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Phosphoethanolamine

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https://www.readbyqxmd.com/read/28203076/light-triggered-liposomal-cargo-delivery-platform-incorporating-photosensitizers-and-gold-nanoparticles-for-enhanced-singlet-oxygen-generation-and-increased-cytotoxicity
#1
Zofia Kautzka, Sandhya Clement, Ewa M Goldys, Wei Deng
We developed light-triggered liposomes incorporating 3-5 nm hydrophobic gold nanoparticles and Rose Bengal (RB), a well-known photosensitizer used for photodynamic therapy. Singlet oxygen generated by these liposomes with 532 nm light illumination was characterized for varying the molar ratio of lipids and gold nanoparticles while keeping the amount of RB constant. Gold nanoparticles were found to enhance the singlet oxygen generation rate, with a maximum enhancement factor of 1.75 obtained for the molar ratio of hydrogenated soy l-α-phosphatidylcholine:1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(hexanoylamine):gold of 57:5:17 compared with liposomes loaded with RB alone...
2017: International Journal of Nanomedicine
https://www.readbyqxmd.com/read/28193899/structure-of-a-lipid-a-phosphoethanolamine-transferase-suggests-how-conformational-changes-govern-substrate-binding
#2
Anandhi Anandan, Genevieve L Evans, Karmen Condic-Jurkic, Megan L O'Mara, Constance M John, Nancy J Phillips, Gary A Jarvis, Siobhan S Wills, Keith A Stubbs, Isabel Moraes, Charlene M Kahler, Alice Vrielink
Multidrug-resistant (MDR) gram-negative bacteria have increased the prevalence of fatal sepsis in modern times. Colistin is a cationic antimicrobial peptide (CAMP) antibiotic that permeabilizes the bacterial outer membrane (OM) and has been used to treat these infections. The OM outer leaflet is comprised of endotoxin containing lipid A, which can be modified to increase resistance to CAMPs and prevent clearance by the innate immune response. One type of lipid A modification involves the addition of phosphoethanolamine to the 1 and 4' headgroup positions by phosphoethanolamine transferases...
February 13, 2017: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/28191842/synthesis-and-functional-characterization-of-novel-sialyl-lewisx-mimic-decorated-liposomes-for-e-selectin-mediated-targeting-to-inflamed-endothelial-cells
#3
Chanikarn Chantarasrivong, Akiharu Ueki, Ryutaro Ohyama, Johan Unga, Shinya Nakamura, Isao Nakanishi, Yuriko Higuchi, Shigeru Kawakami, Hiromune Ando, Akihiro Imamura, Hideharu Ishida, Fumiyoshi Yamashita, Makoto Kiso, Mitsuru Hashida
Sialyl LewisX (sLeX) is a natural ligand of E-selectin that is overexpressed by inflamed and tumor endothelium. Although sLeX is a potential ligand for drug targeting, synthesis of the tetrasaccharide is complicated with many reaction steps. In this study, structurally simplified novel sLeX analogs were designed and linked with 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-polyethyleneglycol-2000 (DSPE-PEG) for E-selectin-mediated liposomal delivery. The sLeX structural simplification strategies include (1) replacement of the Gal-GlcNAc disaccharide unit with lactose to reduce many initial steps and (2) substitution of neuraminic acid with a negatively charged group, i...
February 13, 2017: Molecular Pharmaceutics
https://www.readbyqxmd.com/read/28167510/preclinical-development-of-a-non-toxic-oral-formulation-of-monoethanolamine-a-lipid-precursor-for-prostate-cancer-treatment
#4
Roopali Saxena, Chunhua Yang, Mukkavilli Rao, Ravi Chakra C Turaga, Chakravarthy Garlapati, Sushma Reddy Gundala, Kimberly Myers, Ahmed Ghareeb, Shristi Bhattarai, Golnaz Kamilinia, Sangina Bristi, Dan Su, Giovanni Gadda, Padmashree Cg Rida, Guilherme Cantuaria, Ritu Aneja
PURPOSE: Most currently-available chemotherapeutic agents target rampant cell division in cancer cells, thereby affecting rapidly-dividing normal cells resulting in toxic side-effects. This non-specificity necessitates identification of novel cellular pathways that are reprogrammed selectively in cancer cells and can be exploited to develop pharmacologically superior and less-toxic therapeutics. Despite growing awareness on dysregulation of lipid metabolism in cancer cells, targeting lipid biosynthesis is still largely uncharted territory...
