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Chemical Compound Review

MOLI001910     guanidine

Synonyms: AC1L9PJM
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Disease relevance of guanidine

  • HBB alone also protects Coxsackie A 9, but not echo virus 9-infected animals, whereas guanidine alone is ineffective in either case [1].
  • Guanidine alkaloid analogs as inhibitors of HIV-1 Nef interactions with p53, actin, and p56lck [2].
  • Purified capsids from which VP26 had been removed in vitro by treatment with guanidine hydrochloride were compared with preparations of the same depleted capsids to which purified VP26 had been rebound and with native (undepleted) capsids [3].
  • Analysis of dark-field scanning transmission electron micrographs of unstained freeze-dried specimens established that the interior of the intact bacteriophage T4 tail tube contains extra density that is missing in tubes artificially emptied by treatment with 3 M guanidine hydrochloride [4].
  • Ssb depletion also decreases toxicity of the overproduced Sup35 and causes extreme sensitivity to the [PSI]-curing chemical agent guanidine hydrochloride [5].

Psychiatry related information on guanidine


High impact information on guanidine

  • Extensive cytoskeleton alterations occur even when guanidine inhibits viral replication, and thus result from small amounts of early viral products [9].
  • The adapter protein CrkL was associated with both phosphorylated Cbl and the guanidine nucleotide-releasing factor C3G, which catalyzes guanosine triphosphate (GTP) exchange on Rap1 [10].
  • Ligation was performed in 6 molar guanidine hydrochloride, thus circumventing limited solubility of protected peptide segments, the principal problem of the classical approach to the chemical synthesis of proteins [11].
  • Gel filtration on Sephadex G100 after solubilization in 5 M guanidine HCl yielded three major components with 14,000, 9,000, and 5,000 mol wt, respectively [12].
  • One allele of his TTF1 gene had a guanidine inserted into codon 86 producing a nonsense protein of 407, rather than 371, amino acids [13].

Chemical compound and disease context of guanidine


Biological context of guanidine

  • The putative promoter region is rich in guanidine and cytosine residues and contains potential binding sites for the transcription factor Sp1 and the liver transcription factor, LF-B1 [19].
  • Phosphagens are phosphorylated guanidino compounds that are linked to energy state and ATP hydrolysis by corresponding phosphagen kinase reactions: phosphagen + MgADP + H(+) <--> guanidine acceptor + MgATP [20].
  • Gel filtration of the 4 M guanidine HCl extract of fine powder on Sepharose CL-6B and the subsequent reconstitution of various column fractions with inactive coarse residue showed that fractions with proteins of 20,000-50,000 mol wt induced new bone formation [21].
  • The kinetics of the refolding reaction of ribonuclease A from high concentrations of guanidine hydrochloride or urea are biphasic, and show two refolding reactions whose rates differ 450-fold at pH 5.8 and 25 degrees [22].
  • We report here the synthesis and characterization of a tritiated, symmetrically substituted guanidine derivative, 1,3-di(2-[5-3H]tolyl)guanidine ([3H]Tol2Gdn), that binds with high affinity to a single population of binding sites in guinea pig brain membrane preparations [23].

Anatomical context of guanidine

  • To determine whether alkaline phosphatase (ALP) can cause the mineralization of collagenous matrices in vivo, bovine intestinal ALP was covalently bound to slices of guanidine-extracted demineralized bovine dentin (DDS) [24].
  • To determine the possible biochemical potential of fine matrix to induce bone, the matrix was extracted in 4 M guanidine HCl and the extract was reconstituted with biologically inactive 4 M guanidine HCl-treated coarse bone matrix residue [21].
  • Nidogen was purified in its genuine form with a mol. wt. of 150 000 (Nd-150) and as fragments with mol. wts. of 100 000 (Nd-100) and 80 000 (Nd-80) from a mouse tumor basement membrane by preventing activity of endogenous proteases with 6 M guanidine and protease inhibitors [25].
  • Reconstitution of the whole guanidine extract on Millipore filters coated with gels of tendon collagen (type I) and subsequent culture with minced skeletal muscle also resulted in cartilage induction in vitro [26].
  • The endothelial cell inhibitor not only survived exposure to NaDodSO4 but also was active after incubation at pH 12 or treatment with 5% (vol/vol) 2-mercaptoethanol, 6 M urea, 4 M guanidine hydrochloride, or 1 M acetic acid [27].

Associations of guanidine with other chemical compounds


Gene context of guanidine

  • We demonstrate here, two different curing mechanisms: the inhibition of [URE3] replication by guanidine hydrochloride and its destruction by Ure2p aggregation [33].
  • One was soluble in both the prion and the nonprion form, mitotically stable but meiotically unstable, and cured by guanidine HCl but not by alterations in heat shock protein 104 (Hsp104p) [34].
  • ADAMTS13 could cleave approximately 14% of VWF pretreated with guanidine HCl, suggesting that this substrate is heterogeneous in susceptibility to proteolysis [35].
  • GM-CSF had a m.w. of 25,000 to 30,000 by gel filtration in PBS and about 23,000 in guanidine hydrochloride [36].
  • SAA4, however, increased turbidity at molar ratios of 1:250 and 1:100 even when preincubated in guanidine HCl before addition to liposomes [37].

