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  1. Article ; Online: Controlling the G-Quadruplex Topology: Toward the Formation of a Lipid Thrombin Binding Aptamer Prodrug.

    Vialet, Brune / Bansode, Nitin D / Gissot, Arnaud / Barthélémy, Philippe

    Bioconjugate chemistry

    2023  Volume 34, Issue 7, Page(s) 1198–1204

    Abstract: Important efforts have been devoted toward the development of modified oligonucleotides capable of controlling the secondary structures of the G-quadruplex (G4). Herein, we introduce a photocleavable, lipidated construct of the well-known Thrombin ... ...

    Abstract Important efforts have been devoted toward the development of modified oligonucleotides capable of controlling the secondary structures of the G-quadruplex (G4). Herein, we introduce a photocleavable, lipidated construct of the well-known Thrombin Binding Aptamer (TBA) whose conformation can be dual-controlled by light and/or the ionic strength of the aqueous solution. This novel lipid-modified TBA oligonucleotide spontaneously self-assembles and switches from the conventional antiparallel aptameric fold at low ionic strength to the parallel, inactive conformation of the TBA oligonucleotide strands under physiologically relevant conditions. The latter parallel conformation can be readily and chemoselectively switched back to the antiparallel native aptamer conformation upon light irradiation. Our lipidated construct constitutes an original prodrug of the original TBA with properties that are prone to improving the pharmacodynamic profile of the unmodified TBA.
    MeSH term(s) Thrombin/chemistry ; Prodrugs/pharmacology ; G-Quadruplexes ; Aptamers, Nucleotide/chemistry ; Lipids
    Chemical Substances Thrombin (EC 3.4.21.5) ; Prodrugs ; Aptamers, Nucleotide ; Lipids
    Language English
    Publishing date 2023-06-21
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 1024041-x
    ISSN 1520-4812 ; 1043-1802
    ISSN (online) 1520-4812
    ISSN 1043-1802
    DOI 10.1021/acs.bioconjchem.3c00170
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  2. Article ; Online: Intramolecular Michael Additions in Uridine Derivatives: Isolation of the Labile 5'O-C6 Cyclonucleoside.

    Gissot, Arnaud / Massip, Stéphane / Barthélémy, Philippe

    ACS omega

    2020  Volume 5, Issue 38, Page(s) 24746–24753

    Abstract: Uridine derivatives undergo a diastereospecific intramolecular hetero Michael addition onto uracil C6 to give cyclo-adducts. In contrast to the potent amine and thiol nucleophiles at the 5' position of ribose, which readily give ... ...

    Abstract Uridine derivatives undergo a diastereospecific intramolecular hetero Michael addition onto uracil C6 to give cyclo-adducts. In contrast to the potent amine and thiol nucleophiles at the 5' position of ribose, which readily give the
    Language English
    Publishing date 2020-09-15
    Publishing country United States
    Document type Journal Article
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.0c03348
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  3. Article ; Online: Intramolecular Michael Additions in Uridine Derivatives

    Arnaud Gissot / Stéphane Massip / Philippe Barthélémy

    ACS Omega, Vol 5, Iss 38, Pp 24746-

    Isolation of the Labile 5′O-C6 Cyclonucleoside

    2020  Volume 24753

    Keywords Chemistry ; QD1-999
    Language English
    Publishing date 2020-09-01T00:00:00Z
    Publisher American Chemical Society
    Document type Article ; Online
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  4. Article ; Online: An analytical study of lipid-oligonucleotide aggregation properties.

    Barakat, Fatima / Gaudin, Karen / Vialet, Brune / Gissot, Arnaud / Darbary, Alexandre / Barthélémy, Philippe / Ferey, Ludivine

    Journal of pharmaceutical and biomedical analysis

    2021  Volume 205, Page(s) 114327

    Abstract: Lipid-oligonucleotides (LON) attract great interest as supramolecular scaffolds to improve the intracellular delivery of nucleic acids. Analytical characterization of LON assemblies is critical to formulation development, understanding in-vivo ... ...

