Publications de l’équipe/Brevets
(IBMM, UMR 5247 CNRS-UM1-UM2) 2006-2010
a) Publications (journaux à comité de lecture)
2006
1) Parey, N. ; Baraguey, C. ; Vasseur, J. J. ; Debart, F., First evaluation of acyloxymethyl or acylthiomethyl groups as biolabile 2’-O-protections of RNA. Org Lett. 2006, 8, (17), 3869-3872.
2) Johnson, A. A. ; Sayer, J. M. ; Yagi, H. ; Patil, S. S. ; Debart, F. ; Maier, M. A. ; Corey, D. R. ; Vasseur, J. J. ; Burke, T. R., Jr. ; Marquez, V. E. ; Jerina, D. M. ; Pommier, Y., Effect of DNA modifications on DNA processing by HIV-1 integrase and inhibitor binding : role of DNA backbone flexibility and an open catalytic site. J Biol Chem. 2006, 281, (43), 32428-32438.
3) Deglane, G. ; Abes, S. ; Michel, T. ; Prevot, P. ; Vives, E. ; Debart, F. ; Barvik, I. ; Lebleu, B. ; Vasseur, J. J., Impact of the guanidinium group on hybridization and cellular uptake of cationic oligonucleotides. Chembiochem. 2006, 7, (4), 684-692.
4) Bouillon, C. ; Meyer, A. ; Vidal, S. ; Jochum, A. ; Chevolot, Y. ; Cloarec, J. P. ; Praly, J. P. ; Vasseur, J. J. ; Morvan, F., Microwave assisted “click” chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support. J Org Chem. 2006, 71, (12), 4700-4702.
5) Fraternale, A. ; Paoletti, M. F. ; Casabianca, A. ; Oiry, J. ; Clayette, P. ; Vogel, J. U. ; Cinatl, J., Jr. ; Palamara, A. T. ; Sgarbanti, R. ; Garaci, E. ; Millo, E. ; Benatti, U. ; Magnani, M., Antiviral and immunomodulatory properties of new pro-glutathione (GSH) molecules. Curr Med Chem. 2006, 13, (15), 1749-1755.
6) Ohara, K. ; Smietana, M. ; Vasseur, J. J., Characterization of specific noncovalent complexes between guanidinium derivatives and single-stranded DNA by MALDI. J Am Soc Mass Spectrom. 2006, 17, (3), 283-291.
7) Moukha-Chafiq, O. ; Taha, M. L. ; Lazrek, H. B. ; Vasseur, J. J. ; Clercq, E. D., Synthesis and antiviral activity of some C2-, C4-, and C6-substituted pyrazolo[3,4-D]pyrimidine acyclonucleosides with the alkylating chains of ACV, HBG, and ISO-DHPG. Nucleosides Nucleotides Nucleic Acids. 2006, 25, (8), 849-860.
8) Adamo, I. ; Dueymes, U. ; Schonberger, A. ; Navarro, A. E. ; Meyer, A. ; Lange, M. ; Imbach, J. L. ; Link, F. ; Morvan, F. ; Vasseur, J. J., Solution-phase synthesis of phosphorothioate oligonucleotides using a solid-supported acyl chloride with H-phosphonate chemistry. European Journal of Organic Chemistry 2006, (2), 436-448.
9) Meyer, A. ; Bouillon, C. ; Vidal, S. ; Vasseur, J. J. ; Morvan, F., A versatile reagent for the synthesis of 5 ‘-phosphorylated, 5 ‘-thiophosphorylated or 5 ‘-phosphoramidate-conjugated oligonucleotides. Tetrahedron Letters 2006, 47, (50), 8867-8871.
10) Zlatev, I. ; Kato, Y. ; Meyer, A. ; Vasseur, J. J. ; Morvan, F., Use of a solid-supported coupling reagent for a selective phosphitylation of the primary alcohol of N-2-isobutyryl-2’-deoxy or 2 ‘-O-methyl guanosine. Tetrahedron Letters 2006, 47, (47), 8379-8382.
