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Chemical Compound Review

Butanamine     butan-1-amine

Synonyms: Butylamine, Norvalamine, Monobutilamina, Monobutylamime, Monobutylamine, ...
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Disease relevance of N-BUTYLAMINE

  • Although the wild-type strain of Paracoccus denitrificans produced an active, mature enzyme upon induction with n-butylamine, a mutant strain in which the ORF2 gene had been mostly deleted, neither grew in the n-butylamine medium nor showed QHNDH activity [1].
  • Although benomyl--or rather its non-enzymatic breakdown product methyl benzimidazol-2-yl carbamate (MBC)--was partially degraded to 2-AB, most probably n-butylamine, which arises after splitting off of the butylcarbamoyl side chain, was the actual carbon source for the Pseudomonas isolates [2].
  • Developmental toxicity of oral n-butylamine hydrochloride and inhaled n-butylamine in rats [3].
  • Inhaled n-butylamine produced concentration-dependent nasal epithelial hyperplasia and squamous metaplasia, inflammation and necrosis; the maternal NOAEL was less than 17 ppm [3].
  • Butylamine and pentylamine derivatives of PSMA copolymers exhibited more than 80% hemolysis at endosomal pH values, which suggests their potential as a platform of "smart" polymeric carriers for enhanced cytoplasmic delivery of a variety of therapeutic macromolecules [4].

High impact information on N-BUTYLAMINE

  • A putative [Fe-S]-cluster-binding protein (ORF2 protein) encoded between the structural genes for thealpha- andgamma-subunits of QHNDH in the n-butylamine-utilizing operon likely belongs to a Radical SAM (S-Ado-Met) superfamily that includes many proteins involved in vitamin biosynthesis and enzyme activation [1].
  • When the mutant strain was transformed with an expression plasmid for the ORF2 protein, n-butylamine-dependent bacterial growth and QHNDH activity were restored [1].
  • It is formed posttranslationally in the precursor of eukaryotic initiation factor 5A (eIF5A) by deoxyhypusine synthase, employing spermidine as a butylamine donor [5].
  • Separate experiments showing efficient transfer of labeled butylamine moiety from enzyme intermediate to eIF-5A precursor strongly support a reaction mechanism involving an imine intermediate [6].
  • The addition of n-butylamine to assay mixtures containing lysyl oxidase and TNM markedly increased the background rate of nitroform release [7].

Biological context of N-BUTYLAMINE


Anatomical context of N-BUTYLAMINE

  • The effect of the known inhibitors of iron uptake, n-butylamine and NH4Cl, was examined at the molecular level to more precisely define the mechanisms by which these lysosomotropic agents block iron uptake by rabbit reticulocytes [13].
  • Supercoiled enriched PM-2 DNA has been relaxed by treating with calf thymus topoisomerase I and used in the preparation of a family of n-butylamine adducts of varying levels of substitution [14].
  • Tris and two of its hydroxylated amine analogs were examined in a metal-free, universal n-butylamine buffer, for their interaction with intestinal brush border sucrase [15].
  • Formation of O6-ethyldeoxyguanosine from NEBA, however, was twice as high in liver as in nasal mucosa and lung and four times as high in liver as in oesophagus [16].
  • Motile and immotile mouse spermatozoa became resistant to n-butylamine when aged in physiologic medium and buffer, respectively [17].

Associations of N-BUTYLAMINE with other chemical compounds


Gene context of N-BUTYLAMINE

  • In a model study, succinimidyl N-[N'-(4-azidobenzoyl)tyrosyl]-beta-alanate (16A) was coupled to n-butylamine (a Lys surrogate), iodinated, and cleaved with chymotrypsin in the presence of tyrosylamide to afford the desired adduct (N-(N'-(4-azidobenzoyl)-3-iodotyrosyl)tyrosinamide, thereby demonstrating the feasibility of the enzymatic cleavage [22].
  • A mobile phase of 0.5% n-butylamine in methanol-hexane-methyl tert. butyl ether (1:1:1) is used in the analysis [23].
  • The use of proton nuclear magnetic resonance spectrometry (1H NMR) for monitoring the reaction of epoxides with butylamine and predictive capabilities of the relative alkylation index (RAI) for skin sensitization by epoxides [24].
  • Such an analysis allows to dissect the contributions due to the primary recognition subsite, where small mono-functional ligands (e.g., n-butylamine) bind, from those of the secondary subsite(s), which are additional recognition clefts for macromolecular inhibitors (e.g., BPTI and PSTI) [25].
  • We examined the formation of quaternary pyridinium crosslinks of elastin formed by condensation of lysine and allysine residues using the model compounds propanal (allysine) and n-butylamine (lysine) under quasi-physiological conditions [26].

