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Chemical Compound Review

AC1MHURQ     guanidine; hydrogen(+1) cation

Synonyms: 25215-10-5, guanidine; hydron, Guanidine, conjugate monoacid
This record was replaced with 3520.
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Disease relevance of guanidine


Psychiatry related information on guanidine

  • Total cellular polyadenylated RNA (poly(A)+ RNA, mRNA) was prepared after guanidinium thiocyanate extraction of frozen brain tissue from age-matched controls and patients suffering from schizophrenia and unipolar depression [6].

High impact information on guanidine


Chemical compound and disease context of guanidine


Biological context of guanidine

  • Thus, the stabilizing effect of the positively charged guanidinium group does not appear to play a major role in the rate-limiting step for substrate hydrolysis [2].
  • The guanidinium group of arginine-166 has been postulated to act as an electrophilic species during phosphorylation of alkaline phosphatase [2].
  • These findings indicate that mu-conotoxins must be classified in the same group of Na channel inhibitors as guanidinium toxins, since they competed with guanidinium toxins for binding sites on the Na channel [17].
  • Mu-Conotoxins (CGIIIA and CGIIIB) and guanidinium toxins (TTX and saxitoxin) inhibited 3H-Pr-CGIIIA (1 nM) binding to electroplax membranes with IC50 values of 0.6, 1.1, 7.1, and 2.2 nM, respectively [17].
  • One type which is resistant to 5.2 M guanidinium chloride is most likely a D-loop that depends only on heteroduplex base pairing for its stability [18].

Anatomical context of guanidine

  • Structure/activity studies based on transport measurements in vesicles prepared from guinea pig left ventricle indicate that hydrophobic substitutions at the terminal nitrogen atom of the guanidinium moiety of amiloride improved the inhibitory potency almost 100-fold over that of the parent compound [19].
  • Treatment of macaques with 2 mg/kg of the guanidinium compounds resulted in patches of small-cell infiltrate, slight neuronal loss, and degenerative alterations in the sympathetic ganglia [20].
  • Low density proteoglycans (PG-III) were isolated from bovine articular cartilage by extraction with 4 M guanidinium chloride followed by sedimentation in a dissociative CsCl density gradient and fractionation by chromatography on DEAE-cellulose and Sepharose CL-6B columns [21].
  • Based on these results, we propose that the guanidinium group binds to a relatively wide vestibule at the cytoplasmic surface; but, unlike Na+ or K+ ions, it cannot pass into a narrower region of the cation transport path within the membrane [22].
  • Static and dynamic light-scattering methods have been used to investigate the structure of chick limb bud chondrocyte proteoglycan aggregate in 0.4 M guanidinium chloride [23].

Associations of guanidine with other chemical compounds


Gene context of guanidine

  • Imidazoline/guanidinium binding domains on monoamine oxidases. Relationship to subtypes of imidazoline-binding proteins and tissue-specific interaction of imidazoline ligands with monoamine oxidase B [29].
  • However, [KIL-d] is distinct from the known yeast prions in its relative guanidinium hydrochloride incurability and independence of Hsp104 protein for its maintenance [30].
  • Human gastric mucin was isolated by successive CsCl-gradient ultracentrifugation in the presence of guanidinium hydrochloride to prevent degradation of the polypeptide moieties of the molecules [31].
  • Extraction of the recombinant proteins from inclusion bodies by guanidinium chloride, followed by two column chromatography steps, produced high yields of pure CNTF that supported survival and neurite outgrowth from embryonic chick ciliary neurons in culture [32].
  • In HSMSL saliva, MUC5B was found in the gel phase; however, most of the material was 'insoluble' in guanidinium chloride and was only brought into solution by reduction [33].

