Disease relevance of ALLYLAMINE

• Ultrastructural alterations in allylamine cardiovascular toxicity. Late myocardial and vascular lesions [1].
• Terbinafine, an allylamine used to treat onychomycosis, has been reported to be active against rat Pneumocystis carinii in vitro and in vivo [2].
• A new subclass, which features an acetylene group conjugated with the allylamine double bond, is characterized by enhanced antifungal activity, especially on oral treatment of guinea pig dermatophytoses [3].
• Ultrastructural alterations in allylamine- induced cardiomyopathy: early lesions [4].
• To study the complex interaction between oxidative injury and the pathogenesis of vascular disease, vascular gene expression was examined in male Sprague-Dawley rats given 35 or 70 mg/kg allylamine, a synthetic amine converted to acrolein and hydrogen peroxide within the vascular wall [5].

High impact information on ALLYLAMINE

• This review focuses on the deregulation of gene transcription by redox-activated trans-acting factors after benzo(a)pyrene challenge and the modulation of extracellular matrix signaling in vascular smooth muscle cells by allylamine-induced oxidative injury [6].
• In this study, we demonstrate that allylamine, a selective cardiovascular toxin in vivo, is actively metabolized in vitro by a purified vascular enzyme (semicarbazide-sensitive amine oxidase), which has been localized recently to vascular smooth muscle cells [7].
• Oxidative deamination of allylamine to a highly toxic aldehyde, acrolein, was blocked through enzyme inhibition by semicarbazide-sensitive amine oxidase suggests that this vascular enzyme's physiological role may include metabolism of exogenous amines [7].
• This deduced rat SE sequence is 30.2% identical to the ERG 1 gene, which encodes SE from an allylamine-resistant Saccharomyces cerevisiae mutant [8].
• Under these same denaturing conditions, 96% of the radioactivity associated with the enzyme remained bound, therefore indicating that allylamine attachment is not to the flavin coenzyme but rather to an active site amino acid residue [9].

Chemical compound and disease context of ALLYLAMINE

• Clinical trials have also shown significant differences favoring allylamine/benzylamine drugs over imidazoles in the treatment of dermatophytosis [10].
• Ethanol ingestion on allylamine-induced experimental subendocardial fibrosis [11].
• A third subgroup of nine muscles from allylamine-treated rats but with normal left ventricular hydroxyproline concentration and fibrosis as determined by point counting served as another control group (AL-A) for the evaluation of effects of allylamine not due to fibrosis [12].

Biological context of ALLYLAMINE

• Altered protein secretion and extracellular matrix deposition is associated with the proliferative phenotype induced by allylamine in aortic smooth muscle cells [13].
• Interestingly, enhanced DNA synthesis of allylamine cells was associated with increased cell numbers only when seeded on a glass surface [13].
• Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics [14].
• Injury of vascular smooth muscle cells (VSMCs) by allylamine (AAM) leads to phenotypic changes associated with atherogenic progression including increased proliferation, migration, and alterations in cell adhesion [15].
• Biotransformation of the cardiovascular toxin, allylamine, by rat and human cardiovascular tissue [16].

Anatomical context of ALLYLAMINE

• Repeated cycles of allylamine-induced aortic injury in vivo modulate the proliferative potential of smooth muscle cells (SMCs) during serial propagation in vitro [13].
• In vivo alpha(7)-mRNA and protein expression were enhanced in the aortas of AAM-treated rats [15].
• Ultrastructural studies were made of the early changes induced in left ventricular myocardium by allylamine given to rats either in drinking water (10.7 mM for 1 to 7 days) or by gavage (100 mg. per kg. per day for 1 or 2 days) [4].
• Acrolein was detected in homogenates of rat aorta, lung, skeletal muscle, and heart incubated with allylamine [17].
• The adhesion of mouse STO fibroblast cells was accelerated by the immobilization of polyallylamine [18].

Associations of ALLYLAMINE with other chemical compounds

• The allylamine derivative terbinafine is the first antifungal agent with primary fungicidal properties against dermatophytes which acts systemically after oral application as well as locally after topical application [19].
• The layer was overcoated with an electrically insulating layer of polyaziridine-cross-linked poly(allylamine), on which an immobilized interference-eliminating horseradish peroxidase based film was deposited [20].
• Naftifine, a new antimycotic drug of the allylamine class, is a potent inhibitor of ergosterol biosynthesis in Candida albicans [21].
• From readily available allylamine, aldehyde and isocyanoacetamide, a three-component reaction followed by a Pummerer cyclization provided tetracyclic ring systems (6-7-5-6 and 6-6-5-6) in excellent overall yields [22].
• The lipid coating introduced directly on (polystyrene sulfonate/polyallylamine hydrochloride)5 polyelectrolyte microcapsule surfaces significantly reduces the permeability of capsule walls estimated by fluorescence recovery after photobleaching (FRAP) [23].

Gene context of ALLYLAMINE

• The allylamine antimycotic terbinafine prevents the formation of sterols by specifically inhibiting squalene epoxidase (SE) [24].
• Modulation of cyclin dependent kinase inhibitor proteins and ERK1/2 activity in allylamine-injured vascular smooth muscle cells [25].
• Redox polyelectrolyte multilayers have been assembled with use of the layer-by-layer (LBL) deposition technique with cationic poly(allylamine) modified with Os(bpy)(2)ClPyCHO (PAH-Os) and anionic poly(styrene)sulfonate (PSS) or poly(vinyl)sulfonate (PVS) [26].
• Here we report the structural and conformational properties of a peptide-conjugated graft copolymer, poly(gamma-methyl-L-glutamate) grafted polyallylamine (1) in a water-2,2,2-trifluoroethanol solution as a simple model for amyloid formation [27].
• Acrolein was also produced from allylamine by bovine plasma amine oxidase and porcine kidney diamine oxidase but not by rat liver or brain homogenates [17].

Analytical, diagnostic and therapeutic context of ALLYLAMINE

• Naftifine is an allylamine derivative for topical administration with a mechanism of action distinct from that of other classes of antifungal agents [28].
• In this work, we demonstrate that a polymer thin film, produced by pulsed rf plasma polymerization of allylamine and deposited directly on a MALDI probe, can be subsequently biotinylated to develop a bioaffinity capture MALDI probe [29].
• A bioassay with Trichophyton mentagrophytes is described for SF 86-327, an allylamine antifungal agent [30].
• Rats on the drinking water protocol developed myocardial alterations evident by light and electron microscopy within 2 days; those given allylamine by gavage developed lesions after 24 hours [4].
• A polyion complex (PIC) membrane composed of DNA and poly(allylamine) (PAA) functioned as a support matrix for immobilization of electrocatalytic element-copper ion [31].

References