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  1. Article ; Online: Solvent-Assisted Mechanochemical Synthesis of a Nucleotide Dimer.

    Johnston, Christopher / Migaud, Marie E

    Current protocols

    2022  Volume 2, Issue 4, Page(s) e418

    Abstract: This article contains a synthetic protocol for solvent-assisted mechanochemical synthesis of a nucleotide dimer. First, a dinucleoside phosphite is prepared by solvent-assisted mechanochemistry via the phosphoramidite method. Second, the dinucleoside ... ...

    Abstract This article contains a synthetic protocol for solvent-assisted mechanochemical synthesis of a nucleotide dimer. First, a dinucleoside phosphite is prepared by solvent-assisted mechanochemistry via the phosphoramidite method. Second, the dinucleoside phosphite is oxidized to form the dinucleotide under mechanochemical conditions. Finally, the dinucleotide is purified by column chromatography. Support protocols are also provided for preparing the acidic salts that can be utilized for phosphoramidite couplings and for demonstrating that the reaction occurs under mechanochemical conditions rather than as a result of solvent added for analysis. Mechanochemistry as applied to synthesis of dinucleotides is a recent development and it is anticipated that the principles in this protocol will be widely applicable to a range of nucleoside and ribonucleoside monomers. The advantages of mechanochemistry over traditional solution-phase chemistry are the simplicity of the procedure, improved hydrolytic stability, and elimination of the need to solubilize poorly soluble compounds. © 2022 Wiley Periodicals LLC. Basic Protocol: Solvent-assisted mechanochemical synthesis of a nucleotide dimer Supplementary Protocol 1: Synthesis of N-methylimidazolium triflate Supplementary Protocol 2: Synthesis of pyridinium trifluoroacetate Supplementary Protocol 3: Confirmation of the efficacy of mechanochemical conditions.
    MeSH term(s) Nucleosides ; Nucleotides ; Oligonucleotides ; Phosphites ; Polymers/chemistry ; Solvents
    Chemical Substances Nucleosides ; Nucleotides ; Oligonucleotides ; Phosphites ; Polymers ; Solvents
    Language English
    Publishing date 2022-04-21
    Publishing country United States
    Document type Journal Article
    ISSN 2691-1299
    ISSN (online) 2691-1299
    DOI 10.1002/cpz1.418
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  2. Article ; Online: A tipping point in dihydroxyacetone exposure: mitochondrial stress and metabolic reprogramming alter survival in rat cardiomyocytes H9c2 cells.

    Hernandez, Arlet / Belfleur, Luxene / Migaud, Marie / Gassman, Natalie R

    Chemico-biological interactions

    2024  Volume 394, Page(s) 110991

    Abstract: Exogenous exposures to the triose sugar dihydroxyacetone (DHA) occur from sunless tanning products and electronic cigarette aerosol. Once inhaled or absorbed, DHA enters cells, is converted to dihydroxyacetone phosphate (DHAP), and incorporated into ... ...

