The interactions between the fluorescent dye thiazole orange and DNA

Nygren, Jan; Svanvik, Nicke; Kubista, Mikael

doi:10.1002/(sici)1097-0282(199807)46:1<39::aid-bip4>3.3.co;2-m

Cited by 140 publications

(292 citation statements)

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“…Thiazole orange has been reported to be significantly more fluorescent in the presence of DNA than in dilute solutions (9). Connection of this fluorophore to an oligonucleotide should yield a probe, which upon hybridization with the complementary sequence would be predicted to be more fluorescent.…”

Section: Discussionmentioning

confidence: 99%

Fluorescent Properties of Oligonucleotide-conjugated Thiazole Orange Probes¶

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Melvin

Mérola

et al. 2007

Photochemistry and Photobiology

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The fluorescence properties of thiazole orange, linked via a (1) hydrophobic alkyl or a (2) hydrophilic ethylene glycol chain to the central internucleotidic phosphate group of a pentadeca‐2′‐deoxyriboadenylate (dA15), are evaluated. Linkage at the phosphate group yields two stereoisomers, S‐isomer of the phosphorus chiral center (Sp) and R‐isomer of the phosphorus chiral center (Rp); these are studied separately. The character of the linkage chain and the chirality of the internucleotidic phosphate linkage site influence the fluorescent properties of these thiazole orange–oligonucleotide conjugates (TO‐probes). Quantum yields of fluorescence (Φfl) of between 0.04 and 0.07 were determined for the single‐stranded conjugates. The fluorescence yield increased by up to five times upon hybridization with the complementary sequence (d5′[CACT15CAC3′]); Φfl values of between 0.06–0.35 were determined for the double‐stranded conjugates. The Φfl value (0.17) of thiazole orange, 1‐(N,N′‐trimethylaminopropyl)‐4‐[3‐methyl‐2,3‐dihydro‐(benzo‐1,3‐thiazole)‐2‐methylidene]‐quinolinium iodide (TO‐Pro 1) in the presence of the oligonucleotide duplex (TO‐Pro 1: dA15·d5′[CACT15CAC3′] (1:1)) is much less than that for some of the hybrids of the conjugates. Our studies, using steady‐state and time‐resolved fluorescence experiments, show that a number of discrete fluorescent association species between the thiazole orange and the helix are formed. Time‐resolved studies on the four double‐stranded TO‐probes revealed that the fluorescent oligonucleotide–thiazole orange complexes are common, only the distribution of the species varies with the character of the chain and the chirality at the internucleotidic phosphate site. Those TO‐probes in which the isomeric structure of the phosphate‐chain linkage is Rp, and therefore such that the fluorophore is directed toward the minor groove, have higher Φfl values than the Sp isomer. Of the systems studied, thiazole orange linked by an alkyl chain to the internucleotidic phosphate (Rp isomer) has the highest Φfl and the greatest fraction of the longest‐lived fluorescent thiazole orange species (in the hybrid form).

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Section: Discussionmentioning

confidence: 99%

Fluorescent Properties of Oligonucleotide-conjugated Thiazole Orange Probes¶

Privat

Melvin

Mérola

et al. 2007

Photochemistry and Photobiology

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“…TO binds with high affinity to dsDNA, which is accompanied by high fluorescence quantum yields. Binding to ssDNA is less pronounced (Nygren et al, 1998). Therefore, the increased TO fluorescence intensity is most likely due to an increased accessibility of aberrant dsDNA in the dying bacteria.…”

Section: Discussionmentioning

confidence: 99%

Differential effect of auxotrophies on the release of macromolecules by Salmonella enterica vaccine strains

Loessner

Endmann

Rohde

et al. 2006

FEMS Microbiology Letters

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Attenuated Salmonella enterica strains have been widely used as live carriers for vaccines and therapeutic molecules. Appropriate attenuation has been introduced into such bacteria for safety reasons and the improvement of strain properties. Here, we compared two strains that were rendered auxotroph for diaminopimelic acid or thymidine monophosphate precursors by deletion of the genes asd or thyA, respectively. Upon removal of the complementing compound from bacterial cultures, both strains quickly lose their property to form colonies. However, while the Deltaasd bacteria lysed almost immediately under such conditions, DeltathyA bacteria remained physically intact during the observation period. As a consequence, the Deltaasd bacteria released their intracellular content such as proteins or plasmids into the supernatant. In contrast, no intracellular component, either proteins or plasmids, could be recovered from the supernatants of DeltathyA bacteria upon depletion of thymidine. Thus, the release of macromolecules from the bacterial carrier occurs as a consequence of appropriate lethal attenuation. This might substitute for sophisticated secretion systems.

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“…[18] The core fluorophore of these dyes is essentially thiazoleo range (TO), [19] with a F F dsDNA value that is reported to be quite low (0.22). [20] We considered that uncovering the molecular basis of the high fluorescenceo fSG and PG could lead to the rational design of new fluorescent turn-on DNA probes. Herein, we synthesized as eries of TO derivatives and studied how SG and PG express high F F dsDNA values.…”

Section: Introductionmentioning

confidence: 99%

Key Structural Elements of Unsymmetrical Cyanine Dyes for Highly Sensitive Fluorescence Turn‐On DNA Probes

Uno

Sasaki

Sugimoto

et al. 2016

Chemistry An Asian Journal

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Unsymmetrical cyanine dyes, such as thiazole orange, are useful for the detection of nucleic acids with fluorescence because they dramatically enhance the fluorescence upon binding to nucleic acids. Herein, we synthesized a series of unsymmetrical cyanine dyes and evaluated their fluorescence properties. A systematic structure-property relationship study has revealed that the dialkylamino group at the 2-position of quinoline in a series of unsymmetrical cyanine dyes plays a critical role in the fluorescence enhancement. Four newly designed unsymmetrical cyanine dyes showed negligible intrinsic fluorescence in the free state and strong fluorescence upon binding to double-stranded DNA (dsDNA) with a quantum yield of 0.53 to 0.90, which is 2 to 3 times higher than previous unsymmetrical cyanine dyes. A detailed analysis of the fluorescence lifetime revealed that the dialkylamino group at the 2-position of quinoline suppressed nonradiative decay in favor of increased fluorescence quantum yield. Moreover, these newly developed dyes were able to stain the nucleus specifically in fixed HeLa cells examined by using a confocal laser-scanning microscope.

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The interactions between the fluorescent dye thiazole orange and DNA

Cited by 140 publications

References 0 publications

Fluorescent Properties of Oligonucleotide-conjugated Thiazole Orange Probes¶

Fluorescent Properties of Oligonucleotide-conjugated Thiazole Orange Probes¶

Differential effect of auxotrophies on the release of macromolecules by Salmonella enterica vaccine strains

Key Structural Elements of Unsymmetrical Cyanine Dyes for Highly Sensitive Fluorescence Turn‐On DNA Probes

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