    Abstract Lipid-oligonucleotides (LON) attract great interest as supramolecular scaffolds to improve the intracellular delivery of nucleic acids. Analytical characterization of LON assemblies is critical to formulation development, understanding in-vivo performance, as well as quality control. For this study, we selected LONs featuring different modifications on both oligonucleotide (with or without a G4 prone sequence) and lipid (mono or bis-alkyl chain covalently attached to the oligonucleotide sequence). Size exclusion chromatography (SEC) and, for the first time, capillary electrophoresis (CE) were investigated to study LON supramolecular self-assemblies. Results were correlated to those obtained with conventional physico-chemical characterization techniques i.e. gel electrophoresis, dynamic light scattering, and circular dichroism. In SEC, a separation between LON monomers and micelles was achieved in 5min on a TSK-gel G3000PW column at 70°C with 100% water, as mobile phase. CE conditions were optimized using a fused-silica capillary length of 10.0cm effective length at 15°C. Different background electrolytes were tested by varying the nature and the concentration of salts added. A sodium tetraborate buffer with 75mM NaCl appeared suitable to promote LON assembly. CE offers benefits to LON micelle analysis in terms of speed of analysis, high resolution, and low quantity of sample injected. Moreover, CE provides an appropriate tool to assess the impact of media of biological relevance on LON self-assembly. In this work, the key role of lipophilic tails and the formation of tetramolecular G-quadruplexes on the stability of LON micelles was confirmed.
    MeSH term(s) Chromatography, Gel ; Electrophoresis, Capillary ; Lipids ; Micelles ; Oligonucleotides
    Chemical Substances Lipids ; Micelles ; Oligonucleotides
    Language English
    Publishing date 2021-08-12
    Publishing country England
    Document type Journal Article
    ZDB-ID 604917-5
    ISSN 1873-264X ; 0731-7085
    ISSN (online) 1873-264X
    ISSN 0731-7085
    DOI 10.1016/j.jpba.2021.114327
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  5. Article ; Online: Controlling G-quadruplex formation via lipid modification of oligonucleotide sequences.

    Vialet, Brune / Gissot, Arnaud / Delzor, Romain / Barthélémy, Philippe

    Chemical communications (Cambridge, England)

    2017  Volume 53, Issue 84, Page(s) 11560–11563

    Abstract: G-quadruplexes (G4) represent attractive supramolecular scaffolds. In this communication, we show that the lipid modification of a G4 prone oligonucleotide sequence drastically increases the probability of forming tetramolecular parallel G4s with ... ...

    Abstract G-quadruplexes (G4) represent attractive supramolecular scaffolds. In this communication, we show that the lipid modification of a G4 prone oligonucleotide sequence drastically increases the probability of forming tetramolecular parallel G4s with unprecedented conformational control over other unspecific oligomers or folds.
    Language English
    Publishing date 2017-10-19
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/c7cc05693a
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  6. Article ; Online: Bioconjugated Oligonucleotides: Recent Developments and Therapeutic Applications.

    Benizri, Sebastien / Gissot, Arnaud / Martin, Andrew / Vialet, Brune / Grinstaff, Mark W / Barthélémy, Philippe

    Bioconjugate chemistry

    2019  Volume 30, Issue 2, Page(s) 366–383

    Abstract: Oligonucleotide-based agents have the potential to treat or cure almost any disease, and are one of the key therapeutic drug classes of the future. Bioconjugated oligonucleotides, a subset of this class, are emerging from basic research and being ... ...

