Features, roles and chiral analyses of proteinogenic amino acids

Ayon, Navid J.

doi:10.3934/molsci.2020011

Cited by 22 publications

(24 citation statements)

References 106 publications

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“…Despite this, stereoisomers are still overlooked in various tissues and/or physiological fluids, in peptide characterization experiments, and in the metabolomics process, thus demanding stereochemical analytical protocols [ 15 , 16 , 17 ].…”

Section: Chiral Metabolites and Lipids Separation By Liquid Chromatographymentioning

confidence: 99%

Enantioselectivity Effects in Clinical Metabolomics and Lipidomics

2021

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Metabolomics and lipidomics have demonstrated increasing importance in underlying biochemical mechanisms involved in the pathogenesis of diseases to identify novel drug targets and/or biomarkers for establishing therapeutic approaches for human health. Particularly, bioactive metabolites and lipids have biological activity and have been implicated in various biological processes in physiological conditions. Thus, comprehensive metabolites, and lipids profiling are required to obtain further advances in understanding pathophysiological changes that occur in cells and tissues. Chirality is one of the most important phenomena in living organisms and has attracted long-term interest in medical and natural science. Enantioselective separation plays a pivotal role in understanding the distribution and physiological function of a diversity of chiral bioactive molecules. In this context, it has been the goal of method development for targeted and untargeted metabolomics and lipidomic assays. Herein we will highlight the benefits and challenges involved in these stereoselective analyses for clinical samples.

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Section: Chiral Metabolites and Lipids Separation By Liquid Chromatographymentioning

confidence: 99%

Enantioselectivity Effects in Clinical Metabolomics and Lipidomics

2021

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“…The seven essential amino acids in leaves that were present in high concentration included isoleucine (7965 µg/g), L-leucine (6955 µg/g), L-lysine (866 µg/g), L-methionine (398 µg/g), L-phenylalanine (6032 µg/g), L-threonine (2701 µg/g), L-tryptophan (1186 µg/g), and L-valine (6151 µg/g). As for the total amino acids content in C. sativus leaves, it exceeds 43,174 µg/g and shows that this raw material can be an excellent and underestimated source of proteinogenic amino acids [48], especially glutamine, phenylalanine, isoleucine, alanine, and leucine.…”

Section: Gc-ms Analysis Of Amino Acids and Short-chained And Long-chain Carboxylic Acidsmentioning

confidence: 99%

Characterization of Phytochemical Components of Crocus sativus Leaves: A New Attractive By-Product

et al. 2021

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Crocus sativus L. is one of the world’s most famous saffron production crops and its enormous by-products, such as leaves, are an excellent source of bioactive compounds with potential nutritional applications. The total phenolic content of Crocus leaves was 5.44 ± 0.01 mg GAE/g, and the total flavonoid content was 2.63 ± 0.05 mg RE/g, respectively. The main bioactive compounds in the leaves, such as polyphenols, flavonoids by HPLC and carboxylic acids, and amino acids, were also identified by GC-MS. HPLC analyses revealed mangiferin as a dominant constituent (1.26 ± 0.02 mg/g). C. sativus contains seven essential amino acids (ILE, LEU, LYS, MET, PHE, THR, TRP, VAL) in high concentration. Among them, isoleucine (7965 µg/g) was the dominant compound. In addition, the K and Ca concentrations in the leaves were significant (p < 0.05). The chemical composition revealed α-linolenic acid (22,490 µg/g) and linoelaidic acid (9880 µg/g) to be major constituents among all the acids found in the Crocus leaves. The extracts of C. sativus leaves showed the highest inhibitory activity for Gram-positive (B. subtilis and S. aureus) bacteria in the in vitro assay. The current results identify and underline the potential of natural products from C. sativus leaves that can add value to saffron production.

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“…Since protein biosynthesis is also upregulated in many tumors, a higher protein incorporation rate could facilitate the sustained trapping of PET tracers in tumor tissues, thereby increasing the tumor-to-background ratio (TBR) and improving the image quality. The naturally occurring amino acid l -phenylalanine ( l -Phe) is an essential proteinogenic amino acid [ 18 ]. Therefore, its radiofluorination in the 3-position of the aromatic ring could provide a probe that combines high LAT1 affinity with high protein incorporation rates and might thus serve as a marker for increased protein biosynthesis [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of 3-l- and 3-d-[18F]Fluorophenylalanines as PET Tracers for Tumor Imaging

Krämer

Gröner

Hoffmann

et al. 2021

Cancers

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Purpose: The preclinical evaluation of 3-l- and 3-d-[18F]FPhe in comparison to [18F]FET, an established tracer for tumor imaging. Methods: In vitro studies were conducted with MCF-7, PC-3, and U87 MG human tumor cell lines. In vivo µPET studies were conducted in healthy rats with/without the inhibition of peripheral aromatic l-amino acid decarboxylase by benserazide pretreatment (n = 3 each), in mice bearing subcutaneous MCF-7 or PC-3 tumor xenografts (n = 10), and in rats bearing orthotopic U87 MG tumor xenografts (n = 14). Tracer accumulation was quantified by SUVmax, SUVmean and tumor-to-brain ratios (TBrR). Results: The uptake of 3-l-[18F]FPhe in MCF-7 and PC-3 cells was significantly higher relative to [18F]FET. The uptake of all three tracers was significantly reduced by the suppression of amino acid transport systems L or ASC. 3-l-[18F]FPhe but not 3-d-[18F]FPhe exhibited protein incorporation. In benserazide-treated healthy rats, brain uptake after 42–120 min was significantly higher for 3-d-[18F]FPhe vs. 3-l-[18F]FPhe. [18F]FET showed significantly higher uptake into subcutaneous MCF-7 tumors (52–60 min p.i.), while early uptake into orthotopic U87 MG tumors was significantly higher for 3-l-[18F]FPhe (SUVmax: 3-l-[18F]FPhe, 107.6 ± 11.3; 3-d-[18F]FPhe, 86.0 ± 4.3; [18F]FET, 90.2 ± 7.7). Increased tumoral expression of LAT1 and ASCT2 was confirmed immunohistologically. Conclusion: Both novel tracers enable accurate tumor delineation with an imaging quality comparable to [18F]FET.

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Features, roles and chiral analyses of proteinogenic amino acids

Cited by 22 publications

References 106 publications

Enantioselectivity Effects in Clinical Metabolomics and Lipidomics

Enantioselectivity Effects in Clinical Metabolomics and Lipidomics

Characterization of Phytochemical Components of Crocus sativus Leaves: A New Attractive By-Product

Evaluation of 3-l- and 3-d-[18F]Fluorophenylalanines as PET Tracers for Tumor Imaging

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