Analytical, diagnostic and therapeutic context of N-BUTYLAMINE


  1. Involvement of a Putative [Fe-S]-cluster-binding Protein in the Biogenesis of Quinohemoprotein Amine Dehydrogenase. Ono, K., Okajima, T., Tani, M., Kuroda, S., Sun, D., Davidson, V.L., Tanizawa, K. J. Biol. Chem. (2006) [Pubmed]
  2. Bacterial breakdown of benomyl. I. Pure cultures. Fuchs, A., de Vries, F.W. Antonie Van Leeuwenhoek (1978) [Pubmed]
  3. Developmental toxicity of oral n-butylamine hydrochloride and inhaled n-butylamine in rats. Gamer, A.O., Hellwig, J., van Ravenzwaay, B., Heliwig, J. Food Chem. Toxicol. (2002) [Pubmed]
  4. pH-responsive poly(styrene-alt-maleic anhydride) alkylamide copolymers for intracellular drug delivery. Henry, S.M., El-Sayed, M.E., Pirie, C.M., Hoffman, A.S., Stayton, P.S. Biomacromolecules (2006) [Pubmed]
  5. Deoxyhypusine synthase generates and uses bound NADH in a transient hydride transfer mechanism. Wolff, E.C., Wolff, J., Park, M.H. J. Biol. Chem. (2000) [Pubmed]
  6. Enzyme-substrate intermediate formation at lysine 329 of human deoxyhypusine synthase. Wolff, E.C., Folk, J.E., Park, M.H. J. Biol. Chem. (1997) [Pubmed]
  7. Alpha-proton abstraction and carbanion formation in the mechanism of action of lysyl oxidase. Williamson, P.R., Kagan, H.M. J. Biol. Chem. (1987) [Pubmed]
  8. Organogermanium reactive intermediates. The direct detection and characterization of transient germylenes and digermenes in solution. Leigh, W.J., Harrington, C.R., Vargas-Baca, I. J. Am. Chem. Soc. (2004) [Pubmed]
  9. Synthesis and characterization of a heterobifunctional mercurial cross-linking agent: incorporation into cobratoxin and interaction with the nicotinic acetylcholine receptor. Wohlfeil, E.R., Hudson, R.A. Biochemistry (1991) [Pubmed]
  10. Biochemical and electrochemical characterization of quinohemoprotein amine dehydrogenase from Paracoccus denitrificans. Takagi, K., Torimura, M., Kawaguchi, K., Kano, K., Ikeda, T. Biochemistry (1999) [Pubmed]
  11. A fluorescent substrate of transglutaminase for detection and characterization of glutamine acceptor compounds. Pasternack, R., Laurent, H.P., Rüth, T., Kaiser, A., Schön, N., Fuchsbauer, H.L. Anal. Biochem. (1997) [Pubmed]
  12. The use of proton nuclear magnetic resonance spectrometry (1H NMR) for monitoring the reaction of epoxides with butylamine and predictive capabilities of the relative alkylation index (RAI) for skin sensitization by epoxides. Betso, J.E., Carreon, R.E., Miner, V.M. Toxicol. Appl. Pharmacol. (1991) [Pubmed]
  13. Amines as inhibitors of iron transport in rabbit reticulocytes. Glass, J., Nunez, M.T. J. Biol. Chem. (1986) [Pubmed]
  14. Effects of charge modification on the helical period of duplex DNA. Kilkuskie, R., Wood, N., Ringquist, S., Shinn, R., Hanlon, S. Biochemistry (1988) [Pubmed]
  15. pH-dependent inhibitory effects of tris and lithium ion on intestinal brush-border sucrase. Vasseur, M., Frangne, R., Caüzac, M., Mahmood, A., Alvarado, F. J. Enzym. Inhib. (1990) [Pubmed]
  16. Bioactivation of asymmetric N-dialkylnitrosamines in rat tissues derived from the ventral entoderm. Ludeke, B., Meier, T., Kleihues, P. IARC Sci. Publ. (1991) [Pubmed]
  17. Cross-link formation at the head-tail junction of mammalian spermatozoa during aging is dependent on sperm motility. Young, R.J. Arch. Androl. (1985) [Pubmed]
