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New series of non-toxic DNA intercalators, mitochondria targeting fluorescent dyes

Kurutos, Atanas; Orehovec, Iva; Tomašić Paić, Ana; Crnolatac, Ivo; Horvat, Lucija; Gadjev, Nikolai; Piantanida, Ivo; Deligeorgiev, Todor (2018) New series of non-toxic DNA intercalators, mitochondria targeting fluorescent dyes. Dyes and Pigments, 148 . pp. 452-459. ISSN 0143-7208

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Abstract

Five novel benzoxazolium and benzothiazolium derived asymmetric dicationic monomethine cyanine dyes, bearing a thioester group have been synthesised via condensation of quaternary nitrogen containing heterocyclic salts in various anhydrides. Their chemical structures were evaluated by NMR, ESI/MS, IR spectroscopy, and melting point temperatures. Photophysical studies on the title compounds were performed in methanol solutions. The longest wavelength absorption maxima λmax of the studied dyes are in the region 453-508 nm. The corresponding fluorescence maxima λfl were registered within the 489-553 nm. Further spectroscopy and calorimetric techniques including circular dichroism (CD), UV-Vis, fluorescence, thermal denaturation and isothermal titration calorimetry have been applied to the studied dyes in the presence of biopolymers, in order to evaluate their staining ability as fluorescent markers. In aqueous solution the compounds exhibit no intrinsic fluorescence, however upon binding to dsDNA and dsRNA they show considerable enhancement of fluorescence intensity. Binding constants Ks of the complexes [dye–polynucleotide] have been evaluated from fluorescence spectral titrations. Although the intercalation is the predominant binding mode, the compounds show little or no effect on the cell proliferation. Upon fast cell internalization the compounds accumulate in the mitochondrial space.

Item Type: Article
Additional Information: AK, NG and TD are grateful for the financial support to "Funding of research projects in support of PhD students"-University of Sofia "St. Kliment Ohridski" - Project No 098/08.05.2014 and IC, IO, ATP and IP gratefully acknowledge financial support of ESF project HR.3.2.01 0254 and Croatian Science Foundation Grant No 1477: DNA/RNA-MolSense.
Uncontrolled Keywords: monomethine cyanine dyes ; DNA/RNA ; ITC ; circular dichroism ; binding parameters ; mitochondria
Subjects: NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
UNSPECIFIEDUNSPECIFIEDHR.3.2.01 0254UNSPECIFIED
Višenamjensko očitavanje DNA / RNA sekundarne strukture molekularnim kemijskim senzorima-DNA/RNA-MolSenseIvo PiantanidaIP-2013-11-1477HRZZ
Depositing User: Iva Orehovec
Date Deposited: 03 Dec 2019 13:21
Last Modified: 03 Dec 2019 13:21
URI: http://fulir.irb.hr/id/eprint/5203
DOI: 10.1016/j.dyepig.2017.09.049

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