Analytical, diagnostic and therapeutic context of guanidine


  1. Successful treatment of enterovirus-infected mice by 2-(alpha-hydroxybenzyl)-benzimidazole and guanidine. Eggers, H.J. J. Exp. Med. (1976) [Pubmed]
  2. Guanidine alkaloid analogs as inhibitors of HIV-1 Nef interactions with p53, actin, and p56lck. Olszewski, A., Sato, K., Aron, Z.D., Cohen, F., Harris, A., McDougall, B.R., Robinson, W.E., Overman, L.E., Weiss, G.A. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  3. Finding a needle in a haystack: detection of a small protein (the 12-kDa VP26) in a large complex (the 200-MDa capsid of herpes simplex virus). Booy, F.P., Trus, B.L., Newcomb, W.W., Brown, J.C., Conway, J.F., Steven, A.C. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  4. Mass distribution of a probable tail-length-determining protein in bacteriophage T4. Duda, R.L., Wall, J.S., Hainfeld, J.F., Sweet, R.M., Eiserling, F.A. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  5. Evidence for a protein mutator in yeast: role of the Hsp70-related chaperone ssb in formation, stability, and toxicity of the [PSI] prion. Chernoff, Y.O., Newnam, G.P., Kumar, J., Allen, K., Zink, A.D. Mol. Cell. Biol. (1999) [Pubmed]
  6. Viral particles are required for infection in neurodegenerative Creutzfeldt-Jakob disease. Manuelidis, L., Sklaviadis, T., Akowitz, A., Fritch, W. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  7. Histochemical classification of systemic amyloid fibril proteins. Alkaline guanidine method. Tashima, T., Kitamoto, T., Tateishi, J. Arch. Pathol. Lab. Med. (1986) [Pubmed]
  8. Methylamine: a new endogenous modulator of neuron firing? Pirisino, R., Ghelardini, C., De Siena, G., Malmberg, P., Galeotti, N., Cioni, L., Banchelli, G., Raimondi, L. Med. Sci. Monit. (2005) [Pubmed]
  9. The cytoskeletal framework and poliovirus metabolism. Lenk, R., Penman, S. Cell (1979) [Pubmed]
  10. Maintenance of human T cell anergy: blocking of IL-2 gene transcription by activated Rap1. Boussiotis, V.A., Freeman, G.J., Berezovskaya, A., Barber, D.L., Nadler, L.M. Science (1997) [Pubmed]
  11. Constructing proteins by dovetailing unprotected synthetic peptides: backbone-engineered HIV protease. Schnölzer, M., Kent, S.B. Science (1992) [Pubmed]
  12. A variant of prealbumin from amyloid fibrils in familial polyneuropathy of Jewish origin. Pras, M., Franklin, E.C., Prelli, F., Frangione, B. J. Exp. Med. (1981) [Pubmed]
  13. Partial deficiency of thyroid transcription factor 1 produces predominantly neurological defects in humans and mice. Pohlenz, J., Dumitrescu, A., Zundel, D., Martiné, U., Schönberger, W., Koo, E., Weiss, R.E., Cohen, R.N., Kimura, S., Refetoff, S. J. Clin. Invest. (2002) [Pubmed]
  14. Tumor-associated antigens of rat moloney sarcoma cells. I. Cell-surface antigens. Leung, K., Jones, J.M., Feldman, J.D. J. Immunol. (1978) [Pubmed]
  15. Impaired intracellular migration and altered solubility of nonglycosylated glycoproteins of vesicular stomatitis virus and Sindbis virus. Leavitt, R., Schlesinger, S., Kornfeld, S. J. Biol. Chem. (1977) [Pubmed]
  16. Modification of phospholipase C and phospholipase A2 activities during poliovirus infection. Guinea, R., López-Rivas, A., Carrasco, L. J. Biol. Chem. (1989) [Pubmed]
  17. Structure-function relationships of sea anemone toxin II from Anemonia sulcata. Barhanin, J., Hugues, M., Schweitz, H., Vincent, J.P., Lazdunski, M. J. Biol. Chem. (1981) [Pubmed]
  18. Foot-and-mouth disease virus and poliovirus particles contain proteins of the replication complex. Newman, J.F., Brown, F. J. Virol. (1997) [Pubmed]
  19. Frameshift and splice-junction mutations in the sterol 27-hydroxylase gene cause cerebrotendinous xanthomatosis in Jews or Moroccan origin. Leitersdorf, E., Reshef, A., Meiner, V., Levitzki, R., Schwartz, S.P., Dann, E.J., Berkman, N., Cali, J.J., Klapholz, L., Berginer, V.M. J. Clin. Invest. (1993) [Pubmed]
  20. Evolution and physiological roles of phosphagen systems. Ellington, W.R. Annu. Rev. Physiol. (2001) [Pubmed]
  21. Importance of geometry of the extracellular matrix in endochondral bone differentiation. Sampath, T.K., Reddi, A.H. J. Cell Biol. (1984) [Pubmed]
