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Amino Acids: The Forum for Amino Acid, Peptide and Protein Research (v.30, #3)

When quinones meet amino acids: chemical, physical and biological consequences by S. Bittner (pp. 205-224).

Quinones and amino acids are usually compartmentally separated in living systems, however there are several junctions in which they meet, react and influence. It occurs mainly in wounded, cut or crushed plant material during harvest, ensiling or disintegrating cells. Diffusing polyphenols are oxidized by polyphenol oxidases (PPOs) to quinonic compounds, which associate reversibly or irreversibly with amino acids and proteins. The reaction takes place with the free nucleophilic functional groups such as sulfhydryl, amine, amide, indole and imidazole substituents. It results in imine formation, in 1,4-Michael addition via nitrogen or sulphur and in Strecker degradation forming aldehydes. The formation and activity of quinone–amino acids conjugates influences the colour, taste, and aroma of foods. Physical and physiological phenomena such as browning of foods, discoloration of plants during processing, alteration of solubility and digestibility, formation of humic substances, germicidal activity, cytotoxicity and more occur when quinones from disintegrating cells meet amino acids. The mechanisms of toxicity and the pathways by which PCBs may be activated and act as a cancer initiator include oxidation to the corresponding quinones and reaction with amino acids or peptides. Sclerotization of insect cuticle is a biochemical process involving also the reaction between quinones and amino acid derivatives.

Keywords: Keywords: Quinones – Amino acids – Polyphenols – Polyphenyloxidase – Browning of foods – Catechol amino acid adducts

Asymmetrical (ADMA) and symmetrical dimethylarginine (SDMA) as potential risk factors for cardiovascular and renal outcome in chronic kidney disease – possible candidates for paradoxical epidemiology? by M. Busch; C. Fleck; G. Wolf; G. Stein (pp. 225-232).

Background: Asymmetrical dimethylarginine (ADMA) is an inhibitor of nitric-oxide synthase. It has been linked to atherosclerotic risk in the general population as well as in end-stage renal disease patients (ESRD), whereas symmetrical dimethylarginine (SDMA) is thought to be biological inactive. Prospective data concerning the role of both dimethylarginines are rare in patients with chronic kidney disease.Methods: 200 patients with chronic kidney disease (mean age 57.6 ± 13.0 years, 69 female, 131 male); 82 with chronic renal failure (CRF), 81 on maintenance haemodialysis (HD) and 37 renal transplant recipients (RTR) were prospectively followed for 24 months. ADMA and SDMA were measured by HPLC. The relation of plasma levels of ADMA and SDMA together with conventional risk factors for the cardiovascular and renal outcome was investigated with Cox proportional hazards model.Results: Mean serum levels of SDMA were significantly increased in all groups compared to the control group (P ≤ 0.0005), ADMA was increased only in HD and RTR (P ≤ 0.004). Forty-seven cardiovascular events (CVE) occurred during follow-up, 35 patients died, and 39 patients reached ESRD. Multivariate analysis showed diabetes (RR 3.072, P = 0.01), ESRD (RR 11.915, P < 0.0005), elevated CRP levels (RR 3.916, P < 0.0005) and surprisingly a lower ADMA level (RR 0.271, P = 0.008) as independent risk factors for CVE. Serum creatinine (RR 11.378, P = 0.001), haemoglobin (RR 0.710, P = 0.038 for an increment of 1 mmol/l), and SDMA levels (RR 1.633, P = 0.006, per 1 µmol/l increment) were predictors for the progression to ESRD.Conclusions: Data from a heterogeneous group of patients with chronic kidney disease provide evidence that conventional risk factors seem to play a more important role than elevated serum levels of ADMA or SDMA for cardiovascular events. Increasing serum SDMA concentration seems to play an additive role for the renal outcome besides serum creatinine and haemoglobin levels. Whether ADMA might possibly be a candidate for the phenomenon of “paradoxical epidemiology” in chronic kidney disease needs further investigation.

Keywords: Keywords: Chronic renal failure – Haemodialysis – Renal transplantation – Cardiovascular risk – ADMA – SDMA

GABA-mediated effects of some taurine derivatives injected i.c.v. on rabbit rectal temperature and gross motor behavior by M. Frosini; L. Ricci; S. Saponara; M. Palmi; M. Valoti; G. Sgaragli (pp. 233-242).

