New cyanine dyes as base surrogates in PNA: Forced intercalation probes (FIT-probes) for homogeneous SNP detection

Bethge, Lucas; Jarikote, Dilip V.; Seitz, Oliver

doi:10.1016/j.bmc.2006.12.044

Cited by 90 publications

(73 citation statements)

References 39 publications

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“…Whereas the synthesis of SG and PG remains unclear despite their famous names and practical uses, we established a new synthetic procedure for a series of dialkylamino‐substituted derivatives of TO and YO (Scheme ). The synthesis of monomethine dyes ( YONEt 2 and TONEt 2 ) began with the reaction of 2‐iodo‐1,4‐dimethyl‐1‐quinolinium iodide ( 1 ) and dimethyloxazolinium salt 2 or dimethylthiazolinium salt 3 with triethylamine. After workup with concentrated hydrochloric acid, the obtained crude chloro‐substituted compounds ( YOCl and TOCl ) were further reacted with diethylamine to give YONEt 2 and TONEt 2 in overall yields of 26 and 22 %, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The absorbance of unsymmetrical cyanine dyes has been modified to fit conventional laser sources. By simply changing the number of methine units [11] or the substituents aroundt he terminal nitrogen atoms, [12] their absorption regionsc an be tuned between theu ltraviolet and near-infrared regions. The fluorescences ensitivity can be improved by the homodimerization of unsymmetricalc yanine dyes, which are referred to as TOTOa nd YOYO series dyes ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

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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“…Cyanine dyes have been introduced as a PNA surrogate base to detect mismatches with complementary DNA. 76 A DNA molecular beacon has been used as a probe to detect strand invasion of a DNA duplex by PNA. The molecular beacon is complementary to the single stranded region left by PNA strand invasion, and it is able to bind to that region giving a fluorescent signal upon binding to it.…”

Section: Oligonucleotide Synthesismentioning

confidence: 99%

Nucleotides and Nucleic Acids; Oligo- and Polynucleotides

Loakes

2010

Organophosphorus Chemistry

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“…112 These FIT-PNA probes contain a single thiazole orange (TO) intercalator serving as an artificial fluorescent nucleobase, providing superior signal-to-background ratios in comparison to MB probes. [112][113][114] The authors successfully applied the probes to the detection of influenza H1N1 mRNA in living infected cells, which represents the first example of an artificial nucleotidic probe that can be used for imaging of mRNA in living cells. 115 The probes achieved an 11-fold increase in TO emission upon hybridization with the complementary RNA target.…”

Section: Fluorescence Imaging With Nucleic Acid Probesmentioning

confidence: 99%

Nucleic Acid Fluorescent Probes for Biological Sensing

Xiao

Zhang

et al. 2012

Appl Spectrosc

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Nucleic acid fluorescent probes are playing increasingly important roles in biological sensing in recent years. In addition to the conventional functions of single-stranded DNA/RNA to hybridize with their complementary strands, affinity nucleic acids (aptamers) with specific target binding properties have also been developed, which has greatly broadened the application of nucleic acid fluorescent probes to the detection of a large variety of analytes, including small molecules, proteins, ions, and even whole cells. Another chemical property of nucleic acids is to act as substrates for various nucleic acid enzymes. This property can be utilized not only to detect those enzymes and screen their inhibitors, but also employed to develop effective signal amplification systems, which implies extensive applications. This review mainly covers the biosensing methods based on the above three types of nucleic acid fluorescent probes. The most widely used intensity-based biosensing assays are covered first, including nucleic acid probe-based signal amplification methods. Then fluorescence lifetime, fluorescence anisotropy, and fluorescence correlation spectroscopy assays are introduced, respectively. As a rapidly developing field, fluorescence imaging approaches are also briefly summarized.

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New cyanine dyes as base surrogates in PNA: Forced intercalation probes (FIT-probes) for homogeneous SNP detection

Cited by 90 publications

References 39 publications

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

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

Nucleotides and Nucleic Acids; Oligo- and Polynucleotides

Nucleic Acid Fluorescent Probes for Biological Sensing

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