Disease relevance of cyclopropanamine

• Cyclopropylamine is a mechanism-based inhibitor of the quinoprotein methylamine dehydrogenase (MADH) from Paracoccus denitrificans [1].
• As part of an effort to understand the role of this enzyme in PGPR, the genes for ACC deaminase from two PGPR, Enterobacter cloacae CAL2 and UW4, have been isolated [2].
• These genes are highly homologous to the ACC deaminase genes from Pseudomonas strains 6G5 and F17 and similar to the ACC deaminase gene from Pseudomonas sp. strain ACP [2].
• In this research, to produce double-stranded (ds)RNA of tomato ACC oxidase, we linked the sense and antisense configurations of DNA fragments with 1,002-bp or 7-nt artificially synthesized fragments, respectively, and then placed these under the control of a modified cauliflower mosaic virus 35S promoter [3].
• Carnation cuttings treated with non-transformed and 1-aminocyclopropane (ACC) deaminase-containing Azospirillum brasilense Cd1843 produced significantly more roots than untreated controls and fewer roots than cuttings treated with 0.1% indolebutyric acid (IBA) [4].

High impact information on cyclopropanamine

• Cyclopropylamine, lacking the benzene moiety of TCP, inhibited lysyl oxidase irreversibly and competitively, and was not a substrate, pointing toward a defining role for the benzene moiety in the interaction of TCP with lysyl oxidase [5].
• The synthetic and analytical methods developed in the course of these studies should facilitate the application of cyclopropylamine-containing probes to reactions catalyzed by cytochrome P450 enzymes [6].
• Aminocyclopropane carboxylic Acid synthase is a regulated step in ethylene-dependent induced conifer defense. Full-length cDNA cloning of a multigene family, differential constitutive, and wound- and insect-induced expression, and cellular and subcellular localization in spruce and douglas fir [7].
• Preincubation of DGD with ACC, like the exchange of Na+ for K+, shifts the conformational distribution, in agreement with the steady-state kinetics [8].
• A possible explanation of drug resistance based on the observation of suicide inactivation of bacterial cytochrome P-450 by the cyclopropylamine moiety has also been proposed and is discussed in this report [9].

Biological context of cyclopropanamine

• The independent (developmental) pathway is responsible for the transcriptional activation of genes such as PG, ACC oxidase, E8, E17, D2, and J49 [10].
• These data, indicate that roots isolated from canola seeds treated with the ACC deaminase-producing E. cloacae UW4 upregulate genes involved in cell division and proliferation but down-regulate stress genes [11].
• We have examined whether or not a positive feedback regulation of gene expression for 1-aminocyclopropane-1-carboxylate (ACC) synthase and ACC oxidase also operates in ripening tomato (Lycopersicon esculentum) fruit during the burst of ethylene production [12].
• Gene silencing by an ACO1 [1-aminocyclopropane-1-carboxylate (ACC) oxidase 1] sense transgene in tomato plants was correlated with the production of small antisense RNAs (asRNAs) of 21-28 nucleotides, which were preferentially generated from the 3' region of the transgene [13].

Anatomical context of cyclopropanamine

• 1-aminocyclopropane-1-carboxylate (ACC) deaminase induced by ACC synthesized and accumulated in Penicillium citrinum intracellular spaces [14].

Associations of cyclopropanamine with other chemical compounds

• Preincubation of DGD-K+ with the competitive inhibitor 1-aminocyclopropane-1-carboxylate (ACC) lowers both kcat and KAIB apparently by drawing the enzyme toward the less active, tighter binding form observed in the pre-steady-state kinetics [8].
• Enzyme inactivation was irreversible, as no restoration of activity was evident after gel filtration of methylamine dehydrogenase which had been incubated with cyclopropylamine in the presence of a reoxidant [15].
• Electron paramagnetic resonance study of the mononuclear Al species formed in the reaction of Al atoms and cyclopropylamine at 77 k in an adamantane matrix [16].
• Wound-induced ethylene synthesis and expression and formation of 1-aminocyclopropane-1-carboxylate (ACC) synthase, ACC oxidase, phenylalanine ammonia-lyase, and peroxidase in wounded mesocarp tissue of Cucurbita maxima [17].

Gene context of cyclopropanamine

• The 2A6 protein shows three domains that are highly conserved among E8, ACC oxidases, and 2-ODDs [18].
• The minimum onset energy of photoionization of cyclopropylamine was calculated to be 201.5 kcal/mol (CCSD(T)) compared to experimental values of between about 201 and 204 kcal/mol [19].

References