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Biochimie Nov 2016In this mini-review, we summarize current knowledge about the lipid-binding characteristics of two types of toxins used to visualize the membrane distribution of... (Review)
Review
In this mini-review, we summarize current knowledge about the lipid-binding characteristics of two types of toxins used to visualize the membrane distribution of phosphoethanolamine-containing lipid species: the glycerophospholipid, phosphatidylethanolamine (PE) and the sphingolipid, ceramide phosphoethanolamine (CPE). The lantibiotic cinnamycin and the structurally-related peptide duramycin produced by some Gram-positive bacteria were among the first toxins characterized by their specificity for PE which is widely present in animal kingdoms from bacteria to mammals. These toxins promoted their binding to PE-containing membranes by changing membrane curvature and by inducing transbilayer lipid movement. The recognition of the conical shape and negative curvature adopted by the PE species within the membrane, is important to understand how lipid-peptide interaction can occur. Three mushroom-derived proteins belonging to the aegerolysin family, pleurotolysin A2, ostreolysin and erylysin A were recently described as efficient tools to visualize the membrane distribution of CPE which is found in trace amounts in mammalian cells but in higher amounts in some developmental stages of lower eukaryotes like Trypanosoma and in invertebrates such as Drosophila. The recent development of lantibiotic-based PE-specific and aegerolysin-based CPE-specific probes is useful to visualize and specify the role of these lipids in various pathophysiological events such as cell division, apoptosis, tumor vasculature and parasite developmental stages.
Topics: Animals; Bacteriocins; Binding, Competitive; Cell Membrane; Ethanolamines; Fungal Proteins; Hemolysin Proteins; Peptides; Peptides, Cyclic; Phosphatidylethanolamines; Protein Binding
PubMed: 27693589
DOI: 10.1016/j.biochi.2016.09.020 -
International Journal of Molecular... Oct 2021The selenoprotein family includes 25 members, many of which are antioxidant or redox regulating enzymes. A unique member of this family is Selenoprotein I (SELENOI),... (Review)
Review
The selenoprotein family includes 25 members, many of which are antioxidant or redox regulating enzymes. A unique member of this family is Selenoprotein I (SELENOI), which does not catalyze redox reactions, but instead is an ethanolamine phosphotransferase (Ept). In fact, the characteristic selenocysteine residue that defines selenoproteins lies far outside of the catalytic domain of SELENOI. Furthermore, data using recombinant SELENOI lacking the selenocysteine residue have suggested that the selenocysteine amino acid is not directly involved in the Ept reaction. SELENOI is involved in two different pathways for the synthesis of phosphatidylethanolamine (PE) and plasmenyl PE, which are constituents of cellular membranes. Ethanolamine phospholipid synthesis has emerged as an important process for metabolic reprogramming that occurs in pluripotent stem cells and proliferating tumor cells, and this review discusses roles for upregulation of SELENOI during T cell activation, proliferation, and differentiation. SELENOI deficiency lowers but does not completely diminish de novo synthesis of PE and plasmenyl PE during T cell activation. Interestingly, metabolic reprogramming in activated SELENOI deficient T cells is impaired and this reduces proliferative capacity while favoring tolerogenic to pathogenic phenotypes that arise from differentiation. The implications of these findings are discussed related to vaccine responses, autoimmunity, and cell-based therapeutic approaches.
