title: (DNS)C: a fluorescent, environmentally sensitive cytidine derivative for the direct detection of GGG triad sequences.
abstract: With the goal of developing a fluorescent nucleoside sensitive to its environment, in this study we synthesized (DNS)C, a novel modified 2'-deoxycytidine bearing a 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) moiety at the N4 position, and tested its properties in monomeric and oligomeric states. (DNS)C undergoes intramolecular photoinduced electron transfer between its dansyl and cytosine units, resulting in remarkable changes in fluorescence that depend on the choice of solvent. In addition, the fluorescence behavior and thermal stability of oligonucleotides containing (DNS)C are dependent on the nature of the flanking and neighboring bases. Notably, (DNS)C exhibits fluorescence enhancement only in fully matched duplex DNA containing a GGG triad sequence. The environmental sensitivity of (DNS)C can be exploited as a fluorescence tool for monitoring the interactions of DNA with other biomolecules, including DNA, RNA, and proteins.
authors.affiliation: Department of Chemistry, BK School of Molecular Science, Pohang University of Science and Technology, Pohang 790-784, South Korea.
authors.forename: Ki Tae
authors.initials: KT
authors.lastname: Kim
authors.forename: Hyun Woo
authors.initials: HW
authors.lastname: Kim
authors.forename: Dohyun
authors.initials: D
authors.lastname: Moon
authors.forename: Young Min
authors.initials: YM
authors.lastname: Rhee
authors.forename: Byeang Hyean
authors.initials: BH
authors.lastname: Kim
mesh_terms: D001483:Base Sequence; D004247:DNA / Q000032:analysis* / Q000235:genetics*; D003619:Dansyl Compounds / Q000737:chemistry*; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D005453:Fluorescence; D008958:Models, Molecular; D015394:Molecular Structure; D013696:Temperature
chemical_list: D003619:Dansyl Compounds; D003841:Deoxycytidine; D004247:DNA