Thiazole Orange
Title: Thiazole Orange
Additional Names: 1-Methyl-4-[(3-methyl-2(3H)-benzothiazolylidene)methyl] quinolinium; TO
Molecular Formula: [C19H17N2S]+
Literature References: Asymmetric cyanine dye; fluoresces when intercalated with DNA or RNA. Prepn of tosylate and use in reticulocyte analysis: L. G. Lee et al., Cytometry 7, 508 (1986). Interactions with DNA: J. Nygren et al., Biopolymers 46, 39 (1998). Use in detection of reticulated platelets: T. Fujii et al., Thromb. Res. 97, 431 (2000); L. Joutsi-Korhonen et al., Eur. J. Haematol. 65, 66 (2000); in fluorescent intercalator displacement assays: D. L. Boger, W. C. Tse, Bioorg. Med. Chem. 9, 2511 (2001).
 
Derivative Type: Dimer
CAS Registry Number: 143413-84-7
CAS Name: 1,1¢-[1,3-Propanediylbis[(dimethylimino)-3,1-propanediyl]]bis[4-(3-methyl-2(3H)-benzothiazolylidene)methyl] quinolinium tetraiodide
Additional Names: TOTO
Molecular Formula: C49H58I4N6S2
Molecular Weight: 1302.77
Percent Composition: C 45.17%, H 4.49%, I 38.96%, N 6.45%, S 4.92%
Literature References: Synthesis and characterization: H. S. Rye et al., Nucleic Acids Res. 20, 2803 (1992). 1H NMR soln structure of complex with DNA: H. P. Spielmann et al., Biochemistry 34, 8542 (1995). Interactions with DNA: J. Bunkenborg et al., Bioconjugate Chem. 11, 861 (2000).
Properties: Absorption max (4 mM TAE, pH 8.2): 481 nm. e507 131.7´103 in methanol.
Absorption maximum: Absorption max (4 mM TAE, pH 8.2): 481 nm
 
Derivative Type: Iodide
CAS Registry Number: 24147-36-2
Molecular Formula: C19H17IN2S
Molecular Weight: 432.32
Percent Composition: C 52.79%, H 3.96%, I 29.35%, N 6.48%, S 7.42%
Properties: Absorption max (4 mM TAE, pH 8.2): 501 nm. e502 77.0´103 in methanol.
Absorption maximum: Absorption max (4 mM TAE, pH 8.2): 501 nm
 
Derivative Type: Methyl Sulfate
CAS Registry Number: 172668-52-9
Molecular Formula: C19H17N2S.CH3O4S
Molecular Weight: 416.51
Percent Composition: C 57.67%, H 4.84%, N 6.73%, S 15.40%, O 15.37%
Literature References: Prepn: T. G. Deligeorgiev et al., Dyes Pigments 29, 315 (1995).
Properties: Crystals from acetone, mp 225-227°. Absorption max (methanol): 500 nm (e 80700).
Melting point: mp 225-227°
Absorption maximum: Absorption max (methanol): 500 nm (e 80700)
 
Derivative Type: Tosylate
CAS Registry Number: 107091-89-4
Molecular Formula: C19H17N2S.C7H7O3S
Molecular Weight: 476.61
Percent Composition: C 65.52%, H 5.08%, N 5.88%, S 13.46%, O 10.07%
Properties: Sol in methanol. Absorption max (methanol): 512 nm.
Absorption maximum: Absorption max (methanol): 512 nm
 
NOTE: The term "thiazole orange" is used to describe various salt forms in the chemical literature.
Use: Stains DNA or RNA in flow cytometry reticulocyte analysis, in agarose gels, in capillary electrophoresis.

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