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Article

Flavylium Dye as pH-Tunable Fluorescent and CD Probe for Double-Stranded DNA and RNA

1
Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, HR-10002 Zagreb, Croatia
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LAQV-Laboratório Associado para a Química Verde-REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal
3
Department of Physical Chemistry, Faculty of Science/Chemistry, Horvatovac 102A, HR-10000 Zagreb, Croatia
*
Authors to whom correspondence should be addressed.
Chemosensors 2020, 8(4), 129; https://doi.org/10.3390/chemosensors8040129
Received: 12 November 2020 / Revised: 4 December 2020 / Accepted: 11 December 2020 / Published: 13 December 2020
(This article belongs to the Special Issue New insides in Fluorescent and Colorimetric Probes)
The interaction of 4′-(N,N-dimethylamino)-6-hydroxyflavylium cation with double stranded (ds-) DNA/RNA was studied by UV/Vis spectrophotometry, circular dichroism (CD), and also steady-state and time-resolved emission spectroscopies at neutral and weakly acidic conditions. At pH 5, the studied molecule, in its flavylium cationic form, showed considerable binding affinities (5 < logKs < 6) for all ds-DNA/RNA, contrary to chalcones forms (dominant at pH 7), which did not show binding to polynucleotides. Flavylium cation intercalated into ds-DNAs at variance to dominant groove aggregation within ds-RNA, which was reported by RNA-specific bisignate induced CD spectrum (ICD) bands. The intrinsically negligible fluorescence of flavylium was strongly increased upon the addition of DNA or RNA, whereby both the fluorescence intensity and emission lifetimes of complexes differed considerably: the strongest emission increase was observed for AU-RNA (detection limit estimated to 10 nM) followed by AT-DNAs and the much weaker effect of GC-DNAs. Both fluorescence sensitivity on the ds-DNA/RNA secondary structure and sequence-selective ICD bands make the flavylium–chalcones system an intriguing pH-switchable new probe for distinguishing between various polynucleotide sequences. View Full-Text
Keywords: flavylium cation; chalcones; pH control; DNA/RNA binding; fluorescence, circular dichroism flavylium cation; chalcones; pH control; DNA/RNA binding; fluorescence, circular dichroism
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MDPI and ACS Style

Crnolatac, I.; Giestas, L.; Horvat, G.; Parola, A.J.; Piantanida, I. Flavylium Dye as pH-Tunable Fluorescent and CD Probe for Double-Stranded DNA and RNA. Chemosensors 2020, 8, 129. https://doi.org/10.3390/chemosensors8040129

AMA Style

Crnolatac I, Giestas L, Horvat G, Parola AJ, Piantanida I. Flavylium Dye as pH-Tunable Fluorescent and CD Probe for Double-Stranded DNA and RNA. Chemosensors. 2020; 8(4):129. https://doi.org/10.3390/chemosensors8040129

Chicago/Turabian Style

Crnolatac, Ivo, Letícia Giestas, Gordan Horvat, António J. Parola, and Ivo Piantanida. 2020. "Flavylium Dye as pH-Tunable Fluorescent and CD Probe for Double-Stranded DNA and RNA" Chemosensors 8, no. 4: 129. https://doi.org/10.3390/chemosensors8040129

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