Some synthetic taurine analogues, namely ethanolamine-O-sulphate (EOS), N,N-dimethyltaurine (DMT), N,N,N-trimethyltaurine (TMT) and 2-aminoethylphosphonic acid (AEP) were shown to interact with rabbit brain GABA_A- or GABA_B-receptors, while (±)piperidine-3-sulfonic acid (PSA) inhibited the activity of rabbit brain 4-aminobutyrate transaminase. This suggests that they behave like direct/indirect GABA agonists or GABA antagonists and affect thermoregulation and gross motor behaviour (GMB) which are under GABA control. In the present study micromole (1.2–48) amounts of these compounds were i.c.v. injected in conscious, restrained rabbits while monitoring rectal temperature (RT), ear skin temperature (EST) and GMB. AEP, EOS, DMT and TMT induced a dose-related hyperthermia, ear vasoconstriction and excitation of GMB, while PSA induced a dose-related hypothermia, ear vasodilation and inhibition of GMB. EOS antagonized in a dose-related fashion hypothermia induced by 60 nmol THIP, a GABA_A agonist, while AEP, DMT and TMT counteracted that induced by 8 nmol R(-)Baclofen, a GABA_B agonist.In conclusion, EOS and AEP, DMT, TMT seem to act as GABA_A and GABA_B antagonists, respectively, while PSA behaves like an indirect GABA agonist, all affecting the central mechanisms which drive rabbit thermoregulation.

Keywords: Keywords: Taurine – Taurine derivatives – GABA – GABA_A – GABA_B agonist/antagonist – Thermoregulation

Solid-phase S-3CR generates N-substituted α-aminonitriles for the synthesis of α-phenyl-α-(1-piperazinyl) substituted amino acids by K. C. Probst; G. Jung (pp. 243-250).

Structurally diverse amino acids were prepared as versatile synthons for combinatorial chemistry. Using an optimized solid-phase synthesis by Strecker-three-component-reaction (S-3CR), two different polymer linker constructs carrying piperazine were investigated. (a) Acrylate derived base-labile linker yielded α-aminonitriles with N-alkylated piperazines via Hofmann elimination after quarternisation with an alkyl halide. The crude product purities were in the range of 54–87%. (b) A urethane type linker yielded α-aminonitriles with the free piperazine nitrogen when cleaved with acid and the product purities were 72–93%. The α-aminonitriles were easily converted to novel N^ɛ – Fmoc-protected α-amino acids with α-(1-piperazinyl) and α-phenyl substituents.

Keywords: Keywords: Amino acid synthesis – Strecker reaction – Solid-phase synthesis – Combinatorial chemistry – Multicomponent reaction

Surprising insights that aren’t so surprising in the modeling of sulfur amino acid metabolism by M. H. Stipanuk; J. E. Dominy Jr (pp. 251-256).

The modeling of whole organism sulfur amino acid flux control has been aided in recent years by advancements in proteomics and mass spectroscopy-based metabolite analysis. The convergence of these two fields and their respective techniques, as demonstrated by a new study using yeast by Lafaye et al., has shown that researchers seeking to model whole cell/organism metabolism should give careful consideration to the relationships connecting enzyme concentration, enzyme activity, substrate concentration, and metabolic flux. In this paper, we outline some of the fundamental concepts for modeling sulfur amino acid metabolism and how they relate to our current understanding of mammalian sulfur amino acid metabolism.

Keywords: Keywords: Sulfur – Metabolism – Amino acid

Chronic intake of caffeine during gestation down regulates metabotropic glutamate receptors in maternal and fetal rat heart by I. Iglesias; D. León; M. A. Ruiz; J. L. Albasanz; M. Martín (pp. 257-266).

Caffeine is the most widely consumed substance in the world which antagonizes adenosine effects. Adenosine acting through A₁ receptors inhibits glutamate release which binds to metabotropic glutamate receptors (mGluRs). Recently, we have shown that maternal caffeine intake during gestation causes down-regulation of A₁ and metabotropic glutamate receptors in the brain of both rat mothers and fetuses. In the present work we provide evidence that caffeine also affects receptors in hearts, causing a decrease in mGluRs from both maternal and fetal hearts. A decrease in G_q/11 and PLC β₁ proteins level was also observed in both tissues. However, phospholipase C activity was only affected in fetal heart, being significantly decreased. These results suggest an in vivo cross-talk mechanism between adenosine and glutamate receptors in peripheral tissues. Therefore, special attention should be paid to caffeine ingestion during gestation.

