9308. Thiazole Orange

Nomenclature

1-Methyl-4-[(3-methyl-2(3H)-benzothiazolylidene)methyl] quinolinium; TO.
[C19H17N2S]+.

Description and 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).

Chemical structure

Derivative

Dimer.

Nomenclature

CAS number: 143413-84-7
1,1′-[1,3-Propanediylbis[(dimethylimino)-3,1-propanediyl]]bis[4-(3-methyl-2(3H)-benzothiazolylidene)methyl] quinolinium tetraiodide; TOTO.
C49H58I4N6S2; mol wt 1302.77.
C 45.17%, H 4.49%, I 38.96%, N 6.45%, S 4.92%.

Description and 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. ε507 131.7×103 in methanol.

Derivative

Iodide.

Nomenclature

CAS number: 24147-36-2
C19H17IN2S; mol wt 432.32.
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. ε502 77.0×103 in methanol.

Derivative

Methyl Sulfate.

Nomenclature

CAS number: 172668-52-9
C19H17N2S.CH3O4S; mol wt 416.51.
C 57.67%, H 4.84%, N 6.73%, S 15.40%, O 15.37%.

Description and references

Prepn: T. G. Deligeorgiev et al., Dyes Pigm. 29, 315 (1995).

Properties

Crystals from acetone, mp 225-227°. Absorption max (methanol): 500 nm (ε 80700).

Derivative

Tosylate.

Nomenclature

CAS number: 107091-89-4
C19H17N2S.C7H7O3S; mol wt 476.61.
C 65.52%, H 5.08%, N 5.88%, S 13.46%, O 10.07%.

Properties

Sol in methanol. 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.