11) Luvino, D. ; Smietana, M. ; Vasseur, J. J., Selective fluorescence-based detection of dihydrouridine with boronic acids. Tetrahedron Letters 2006, 47, (52), 9253-9256.
12) Lazrek, H. B. ; Ouzebla, D. ; Rochdi, A. ; Redwane, N. ; Vasseur, J. J., A one-pot synthesis of D-ribonucleosides using natural phosphate doped with KI in HMDS. Letters in Organic Chemistry 2006, 3, (4), 313-314.
2007
13) Morvan, F. ; Meyer, A. ; Jochum, A. ; Sabin, C. ; Chevolot, Y. ; Imberty, A. ; Praly, J. P. ; Vasseur, J. J. ; Souteyrand, E. ; Vidal, S., Fucosylated pentaerythrityl phosphodiester oligomers (PePOs) : Automated synthesis of DNA-Based glycoclusters and binding to Pseudomonas aeruginosa lectin (PA-IIL). Bioconjugate Chemistry 2007, 18, (5), 1637-1643.
14) Debart, F. ; Abes, S. ; Deglane, G. ; Moulton, H. M. ; Clair, P. ; Gait, M. J. ; Vasseur, J. J. ; Lebleu, B., Chemical modifications to improve the cellular uptake of oligonucleotides. Current Topics in Medicinal Chemistry 2007, 7, (7), 727-737.
15) Chevolot, Y. ; Bouillon, C. ; Vidal, S. ; Morvan, F. ; Meyer, A. ; Cloarec, J. P. ; Jochum, A. ; Praly, J. P. ; Vasseur, J.-J. ; Souteyrand, E., DNA-based carbohydrate biochips : a platform for surface glyco-engineering. Angewandte Chemie International Edition 2007, 46, 2398-2402.
16) Deglane, G. ; Morvan, F. ; Debart, F. ; Vasseur, J.-J., 5-propynylamino alpha-deoxyuridine promotes DNA duplex stabilization of anionic and neutral but not cationic alpha-oligonucleotides. Bioorganic and Medicinal Chemistry Letters 2007, 17, 951-954.
17) Peyrane, F. ; Selisko, B. ; Decroly, E. ; Vasseur, J. J. ; Benarroch, D. ; Canard, B. ; Alvarez, K., High-yield production of short GpppA- and 7MeGpppA-capped RNAs and HPLC-monitoring of methyltransfer reactions at the guanine-N7 and adenosine-2’-O positions. Nucleic Acids Research 2007, 35, (4), 1-11.
18) Froeyen, M. ; Morvan, F. ; Vasseur, J. J. ; Nielsen, P. ; Van Aerschot, A. ; Rosemeyer, H. ; Herdewijn, P., Conformational and Chiral Selection of Oligonucleotides. Chemistry & Biodiversity 2007, 4, 803-817.
19) Moukha-Chafiq, O. ; Taha, M. L. ; Mouna, A. ; Lazrek, H. B. ; Vasseur, J. J., Synthesis and biological evaluation of some alpha-[6-(1 ‘-carbamoylalkylthio)-1H-pyrazolo[3,4-D]pyrimidin-4-yl]thioalkylcarboxamide acyclonucleosides. Nucleosides Nucleotides & Nucleic Acids 2007, 26, (4), 335-345.
20) Luvino, D. ; Amalric, C. ; Smietana, M. ; Vasseur, J. J., Sequential Seyferth-Gilbert/CuAAC reactions : Application to the one-pot synthesis of triazoles from aldehydes. Synlett 2007, (19), 3037-3041.
21) Lietard, J. ; Meyer, A. ; Vasseur, J. J. ; Morvan, F., An efficient reagent for 5 ‘-azido oligonucleotide synthesis. Tetrahedron Letters 2007, 48, (50), 8795-8798.
22) Perzyna, A. ; Zotto, C. ; Durand, J. O. ; Granier, M. ; Smietana, M. ; MeInyk, O. ; Stara, I. G. ; Stary, I. ; Klepetarova, B. ; Saman, D., Reaction of isocyanate-functionalised silicon wafers with complex amino compounds. European Journal of Organic Chemistry 2007, (24), 4032-4037.
