title: Synthesis and binding properties of oligo-2'-deoxyribonucleotides covalently linked to a thiazole orange derivative.
abstract: Thiazole orange label was coupled to the eighth phosphate of a pentadeca-2'-deoxyriboadenylate via a phosphoramidate linkage using different linkers. The stereoisomers were separated, and their absolute configurations were determined. Finally, the thiazole orange moiety was also linked to the tenth phosphate of icosathymidylates in both the alpha and the beta series via a phosphoramidate linkage. Once again, the thiazole orange-icosathymidylate conjugates were obtained as pure stereoisomers. The binding properties of these oligo-2'-deoxyribonucleotide-thiazole orange conjugates with their complementary sequences were studied by absorption spectroscopy. The covalent attachment of the thiazole orange derivatives to the oligoadenylates stabilizes the complexes formed with both the DNA and RNA targets. On the contrary, when the thiazole orange is tethered to the oligo-alpha-thymidylate or oligo-beta-thymidylate, no significant stabilization of the duplexes formed with poly r(A) can be observed.
authors.affiliation: Centre de Biophysique Moléculaire, UPR 4301 CNRS. Affiliated with the University of Orléans and with INSERM, Rue Charles Sadron, 45071 Orléans Cedex 02, France.
authors.forename: E
authors.initials: E
authors.lastname: Privat
authors.forename: U
authors.initials: U
authors.lastname: Asseline
mesh_terms: D000577:Amides / Q000737:chemistry; D052160:Benzothiazoles; D003432:Cross-Linking Reagents; D004355:Drug Stability; D005456:Fluorescent Dyes / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D009693:Nucleic Acid Hybridization / Q000187:drug effects*; D015341:Nucleic Acid Probes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D010756:Phosphoric Acids / Q000737:chemistry; D011061:Poly A / Q000737:chemistry / Q000378:metabolism; D011804:Quinolines; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000577:Amides; D052160:Benzothiazoles; D003432:Cross-Linking Reagents; D005456:Fluorescent Dyes; D015341:Nucleic Acid Probes; D009838:Oligodeoxyribonucleotides; D010756:Phosphoric Acids; D011804:Quinolines; D013844:Thiazoles; C051000:thiazole orange; D011061:Poly A; C011067:phosphoramidic acid