inhibitory activity. Vázquez, F., Hastings, G., Ortega, M.A., Lane, T.F., Oikemus, S., Lombardo, M., Iruela-Arispe, M.L. J. Biol. Chem. (1999) [Pubmed]
  34. Stabilization of MyoD by direct binding to p57(Kip2). Reynaud, E.G., Leibovitch, M.P., Tintignac, L.A., Pelpel, K., Guillier, M., Leibovitch, S.A. J. Biol. Chem. (2000) [Pubmed]
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