Solid-phase synthesis of asymmetric cyanine dyes

Isacsson, J; Westman, Gunnar

doi:10.1016/s0040-4039(01)00365-3

Cited by 36 publications

(21 citation statements)

References 8 publications

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“…While TO has found numerous applications in DNA hybridization, BO has been used rather less often ( 29 – 31 ). BO has an excitation maximum at a lower wavelength than TO (444 nm as opposed to 510 nm), ( 32 ) and intercalates into DNA with a large increase in fluorescence intensity ( 33 ). Although BO forms a less stable intercalation complex than TO, the barrier to complex formation is significantly lower, presumably as a result of its smaller hydrophobic surface ( 32 ).…”

Section: Resultsmentioning

confidence: 99%

Combination probes with intercalating anchors and proximal fluorophores for DNA and RNA detection

et al. 2016

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A new class of modified oligonucleotides (combination probes) has been designed and synthesised for use in genetic analysis and RNA detection. Their chemical structure combines an intercalating anchor with a reporter fluorophore on the same thymine nucleobase. The intercalator (thiazole orange or benzothiazole orange) provides an anchor, which upon hybridisation of the probe to its target becomes fluorescent and simultaneously stabilizes the duplex. The anchor is able to communicate via FRET to a proximal reporter dye (e.g. ROX, HEX, ATTO647N, FAM) whose fluorescence signal can be monitored on a range of analytical devices. Direct excitation of the reporter dye provides an alternative signalling mechanism. In both signalling modes, fluorescence in the unhybridised probe is switched off by collisional quenching between adjacent intercalator and reporter dyes. Single nucleotide polymorphisms in DNA and RNA targets are identified by differences in the duplex melting temperature, and the use of short hybridization probes, made possible by the stabilisation provided by the intercalator, enhances mismatch discrimination. Unlike other fluorogenic probe systems, placing the fluorophore and quencher on the same nucleobase facilitates the design of short probes containing multiple modifications. The ability to detect both DNA and RNA sequences suggests applications in cellular imaging and diagnostics.

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Section: Resultsmentioning

confidence: 99%

Combination probes with intercalating anchors and proximal fluorophores for DNA and RNA detection

et al. 2016

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“…TO-3 was synthesized as described [47], and its purity was spectroscopically determined. A stock solution (3.1×10 −3 M) was prepared by dissolving solid TO-3 in pure ethanol.…”

Section: Methodsmentioning

confidence: 99%

“…The fluorescence spectra have the biphasic behavior. Initially, at low BP/D ratio, the addition of DNA quenches the fluorescence of the dye with λ max =567 nm to approximately 75% along with the bathochromic shift of the emission spectra (BP/D< 0.65), and upon the addition of more DNA, a new emission peak at around 580 nm appears, which has enhanced strong fluorescence associated with the restricted rotation upon intercalation [47,65], as reported previously by Milanovich et al [69]. We may conclude that there are at least two modes of interactions.…”

Section: Dna Binding Studymentioning

confidence: 99%

Spectroscopic Characterization of Thiazole Orange-3 DNA Interaction

Ghasemi

Ahmadi

Ahmad

et al. 2008

Appl Biochem Biotechnol

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The interaction of a new derivative of thiazole orange (TO-3) with calf thymus DNA (ctDNA) has been investigated by fluorescence and absorption spectroscopy. When TO-3 binds to ctDNA, absorption bands exhibit significant hypochromicity at low base pair/dye ratio (BP/D ratio), and high BP/D show hyperchromicity with red shift. The spectral changes are attributed to the different species formed between TO-3 and ctDNA in the titration course of the dye molecule with DNA. Multivariate curve resolutions-alternating least squares (MCR-ALS) is applied to the absorption measurements recorded to recover the concentration profiles and the pure spectra of the DNA/TO-3 complexes involved in the process. The binding constant and size of the binding site have been determined spectrophotometrically using the McGhee von Hippel equation. MCR-ALS has been used to reveal the precise concentration profiles of all detectable species formed between ctDNA and TO-3 and their pure spectral profiles.

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“…Solid-phase organic synthesis and combinatorial chemistry are well-known approaches, involving the use of resins, for the synthesis of peptides and drugs [31,32]. However, in the last years they have found a broader application in the synthesis of different type of dyes such as styryl dyes, BODIPYs, phthalocyanines and cyanines [33][34][35][36][37][38][39][40][41][42]. In particular, the use of solid-phase synthesis has become a powerful technique to cleanly synthesize asymmetrical CDs with high degree of purity and without tricky and expensive purification protocols.…”

Section: Solid-phase Synthesis Of Asymmetrical Cyaninesmentioning

confidence: 99%

Solid-Phase Synthesis of Asymmetric Cyanine Dyes

Giordano

Renno

Quagliotto

et al. 2021

COC

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: Cyanine dyes (CD) are a functional class of organic molecules used in several applications ranging from photography to bioimaging. CDs most well-known features reside on high molar extinction coefficients up to 105 L mol-1cm-1 and on the absorption spectra, ranging from 500 to 1000 nm, which can be fine-tuned both by extending the length of the central methylene bridge or by modulating the terminal heterocycles. In the last decades, new synthetic methodologies, namely microwave-assisted and the solid-phase procedure, have been developed to overcome the limitation of the classical synthetic protocols. While the microwave approach usually reduces the exposure time of the reagents and products to thermal degradation, the solid-phase methodology allows easier synthetic protocols, which are translated into higher yields and simpler product purification. In the present review, a comprehensive analysis of the solid-phase methods for the synthesis of asymmetrical CDs is discussed, with a critical evaluation of the difference among the currently available solid-state approaches.

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Solid-phase synthesis of asymmetric cyanine dyes

Cited by 36 publications

References 8 publications

Combination probes with intercalating anchors and proximal fluorophores for DNA and RNA detection

Combination probes with intercalating anchors and proximal fluorophores for DNA and RNA detection

Spectroscopic Characterization of Thiazole Orange-3 DNA Interaction

Solid-Phase Synthesis of Asymmetric Cyanine Dyes

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