    Abstract Oligonucleotide-based agents have the potential to treat or cure almost any disease, and are one of the key therapeutic drug classes of the future. Bioconjugated oligonucleotides, a subset of this class, are emerging from basic research and being successfully translated to the clinic. In this Review, we first briefly describe two approaches for inhibiting specific genes using oligonucleotides-antisense DNA (ASO) and RNA interference (RNAi)-followed by a discussion on delivery to cells. We then summarize and analyze recent developments in bioconjugated oligonucleotides including those possessing GalNAc, cell penetrating peptides, α-tocopherol, aptamers, antibodies, cholesterol, squalene, fatty acids, or nucleolipids. These novel conjugates provide a means to enhance tissue targeting, cell internalization, endosomal escape, target binding specificity, resistance to nucleases, and more. We next describe those bioconjugated oligonucleotides approved for patient use or in clinical trials. Finally, we summarize the state of the field, describe current limitations, and discuss future prospects. Bioconjugation chemistry is at the centerpiece of this therapeutic oligonucleotide revolution, and significant opportunities exist for development of new modification chemistries, for mechanistic studies at the chemical-biology interface, and for translating such agents to the clinic.
    MeSH term(s) Animals ; Drug Delivery Systems/methods ; Gene Silencing ; Humans ; Oligonucleotides, Antisense/administration & dosage ; Oligonucleotides, Antisense/chemistry ; Oligonucleotides, Antisense/therapeutic use ; RNA Interference ; RNA, Small Interfering/administration & dosage ; RNA, Small Interfering/chemistry ; RNA, Small Interfering/therapeutic use ; Transfection/methods
    Chemical Substances Oligonucleotides, Antisense ; RNA, Small Interfering
    Language English
    Publishing date 2019-01-29
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Review
    ZDB-ID 1024041-x
    ISSN 1520-4812 ; 1043-1802
    ISSN (online) 1520-4812
    ISSN 1043-1802
    DOI 10.1021/acs.bioconjchem.8b00761
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  7. Article ; Online: Changes in cerebral connectivity and brain tissue pulsations with the antidepressant response to an equimolar mixture of oxygen and nitrous oxide: an MRI and ultrasound study.

    Desmidt, Thomas / Dujardin, Paul-Armand / Andersson, Frédéric / Brizard, Bruno / Réméniéras, Jean-Pierre / Gissot, Valérie / Arlicot, Nicolas / Barantin, Laurent / Espitalier, Fabien / Belzung, Catherine / Tanti, Arnaud / Robert, Gabriel / Bulteau, Samuel / Gallet, Quentin / Kazour, François / Cognet, Sandrine / Camus, Vincent / El-Hage, Wissam / Poupin, Pierre /
    Karim, Helmet T

    Molecular psychiatry

    2023  Volume 28, Issue 9, Page(s) 3900–3908

    Abstract: Nitrous oxide ( ... ...

    Abstract Nitrous oxide (N
    MeSH term(s) Female ; Humans ; Nitrous Oxide/therapeutic use ; Depressive Disorder, Major/drug therapy ; Oxygen/therapeutic use ; Magnetic Resonance Imaging/methods ; Brain/diagnostic imaging ; Antidepressive Agents/pharmacology ; Antidepressive Agents/therapeutic use ; Gyrus Cinguli/diagnostic imaging
    Chemical Substances Nitrous Oxide (K50XQU1029) ; Oxygen (S88TT14065) ; Antidepressive Agents
    Language English
    Publishing date 2023-08-17
    Publishing country England
    Document type Journal Article
    ZDB-ID 1330655-8
    ISSN 1476-5578 ; 1359-4184
    ISSN (online) 1476-5578
    ISSN 1359-4184
    DOI 10.1038/s41380-023-02217-6
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  8. Article ; Online: Controlling G-quadruplex formation via lipid modification of oligonucleotide sequences

    Vialet, Brune / Gissot, Arnaud / Delzor, Romain / Barthélemy, Philippe

    Chemical communications. 2017 Oct. 19, v. 53, no. 84 p.11560-11563

    2017  

    Abstract: G-quadruplexes (G4) represent attractive supramolecular scaffolds. In this communication, we show that the lipid modification of a G4 prone oligonucleotide sequence drastically increases the probability of forming tetramolecular parallel G4s with ... ...

