N-alkylaryl styrylcyanine dyes as fluorescent probes for nucleic acids detection

• DOI: 10.7124/bc.000987
• Publication Date: 2018-12-28T18:18:51Z
• Authors: M. V. Kuperman; Y. V. Snihirova; D. V. Kryvorotenko; M. Yu. Losytskyy; V. B. Kovalska; S. M. Yarmoluk
• Keywords: Nucleic acid quantitation

Aim.To synthesize and characterize a series of N-alkylaryl benzothiazole styrylcyanine dyes as potential fluorescent probes for nucleic acids (NA) detection.Methods.Synthesis, absorption fluorescence spectroscopy, gel electrophoresis.Results.The modification N-alkyl by variation aromatic moieties insignificantly affected its inherent properties.Weakly in an unbound state, the noticeably increased their emission upon binding to dsDNA/RNA (up 83-fold derivative with N-alkylbenzylamine group (Sbt1) complexed dsDNA: constant (Kb) 5.0 × 10 4 M -1 , detection limit dsDNA solution 6.2 -7 Mbp (0.4 µg)).When bound dsDNA, styrylcyanines have moderate quantum yields ~22 %).The structure terminal allowed discriminate between RNA: Sbt2 dye N-alkylphenantroline 14 55-fold, respectively.A higher discernibility post-electrophoretic staining at low DNA concentrations (3.6 ng/lane) Sbt3 N-alkyldipyridyl was observed compared commonly used ethidium bromide.Conclusions.Due sensitivity novel NA electrophoresis, they could be proposed photostable, low-toxic inexpensive laboratory use.K e y w o r d s: styrylcyanines, detection, probes.N-alkylaryl Yield: 78 %.M. p. (dec.):236-238 °C.1H-NMR (DMSO-d6): δ(ppm)= 2.08 (2H, m), 2.28 3.14 (6H, s), 4.90 t, J=6.5 Hz), 5.92 6.80 d, J=8.5 7.53 (1H, J=15.0 7.69-7.87(4H, 7.99-8.13(3H, 8.30 J=8.0 8. 8.81 J=7.7 9.11 dd, J=5.5 9.38 J=8.3 9.58 Hz).Anal.calcd.for C34H33N3SI2: C, 53.07; H, 4.32; N, 5.46.Found: 53.14; 4.28; N,2']Bipyridinyl-1-ium-butyl)-2-[2-( -D i m t h l n -p ) -v ]benzothiazol-3-ium diiodide (Sbt3)Yield: 95 (dec.):182-184 1.93 (4H, 3.10 4.82 6.83 J=9.0 7.44 7.57 7.67 7.77 J=7.8 7.93 8.07 8.14 8.29 J=7.9 8.37 8.67 m).Anal.calcd.for C31H32N4SI2: 49.88; 7.51.Found: 49.92; 4.27; N,-vinyl]-3-(4-4,4'-dimethyl-[2,2']bipyridinyl-1-iumbutyl)-benzothiazol-3-ium (Sbt4) (dec.):242-244 2.41 3.11 4.83 J=5.7 6.84 J=8.2 7.29 J=15.3 7.78 J=7.2 7.92 J=15.7 8.24 J=7.5 8.52 C33H36N4SI2: 51.17; H,4.68; 7.23.