Topics: Cellular Reprogramming; Ethanolamine; Ethanolaminephosphotransferase; Humans; Lymphocyte Activation; Phosphatidylethanolamines; Phospholipids; Selenium; Selenocysteine; Selenoproteins; T-Lymphocytes; Up-Regulation
PubMed: 34681834
DOI: 10.3390/ijms222011174 -
Journal of Drug Targeting Apr 2015PEG-lipid micelles, primarily conjugates of polyethylene glycol (PEG) and distearyl phosphatidylethanolamine (DSPE) or PEG-DSPE, have emerged as promising drug-delivery... (Review)
Review
PEG-lipid micelles, primarily conjugates of polyethylene glycol (PEG) and distearyl phosphatidylethanolamine (DSPE) or PEG-DSPE, have emerged as promising drug-delivery carriers to address the shortcomings associated with new molecular entities with suboptimal biopharmaceutical attributes. The flexibility in PEG-DSPE design coupled with the simplicity of physical drug entrapment have distinguished PEG-lipid micelles as versatile and effective drug carriers for cancer therapy. They were shown to overcome several limitations of poorly soluble drugs such as non-specific biodistribution and targeting, lack of water solubility and poor oral bioavailability. Therefore, considerable efforts have been made to exploit the full potential of these delivery systems; to entrap poorly soluble drugs and target pathological sites both passively through the enhanced permeability and retention (EPR) effect and actively by linking the terminal PEG groups with targeting ligands, which were shown to increase delivery efficiency and tissue specificity. This article reviews the current state of PEG-lipid micelles as delivery carriers for poorly soluble drugs, their biological implications and recent developments in exploring their active targeting potential. In addition, this review sheds light on the physical properties of PEG-lipid micelles and their relevance to the inherent advantages and applications of PEG-lipid micelles for drug delivery.
Topics: Animals; Chemical Phenomena; Chemistry, Pharmaceutical; Drug Carriers; Humans; Micelles; Models, Biological; Phosphatidylethanolamines; Polyethylene Glycols
PubMed: 25547369
DOI: 10.3109/1061186X.2014.997735 -
The Journal of Biological Chemistry Jul 2014Recently, synthetic prions with a high level of specific infectivity have been produced from chemically defined components in vitro. A major insight arising from these... (Review)
Review
Recently, synthetic prions with a high level of specific infectivity have been produced from chemically defined components in vitro. A major insight arising from these studies is that various classes of host-encoded cofactor molecules such as phosphatidylethanolamine and RNA molecules are required to form and maintain the specific conformation of infectious prions. Synthetic mouse prions formed with phosphatidylethanolamine exhibit levels of specific infectivity ∼1 million-fold greater than "protein-only" prions (Deleault, N. R., Walsh, D. J., Piro, J. R., Wang, F., Wang, X., Ma, J., Rees, J. R., and Supattapone, S. (2012) Proc. Natl. Acad. Sci. U.S.A. 109, E1938-E1946). Moreover, cofactor molecules also appear to regulate prion strain properties by limiting the potential conformations of the prion protein (see Deleault et al. above). The production of fully infectious synthetic prions provides new opportunities to study the mechanism of prion infectivity directly by structural and biochemical methods.
Topics: Animals; Cricetinae; Mice; Phosphatidylethanolamines; PrPSc Proteins; Prion Diseases; Prions; Protein Conformation
PubMed: 24860097
DOI: 10.1074/jbc.R113.511329 -
Progress in Lipid Research Jul 2015Host defence peptides (HDPs) are antimicrobial agents produced by organisms across the prokaryotic and eukaryotic kingdoms. Many prokaryotes produce HDPs, which utilise... (Review)
Review
Host defence peptides (HDPs) are antimicrobial agents produced by organisms across the prokaryotic and eukaryotic kingdoms. Many prokaryotes produce HDPs, which utilise lipid and protein receptors in the membranes of bacterial competitors to facilitate their antibacterial action and thereby survive in their niche environment. As a major example, it is well established that cinnamycin and duramycins from Streptomyces have a high affinity for phosphatidylethanolamine (PE) and exhibit activity against other Gram-positive organisms, such as Bacillus. In contrast, although eukaryotic HDPs utilise membrane interactive mechanisms to facilitate their antimicrobial activity, the prevailing view has long been that these mechanisms do not involve membrane receptors. However, this view has been recently challenged by reports that a number of eukaryotic HDPs such as plant cyclotides also use PE as a receptor to promote their antimicrobial activities. Here, we review current understanding of the mechanisms that underpin the use of PE as a receptor in the antimicrobial and other biological actions of HDPs and describe medical and biotechnical uses of these peptides, which range from tumour imaging and detection to inclusion in topical microbicidal gels to prevent the sexual transmission of HIV.