February 6, 2017: Clinical Cancer Research: An Official Journal of the American Association for Cancer Research
https://www.readbyqxmd.com/read/28154264/modifying-cationic-liposomes-with-cholesteryl-peg-prevents-their-aggregation-in-human-urine-and-enhances-cellular-uptake-by-bladder-cancer-cells
#5
Takashi Nakamura, Yosuke Noma, Yu Sakurai, Hideyoshi Harashima
Intravesical drug delivery by cationic liposomes (Cat-LPs) represents a potent nanotechnology for enhancing therapeutic effects against bladder disorders. However, preventing the aggregation of Cat-LPs in urine poses a significant barrier. We report on an examination of the effect of modifying liposomes with polyethylene glycol (PEG) lipids to prevent Cat-LPs from aggregating in human urine. Although Cat-LPs underwent significant aggregation in human urine, introducing 5 mol% of PEG2k lipid or 2 mol% of PEG5k lipid completely inhibited the aggregation of the Cat-LPs...
2017: Biological & Pharmaceutical Bulletin
https://www.readbyqxmd.com/read/28137464/a-ph-sensitive-micelle-composed-of-heparin-phospholipids-and-histidine-as-the-carrier-of-photosensitizers-application-to-enhance-photodynamic-therapy-of-cancer
#6
Tilahun Ayane Debele, Shewaye Lakew Mekuria, Hsieh-Chih Tsai
In this study, we describe the synthesis of a stable, pH-sensitive micelle composed of heparin, 1, 2-distearoyl-sn-glycerol-3-phosphoethanolamine, and l-histidine (HDH) through 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC)/N-hydroxysuccinimide (NHS) chemistry. (1)H-Nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FTIR) analyses confirmed the formation of HDH copolymers and dynamic light scattering (DLS) measurements indicated a particle size of 111.57±12.36nm and zeta potential of -59...
January 27, 2017: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/28127097/synthesis-of-3-o-and-4-o-2-aminoethylphosphono-derivatives-of-methyl-l-glycero-%C3%AE-d-manno-heptopyranoside
#7
Martin Walter, Claudia Kohout, Markus Blaukopf, Paul Kosma
ABSTRACT: Phosphoethanolamine derivatives of the bacterial saccharide l-glycero-d-manno-heptose have been prepared using a phosphoramidite-based coupling reaction at position 4 of a side-chain-protected 2,3-O-orthoester methyl heptoside and at position 3 of a 3,4-diol heptoside, respectively. Global deprotection afforded the corresponding 2-aminoethylphosphodiester derivatives as substrates for crystallographic and binding studies with lectins and antibodies targeting the inner core structure of bacterial lipopolysaccharides...
2017: Monatshefte Für Chemie
https://www.readbyqxmd.com/read/28125111/direct-demonstration-of-lipid-phosphorylation-in-the-lipid-bilayer-of-the-biomimetic-bicontinuous-cubic-phase-using-the-confined-enzyme-lipid-a-phosphoethanolamine-transferase
#8
Leonie van 't Hag, Anandhi Anandan, Shane A Seabrook, Sally L Gras, Calum J Drummond, Alice Vrielink, Charlotte E Conn
Retention of amphiphilic protein activity within the lipid bilayer membrane of the nanostructured biomimetic bicontinuous cubic phase is crucial for applications utilizing these hybrid protein-lipid self-assembly materials, such as in meso membrane protein crystallization and drug delivery. Previous work, mainly on soluble and membrane-associated enzymes, has shown that enzyme activity may be modified when immobilized, including membrane bound enzymes. The effect on activity may be even greater for amphiphilic enzymes with a large hydrophilic domain, such as the Neisserial enzyme lipid A phosphoethanolamine transferase (EptA)...
