Thiazole orange

CE is also potentially a useful alternative analytical tool for monitoring of chemicals (dyes, flame retardants and lubricants) involved in various steps of the textile fibre manufacturing process. In this area, CE compares favourably with existing techniques. CZE-MSn was used for the analysis of sulfonated azo dyes [942]. A variety of fluorescent analytes including thiazole orange dyes have been characterised by CE-FLNS [943]. 

Fig. 7 Structures of the dyes forming aggregates on DNA (a) l-methyI-4-[[3-methyl-2(3//)-benzothiazolylidene]methyl]-quinolinium (Thiazole Orange, TO), (b) 3,3 -diethyIthiadicarbo-cyanine (DiSC2(5)), (c) 3,3 -trimethylammoniopropylthiadicarbocyanine (DiSC3+(5)), (d) 2- [(Z)-2-(2,5-dihydro-2-thienyl)-3 - [3 -methyl-2(3/f)-benzothiazolylidene] -1 -propenyl] -3 -methyl -benzothiazol-3-ium (L-21), (e) 2-[( )-3-[3,7-diethyT6-[( ,2 )-3-(l-ethyl-3,3-dimethyl-3/7-indo-lium-2-yl)-2-propenylidene]-6,7-dihydrothiazolo[5,4-/]benzothiazol-2(3//)-ylidene]-l-propenyl]-l-ethyl-3,3-dimethyl-3//-indolium (BCD), (f) 3-methyl-2-[( )-3-methyl-2-[[3-methyl-2(3/f)-ben-zothiazolylidene]methyl]-l-butenyl]-benzothiazol-3-ium (Cyan ]3iPr)...

Nygren J, Svanvik N, Kubista M (1998) The interactions between the fluorescent dye thiazole orange and DNA. Biopolymers 46 39-51... 

Liu B, Bazan GC (2007) Energy transfer between a cationic conjugated poly(lluorene-co-phenylene) and thiazole orange for DNA hybridization detection involving G-rich sequences. Macromol Rapid Commun 28 1804—1808... 

Li K, Liu B (2009) Conjugated polyelectrolyte amplified thiazole orange emission for label free sequence specific DNA detection with single nucleotide polymorphism selectivity. Anal Chem 81 4099-4105... 

Thiazole orange derivatives have also been covalently attached to oligonucleotides to generate a fluorescently labelled probe oligonucleotide capable... 

Alternatively to the DNA modifications in the previous two sections where the chromophore was attached to one of the four DNA bases, chromophores can be incorporated as artificial DNA bases substituting a natural base or even a whole base-pair. There is a large number of recently reported syntheses of chromophores as DNA base surrogates, e.g. flavine derivatives [26] and thiazole orange derivatives [42]. Additionally, a variety of phosphoramidites as DNA building blocks for the introduction of fluorophores into DNA are commercially available, e.g. acridine derivatives. Clearly, the synthetic protocols for this kind of DNA modification do not follow a principle strategy which can be applied in a versatile fashion, as is the case for the DNA base modifications mentioned in the previous sections. It is important to point out that in many cases it turned out to be useful to replace the 2 -deoxyribose moiety with acyclic linker systems. This was also the case during our attempts to synthesize ethidium-modified DNA, which will be described here briefly. 

Schwartz HE, Ulfelder KJ (1992) Capillary electrophoresis with laser-induced fluorescence detection of PCR fragments using thiazole orange. Anal Chem 64 1737-1740. 

Nucleic acids do not display the same promiscuous chemical reactivity of proteins. Instead, individual synthetic nucleotides can display a unique functional group that can be exploited even more for direct attachment of probes (117). The simplest method of labeling DNA uses high-affinity bis-intercalating dyes such as ethidium bromide, acridine, and thiazole orange monomers... 

FON probes labeled at their 5 -ends with thiazole orange can discern perfect duplexes from those that involve a terminal mismatch, as well as those that involve mismatches at the penultimate or last two positions under nonstringent conditions (31). 

Privat E, Melvin T. Asseline U, Vigny P. Oligonucleotide conjugated thiazole orange probes as Tight-up probes for mes-senge RNA molecules in living cells. Photochem. Photobiol. B. 2001 74 532-541. 

Privat E, Asseline U. Synthesis and properties of oligonucleotide-conjugated thiazole orange. Bioconjugate Chem. 2001 12 757-769. 

Kohler O, Jarikote DV, Seitz O. Forced Intercalation Probes (FIT Probes) Thiazole orange as a fluorescent base in peptide nucleic 39. acids for homogeneous single-nucleotide-polymorphism detection. ChemBioChem. 2005 6 69-77. 

UV spectroscopic methods were used to determine equilibrium constants between cyanine dyes (thiazole orange) and nucleic acid <2005JA3339, 2002PCB4838,1999ABI278>, quantification of DNA <1998AEM3238>, and Ru(n), and Ni(ll) complexes containing thiazoles <2003IC8038>. 

The interaction between DNA and the fluorescent dye thiazole orange was studied using absorption and fluorescence spectroscopic techniques. A drastic fluorescence intensity enhancement (up to 103 times) was observed in the presence of DNA <2003FMA528>. Fluorescence measurement was also used to evaluate the inhibitory potency of 5-(bis(trifluoromethyl)methyl)-2-aminothiazoles <2006JFC(127)1522>. 

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