title: Construction of highly reactive probes for abasic site detection by introduction of an aromatic and a guanidine residue into an aminooxy group.
abstract: Abasic sites (AP sites) arise from hydrolysis of glycosidic bonds of DNA that is damaged by various external and internal processes; unrepaired AP sites give rise to genetic mutations. We have constructed highly reactive AP-site-detecting probes by introducing a hydrophobic and a hydrophilic residue in an aminooxy group. Synthesized probes containing either a naphthalene or a guanidine residue conjugate effectively with AP sites. In particular, a probe containing both functional groups shows the highest reaction rate, indicating that the hydrophobic and hydrophilic interactions act cooperatively in reaction with AP sites. The guanidine residue also contributes to the solubility of the molecules in aqueous media. The biotinylated probes provide much more sensitive detection of AP sites in genomic DNA than the conventional aldehyde-reactive probe.
authors.affiliation: Research Institute of Genome-based Biofactory, National Institute of Advanced Industrial Science and Technology, 2-17-2-1 Tsukisamu-Higashi, Toyohira-ku, Sapporo 062-8517, Japan.
authors.forename: Naoshi
authors.initials: N
authors.lastname: Kojima
authors.forename: Toshie
authors.initials: T
authors.lastname: Takebayashi
authors.forename: Akiko
authors.initials: A
authors.lastname: Mikami
authors.forename: Eiko
authors.initials: E
authors.lastname: Ohtsuka
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Komatsu
mesh_terms: D000818:Animals; D001483:Base Sequence; D002417:Cattle; D004247:DNA / Q000737:chemistry* / Q000235:genetics*; D019791:Guanidine / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D007700:Kinetics; D015335:Molecular Probes / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry / Q000235:genetics; D013329:Structure-Activity Relationship
chemical_list: D015335:Molecular Probes; D009838:Oligodeoxyribonucleotides; D004247:DNA; D019791:Guanidine