    Abstract Exogenous exposures to the triose sugar dihydroxyacetone (DHA) occur from sunless tanning products and electronic cigarette aerosol. Once inhaled or absorbed, DHA enters cells, is converted to dihydroxyacetone phosphate (DHAP), and incorporated into several metabolic pathways. Cytotoxic effects of DHA vary across the cell types depending on the metabolic needs of the cells, and differences in the generation of reactive oxygen species (ROS), cell cycle arrest, and mitochondrial dysfunction have been reported. We have shown that cytotoxic doses of DHA induced metabolic imbalances in glycolysis and oxidative phosphorylation in liver and kidney cell models. Here, we examine the dose-dependent effects of DHA on the rat cardiomyocyte cell line, H9c2. Cells begin to experience cytotoxic effects at low millimolar doses, but an increase in cell survival was observed at 2 mM DHA. We confirmed that 2 mM DHA increased cell survival compared to the low cytotoxic 1 mM dose and investigated the metabolic differences between these two low DHA doses. Exposure to 1 mM DHA showed changes in the cell's fuel utilization, mitochondrial reactive oxygen species (ROS), and transient changes in the glycolysis and mitochondrial energetics, which normalized 24 h after exposure. The 2 mM dose induced robust changes in mitochondrial flux through acetyl CoA and elevated expression of fatty acid synthase. Distinct from the 1 mM dose, the 2 mM exposure increased mitochondrial ROS and NAD(P)H levels, and sustained changes in LDHA/LDHB and acetyl CoA-associated enzymes were observed. Although the cells were exposed to low cytotoxic (1 mM) and non-cytotoxic (2 mM) acute doses of DHA, significant changes in mitochondrial metabolic pathways occurred. Further, the proliferation increase at the acute 2 mM DHA dose suggests a metabolic adaption occurred with sustained consequences in survival and proliferation. With increased exogenous exposure to DHA through e-cigarette aerosol, this work suggests cell metabolic changes induced by acute or potentially chronic exposures could impact cell function and survival.
    MeSH term(s) Animals ; Rats ; Dihydroxyacetone/metabolism ; Cell Survival/drug effects ; Reactive Oxygen Species/metabolism ; Myocytes, Cardiac/drug effects ; Myocytes, Cardiac/metabolism ; Myocytes, Cardiac/pathology ; Mitochondria/metabolism ; Mitochondria/drug effects ; Cell Line ; Glycolysis/drug effects ; Metabolic Reprogramming
    Chemical Substances Dihydroxyacetone (O10DDW6JOO) ; Reactive Oxygen Species
    Language English
    Publishing date 2024-04-04
    Publishing country Ireland
    Document type Journal Article
    ZDB-ID 218799-1
    ISSN 1872-7786 ; 0009-2797
    ISSN (online) 1872-7786
    ISSN 0009-2797
    DOI 10.1016/j.cbi.2024.110991
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    Zs.A 686: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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  3. Article ; Online: Defining NAD(P)(H) Catabolism.

    Dhuguru, Jyothi / Dellinger, Ryan W / Migaud, Marie E

    Nutrients

    2023  Volume 15, Issue 13

    Abstract: Dietary vitamin B3 components, such as nicotinamide and nicotinic acid, are precursors to the ubiquitous redox cofactor nicotinamide adenine dinucleotide ( ... ...

    Abstract Dietary vitamin B3 components, such as nicotinamide and nicotinic acid, are precursors to the ubiquitous redox cofactor nicotinamide adenine dinucleotide (NAD
    MeSH term(s) NAD/metabolism ; Niacinamide/metabolism ; Niacin ; Metabolome ; Oxidation-Reduction ; Biomarkers/metabolism
    Chemical Substances NAD (0U46U6E8UK) ; Niacinamide (25X51I8RD4) ; Niacin (2679MF687A) ; Biomarkers
    Language English
    Publishing date 2023-07-07
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 2518386-2
    ISSN 2072-6643 ; 2072-6643
    ISSN (online) 2072-6643
    ISSN 2072-6643
    DOI 10.3390/nu15133064
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  4. Article: Editorial: NAD+ metabolism as a novel target against infection-Volume II.

    Balducci, Enrico / Braidy, Nady / Migaud, Marie

    Frontiers in molecular biosciences

    2022  Volume 9, Page(s) 1087897

    Language English
    Publishing date 2022-11-21
    Publishing country Switzerland
    Document type Editorial
    ZDB-ID 2814330-9
    ISSN 2296-889X
    ISSN 2296-889X
    DOI 10.3389/fmolb.2022.1087897
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  5. Article ; Online: Conformational Preferences of Pyridone Adenine Dinucleotides from Molecular Dynamics Simulations.

    Buckley, David P / Migaud, Marie E / Tanner, John J

    International journal of molecular sciences

    2022  Volume 23, Issue 19

    Abstract: Pyridone adenine dinucleotides (ox-NADs) are redox inactive derivatives of the enzyme cofactor and substrate nicotinamide adenine dinucleotide (NAD) that have a carbonyl group at the C2, C4, or C6 positions of the nicotinamide ring. These aberrant ... ...

