Editing DNA Dye 29

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Preparation of TOTO-13 (Dye No. 29 of Table 1) 

The compound (102 mg) was prepared by using the procedure to synthesize AOAO-2 (Dye No. 7 of Table 1) from N-carboxypentyl thiazole orange (102 mg, 0.23 mmole) (Example 31) and 4,7,10-trioxa-1,13-tridecanediamine (23 mg, 0.1 mole). 

Example 31 Preparation of N-Carboxypentyl Thiazole Orange (Shown Directly Below) 

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The dye was prepared using published procedure (Carreon, et al., Org. Let. 6(4), 517 (2004)). 

Product Name Thiazole Orange *UltraPure Grade* Size 100 mg Catalog # 83227 US$ $66 Description 

Excellent DNA stain for reticulocyte analysis http://www.anaspec.com/products/product.asp?id=29655 

http://www.polysciences.com/Core/Display.aspx?pageId=98&amp;categoryId=13&amp;productId=1105 19352-25 Size: 25 mg $375.00 Fluorescent dye for reticulocyte analysis. Also useful for Plasmodium species analysis. 

Thiazole orange, a benzothiazole ring covalently linked to a quinoline ring through a monomethine bridge, has been widely used as the embedded cyanine dye for labeling nucleic acids, allowing the detection of DNA and RNA in gels, flow cytometry, or microscopy. Embedded fluorescent dyes such as Thiazole Orange (TO) and Oxazole Yellow (YO) are of particular interest because they have lower quantum yield and weaker fluorescence in solution, while larger fluorescence enhancements are observed when bound to DNA or RNA partner The obvious distinction of fluorescence between free dye and nucleic acid-bound dye provides an excellent way to image, label and detect cancer. TO and its derivatives can be synthesized in liquid phase by several different routes: (1) 2-mercaptobenzothiazole reacts with lepidine derivatives to yield TO [7-11]; (2) 2-aminobenzothiazole, instead of 2-mercaptobenzothiazole, reacts with lepidine derivatives to afford TO [12, 13]; (3) TO and its derivatives can also be prepared by reacting 2-methylbenzothiazole with lepidine derivatives. 

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http://www.chemie.hu-berlin.de/seitz/research.htm 

Î» max 512nm 

<br> The dyes TO-N-5-COOH (N-carboxypentyl-4-[(3'-methyl-1',3'-benzothiazol-2'-yl) methylenyl]quinolinium iodide), TO-N-5-S (succinimidyl ester of N-carboxypentyl-4-[(3'-methyl-1',3'-benzothiazol-2Ð-yl)methylenyl]quinolinium iodide), and TO-NÐ-10-COOH (N-methyl-4-[(3'-carboxydecyl-1',3'-benzothiazol-2'-yl)methylenyl]quinolinium iodide) were synthesized by a somewhat modified procedure of Zhou et al. (14). The benzothiazolium and quinolinium salts of the dyes were prepared via suaternization by heating equimolar amount of the heterocyclic compound (2-methylbenzothizole or quinoline) with either methyl p-toluene sulfonate or gama-bromocarboxylic acid (5-bromohexanoic acid or 10-bromoundecanoic acid) at 110°C for 4 h. The methyl salts were obtained in almost 100% yields and the gama-carboxylic acid salts were obtained in 20 â 60% yield. The dyes were synthesized in 20 â 40% yield by condensation of the corresponding benzothiazolium and quinolinium salts by stirring equimolar amounts of the two salts and five mole equivalents of triethylamine (Et<sub>3</sub>N) in dichloromethane at room temperature overnight. The reactions were quenched by addition of 30% KI<sub>aq</sub> solution and the products were purified by recrystallization from MeOH/H2O. 

[[Category:Compounds_Synthesis]] [[Category:Paul]]