1998
DOI: 10.1089/oli.1.1998.8.469
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A Fluorescent Base Analog for Probing Triple Helix Formation

Abstract: Benzo[gJquinazoline-2,4-(l//,3//)-dione (BgQ), a fluorescent thymine analog, was incorporated into an oligopyrimidine (III) able to give rise to a triple-stranded structure by clamping a purine 11-mer (I). The formation of the 1-111 complex resulted in both a shift of the fluorescence emission maximum and a decreased fluorescence intensity. No such variations were observed on the formation of a Watson-Crick duplex between I and the complementary strand in which a T residue was substituted for BgQ. Therefore, t… Show more

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Cited by 12 publications
(12 citation statements)
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“… a λ, ε, and τ are given in nm, 10 3 M −1 cm −1 , and ns respectively. b Data from Wilson and Kool,427 and Moreau 461. Photophysical properties measured in buffer at:…”
Section: Figuresmentioning
confidence: 99%
“… a λ, ε, and τ are given in nm, 10 3 M −1 cm −1 , and ns respectively. b Data from Wilson and Kool,427 and Moreau 461. Photophysical properties measured in buffer at:…”
Section: Figuresmentioning
confidence: 99%
“…As regular nucleobases are virtually nonfluorescent, fluorescence has to be introduced into the third strand. Various protocols were developed to probe triplex melting by fluorescence: 1) fluorescent dyes (pyrene) were linked to the triplex, [26,35] 2) the third strand of the 5'-terminus of an oligonucleotide was not labelled with a fluorescent dye but with a quencher, while the purine-rich strand contained a fluorescent dye nearby the quencher, [37] 3) a fluorescence dye was used in intercalator displacement experiments, [38] and 4) base surrogates such as a fluorescent 2'-deoxyuridine with an annealed naphthalene moiety were employed, [39] or the fluorescent 2-aminopurine 2'-deoxyribonucleoside was used instead of 2'-deoxyadenosine within the antiparallel dA-dT-dA triplex motif. [40] To the best of our knowledge, no fluorescent analogue of protonated dC was employed within the dCH + -dG-dC triad.…”
Section: Triplexmentioning
confidence: 99%
“…[21][22][23][24] Like 2-AP, these probes have a high fluorescent quantum yields in their free form, 88% and 70% respectively, 22 but exhibit a substantial reduction in quantum yields, up to 25-fold, upon incorporation into oligonucleotides. Another new group of fluorescent base analogues with promising properties are the benzoquinazolines, [25][26][27] which were originally designed to increase the stability of triple helices. Interestingly, they display high fluorescence quantum yield both free and when included in oligonucleotide duplexes.…”
Section: Introductionmentioning
confidence: 99%
“…Interestingly, they display high fluorescence quantum yield both free and when included in oligonucleotide duplexes. 25 Although these base analogues are quenched when a third strand anneals to the duplex they might have potential in selective detection of triplexes over duplexes.…”
Section: Introductionmentioning
confidence: 99%