January 26, 2017: Soft Matter
https://www.readbyqxmd.com/read/28122817/structural-and-biological-characteristics-of-different-forms-of-vitreoscilla-filiformis-lipid-a-use-of-mass-spectrometry-to-highlight-structural-discrepancies
#9
Aude Breton, Alexey Novikov, Richard Martin, Pierre Tissieres, Martine Caroff
Vitreoscilla filiformis is a Gram-negative bacterium, isolated from spa waters, and described for its beneficial effects on the skin. We characterized the detailed structure of its LPS lipid A moiety, an active component of the bacterium, that contributes to the observed skin activation properties. Two different batches, differing in post-culture cells recovery, were tested. Chemical analyses and mass spectra, obtained before and after mild-alkali treatments, revealed these lipid A share the common bisphosphorylated -(16)-linked d-glucosamine disaccharide with hydroxydecanoic acid in an amide linkage...
January 25, 2017: Journal of Lipid Research
https://www.readbyqxmd.com/read/28120887/er-residency-of-the-ceramide-phosphoethanolamine-synthase-smsr-relies-on-homotypic-oligomerization-mediated-by-its-sam-domain
#10
Birol Cabukusta, Matthijs Kol, Laura Kneller, Angelika Hilderink, Andreas Bickert, John G M Mina, Sergei Korneev, Joost C M Holthuis
SMSr/SAMD8 is an ER-resident ceramide phosphoethanolamine synthase with a critical role in controlling ER ceramides and suppressing ceramide-induced apoptosis in cultured cells. SMSr-mediated ceramide homeostasis relies on the enzyme's catalytic activity as well as on its N-terminal sterile α-motif or SAM domain. Here we report that SMSr-SAM is structurally and functionally related to the SAM domain of diacylglycerol kinase DGKδ, a central regulator of lipid signaling at the plasma membrane. Native gel electrophoresis indicates that both SAM domains form homotypic oligomers...
January 25, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28120533/comparative-binding-to-dr4-and-dr5-receptors-of-trail-and-bnnts-pahe-mpeg-dspe-trail-nanoparticles
#11
Yves Claude Guillaume, Claire André
TRAIL is a member of the tumor necrosis factor family of cytokines, which induces apoptosis of cancer cells, thanks to its binding to its cognate receptors DR5 and DR4. We have recently demonstrated that nanovectorization of TRAIL with single-walled carbon nanotubes enhanced TRAIL affinity to DR5. In this paper, 1-pyrenebutyric acid N-hydroxysuccinimide ester functionalized boron nitride nanotubes (BNNTs) were used to anchor the TRAIL protein. The resulting BNNT/1-pyrenebutyric acid N-hydroxysuccinimide ester nanotubes were mixed with methoxy-poly(ethylene glycol)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-conjugates so as to allow a good dispersion of these nanoparticle TRAIL (NPT) in aqueous solution...
January 25, 2017: Journal of Molecular Recognition: JMR
https://www.readbyqxmd.com/read/28103719/pegylated-nanoliposomal-clusterin-for-amyloidogenic-light-chain-induced-endothelial-dysfunction
#12
Diana Guzman-Villanueva, Raymond Q Migrino, Seth Truran, Nina Karamanova, Daniel A Franco, Camelia Burciu, Subhadip Senapati, Dobrin Nedelkov, Parameswaran Hari, Volkmar Weissig
Light chain (AL) amyloidosis is a disease associated with significant morbidity and mortality arising from multi-organ injury induced by amyloidogenic light chain proteins (LC). There is no available treatment to reverse the toxicity of LC. We previously showed that chaperone glycoprotein clusterin (CLU) and nanoliposomes (NL), separately, restore human microvascular endothelial function impaired by LC. In this work, we aim to prepare PEGylated-nanoliposomal clusterin (NL-CLU) formulations that could allow combined benefit against LC while potentially enabling efficient delivery to microvascular tissue, and test efficacy on human arteriole endothelial function...