Keywords: Keywords: Heart – Metabotropic glutamate receptor – Caffeine – Pregnancy

Increased transglutaminase activity was associated with IL-6 release in cultured human gingival fibroblasts exposed to dental cast alloys by G. Matarese; I. Picerno; D. Caccamo; P. Spataro; G. Cordasco; R. Ientile (pp. 267-271).

Molecular mechanisms underlying gingival and periodontal inflammation caused by dental alloys are still poorly understood. Recently, it has been demonstrated that tissue transglutaminase can be involved in inflammatory cell response. The aim of this study was to evaluate effects of exposure to orthodontic materials on transglutaminase in cultured human gingival fibroblasts. The incubation with Ni–Ti heat-activated (T3) or Ni–Ti super-elastic (T4), and with Ni–Cr–Co (T2) alloys produced respectively 2.5-fold and 8-fold increases in IL-6 release compared with control cultures. Transglutaminase activity was significantly increased in cells exposed to T3 and T4 alloys (about 170% of control; p < 0.05), where it was mainly localized close to inner part of cell membrane. The exposure to T3 and T4 specimens significantly up-regulated also tTG expression compared with control cultures. These data first show an association between IL-6 release and tissue transglutaminase increases, suggesting that TGase-mediated reactions may play a major role in periodontal inflammation.

Keywords: Keywords: Inflammation – Tissue transglutaminase – Interleukins – Fibroblasts – Dental alloys

Study of taurine and tauret content in the compound eye of locust with light and dark adaptation by A. M. Petrosian; L. A. Poghosyan; J. E. Haroutounian (pp. 273-278).

Taurine as well as tauret (retinyliden taurine) levels were measured in locust Locusta migratoria compound eyes. HPLC measurements revealed relatively low taurine levels (1.9 ± 0.16 mM) in dark-adapted eyes. Glutamate, aspartate and glycine levels were 2.0 ± 0.2, 2.7 ± 0.4 and 3.0 ± 0.37 mM, respectively, while GABA was present only in trace amounts. After about 4 h of light adaptation at 1500–2000 lx, amino acid levels in the compound eye were as follows: taurine, 1.8 ± 0.17 mM; glutamate, no change at 2.1 ± 0.2 mM; aspartate sharply increased to 4.7 ± 0.7 mM; glycine slightly decreased to 2.8 ± 0.3 mM; and GABA trace levels. In the compound eye of locust Locusta migratoria, the existence of endogenous tauret in micro-molar range was established. In the dark, levels were several times higher compared with compound eye after light adaptation 1500 lx for 3 h, as estimated by TLC in combination with spectral measurements. Existence of tauret in compound eye is of special interest because in the compound eye, rhodopsin regeneration is based on photoregeneration.

Keywords: Keywords: Taurine – Tauret – Compound eye – Aspartate – Glutamate glycine

The absorption of orally supplied β-alanine and its effect on muscle carnosine synthesis in human vastus lateralis by R. C. Harris; M. J. Tallon; M. Dunnett; L. Boobis; J. Coakley; H. J. Kim; J. L. Fallowfield; C. A. Hill; C. Sale; J. A. Wise (pp. 279-289).

β-Alanine in blood-plasma when administered as A) histidine dipeptides (equivalent to 40 mg · kg⁻¹ bwt of β-alanine) in chicken broth, or B) 10, C) 20 and D) 40 mg · kg⁻¹ bwt β-alanine (CarnoSyn™, NAI, USA), peaked at 428 ± SE 66, 47 ± 13, 374 ± 68 and 833 ± 43 µM. Concentrations regained baseline at 2 h. Carnosine was not detected in plasma with A) although traces of this and anserine were found in urine. Loss of β-alanine in urine with B) to D) was <5%. Plasma taurine was increased by β-alanine ingestion but this did not result in any increased loss via urine. Pharmacodynamics were further investigated with 3 × B) per day given for 15 d. Dietary supplementation with I) 3.2 and II) 6.4 g · d⁻¹ β-alanine (as multiple doses of 400 or 800 mg) or III) L-carnosine (isomolar to II) for 4 w resulted in significant increases in muscle carnosine estimated at 42.1, 64.2 and 65.8%.