Topics: Amino Acid Sequence; Animals; Antimicrobial Cationic Peptides; Humans; Immunity, Innate; Lipid Bilayers; Molecular Dynamics Simulation; Molecular Sequence Data; Phosphatidylethanolamines; Protein Binding
PubMed: 25936689
DOI: 10.1016/j.plipres.2015.02.003 -
Comprehensive Identification of Amadori Compound-Modified Phosphatidylethanolamines in Human Plasma.Chemical Research in Toxicology Jul 2019Amadori compound modified lipids are the result of nonenzymatic glycation and play an important role in several physiological and pathological processes. However,...
Amadori compound modified lipids are the result of nonenzymatic glycation and play an important role in several physiological and pathological processes. However, glycation of phosphatidylethanolamine (PE), the most abundant amine-containing lipid in blood plasma, is underexplored and so far only a few glycated PEs have been reported. Herein, we report comprehensive profiling of Amadori-PE and -LysoPE species in human plasma. Using synthetic standards, we first optimized the enrichment procedure for extracting Amadori-PE/LysoPE from plasma. On the basis of the characteristic neutral losses of 303 Da in positive and 162 Da in negative ionization mode, we then applied neural loss scanning-liquid chromatography tandem mass spectrometry (LC-NLS-MS) to identify potentially glycated PE and LysoPE, which was followed by targeted product ion scanning (LC-PIS-MS) to confidently confirm the fatty acyl substitutions of the modified lipids. A total of 20 Amadori-LysoPE and 62 Amadori-PE species, including diacyl, plasmanyl, and plasmenyl, were identified. Among them, the concentrations of 12 Amarodi-LysoPE and 54 Amadori-PE were also quantified in native human plasma, using stable isotope labeled Amadori lipids as internal standards.
Topics: Chromatography, Liquid; Glycosylation; Humans; Molecular Structure; Phosphatidylethanolamines; Tandem Mass Spectrometry
PubMed: 31188577
DOI: 10.1021/acs.chemrestox.9b00158 -
Methods in Molecular Biology (Clifton,... 2016N-acyl-phosphatidylethanolamine (NAPE)-hydrolyzing phospholipase D (NAPE-PLD) is a prominent enzyme involved in the biosynthesis of fatty acid amides (FAAs), a family of...
N-acyl-phosphatidylethanolamine (NAPE)-hydrolyzing phospholipase D (NAPE-PLD) is a prominent enzyme involved in the biosynthesis of fatty acid amides (FAAs), a family of bioactive lipids including anandamide (AEA) as the prototypical member. Here, we describe a NAPE-PLD assay based on radioactive substrates and product separation by thin-layer chromatography (TLC).
Topics: Cell Line; Chromatography, Thin Layer; Enzyme Activation; Enzyme Assays; Isotope Labeling; Phosphatidylethanolamines; Phospholipase D; Substrate Specificity
PubMed: 27245898
DOI: 10.1007/978-1-4939-3539-0_13 -
Archives of Microbiology Aug 2021A Gram-stain-negative, rod-shaped, aerobic and non-motile bacterium, designated P2-65, was isolated from Moonsan stream water in the Republic of Korea. The temperature,...
A Gram-stain-negative, rod-shaped, aerobic and non-motile bacterium, designated P2-65, was isolated from Moonsan stream water in the Republic of Korea. The temperature, NaCl concentration and pH ranges for growth of strain P2-65 were 10-37 °C, 0.0-3.0% (w/v) and 6.5-8.5 with optimum growth at 25-30 °C, 0.0-1.0% and 7.0-7.5, respectively. Comparison of 16S rRNA gene sequence showed that strain P2-65 was closely related to Flavobacterium cauense (95.4%) and Flavobacterium cheniae (95.3%). The major fatty acids were iso-C, iso C 3-OH, summed feature 3 (Cω7c and/or Cω6c), summed feature 9 (iso-C ω9c and/or 10-methyl C) and iso-C 3-OH. The predominant respiratory quinone was menaquinone-6 (MK-6). The major polar lipids detected in the strain were phosphatidylethanolamine, one aminophospholipid, one unidentified aminolipid and one unidentified polar lipid. The G + C content of the genomic DNA was 39.7%. The average nucleotide identity (ANI) and digital DNA-DNA hybridization (dDDH) values for strain P2-65 with closely related Flavobacterium species were below 74.8% and 20%, respectively. Based on polyphasic features, strain P2-65 is considered to represent a novel species of the genus Flavobacterium, for which the name Flavobacterium inviolabile sp. nov. is proposed. The type strain is P2-65 (= KCTC 62055 = NBRC 112953).