  18. Cross-reactivity between a penicillin and a cephalosporin with the same side chain. Miranda, A., Blanca, M., Vega, J.M., Moreno, F., Carmona, M.J., García, J.J., Segurado, E., Justicia, J.L., Juarez, C. J. Allergy Clin. Immunol. (1996) [Pubmed]
  19. Liquid-chromatographic determination of amoxapine and 8-hydroxyamoxapine in human serum. Tasset, J.J., Hassan, F.M. Clin. Chem. (1982) [Pubmed]
  20. 2,5-Dihydroxybenzoic acid butylamine and other ionic liquid matrixes for enhanced MALDI-MS analysis of biomolecules. Mank, M., Stahl, B., Boehm, G. Anal. Chem. (2004) [Pubmed]
  21. [eta 5-Cyclopentadienyl]metal tricarbonyl pyrylium salts: novel reagents for the specific conjugation of proteins with transition organometallic labels. Salmain, M., Malisza, K.L., Top, S., Jaouen, G., Sénéchal-Tocquer, M.C., Sénéchal, D., Caro, B. Bioconjug. Chem. (1994) [Pubmed]
  22. Photoaffinity heterobifunctional cross-linking reagents based on N-(azidobenzoyl)tyrosines. Imai, N., Kometani, T., Crocker, P.J., Bowdan, J.B., Demir, A., Dwyer, L.D., Mann, D.M., Vanaman, T.C., Watt, D.S. Bioconjug. Chem. (1990) [Pubmed]
  23. Analysis of blood and urine samples for hydroxychloroquine and three major metabolites by high-performance liquid chromatography with fluorescence detection. Williams, S.B., Patchen, L.C., Churchill, F.C. J. Chromatogr. (1988) [Pubmed]
  24. The use of proton nuclear magnetic resonance spectrometry (1H NMR) for monitoring the reaction of epoxides with butylamine and predictive capabilities of the relative alkylation index (RAI) for skin sensitization by epoxides. Roberts, D.W. Toxicol. Appl. Pharmacol. (1992) [Pubmed]
  25. Thermodynamic modeling of internal equilibria involved in the activation of trypsinogen. Coletta, M., Ascenzi, P., Bravin, L., Amiconi, G., Bolognesi, M., Guarneri, M., Menegatti, E. J. Biomol. Struct. Dyn. (1990) [Pubmed]
  26. Mechanism of formation of elastin crosslinks. Akagawa, M., Suyama, K. Connect. Tissue Res. (2000) [Pubmed]
  27. Circular dichroism spectral properties of covalent complexes of deoxyribonucleic acid and n-butylamine. Chen, C., Kilkuskie, R., Hanlon, S. Biochemistry (1981) [Pubmed]
  28. Conformational characteristics of deoxyribonucleic acid-butylamine complexes with C-type circular dichroism spectra. 2. A Raman spectroscopic study. Fish, S.R., Chen, C.Y., Thomas, G.J., Hanlon, S. Biochemistry (1983) [Pubmed]
  29. High-performance liquid chromatographic method for resolving the enantiomers of mexiletine and two major metabolites isolated from microbial fermentation media. Freitag, D.G., Foster, R.T., Coutts, R.T., Pasutto, F.M. J. Chromatogr. (1993) [Pubmed]
  30. Determination of butylamine in air samples by isotachophoresis. Hansén, L., Sollenberg, J., Wiberg, K. J. Chromatogr. (1984) [Pubmed]
  31. Two distinct quinoprotein amine oxidases are induced by n-butylamine in the mycelia of Aspergillus niger AKU 3302. Purification, characterization, cDNA cloning and sequencing. Frébort, I., Tamaki, H., Ishida, H., Pec, P., Luhová, L., Tsuno, H., Halata, M., Asano, Y., Kato, Y., Matsushita, K., Toyama, H., Kumagai, H., Adachi, O. Eur. J. Biochem. (1996) [Pubmed]
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