23) Zlatev, I. ; Vasseur, J.-J. ; Morvan, F., Convenient synthesis of N2-isobutyryl-2’-O-methyl guanosine by efficient alkylation of O6-trimethylsilylethyl-3’,5’-di-tert-butylsilanediyl guanosine. Tetrahedron 2007, 63, (45), 11174-11178.
24) Ohara, K. ; Smietana, M. ; Restouin, A. ; Mollard, S. ; Borg, J. P. ; Collette, Y. ; Vasseur, J. J., Amine-guanidine switch : A promising approach to improve DNA binding and antiproliferative activities. Journal of Medicinal Chemistry 2007, 50, (26), 6465-6475.
2008
25) Mourgues, S. ; Trzcionka, J. ; Vasseur, J. J. ; Pratviel, G. ; Meunier, B., Incorporation of Oxidized Guanine Nucleoside 5’ ;-Triphosphates in DNA with DNA Polymerases and Preparation of Single-Lesion Carrying DNA. Biochemistry 2008, 47, (16), 4788-4799.
26) Lietard, J. ; Meyer, A. ; Vasseur, J. J. ; Morvan, F., New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves. Journal of Organic Chemistry 2008, 73, (1), 191-200.
27) Lavergne, T. ; Bertrand, J. R. ; Vasseur, J. J. ; Debart, F., A Base-Labile Group for 2 ‘-OH Protection of Ribonucleosides : A Major Challenge for RNA Synthesis. Chemistry a European Journal 2008, 14, (30), 9135-9138.
28) Fratemale, A. ; Paoletti, M. F. ; Casabianca, A. ; Orlandi, C. ; Schiavano, G. F. ; Chiarantini, L. ; Clayette, P. ; Oiry, J. ; Vogel, J. U. ; Cinatl, J. ; Magnani, M., Inhibition of murine AIDS by pro-glutathione (GSH) molecules. Antiviral Research 2008, 77, (2), 120-127.
29) Zlatev, I. ; Vasseur, J.-J. ; Morvan, F., Deoxygenation of 5-O-benzoyl-1,2-isopropylidene-3-O-imidazolylthiocarbonyl-[alpha]-d-xylofuranose using dimethyl phosphite : an efficient alternate method towards a 3’-deoxynucleoside glycosyl donor. Tetrahedron Letters 2008, 49, (20), 3288-3290.
30) Luvino, D. ; Baraguey, C. ; Smietana, M. ; Vasseur, J. J., Borononucleotides : synthesis, and formation of a new reversible boronate internucleosidic linkage. Chemical Communications 2008, (20), 2352-2354.
31) Smietana, M. ; Clayette, P. ; Mialocq, P. ; Vasseur, J. J. ; Oiry, J., Synthesis of new N-isobutyryl-L-cysteine/MEA conjugates : Evaluation of their free radical-scavenging activities and anti-HIV properties in human macrophages. Bioorganic Chemistry 2008, 36, (1-3), 133-140.
32) Pourceau, G. ; Meyer, A. ; Vasseur, J. J. ; Morvan, F., Combinatorial and automated synthesis of phosphodiester galactosyl cluster on solid support by click chemistry assisted by microwaves. Journal of Organic Chemistry 2008, 73, (15), 6014-6017.
33) Zlatev, I. ; Dutartre, H. ; Barvik, I. ; Neyts, J. ; Canard, B. ; Vasseur, J.-J. ; Alvarez, K. ; Morvan, F., Phosphoramidate Dinucleosides as Hepatitis C Virus Polymerase Inhibitors. J. Med. Chem. 2008, 51, (18), 5745-5757.
34) Luvino, D. ; Gasparutto, D. ; Reynaud, S. ; Smietana, M. ; Vasseur, J.-J., Boronic acid-based fluorescent receptors for selective recognition of thymine glycol. Tetrahedron Letters 2008, 49, (42), 6075-6078.
2009
35) Ohara, K. ; Jacquinet, J.-C. ; Jouanneau, D. ; Helbert, W. ; Smietana, M. ; Vasseur, J.-J., Matrix-Assisted Laser Desorption/Ionization Mass Spectrometric Analysis of Polysulfated-derived Oligosaccharides Using Pyrenemethylguanidine. Journal of the American Society for Mass Spectrometry 2009, 20, 131-137.
