title: Nucleoterpenes of thymidine and 2'-deoxyinosine: synthons for a biomimetic lipophilization of oligonucleotides.
abstract: 2'-Deoxyinosine (1) and thymidine (7) were N-alkylated with geranyl and farnesyl moieties. These hydrophobic derivatives, 3a and 3b, and 9a and 9b, respectively, represent the first synthetic biomimetic nucleoterpenes and were subsequently 5'-protected and converted into the corresponding 3'-O-phosphoramidites, 5a and 5b and 11a and 11b, respectively. The latter were used to prepare a series of lipophilized oligonucleotide dodecamers, a part of which were additionally labelled with indocarbocyanine fluorescent dyes (Cy3 or Cy5), 18-23. The insertion of the lipooligonucleotides into, as well as duplex formation at artificial lipid bilayers was studied by single-molecule fluorescence spectroscopy and fluorescence microscopy.
authors: Organic Chemistry I - Bioorganic Chemistry, Institute of Chemistry of New Materials, Fachbereich Biologie/Chemie, University of Osnabrück, Barbarastrasse 7, D-49076 Osnabrück, Germany.
authors: Karl
authors: K
authors: Köstler
authors: Emma
authors: E
authors: Werz
authors: Edith
authors: E
authors: Malecki
authors: Malayko
authors: M
authors: Montilla-Martinez
authors: Helmut
authors: H
authors: Rosemeyer
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry*; D002232:Carbocyanines / Q000737:chemistry; D007288:Inosine / Q000031:analogs & derivatives* / Q000737:chemistry; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism; D008856:Microscopy, Fluorescence; D009841:Oligonucleotides / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013936:Thymidine / Q000737:chemistry*
chemical_list: D002232:Carbocyanines; D008051:Lipid Bilayers; D009841:Oligonucleotides; C089187:cyanine dye 3; C085321:cyanine dye 5; D007288:Inosine; C012271:deoxyinosine; D013936:Thymidine