title: 8-Azapurines as isosteric purine fluorescent probes for nucleic acid and enzymatic research.
abstract: The 8-azapurines, and their 7-deaza and 9-deaza congeners, represent a unique class of isosteric (isomorphic) analogues of the natural purines, frequently capable of substituting for the latter in many biochemical processes. Particularly interesting is their propensity to exhibit pH-dependent room-temperature fluorescence in aqueous medium, and in non-polar media. We herein review the physico-chemical properties of this class of compounds, with particular emphasis on the fluorescence emission properties of their neutral and/or ionic species, which has led to their widespread use as fluorescent probes in enzymology, including enzymes involved in purine metabolism, agonists/antagonists of adenosine receptors, mechanisms of catalytic RNAs, RNA editing, etc. They are also exceptionally useful fluorescent probes for analytical and clinical applications in crude cell homogenates.
authors.affiliation: Department of Biophysics, University of Varmia & Masuria, Oczapowskiego 4, 10-719 Olsztyn, Poland. jacek.wie@uwm.edu.pl.
authors.forename: Jacek
authors.initials: J
authors.lastname: Wierzchowski
authors.forename: Jan M
authors.initials: JM
authors.lastname: Antosiewicz
authors.forename: David
authors.initials: D
authors.lastname: Shugar
mesh_terms: D004798:Enzymes / Q000032:analysis / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism*; D006801:Humans; D008958:Models, Molecular; D009696:Nucleic Acids / Q000032:analysis / Q000737:chemistry; D011684:Purine Nucleosides / Q000737:chemistry; D011685:Purine Nucleotides / Q000737:chemistry; D011687:Purines / Q000737:chemistry* / Q000378:metabolism*; D013050:Spectrometry, Fluorescence
chemical_list: C512929:7-deazapurine; D004798:Enzymes; D005456:Fluorescent Dyes; D009696:Nucleic Acids; D011684:Purine Nucleosides; D011685:Purine Nucleotides; D011687:Purines; C015008:triazolopyrimidinone