Halogen-containing thiazole orange analogues – new fluorogenic DNA stains

Autor: Aleksey A. Vasilev, Meglena I. Kandinska, Stanimir S. Stoyanov, Stanislava B. Yordanova, David Sucunza, Juan J. Vaquero, Obis D. Castaño, Stanislav Baluschev, Silvia E. Angelova
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 13, Iss 1, Pp 2902-2914 (2017)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.13.283
Popis: Novel asymmetric monomeric monomethine cyanine dyes 5a–d, which are analogues of the commercial dsDNA fluorescence binder thiazole orange (TO), have been synthesized. The synthesis was achieved by using a simple, efficient and environmetally benign synthetic procedure to obtain these cationic dyes in good to excellent yields. Interactions of the new derivatives of TO with dsDNA have been investigated by absorption and fluorescence spectroscopy. The longest wavelength absorption bands in the UV–vis spectra of the target compounds are in the range of 509–519 nm and these are characterized by high molar absorptivities (63000–91480 L·mol−1·cm−1). All investigated dyes from the series are either not fluorescent or their fluorescence is quite low, but they become strongly fluorescent after binding to dsDNA. The influence of the substituents attached to the chromophores was investigated by combination of spectroscopic (UV–vis and fluorescence spectroscopy) and theoretical (DFT and TDDFT calculations) methods.
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