January 20, 2017: Journal of Liposome Research
https://www.readbyqxmd.com/read/28068143/adaptations-to-excess-choline-in-insulin-resistant-and-pcyt2-deficient-skeletal-muscle
#13
Adrian Taylor, Laila Cigana Schenkel, Maiya Yokich, Marica Bakovic
It was hypothesized that choline supplementation in insulin resistant (IR) CTP:phosphoethanolamine cytidylyltransferase deficient (Pcyt2(+/-)) mice would ameliorate muscle function by remodeling glucose and fatty acid (FA) metabolism. Pcyt2(+/-) mice either received no treatment or were allowed access to 2 mg/mL choline in drinking water for 4 weeks. Skeletal muscle was harvested from choline treated and untreated mice. Lipid analysis and metabolic gene expression and signaling pathways were compared between untreated Pcyt2(+/-) mice, treated Pcyt2(+/-) mice, and Pcyt2(+/+) mice...
September 6, 2016: Biochemistry and Cell Biology, Biochimie et Biologie Cellulaire
https://www.readbyqxmd.com/read/28059088/insights-into-the-mechanistic-basis-of-plasmid-mediated-colistin-resistance-from-crystal-structures-of-the-catalytic-domain-of-mcr-1
#14
Philip Hinchliffe, Qiu E Yang, Edward Portal, Tom Young, Hui Li, Catherine L Tooke, Maria J Carvalho, Neil G Paterson, Jürgen Brem, Pannika R Niumsup, Uttapoln Tansawai, Lei Lei, Mei Li, Zhangqi Shen, Yang Wang, Christopher J Schofield, Adrian J Mulholland, Jianzhong Shen, Natalie Fey, Timothy R Walsh, James Spencer
The polymixin colistin is a "last line" antibiotic against extensively-resistant Gram-negative bacteria. Recently, the mcr-1 gene was identified as a plasmid-mediated resistance mechanism in human and animal Enterobacteriaceae, with a wide geographical distribution and many producer strains resistant to multiple other antibiotics. mcr-1 encodes a membrane-bound enzyme catalysing phosphoethanolamine transfer onto bacterial lipid A. Here we present crystal structures revealing the MCR-1 periplasmic, catalytic domain to be a zinc metalloprotein with an alkaline phosphatase/sulphatase fold containing three disulphide bonds...
January 6, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28050958/non-invasive-prediction-of-blastocyst-implantation-ongoing-pregnancy-and-live-birth-by-mass-spectrometry-lipid-fingerprinting
#15
Edson Borges, Daniela P A F Braga, Amanda Souza Setti, Daniela A Montanni, Elaine Cristina Cabral, Marcos N Eberlin, Edson G Lo Turco, Assumpto Iaconelli
OBJECTIVE: To identify lipid markers of blastocyst implantation and ongoing pregnancy by day three culture medium mass spectrometry (MS) fingerprinting. METHODS: For this study, 33 culture media samples were harvested on day three, from 22 patients undergoing day five embryo transfers. All embryos achieved the blastocyst stage and were split into groups based on their implantation (Negative Implantation, n= 14 and Positive Implantation, n= 19). The positive implantation cycles resulted in successful ongoing pregnancies...