    Abstract Pyridone adenine dinucleotides (ox-NADs) are redox inactive derivatives of the enzyme cofactor and substrate nicotinamide adenine dinucleotide (NAD) that have a carbonyl group at the C2, C4, or C6 positions of the nicotinamide ring. These aberrant cofactor analogs accumulate in cells under stress and are potential inhibitors of enzymes that use NAD(H). We studied the conformational landscape of ox-NADs in solution using molecular dynamics simulations. Compared to NAD
    MeSH term(s) Adenine ; Amides ; Dapsone/analogs & derivatives ; Molecular Dynamics Simulation ; NAD/metabolism ; Niacinamide ; Pyridones ; Ribose
    Chemical Substances Amides ; Pyridones ; NAD (0U46U6E8UK) ; 4-nitro-4'-aminodiphenyl sulfone (1948-92-1) ; Niacinamide (25X51I8RD4) ; Ribose (681HV46001) ; Dapsone (8W5C518302) ; Adenine (JAC85A2161)
    Language English
    Publishing date 2022-10-06
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms231911866
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  6. Article: Imaging and spectroscopic methods to investigate adult neurogenesis

    Just, Nathalie / Chevillard, Pierre-Marie / Migaud, Martine

    Frontiers in neuroscience

    2022  Volume 16, Page(s) 933947

    Abstract: Adult neurogenesis (AN) can be defined as the birth and development of new neurons in adulthood. Until the 1990s, AN was deemed not to happen after birth. Gradually, several groups demonstrated that specific zones of the brain of various species had a ... ...

    Abstract Adult neurogenesis (AN) can be defined as the birth and development of new neurons in adulthood. Until the 1990s, AN was deemed not to happen after birth. Gradually, several groups demonstrated that specific zones of the brain of various species had a neurogenic potential. AN could be the key to treating a large range of neurodegenerative, neuropsychiatric, and metabolic diseases, with a better understanding of the mechanisms allowing for regeneration of new neurons. Despite this promising prospect, the existence of AN has not been validated
    Language English
    Publishing date 2022-08-05
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 2411902-7
    ISSN 1662-453X ; 1662-4548
    ISSN (online) 1662-453X
    ISSN 1662-4548
    DOI 10.3389/fnins.2022.933947
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  7. Article ; Online: Nicotinamide riboside-amino acid conjugates that are stable to purine nucleoside phosphorylase.

    Hayat, Faisal / Migaud, Marie E

    Organic & biomolecular chemistry

    2020  Volume 18, Issue 15, Page(s) 2877–2885

    Abstract: The nutraceutical Nicotinamide Riboside (NR), an efficacious biosynthetic precursor to NAD, is readily metabolized by the purine nucleoside phosphorylase (PNP). Access to the PNP-stable versions of NR is difficult because the glycosidic bond of NR is ... ...

    Abstract The nutraceutical Nicotinamide Riboside (NR), an efficacious biosynthetic precursor to NAD, is readily metabolized by the purine nucleoside phosphorylase (PNP). Access to the PNP-stable versions of NR is difficult because the glycosidic bond of NR is easily cleaved. Unlike NR, NRH, the reduced form of NR, offers sufficient chemical stability to allow the successful functionalisation of the ribosyl-moiety. Here, we report on a series of NRH and NR derived amino acid conjugates, generated in good to excellent yields and show that O5'-esterification prevents the PNP-catalyzed phosphorolysis of these NR prodrugs.
    MeSH term(s) Amino Acids/chemistry ; Amino Acids/metabolism ; Biocatalysis ; Molecular Structure ; Niacinamide/analogs & derivatives ; Niacinamide/chemistry ; Niacinamide/metabolism ; Prodrugs/chemistry ; Prodrugs/metabolism ; Purine-Nucleoside Phosphorylase/chemistry ; Purine-Nucleoside Phosphorylase/metabolism ; Pyridinium Compounds
    Chemical Substances Amino Acids ; Prodrugs ; Pyridinium Compounds ; nicotinamide-beta-riboside (0I8H2M0L7N) ; Niacinamide (25X51I8RD4) ; Purine-Nucleoside Phosphorylase (EC 2.4.2.1)
    Language English
    Publishing date 2020-03-30
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d0ob00134a
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  8. Article: Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives.

    Makarov, Mikhail V / Migaud, Marie E

    Beilstein journal of organic chemistry

    2019  Volume 15, Page(s) 401–430

    Abstract: The β-anomeric form of nicotinamide riboside ( ... ...