Topics: Fatty Acids; Flavobacterium; Phosphatidylethanolamines; Water Microbiology
PubMed: 33993324
DOI: 10.1007/s00203-021-02221-w -
FASEB Journal : Official Publication of... Jan 2021Enzymatic control of lipid homeostasis in the cell is a vital element in the complex organization of life. Phosphatidylserine (PS) is an essential anionic phospholipid... (Review)
Review
Enzymatic control of lipid homeostasis in the cell is a vital element in the complex organization of life. Phosphatidylserine (PS) is an essential anionic phospholipid of cell membranes, and conducts numerous roles for their structural and functional integrity. In mammalian cells, two distinct enzymes phosphatidylserine synthases-1 (PSS1) and -2 (PSS2) in the mitochondria-associated membrane (MAM) in the ER perform de novo synthesis of PS. It is based on base-exchange reactions of the preexisting dominant phospholipids phosphatidylcholine (PC) and phosphatidylethanolamine (PE). While PSS2 specifically catalyzes the reaction "PE → PS," whether or not PSS1 is responsible for the same reaction along with the reaction "PC → PS" remains unsettled despite its fundamental impact on the major stoichiometry. We propose here that a key but the only report that appeared to have put scientists on hold for decades in answering to this issue may be viewed consistently with other available research reports; PSS1 utilizes the two dominant phospholipid classes at a similar intrinsic rate. In this review, we discuss the issue in view of the current information for the enzyme machineries, membrane structure and dynamics, intracellular network of lipid transport, and PS synthesis in health and disease. Resolution of the pending issue is thus critical in advancing our understanding of roles of the essential anionic lipid in biology, health, and disease.
Topics: Animals; Homeostasis; Humans; Lipid Metabolism; Mitochondrial Membranes; Nitrogenous Group Transferases; Phosphatidylethanolamines; Phosphatidylserines
PubMed: 33205488
DOI: 10.1096/fj.202001802R -
Food Research International (Ottawa,... Jul 2022Heat treatment is an important processing technique related to milk quality and nutritional value in the dairy industry. In this study, changes in milk lipids in...
Heat treatment is an important processing technique related to milk quality and nutritional value in the dairy industry. In this study, changes in milk lipids in response to different heat treatments were comprehensively characterized using a lipidomic approach. Ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS) were used to identify and quantify 29 classes and 788 different lipids. In general, heat treatment promoted milk lipid hydrolysis and oxidation; in particular, ultra-high temperature (UHT) treatment resulted in more phospholipid hydrolysis than did pasteurization and extended shelf-life (ESL) treatment. Heat treatment resulted in further lipid oxidation reactions and a reduction in the amount of mild oxidation products. Moreover, the levels of lysophospholipids and free fatty acids (including oxidized free fatty acids) can be used to distinguish UHT-treated milk. In turn, oxidized phosphatidylcholine, oxidized phosphatidylethanolamine, ether-linked phosphatidylethanolamine, diacylglycerol, triacylglycerol, and oxidized triacylglycerol can be used to differentiate raw, pasteurized, and ESL milk. These biomarkers can potentially be used in the dairy industry to monitor the degree and method of heat treatment of milk.
Topics: Animals; Fatty Acids, Nonesterified; Hot Temperature; Lipidomics; Milk; Phosphatidylethanolamines; Triglycerides
PubMed: 35761614
DOI: 10.1016/j.foodres.2022.111345