Analytical, diagnostic and therapeutic context of guanidine


  1. Absence of hepatitis C viral RNA from saliva and semen of patients with chronic hepatitis C. Fried, M.W., Shindo, M., Fong, T.L., Fox, P.C., Hoofnagle, J.H., Di Bisceglie, A.M. Gastroenterology (1992) [Pubmed]
  2. Use of site-directed mutagenesis to elucidate the role of arginine-166 in the catalytic mechanism of alkaline phosphatase. Butler-Ransohoff, J.E., Kendall, D.A., Kaiser, E.T. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  3. Thiocyanate and hydroxyl ions inactivate the scrapie agent. Prusiner, S.B., Groth, D.F., McKinley, M.P., Cochran, S.P., Bowman, K.A., Kasper, K.C. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  4. HOL1 mutations confer novel ion transport in Saccharomyces cerevisiae. Gaber, R.F., Kielland-Brandt, M.C., Fink, G.R. Mol. Cell. Biol. (1990) [Pubmed]
  5. Stability of the asymmetric Escherichia coli chaperonin complex. Guanidine chloride causes rapid dissociation. Todd, M.J., Lorimer, G.H. J. Biol. Chem. (1995) [Pubmed]
  6. Changes in relative levels of specific brain mRNA species associated with schizophrenia and depression. Perrett, C.W., Whatley, S.A., Ferrier, I.N., Marchbanks, R.M. Brain Res. Mol. Brain Res. (1992) [Pubmed]
  7. Clathrin assembly protein AP180: primary structure, domain organization and identification of a clathrin binding site. Morris, S.A., Schröder, S., Plessmann, U., Weber, K., Ungewickell, E. EMBO J. (1993) [Pubmed]
  8. Structures of nitric oxide synthase isoforms complexed with the inhibitor AR-R17477 suggest a rational basis for specificity and inhibitor design. Fedorov, R., Vasan, R., Ghosh, D.K., Schlichting, I. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  9. X-ray structure of sensory rhodopsin II at 2.1-A resolution. Royant, A., Nollert, P., Edman, K., Neutze, R., Landau, E.M., Pebay-Peyroula, E., Navarro, J. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  10. Structural characteristics of supramolecular assemblies formed by guanidinium-cholesterol reagents for gene transfection. Pitard, B., Oudrhiri, N., Vigneron, J.P., Hauchecorne, M., Aguerre, O., Toury, R., Airiau, M., Ramasawmy, R., Scherman, D., Crouzet, J., Lehn, J.M., Lehn, P. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  11. Synthesis, biophysical properties, and nuclease resistance properties of mixed backbone oligodeoxynucleotides containing cationic internucleoside guanidinium linkages: deoxynucleic guanidine/DNA chimeras. Barawkar, D.A., Bruice, T.C. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  12. On the molecular weights of the three nonidentical subunits of citrate lyase from Klebsiella aerogenes. Carpenter, D.E., Singh, M., Richards, E.G., Srere, P.A. J. Biol. Chem. (1975) [Pubmed]
  13. Superoxide dismutase. Reversible removal of manganese and its substitution by cobalt, nickel or zinc. Ose, D.E., Fridovich, I. J. Biol. Chem. (1976) [Pubmed]
  14. Characterization of a partially unfolded high potential iron protein. Bertini, I., Cowan, J.A., Luchinat, C., Natarajan, K., Piccioli, M. Biochemistry (1997) [Pubmed]
  15. Recombinant antineuraminidase single chain antibody: expression, characterization, and crystallization in complex with antigen. Malby, R.L., Caldwell, J.B., Gruen, L.C., Harley, V.R., Ivancic, N., Kortt, A.A., Lilley, G.G., Power, B.E., Webster, R.G., Colman, P.M. Proteins (1993) [Pubmed]
  16. Rapid real-time PCR assay for detection and quantitation of Mycobacterium avium subsp. paratuberculosis DNA in artificially contaminated milk. O'Mahony, J., Hill, C. Appl. Environ. Microbiol. (2004) [Pubmed]
  17. Mu-conotoxins share a common binding site with tetrodotoxin/saxitoxin on eel electroplax Na channels. Yanagawa, Y., Abe, T., Satake, M. J. Neurosci. (1987) [Pubmed]
  18. The formation of paranemic and plectonemic joints between DNA molecules by the recA and single-stranded DNA-binding proteins of Escherichia coli. Riddles, P.W., Lehman, I.R. J. Biol. Chem. (1985) [Pubmed]