    Abstract The β-anomeric form of nicotinamide riboside (NR
    Language English
    Publishing date 2019-02-13
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.15.36
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  9. Article ; Online: Synthesis of Mixed Dinucleotides by Mechanochemistry.

    Hayat, Faisal / Makarov, Mikhail V / Belfleur, Luxene / Migaud, Marie E

    Molecules (Basel, Switzerland)

    2022  Volume 27, Issue 10

    Abstract: We report the synthesis of vitamin B1, B2, and B3 derived nucleotides and dinucleotides generated either through mechanochemical or solution phase chemistry. Under the explored conditions, adenosine and thiamine proved to be particularly amenable to ... ...

    Abstract We report the synthesis of vitamin B1, B2, and B3 derived nucleotides and dinucleotides generated either through mechanochemical or solution phase chemistry. Under the explored conditions, adenosine and thiamine proved to be particularly amenable to milling conditions. Following optimization of the chemistry related to the formation pyrophosphate bonds, mixed dinucleotides of adenine and thiamine (vitamin B1), riboflavin (vitamin B2), nicotinamide riboside and 3-carboxamide 4-pyridone riboside (both vitamin B3 derivatives) were generated in good yields. Furthermore, we report an efficient synthesis of the MW+4 isotopologue of NAD
    MeSH term(s) Niacin/metabolism ; Riboflavin ; Thiamine/analysis
    Chemical Substances Niacin (2679MF687A) ; Riboflavin (TLM2976OFR) ; Thiamine (X66NSO3N35)
    Language English
    Publishing date 2022-05-18
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules27103229
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    Zs.MO 81: Show issues

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  10. Article ; Online: The NADase CD38 is a central regulator in gouty inflammation and a novel druggable therapeutic target.

    Alabarse, Paulo Gil / Oliveira, Patricia / Qin, Huaping / Yan, Tiffany / Migaud, Marie / Terkeltaub, Robert / Liu-Bryan, Ru

    Inflammation research : official journal of the European Histamine Research Society ... [et al.

    2024  Volume 73, Issue 5, Page(s) 739–751

    Abstract: Objectives: Cellular NAD: Methods: We studied cultured mouse wild type and CD38 knockout (KO) murine bone marrow derived macrophages (BMDMs) stimulated by monosodium urate (MSU) crystals and used the air pouch gouty inflammation model.: Results: ... ...

    Abstract Objectives: Cellular NAD
    Methods: We studied cultured mouse wild type and CD38 knockout (KO) murine bone marrow derived macrophages (BMDMs) stimulated by monosodium urate (MSU) crystals and used the air pouch gouty inflammation model.
    Results: MSU crystals induced CD38 in BMDMs in vitro, associated with NAD
    Conclusions: CD38 and NAD
    MeSH term(s) Animals ; ADP-ribosyl Cyclase 1/genetics ; ADP-ribosyl Cyclase 1/metabolism ; Mice, Knockout ; Macrophages/drug effects ; Macrophages/metabolism ; Mice, Inbred C57BL ; Inflammation/drug therapy ; Uric Acid ; Mice ; NAD/metabolism ; Membrane Glycoproteins/genetics ; Membrane Glycoproteins/metabolism ; Male ; NLR Family, Pyrin Domain-Containing 3 Protein/metabolism ; NLR Family, Pyrin Domain-Containing 3 Protein/genetics ; Cells, Cultured ; Arthritis, Gouty/drug therapy ; Arthritis, Gouty/metabolism ; Arthritis, Gouty/genetics ; Inflammasomes/metabolism ; Inflammasomes/drug effects
    Chemical Substances ADP-ribosyl Cyclase 1 (EC 3.2.2.6) ; Cd38 protein, mouse (EC 3.2.2.5) ; Uric Acid (268B43MJ25) ; NAD (0U46U6E8UK) ; Membrane Glycoproteins ; NLR Family, Pyrin Domain-Containing 3 Protein ; Nlrp3 protein, mouse ; Inflammasomes
    Language English
    Publishing date 2024-03-16
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1221794-3
    ISSN 1420-908X ; 1023-3830
    ISSN (online) 1420-908X
    ISSN 1023-3830
    DOI 10.1007/s00011-024-01863-y
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 675: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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