A Study on the Reactions of Plant Copper Amine Oxidase with C3 and C4 Aliphatic Diamines

Šebela, Marek; Frébort, Ivo; Lemr, Karel; Brauner, F; Peč, Pavel

doi:10.1006/abbi.2000.2081

Cited by 17 publications

(13 citation statements)

References 34 publications

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“…A stable yellow intermediate, the Cu(I)-semiquinolamine radical, is observable in anaerobiosis, when the reaction is initiated by substrate addition. By means of rapid scanning, the radical spectrum can be recorded also under admission of air 12 . Figure 2 presents absorption spectra recorded in aerobiosis within first 10 s after rapid mixing of GPAO with DADO in potassium phosphate buffer, pH 7.0.…”

Section: Resultsmentioning

confidence: 99%

“…The peak at 315 nm can be assigned to the Cu(II)-aminoresorcinol form of the cofactor, which is in equilibrium with the Cu(I)-semiquinolamine radical in the presence of air 12 . Similar results were also obtained for LSAO and ELAO.…”

Section: Resultsmentioning

confidence: 99%

“…Protein content was determined using the spectrophotometric method with bicinchoninic acid; BSA served as a standard 21 . Rapid-scan absorption spectroscopy of the reaction mixture in the early phase of GPAO reaction with DADO was performed according to described methodology 12 . For mass spectrometric analysis of oxidation products, 20 mM DADO in 50 mM ammonium bicarbonate was incubated with an excess of GPAO or LSAO at 37 o C for 12h.…”

Section: Methodsmentioning

confidence: 99%

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Interaction of plant amine oxidases with diaminoethers

Šebela¹,

Jarkovská²,

Lenobel³

et al. 2006

Arkivoc

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Polyamines are ubiquitous compounds, which are involved in crucial physiological events including cell growth and differentiation. The catabolic oxidative degradation of polyamines is catalyzed by quinoprotein copper-containing amine oxidases (CAOs) and flavoprotein polyamine oxidases (PAOs). Various synthetic polyamine analogs and polyamine derivatives have been reported, which represent important tools (substrates or inhibitors) in the study of catalytic properties of the enzymes. In this work, two related compounds were studied in the reactions with plant amine oxidases: 1,8-diamino-3,6-dioxaoctane (DADO) and 1,10-bis(2-pyridinylmethyl)-4,7-dioxa-1,10-diazadecane (BPDD). Based on activity and stoichiometry assays together with spectrophotometric measurements, DADO can be considered a good substrate for grass pea, lentil and E. characias CAOs with K m values in the range 10 -4 -10 -3 M.Its oxidative degradation produces the corresponding aminoaldehyde 8-amino-3,6-dioxaoctanal, which does not undergo spontaneous cyclization (as it is known for the oxidation products of natural substrates putrescine, cadaverine and spermidine) or polymerization in the reaction mixture. Conversely, oat PAO does not oxidize DADO and is only weakly inhibited by the compound (K i = 1.6 mM towards putrescine). BPDD was found to be a competitive inhibitor of both CAOs and PAOs with K i values of 10 -4 M. DADO could be suggested as a potential affinity ligand for CAOs.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Interaction of plant amine oxidases with diaminoethers

Šebela¹,

Jarkovská²,

Lenobel³

et al. 2006

Arkivoc

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“…CAO assay was carried out following a previously published protocol [9]. The guaiacol spectrophotometric method was used, which is based on a coupled reaction of horseradish peroxidase [21].…”

Section: Kinetic Measurementsmentioning

confidence: 99%

“…Two reported strategies in designing such inhibitors are the incorporation of either halogen or unsaturation at the b-position of amine substrates, examples being 2-bromoethylamine (BEA) [6] and 1,4-diamino-2-butyne (DABY) [7], respectively. Namely, the inactivating effect of DABY (as a putrescine analog) on plant CAOs has been studied in detail at the molecular level [8][9][10]. Various b-unsaturated compounds were tested in the reaction with bovine plasma CAO [10][11][12][13].…”

