title: Synthesis, photophysical properties and incorporation of a highly emissive and environment-sensitive uridine analogue based on the Lucifer chromophore.
abstract: The majority of fluorescent nucleoside analogues used in nucleic acid studies have excitation maxima in the UV region and show very low fluorescence within oligonucleotides (ONs); hence, they cannot be utilised with certain fluorescence methods and for cell-based analysis. Here, we describe the synthesis, photophysical properties and incorporation of a highly emissive and environment-sensitive uridine analogue, derived by attaching a Lucifer chromophore (1,8-naphthalimide core) at the 5-position of uracil. The emissive nucleoside displays excitation and emission maxima in the visible region and exhibits high quantum yield. Importantly, when incorporated into ON duplexes it retains appreciable fluorescence efficiency and is sensitive to the neighbouring base environment. Notably, the nucleoside signals the presence of purine repeats in ON duplexes with an enhancement in fluorescence intensity, a property rarely displayed by other nucleoside analogues.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research, Pune, Dr. Homi Bhabha Road, Pashan, Pune 411008 (India).
authors.forename: Arun A
authors.initials: AA
authors.lastname: Tanpure
authors.forename: Seergazhi G
authors.initials: SG
authors.lastname: Srivatsan
mesh_terms: D005453:Fluorescence; D015394:Molecular Structure; D053644:Naphthalimides / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry; D055668:Photochemical Processes; D014466:Ultraviolet Rays; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D053644:Naphthalimides; D009841:Oligonucleotides; D014529:Uridine
keywords: G-repeats; RNA; emission spectroscopy; fluorescent nucleoside; nucleoside analogues