  22. Guanidine-unfolded state of ribonuclease A contains both fast- and slow-refolding species. Garel, J.R., Nall, B.T., Baldwin, R.L. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  23. 1,3-Di(2-[5-3H]tolyl)guanidine: a selective ligand that labels sigma-type receptors for psychotomimetic opiates and antipsychotic drugs. Weber, E., Sonders, M., Quarum, M., McLean, S., Pou, S., Keana, J.F. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  24. Alkaline phosphatase induces the mineralization of sheets of collagen implanted subcutaneously in the rat. Beertsen, W., van den Bos, T. J. Clin. Invest. (1992) [Pubmed]
  25. Identification and interaction repertoire of large forms of the basement membrane protein nidogen. Dziadek, M., Paulsson, M., Timpl, R. EMBO J. (1985) [Pubmed]
  26. In vitro transformation of mesenchymal cells derived from embryonic muscle into cartilage in response to extracellular matrix components of bone. Sampath, T.K., Nathanson, M.A., Reddi, A.H. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  27. Detection of an unusually stable fibrinolytic inhibitor produced by bovine endothelial cells. Loskutoff, D.J., van Mourik, J.A., Erickson, L.A., Lawrence, D. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  28. Cell-free synthesis of rat and rabbit gastric proton pump. Smolka, A., Sachs, G., Lorentzon, P. Gastroenterology (1989) [Pubmed]
  29. Mitogenic polypeptide of the mammalian seminiferous epithelium: biochemical characterization and partial purification. Feig, L.A., Klagsbrun, M., Bellvé, A.R. J. Cell Biol. (1983) [Pubmed]
  30. Somatomedin-like peptide(s) isolated from fetal bovine cartilage (cartilage-derived factor): isolation and some properties. Kato, Y., Nomura, Y., Tsuji, M., Kinoshita, M., Ohmae, H., Suzuki, F. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  31. Altered enolase in aged Turbatrix aceti results from conformational changes in the enzyme. Sharma, H.K., Rothstein, M. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  32. Proteoglycan synthesis in two murine bone marrow stromal cell lines. Kirby, S.L., Bentley, S.A. Blood (1987) [Pubmed]
  33. The mechanisms of [URE3] prion elimination demonstrate that large aggregates of Ure2p are dead-end products. Ripaud, L., Maillet, L., Cullin, C. EMBO J. (2003) [Pubmed]
  34. Changes in the middle region of Sup35 profoundly alter the nature of epigenetic inheritance for the yeast prion [PSI+]. Liu, J.J., Sondheimer, N., Lindquist, S.L. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  35. Zinc and calcium ions cooperatively modulate ADAMTS13 activity. Anderson, P.J., Kokame, K., Sadler, J.E. J. Biol. Chem. (2006) [Pubmed]
  36. Biochemical characterization of regulatory factors derived from T cell hybridomas and spleen cells. I. Separation of T cell growth factor and T cell replacing factor from granulocyte-macrophage colony-stimulating factor. Clark-Lewis, I., Schrader, J.W. J. Immunol. (1982) [Pubmed]
  37. Interaction of the serum amyloid A proteins with phospholipid. Bausserman, L.L., Herbert, P.N., Forte, T., Klausner, R.D., McAdam, K.P., Osborne, J.C., Rosseneu, M. J. Biol. Chem. (1983) [Pubmed]
  38. Isolations of a cartilage factor that inhibits tumor neovascularization. Langer, R., Brem, H., Falterman, K., Klein, M., Folkman, J. Science (1976) [Pubmed]
  39. Occurrence of an incomplete C8 molecule in homozygous C8 deficiency in man. Tschopp, J., Esser, A.F., Spira, T.J., Müller-Eberhard, H.J. J. Exp. Med. (1981) [Pubmed]
  40. The structure and function of immunoglobulin domains: studies with beta-2-microglobulin on the role of the intrachain disulfide bond. Isenman, D.E., Painter, R.H., Dorrington, K.J. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  41. Cell-surface heparan sulfate: an intercalated membrane proteoglycan. Kjellén, L., Pettersson, I., Höök, M. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  42. Biosynthesis of O-linked oligosaccharides on proteoglycans by chondrocytes from the swarm rat chondrosarcoma. Thonar, E.J., Lohmander, L.S., Kimura, J.H., Fellini, S.A., Yanagishita, M., Hascall, V.C. J. Biol. Chem. (1983) [Pubmed]
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