Disease relevance of D-Methionine

• Five specific amino acids in Escherichia coli dihydrofolate reductase and Photinus pyralis luciferase were replaced with d-phenylalanine and d-methionine, and the specific activities of the resulting enzymes were determined [1].
• Brain tumor imaging using C-11-labeled L-methionine and D-methionine [2].
• Non selective transport of [11C-methyl]-L-and D-methionine into a malignant glioma [3].
• Growth assays on a synthetic amino acid diet fed to mice showed that substituting D-methionine for the L-isomer resulted in a dose-dependent relative weight gain reaching approximately 76% when D-methionine was fed at a level equivalent to that optimal for the L-form [4].
• Induction of AmpC beta-lactamase in Enterobacter cloacae ATCC 13047 by D-methionine, glycine, or D-tryptophan was accompanied by alterations in peptidoglycan composition and structure; in the case of D-methionine, it was also accompanied by morphologic changes [5].

High impact information on D-Methionine

• A D-methionine-containing peptide, Trp-Lys-Tyr-Met-Val-D-Met-NH(2) (WKYMVm), featuring a unique receptor specificity was investigated with respect to its ability to activate neutrophil effector functions [6].
• The active transport of oxomethylvalerate, a precursor of isoleucine, was prevented by a kauA mutation, the uptake of L-aspartate was competed by 20 mM L-glutamate, and D-methionine was used instead of L-methionine [7].
• Utilization of D-methionine during total parenteral nutrition in postsurgical patients [8].
• The data indicate poor D-methionine utilization by postsurgical patients during total parenteral nutrition when given as DL-methionine in the presence of other amino acids and glucose [8].
• In contrast, supplementation with D-methionine, L-lysine, L-aspartate or L-glutamate had little or no effect on ODC activity, whereas supplemental L-methionine, L-arginine, L-ornithine or L-cysteine was inhibitory [9].

Chemical compound and disease context of D-Methionine

• Certain D-amino acids, such as D-methionine and D-cystine, were incorporated into cells of Escherichia coli under conditions inhibiting protein and cell wall synthesis [10].
• Once-daily injections of histidine or D-methionine were less effective, pointing to the importance of pharmacokinetics in antioxidant protection in vivo.The study presents a simple screening system for agents with the potential to attenuate gentamicin-induced hearing loss [11].
• Because the amino acids 11C L-leucine, 11C L-methionine, and 11C D-methionine are used for examinations of brain tumors with positron emission tomography (PET), the uptake of the corresponding 14C substances and their incorporation into protein was studied in the rat brain [12].

Biological context of D-Methionine

• Difference Fourier syntheses for data collected from crystals soaked in platinum D-methionine and in 6-(4-hydroxy-3,5-di-iodobenzamido)penicilloic acid revealed the likely position of the active site of the enzyme [13].
• The metD D-methionine transporter locus of Escherichia coli is an ABC transporter gene cluster [14].
• D-Methionine attenuated cisplatin-induced vestibulotoxicity through altering ATPase activities and oxidative stress in guinea pigs [15].
• Northern blot experiments showed that no transcriptional activation occurred in the presence of D-methionine [16].
• Moreover, cisplatin exposure led to a significant dose-dependent increase of lipid peroxidation and nitric oxide concentrations of the vestibules, which could be significantly suppressed by D-methionine [15].

Anatomical context of D-Methionine

• The pathways that facilitate the uptake of L-methionine (L-Met), D-methionine (D-Met) and L-2-hydroxy-4-methylthiobutanoic acid (L-HMB) were characterized in chick intestinal brush border membrane vesicles [17].
• In previous studies we have found that porcine kidney fibroblasts will grow in medium containing D-2-hydroxy-4-methylthiobutanoic acid (D-methionine hydroxy analogue, D-MHA) as the sole source of methionine but not in medium containing the L-isomer (L-MHA) alone [18].
• The peptide containing the D-methionine exhibited high-affinity and selectivity for delta opioid receptors in the mouse vas deferens and in rat brain homogenates [19].
• Absorption mechanisms of L- and D-methionine (MET) in an in vitro cultured human intestinal epithelial cell model (Caco-2) and an in situ perfused rat intestinal model were investigated to determine if the kinetic characteristics of absorption are comparable in these two popular absorption models [20].
• In this study, we attempted to examine whether cisplatin-induced vestibulotoxicity and D-methionine protection were correlated with the changes of ATPase activities and oxidative stress of ampullary tissue of vestibules as well as cerebellar cortex (the inhibitory center of VOR system) of guinea pigs [15].

Associations of D-Methionine with other chemical compounds

• PEGylation did not affect steady-state kinetic parameters for oxidative deamination of D-methionine when 2,6-dichloroindophenol replaced dioxygen as the cosubstrate while it caused a ninefold decrease in substrate catalytic efficiency for the dioxygen-dependent reaction [21].
• Histidine and D-methionine were then administered to guinea pigs receiving concurrent treatment with gentamicin (120 mg/kgx19 days) [11].
• Following the r.w. administration, the concentration of radioactive D-methionine and thiourea declined with a terminal half-life of 0.57 and 0.77 h, respectively [22].
• D-Arginine hydrochloride and D-lysine hydroxamate were inactive at doses up to 50 mumols whilst D-methionine methylester (50 mumols) produced small falls in perfusion pressure in only 3 out of 7 preparations studied [23].
• RESULTS: Prolinase activity against prolylglycine in normal and prolidase-deficient erythrocyte lysates was inhibited by L-methionine, NAc-L-methionine and D,L-methionine in a concentration-dependent manner, but D-methionine enhanced the activity in low concentrations (0-20 mmol/l) [24].

Gene context of D-Methionine

• Human methionine aminopeptidase type 2 in complex with L- and D-methionine [25].
• In Salmonella typhimurium, methionine auxotrophs such as metB can use D-methionine as a methionine source [26].
• In contrast, a radical scavenger, D-methionine, or the neurotrophin BDNF suppressed the production of ROS, in turn stimulating NO production [27].
• Since some of the dadA mutants are thermosensitive in D-methionine utilization in vivo and have thermolabile D-amino acid dehydrogenase in vitro, it is proposed that the dadA gene codes for the enzyme structure [28].
• As expected, delta MTS did not catalyze alpha-proton exchange of D-methionine since the enzyme has been shown to be specific for L-amino acids [29].

Analytical, diagnostic and therapeutic context of D-Methionine

• Utilization of intravenously administered D-methionine was measured by morbidly obese subjects fed parenterally after elective gastric bypass surgery [8].
• 11C-labeled L- and D-methionine uptake was measured in seven patients with brain tumors using positron emission tomography [30].
• Plasma and urinary amino acid levels were measured in four normal adult subject administered equimolar quantities (0.0605 mmol/kg body wt) of L-methionine, D-methionine and L-methionine-dl-sulfoxide in a randomized crossover design [31].
• We have studied urinary excretion of methionine isomers in young miniature pigs, adult rabbits, and adult dogs given D-methionine in an attempt to find an animal model that, like man, utilizes the D-isomer poorly [32].
• The effects of a nutrition therapy with D-methionine (Met)-containing solution were investigated in cell cultures of the AH109A cell line [33].

References