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confidence: 99%

1,5‐Diamino‐2‐pentyne is both a substrate and inactivator of plant copper amine oxidases

Lamplot¹,

Šebela²,

Maloň³

et al. 2004

European Journal of Biochemistry

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1,5-Diamino-2-pentyne (DAPY) was found to be a weak substrate of grass pea (Lathyrus sativus, GPAO) and sainfoin (Onobrychis viciifolia, OVAO) amine oxidases. Prolonged incubations, however, resulted in irreversible inhibition of both enzymes. For GPAO and OVAO, rates of inactivation of 0.1-0.3 min )1 were determined, the apparent K I values (half-maximal inactivation) were of the order of 10DAPY was found to be a mechanism-based inhibitor of the enzymes because the substrate cadaverine significantly prevented irreversible inhibition. The N 1 -methyl and N 5-methyl analogs of DAPY were tested with GPAO and were weaker inactivators (especially the N 5 -methyl) than DAPY. Prolonged incubations of GPAO or OVAO with DAPY resulted in the appearance of a yellow-brown chromophore (k max ¼ 310-325 nm depending on the working buffer). Excitation at 310 nm was associated with emitted fluorescence with a maximum at 445 nm, suggestive of extended conjugation. After dialysis, the color intensity was substantially decreased, indicating the formation of a low molecular mass secondary product of turnover. The compound provided positive reactions with ninhydrin, 2-aminobenzaldehyde and Kovacs' reagents, suggesting the presence of an amino group and a nitrogen-containing heterocyclic structure. The secondary product was separated chromatographically and was found not to irreversibly inhibit GPAO. MS indicated an exact molecular mass (177.14 Da) and molecular formula (C 10 H 15 N 3 ). Electrospray ionization-and MALDI-MS/MS analyses yielded fragment mass patterns consistent with the structure of a dihydropyridine derivative of DAPY. Finally, N-(2,3-dihydropyridinyl)-1,5-diamino-2-pentyne was identified by means of 1 H-and 13 C-NMR experiments. This structure suggests a lysine modification chemistry that could be responsible for the observed inactivation.

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Synthesis and crystal structure of a New Diamine complex CuCl₄(H₂tn)

et al. 2004

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In an attempt to synthesize a new pyrimidine complex of copper@) in a solution reaction of CuBrz with 2,2'-bis(hexahydropyrimidine) and hydro-chloric acid, we unexpectedly obtained a bright yellow chip-like crystal of CuC4(H2m) [H,tn = (H3NCH2CH2CH2NH3)'+]. Its structure was determined by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic system, space group Pnma, with cell parameters: a=0.7216(2) nm, b= 1.8308 (6) nm, r=0.7553(3) nm, V=0.9953(6) nm3, Z=4, F(000)=564, Mr=281.49, D,= 1.879 g/cm3. p(Mo Ka)=3.204 m-I, RI=0.0248, wR2=o.0575. The analysis of the crystal structure indicates that the complex has a three-dimensional network structure, which is formed by hydrogen bonds and electrostatic interaction.

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A Study on the Reactions of Plant Copper Amine Oxidase with C3 and C4 Aliphatic Diamines

Cited by 17 publications

References 34 publications

Interaction of plant amine oxidases with diaminoethers

Interaction of plant amine oxidases with diaminoethers

1,5‐Diamino‐2‐pentyne is both a substrate and inactivator of plant copper amine oxidases

Synthesis and crystal structure of a New Diamine complex CuCl₄(H₂tn)

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A Study on the Reactions of Plant Copper Amine Oxidase with C3 and C4 Aliphatic Diamines

Cited by 17 publications

References 34 publications

Interaction of plant amine oxidases with diaminoethers

Interaction of plant amine oxidases with diaminoethers

1,5‐Diamino‐2‐pentyne is both a substrate and inactivator of plant copper amine oxidases

Synthesis and crystal structure of a New Diamine complex CuCl4(H2tn)

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Product

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Synthesis and crystal structure of a New Diamine complex CuCl₄(H₂tn)