1548
OSADCHII et al.
(61%) of ethidium ethyl sulfate (XI), mp 250–252°C
(with decomposition). Found (%): C 62.90, H 5.87,
N 9.65, S 7.30. C23H25N3O4S. Calculated (%): C 62.84,
H 5.74, N 9.56, S 7.29.
3. Using Molecular Marker Technology in Studies on Plant
Genetic Diversity, DNA-based Technologies, PCR-based
Technologies, Sequence-tagged Sites (Microsatellites,
SCARs, CAPS, ISSRs), IPGRI and Cornell University,
2003.
1H NMR spectrum 5% solution in DMSO-d6, δ, ppm,
J, Hz): 1.10 t (3H, J = 7, CH3 of the ethyl sulfate group);
1.40 br.t (3H, J = 7, CH3 group of C2H5N fragment);
3.74 q (2H, J = 7, CH2 group of ethyl sulfate group);
4.47 br.q (2H, J = 7, CH2 group of C2H5N fragment);
5.93 and 6.36, both br.s (each 2H, 2CH2 groups); 6.25 d
(1H, J = 2, H-7); 7.3–7.4 m (2H, H-2, H-4); 7.51 d.d
(1H, J = 9 and J = 2, H-9); 7.7–7.8 m (5H, C6H5;
8.60 and 8.65, both d (each 1H, J = 9, H-10 and H-1,
respectively). The signals in the 1H NMR spectrum were
assigned by analogy with the data of [9] for ethidium
bromide. IR spectrum, ν, cm–1 (KBr): 720, 790, 840,
930, 1030, 1070, 1170, 1190, 1220, 1240, 1280, 1330,
4. Karsten, U. and Wollenberger, A., Anal. Biochem., 1977,
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5. Giache, V., Pirami, L., and Becciolini, A., J. Biolumin.
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6. GB Patent 735438.
7. US Patent 2662082.
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9. Firth, W.J., Watkins, C.L., Graves, D.E., and
Yielding, L.W., J. Heterocycl. Chem., 1983, vol. 20,
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10. RF Patent 2415842.
11. DRP Patent 602 698.
12. Spravochnik khimika (Chemist’s Handbook), vol. 2,
1410, 1480, 1490, 1510, 1640. EAS (MeOH), λmax
,
Nikol’skii, B.P., ED., Leningrad: Khimiya, 1964, p. 656.
nm (log ε): 216 (4.61), 293 (4.81), and 528 (3.81). FS
(H2O): λmax 619 nm. For ethidium bromide from Fluka,
FS (H2O): λmax 619 nm.
13. Semikolenov,V.A., Simakova, I.L., andSadovnichii, G.V.,
Khim. Prom–st’, 1966, no. 3, pp. 184–191.
14. Organic Syntheses, Collective Volume 5, Baumgar-
Results of tests of the detection sensitivity of
a double-stranded DNA with ethidium bromide and
ethidium ethyl sulfate suggest that ethidium ethyl sulfate
is suitable for determination of PCR products in their
electrophoretic analysis and is less expensive, compared
with ethidium bromide, because its synthesis eliminates
need to expend reagents and time for replacement of the
intermediate anion with the bromine anion and isolate
ethidium bromide.
ten, H.E., Ed., New York: J. Wiley and Sons, 1973.
15. Shchori, E., Jagur-Grodzinski, J., and Shporer, M., J. Am.
Chem. Soc., 1973, vol. 95, pp. 3842–3846.
16. Morgan, G.T. and Walls, L.P., J. Soc. Chem. Ind., 1930,
p. 49, p. 15T.
17. Cymerman, J. and Short, W.F., J. Chem. Soc., 1949,
pp. 703–707.
18. Konakahara, T., Wurdeman, R.L., and Gold, B.,
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19. Barber, H.J., Bretherick, L., Elridge, E.M., et al., J. Soc.
Chem. Ind., 1950, vol. 69, no. 3, pp. 82–96.
CONCLUSIONS
20. Yur’ev, Yu.K., Prakticheskie raboty po organicheskoi
khimii (Practical Works in Organic Chemistry), issues 1
and 2, Moscow: Mosk. Gos. Univ., 1964.
(1) Two methods for synthesis of ethidium bromide
were improved. The technological scheme of one of
these methods was implemented at Pilot chemical
shop, Vorozhtsov Institute of Organic Chemistry in
Novosibirsk.
21. Watkins, T.I., J. Chem. Soc., 1952, pp. 3059–3064.
22. Luedtke, N.W., Liu, Q., andTor,Y., ChemistryAEuropean
J., 2005, vol. 11, no. 2, pp. 495–508.
(2) An analog of ethidium bromide, ethidium ethyl
sulfate, was synthesized. This is a new fluorescent dye
suitable for analysis for double-stranded DNA and, in
particular, for analyses for products of the practically
important polymerase chain reaction.
23. Ross, S.A., Pitie, M., and Meunier, B., J. Chem. Soc.,
Perkin Trans. 1, 2000, no. 4, pp. 571–574.
24. Rangarajan, S. and Friedman, S.H., Bioorg. Med. Chem.
Lett., 2007, vol. 17, no. 8, pp. 2267–2273.
25. Aldrich, Katalog–spravochnik khimicheskikh reaktivov,
Rossiya, 2007–2008 (Aldrich, Catalogue–Reference
Book of Chemical Reagents, Russia, 2007–2008).
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