    Abstract G-quadruplexes (G4) represent attractive supramolecular scaffolds. In this communication, we show that the lipid modification of a G4 prone oligonucleotide sequence drastically increases the probability of forming tetramolecular parallel G4s with unprecedented conformational control over other unspecific oligomers or folds.
    Keywords chemical compounds ; chemical reactions ; lipids ; oligonucleotides ; probability
    Language English
    Dates of publication 2017-1019
    Size p. 11560-11563.
    Publishing place The Royal Society of Chemistry
    Document type Article ; Online
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/c7cc05693a
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  9. Book ; Online: Bioconjugated oligonucleotides

    Benizri, Sébastien / Gissot, Arnaud / Martin, Andrew / Vialet, Brune / Grinstaff, Mark / Barthélémy, Philippe

    recent developments and thera-eutic applications

    2020  

    Abstract: Oligonucleotide-based agents have the potential to treat or cure almost any disease, and are one of the key therapeutic drug classes of the future. Bioconjugated oligonucleotides, a subset of this class, are emerging from basic research and being ... ...

    Abstract Oligonucleotide-based agents have the potential to treat or cure almost any disease, and are one of the key therapeutic drug classes of the future. Bioconjugated oligonucleotides, a subset of this class, are emerging from basic research and being successfully translated to the clinic. In this review, we first briefly describe two approaches for inhibiting specific genes using oligonucleotides -- antisense DNA (ASO) and RNA interference (RNAi) -- followed by a discussion on delivery to cells. We then summarize and analyze recent developments in bioconjugated oligonucleotides including those possessing GalNAc, cell penetrating peptides, $\alpha$-tocopherol, aptamers, antibodies, cholesterol, squalene, fatty acids, or nucleolipids. These novel conjugates provide a means to enhance tissue targeting, cell internalization, endosomal escape, target binding specificity, resistance to nucleases, and more. We next describe those bioconjugated oligonucleotides approved for patient use or in clinical trials. Finally, we summarize the state of the field, describe current limitations, and discuss future prospects. Biocon-jugation chemistry is at the centerpiece of this therapeutic oligonucleotide revolution, and significant opportunities exist for development of new modification chemistries, for mechanistic studies at the chemical-biology interface, and for translating such agents to the clinic.
    Keywords Quantitative Biology - Biomolecules
    Subject code 610
    Publishing date 2020-02-26
    Publishing country us
    Document type Book ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  10. Article ; Online: Hybrid lipid oligonucleotide conjugates: synthesis, self-assemblies and biomedical applications.

    Patwa, Amit / Gissot, Arnaud / Bestel, Isabelle / Barthélémy, Philippe

    Chemical Society reviews

    2011  Volume 40, Issue 12, Page(s) 5844–5854

    Abstract: Hybrid lipid oligonucleotide conjugates are finding more and more biotechnological applications. This short critical review highlights their synthesis, supramolecular organization as well as their applications in the field of biotechnology (111 ... ...

    Abstract Hybrid lipid oligonucleotide conjugates are finding more and more biotechnological applications. This short critical review highlights their synthesis, supramolecular organization as well as their applications in the field of biotechnology (111 references).
    MeSH term(s) Animals ; Biomedical Research/methods ; Cell Membrane/metabolism ; Chemistry Techniques, Synthetic/methods ; Drug Design ; Lipid Metabolism ; Oligonucleotides/chemical synthesis ; Oligonucleotides/chemistry ; Oligonucleotides/metabolism
    Chemical Substances Oligonucleotides
    Language English
    Publishing date 2011-12
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S. ; Review
    ZDB-ID 1472875-8
    ISSN 1460-4744 ; 0306-0012
    ISSN (online) 1460-4744
    ISSN 0306-0012
    DOI 10.1039/c1cs15038c
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