December 1, 2016: JBRA Assisted Reproduction
https://www.readbyqxmd.com/read/28032377/proton-and-phosphorus-magnetic-resonance-spectroscopy-of-the-healthy-human-breast-at-7%C3%A2-t
#16
Wybe J M van der Kemp, Bertine L Stehouwer, Vincent O Boer, Peter R Luijten, Dennis W J Klomp, Jannie P Wijnen
In vivo water- and fat-suppressed (1) H magnetic resonance spectroscopy (MRS) and (31) P magnetic resonance adiabatic multi-echo spectroscopic imaging were performed at 7 T in duplicate in healthy fibroglandular breast tissue of a group of eight volunteers. The transverse relaxation times of (31) P metabolites were determined, and the reproducibility of (1) H and (31) P MRS was investigated. The transverse relaxation times for phosphoethanolamine (PE) and phosphocholine (PC) were fitted bi-exponentially, with an added short T2 component of 20 ms for adenosine monophosphate, resulting in values of 199 ± 8 and 239 ± 14 ms, respectively...
February 2017: NMR in Biomedicine
https://www.readbyqxmd.com/read/28027535/hyaluronic-acid-decorated-pluronic-p85-solid-lipid-nanoparticles-as-a-potential-carrier-to-overcome-multidrug-resistance-in-cervical-and-breast-cancer
#17
Fang Wang, Li Li, Bo Liu, Zhen Chen, Changzhong Li
This work aimed to develop hyaluronic acid (HA) decorated pluronic 85 (P85) coated solid lipid nanoparticles (SLN) loaded with paclitaxel (HA-PTX-P85-SLN) and to evaluate its potential to overcome drug resistance and to increase antitumor efficacy in mice bearing cervical and breast tumor. P85-Distearoyl Phosphoethanolamine (DSPE) was synthesized from P85 and DSPE by coupling in the presence of 1,10-carbonyldiimidazole (CDI) as a catalyst. The SLN were prepared by the hot homogenization technique and electrostatic interaction...
February 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/28005445/preparation-and-in-vivo-safety-evaluations-of-antileukemic-homoharringtonine-loaded-pegylated-liposomes
#18
Dong Liu, Jing Xing, Fei Xiong, Fang Yang, Ning Gu
In order to improve the in vivo safety and specific delivery efficiency of the antileukemic homoharringtonine (HHT) at the targets, the long-circulating PEGylated liposomes loaded with HHT (LCLipo-HHT) were prepared. Their physical characteristics, in vitro drug release, in vivo pharmacokinetic properties and elementary toxicity were evaluated. The mean diameter of the prepared LCLipo-HHT is 75.6 ± 3.2 nm and the zeta potential is -16.9 ± 2.5 mV. The entrapment efficiency (EE) of HHT in the liposomes is 69...
December 22, 2016: Drug Development and Industrial Pharmacy
https://www.readbyqxmd.com/read/28001031/molecular-dynamics-simulation-and-experimental-studies-of-gold-nanoparticle-templated-hdl-like-nanoparticles-for-cholesterol-metabolism-therapeutics
#19
Cheng-Tsung Lai, Wangqiang Sun, Rohun U Palekar, C Shad Thaxton, George C Schatz
High-density lipoprotein (HDL) plays an important role in the transport and metabolism of cholesterol. Mimics of HDL are being explored as potentially powerful therapeutic agents for removing excess cholesterol from arterial plaques. Gold nanoparticles (AuNPs) functionalized with apolipoprotein A-I and with the lipids 1,2-dipalmitoyl-sn-glycero-3-phosphocholine and 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-[3-(2-pyridyldithio)propionate] have been demonstrated to be robust acceptors of cellular cholesterol...
January 18, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28000749/high-resolution-crystal-structure-of-the-catalytic-domain-of-mcr-1
#20
Guixing Ma, Yifan Zhu, Zhicheng Yu, Ashfaq Ahmad, Hongmin Zhang
The newly identified mobile colistin resistant gene (mcr-1) rapidly spread among different bacterial strains and confers colistin resistance to its host, which has become a global concern. Based on sequence alignment, MCR-1 should be a phosphoethanolamine transferase, members of the YhjW/YjdB/YijP superfamily and catalyze the addition of phosphoethanolamine to lipid A, which needs to be validated experimentally. Here we report the first high-resolution crystal structure of the C-terminal catalytic domain of MCR-1 (MCR-1C) in its native state...
December 21, 2016: Scientific Reports
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