36) Pourceau, G. ; Meyer, A. ; Vasseur, J. J. ; Morvan, F., Synthesis of Mannose and Galactose Oligonucleotide Conjugates by Bi-click chemistry. Journal of Organic Chemistry 2009, 74, (3), 1218-1222.
37) Ohara, K. ; Vasseur, J.-J. ; Smietana, M., NIS-promoted guanylation of amines. Tetrahedron Letters 2009, 50, (13), 1463-1465.
38) Lavergne, T. ; Parey, N. ; Debart, F. ; Vasseur, J.-J., Efficient Release of Base-Sensitive Oligonucleotides from Solid Supports Using Fluoride Ions. European Journal of Organic Chemistry 2009, (13), 2190-2194.
39) Zhang, J. ; Pourceau, G. ; Meyer, A. ; Vidal, S. ; Praly, J.-P. ; Souteyrand, E. ; Vasseur, J.-J. ; Morvan, F. ; Chevolot, Y., DNA-directed immobilisation of glycomimetics for glycoarrays application : Comparison with covalent immobilisation, and development of an on-chip IC50 measurement assay. Biosensors and Bioelectronics 2009, 24, 2515-2521.
40) Moni, L.. ; Pourceau, G. ; Zhang, J. ; Meyer, A. ; Vidal, S. ; Souteyrand, E. ; Dondoni, A. ; Morvan, F. ; Chevolot, Y. ; Vasseur, J.-J. ; Marra, A., Design of triazole-tethered glycoclusters exhibiting three different spatial arangements and comparative study of their affinity for PA-IL and RCA 120 using a DNA-based Glycoraray. ChemBioChem 2009, 10, (8), 1369-1378.
41) Martin, A. R. ; Lavergne, T. ; Vasseur, J.-J. ; Debart, F., Assessment of new 2’-O-acetalester protecting groups for regular RNA synthesis and original 2’-modified proRNA. Bioorganic & Medicinal Chemistry Letters 2009, 19, (15), 4046-4049.
42) Pourceau, G. ; Meyer, A. ; Vasseur, J.-J. ; Morvan, F., Azide solid support for 3’-conjugation of oligonucleotides and their circularization by click chemistry. Journal of Organic Chemistry, 2009, 74, (17), 6837-6842.
43) Zlatev, I. ; GirautT, F. ; Morvan, F. ; Herdewijn, P. ; Vasseur, J.-J., delta-Di-Carboxybutyl Phosphoramidate of 2’-Deoxycytidine-5’-Monophosphate as Substrate for DNA Polymerization by HIV-1 Reverse Transcriptase. Bioorganic and Medicinal Chemistry, 2009, 17, (19), 7008-7014.
44) Martin, A.R. ; Mohanan, K. ; Luvino, D. ; Floquet, N. ; Baraguey, C. ; Smietana, M. ; Vasseur, J.-J., Expanding the borononucleotide family : synthesis of boronoanalogues of dCMP, dGMP and dAMP. Organic and Biomolecular Chemistry, 2009, 7, (21), 4369-4377.
45) Zhang, J. ; Pourceau, G. ; Meyer, A. ; Vidal, S. ; Praly, J. P. ; Souteyrand, E. ; Vasseur, J. J. ; Morvan, F. ; Chevolot, Y., Specific recognition of lectins by oligonucleotide glycoconjugates and sorting on a DNA microarray. Chemical Communications, 2009, (44), 6795-6797.
2010
46) Morvan, F. ; Debart, F. ; Vasseur, J.-J., From anionic to cationic alpha anomeric oligodeoxynucleotides. Chemistry & Biodiversity, 2010, 7, (3), 494-535.
47) Mohanan, K. ; Martin, A. R. ; Toupet, L. ; Smietana, M. ; Vasseur, J.-J., Three-Component Reaction Using the Bestmann-Ohira Reagent : A Regioselective Synthesis of Phosphonyl Pyrazole Rings13. Angewandte Chemie International Edition, 2010, 49, (18), 3196-3199.