Keywords: Keywords: Carnosine – β-Alanine – Muscle – Buffering – Intracellular pH

Amino acid analysis by hydrophilic interaction chromatography coupled on-line to electrospray ionization mass spectrometry by T. Langrock; P. Czihal; R. Hoffmann (pp. 291-297).

Collagens form a common family of triple-helical proteins classified in 21 types. This unique structure is further stabilized by specific hydroxylation of distinct lysyl and prolyl residues forming 5-hydroxylysine and hydroxyproline (Hyp) isomers, mostly 4-trans and 3-trans-Hyp. The molecular distribution of the Hyp-isomers among the different collagen types is still not well investigated, even though disturbances in the hydroxylation of collagens are likely to be involved in several diseases such as osteoporosis and autoimmune diseases. Here, a new approach to analyze underivatized amino acids by hydrophilic interaction chromatography (HILIC) coupled on-line to electrospray ionization mass spectrometry (ESI-MS) is reported. This method can separate all three studied Hyp-isomers, Ile, and Leu, which are all isobaric, allowing a direct qualitative and quantitative analysis of collagen hydrolysates. The sensitivity and specificity was increased by a neutral loss scan based on the loss of formic acid (46 u).

Keywords: Keywords: Collagen types – ESI-MS – HILIC – Hydroxyproline – Hyp

A role for ethylene in low-oxygen signaling in rice roots by R. Reggiani (pp. 299-301).

Inhibitors of action and synthesis of ethylene (Ag⁺, norbornadien, Co²⁺) were able to reduce the level of γ-aminobutyric acid (Gaba) in rice roots during the development of an anaerobic environment. The inhibitory effect was reversed by the addition of the G protein activator 5′-guanylylimidodiphosphate. Gaba accumulation was modulated by the presence of CO₂ (inhibitor of ethylene action and synthesis) and stimulated by 2-chloroethylphosphonic acid (ethefon). These findings are consistent with a role of ethylene during a low-oxygen stress.

Keywords: Keywords: γ-Aminobutyric acid – Ethylene – Hypoxia – Oryza sativa – Root – Signal transduction

Phthalocyanine-dyed fibers adsorb allergenic proteins by H. Yano; Y. Sugihara; H. Shirai; Y. Wagatsuma; O. Kusada; T. Matsuda; S. Kuroda; S. Higaki (pp. 303-305).

Phthalocyanine (Pc)-dyed fiber is reported to reduce atopic symptoms in some patients when they use underwear made of the fiber. We investigated the adsorption of allergens on Pc-fiber. Pc-fiber trapped house dust/pollen/food allergens with varied molecular weight and pI. The adsorbed allergens were released in the presence of mild detergent. Pc-fiber did not change the molecular weight or disulfide bonding of the allergens. These observations imply that Pc-fiber is applicable as an “allergen trap” for a wide variety of products.

Keywords: Keywords: Phthalocyanine – Allergen – House dust

Icilin evokes a dose- and time-dependent increase in glutamate within the dorsal striatum of rats by J. L. Werkheiser; S. M. Rawls; A. Cowan (pp. 307-309).

Icilin, the peripheral cold channel agonist, activates TRPM8 and TRPA1, localized on dorsal root ganglia and trigeminal neurons in rats. Icilin precipitates immediate wet-dog shakes in this species, which are antagonized by centrally acting mu and kappa opioid agonists, implicating the central nervous system in the behavioral response. We studied the effect icilin has on glutamate levels in the dorsal striatum, a brain region involved in movement. Icilin (0.25, 0.5 and 0.75 mg/kg, i.p.) elicited a dose- and time-dependent increase in glutamate within the striatum, indicative of icilin’s neurochemical effect in rats.

Keywords: Keywords: Icilin – TRPA1 – TRPM8 – Dorsal striatum – Glutamate

Addendum: Abstracts from the 9th International Congress on Amino Acids and Peptides by Abstracts (pp. 311-316).

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Amino Acids: The Forum for Amino Acid, Peptide and Protein Research (v.30, #3)