  19. Inhibition of Na+/Ca2+ exchange in membrane vesicle and papillary muscle preparations from guinea pig heart by analogs of amiloride. Siegl, P.K., Cragoe, E.J., Trumble, M.J., Kaczorowski, G.J. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  20. Sympathetic neuronal destruction in macaque monkeys by guanethidine and guanacline. Palmatier, M.A., Schmidt, R.E., Plurad, S.B., Johnson, E.M. Ann. Neurol. (1987) [Pubmed]
  21. Isolation and partial characterization of low density proteoglycans from bovine articular cartilage. Swann, D.A., Garg, H.G., Sotman, S.L., Hermann, H. J. Biol. Chem. (1983) [Pubmed]
  22. Guanidinium derivatives act as high affinity antagonists of Na+ ions in occlusion sites of Na+,K(+)-ATPase. David, P., Mayan, H., Cohen, H., Tal, D.M., Karlish, S.J. J. Biol. Chem. (1992) [Pubmed]
  23. Light-scattering studies of chick limb bud proteoglycan aggregate. Shogren, R.L., Blackwell, J., Jamieson, A.M., Carrino, D.A., Pechak, D., Caplan, A.I. J. Biol. Chem. (1983) [Pubmed]
  24. Identification and partial characterization of a nucleolar antigen with a molecular weight of 145,000 found in a broad range of human cancers. Freeman, J.W., McRorie, D.K., Busch, R.K., Gyorkey, F., Gyorkey, P., Ross, B.E., Spohn, W.H., Busch, H. Cancer Res. (1986) [Pubmed]
  25. L-arginine binding to nitric-oxide synthase. The role of H-bonds to the nonreactive guanidinium nitrogens. Babu, B.R., Frey, C., Griffith, O.W. J. Biol. Chem. (1999) [Pubmed]
  26. Unfolding pathway in red kidney bean acid phosphatase is dependent on ligand binding. Cashikar, A.G., Rao, N.M. J. Biol. Chem. (1996) [Pubmed]
  27. Studies on NADH (NADPH)-cytochrome c reductase (FMN-containing) from yeast. Isolation and physicochemical properties of the enzyme from top-fermenting ale yeast. Johnson, M.S., Kuby, S.A. J. Biol. Chem. (1985) [Pubmed]
  28. The active site of C3a anaphylatoxin. Caporale, L.H., Tippett, P.S., Erickson, B.W., Hugli, T.E. J. Biol. Chem. (1980) [Pubmed]
  29. Imidazoline/guanidinium binding domains on monoamine oxidases. Relationship to subtypes of imidazoline-binding proteins and tissue-specific interaction of imidazoline ligands with monoamine oxidase B. Raddatz, R., Parini, A., Lanier, S.M. J. Biol. Chem. (1995) [Pubmed]
  30. The [KIL-d] element specifically regulates viral gene expression in yeast. Tallóczy, Z., Mazar, R., Georgopoulos, D.E., Ramos, F., Leibowitz, M.J. Genetics (2000) [Pubmed]
  31. Cloning and analysis of human gastric mucin cDNA reveals two types of conserved cysteine-rich domains. Klomp, L.W., Van Rens, L., Strous, G.J. Biochem. J. (1995) [Pubmed]
  32. Recombinant human and rat ciliary neurotrophic factors. Masiakowski, P., Liu, H.X., Radziejewski, C., Lottspeich, F., Oberthuer, W., Wong, V., Lindsay, R.M., Furth, M.E., Panayotatos, N. J. Neurochem. (1991) [Pubmed]
  33. Macromolecular organization of saliva: identification of 'insoluble' MUC5B assemblies and non-mucin proteins in the gel phase. Wickström, C., Christersson, C., Davies, J.R., Carlstedt, I. Biochem. J. (2000) [Pubmed]
  34. Reversible unfolding of FtsZ cell division proteins from archaea and bacteria. Comparison with eukaryotic tubulin folding and assembly. Andreu, J.M., Oliva, M.A., Monasterio, O. J. Biol. Chem. (2002) [Pubmed]
  35. Two novel matrix proteins isolated from articular cartilage show wide distributions among connective tissues. Heinegård, D., Larsson, T., Sommarin, Y., Franzén, A., Paulsson, M., Hedbom, E. J. Biol. Chem. (1986) [Pubmed]
  36. Smectic liquid crystals from supramolecular guanidinium alkanesulfonates. Mathevet, F., Masson, P., Nicoud, J.F., Skoulios, A. J. Am. Chem. Soc. (2005) [Pubmed]
  37. The denatured state under native conditions: a non-native-like collapsed state of N-PGK. Reed, M.A., Jelinska, C., Syson, K., Cliff, M.J., Splevins, A., Alizadeh, T., Hounslow, A.M., Staniforth, R.A., Clarke, A.R., Craven, C.J., Waltho, J.P. J. Mol. Biol. (2006) [Pubmed]
  38. Purification and sequencing of radish seed calmodulin antagonists phosphorylated by calcium-dependent protein kinase. Polya, G.M., Chandra, S., Condron, R. Plant Physiol. (1993) [Pubmed]
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