48) Zlatev, I. ; Lavergne, T. ; Debart, F. ; Vasseur, J.-J. ; Manoharan, M. ; Morvan, F., Efficient Solid-Phase Chemical Synthesis of 5’-Triphosphates of DNA, RNA, and their Analogues. Organic Letters, 2010, 12, (10), 2190-2193.
49) Baddi, L. ; Smietana, M. ; Sebti, S. ; Vasseur, J. J. ; Lazrek, H. B., A Procedure for Facile Synthesis of Nucleosides Using N, O-Bistrimethylsilylacetamide in the Presence of Natural Phosphate Coated with Potassium Iodide. Letters in Organic Chemistry, 2010, 7, (3), 196-199.
50) Meyer, A. ; Spinelli, N. ; Dumy, P. ; Vasseur, J. J. ; Morvan, F. ; Defrancq, E., Oligonucleotide Sequential Bis-Conjugation via Click-Oxime and Click-Huisgen Procedures. Journal of Organic Chemistry, 2010, 75, (11), 3927-3930.
b) Chapitres dans des ouvrages
1) Morvan, F. ; Vasseur, J.-J.,”Solution-Phase Synthesis of Di- and Trinucleotides using Polymer-Supported Reagents”, in “Current Protocols in Nucleic Acid Chemistry”, Eds S.L. Beaucage, D.E. Bergstrom, P. Herdewijn, A. Matsuda, Wiley, 2006, 3.14.1-3.14.15.
2) Morvan, F. ; Meyer, A. ; Vasseur, J.-J.,”Universal and recyclable solid support for oligonucleotides synthesis”, in “Current Protocols in Nucleic Acid Chemistry”, Eds S.L. Beaucage, D.E. Bergstrom, P. Herdewijn, A. Matsuda, Wiley, 2007, 3.16.1-3.16.19.
3) Froeyen, M. ; Morvan, F. ; Vasseur, J. J. ; Nielsen, P. ; Van Aerschot, A. ; Rosemeyer, H. ; Herdewijn, P., “Conformational and Chiral Selection of Oligonucleotides”, in “Origin of life : chemical approach”, Eds P. Herdewijn, M.V. Kisakürek, Wiley, 2008, 25.
4) Smietana, M. ; Ohara, K. ; Vasseur, J.-J., « MALDI-TOF Detection of Specific Noncovalent Complexes of Highly Acidic Biomolecules with Pyrenemethylguanidinium » in « Mass Spectrometry of Nucleosides and Nucleic Acids » Eds J. Banoub, P. A. Limbach, CRC Press, 25 oct. 2009
5) Chevolot, Y. ; Vidal, S. ; Laurenceau, E. ; Morvan, F. ; Vasseur, J.-J. ; Souteyrand, E.,« Carbohydrates as recognition receptors in biosensing applications », in « Recognition reception in biosensors », Eds M. Zourob, Spinger, 2009, châp. 7, pages 271-336
c) Brevets
1) « Antioxidants, Preparation Methods and Uses », J. Oiry, J.-Y Puy, J.-L. Imbach, P. Clayette, P. Fretier., US Patent (CNRS/CEA) N° 6,989,372 B1 – Jan. 24, 2006.
2) « Method for preparing oligonucleotides », I. Adamo, C. Dueymes, A. Schoenberger, J.L. Imbach, A. Meyer, F. Morvan, F. Debart, J.J. Vasseur, .M. Lange, F. Link, International Application, WO2004/013154 A1 du 12 Février 2004, US Patent Application 2006/00894994 A1 No : 10/522,854 du 27 Avril 2006
3) « Method for the synthesis of oligonucleotide derivatives », F. Morvan, A. Meyer, J.J. Vasseur, S. VIDAL, J.P.Cloarec, Y. Chevolot, E. Souteyrand, Dépôt d’une demande de brevet US provisoire, 28 Avril 2006, WO2007125429, publié le 08/11/2007
4) « Methode de Synthèse d’ARN », T. Lavergne, J.J. Vasseur, F. Debart FR08 02928, 2008.
