Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA

Pavlović Saftić, Dijana; Krošl Knežević, Ivona; de Lera Garrido, Fernando; Tolosa, Juan; Majhen, Dragomira; Piantanida, Ivo; García Martínez, Joaquín Calixto (2024) Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA. International Journal of Molecular Sciences, 25 (11). ISSN 1422-0067

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Abstract

The wide use of mono- or bis-styryl fluorophores in biomedical applications prompted the presented design and study of a series of trimeric and tetrameric homo-analogues, styryl moieties arranged around a central aromatic core. The interactions with the most common biorelevant targets, ds-DNA and ds-RNA, were studied by a set of spectrophotometric methods (UV-VIS, fluorescence, circular dichroism, thermal denaturation). All studied dyes showed strong light absorption in the 350–420 nm range and strongly Stokes-shifted (+100–160 nm) emission with quantum yields (Φf) up to 0.57, whereby the mentioned properties were finely tuned by the type of the terminal cationic substituent and number of styryl components (tetramers being red-shifted in respect to trimers). All studied dyes strongly interacted with ds-DNA and ds-RNA with 1–10 nM−1 affinity, with dye emission being strongly quenched. The tetrameric analogues did not show any particular selectivity between ds-DNA or ds-RNA due to large size and consequent partial, non-selective insertion into DNA/RNA grooves. However, smaller trimeric styryl series showed size-dependent selective stabilization of ds-DNA vs. ds-RNA against thermal denaturation and highly selective or even specific recognition of several particular ds-DNA or ds-RNA structures by induced circular dichroism (ICD) bands. The chiral (ICD) selectivity was controlled by the size of a terminal cationic substituent. All dyes entered efficiently live human cells with negligible cytotoxic activity. Further prospects in the transfer of ICD-based selectivity into fluorescence-chiral methods (FDCD and CPL) is proposed, along with the development of new analogues with red-shifted absorbance properties.

Item Type:	Article
Uncontrolled Keywords:	styryl dyes; DNA binding; RNA binding; fluorescence; circular dichroism; cell non-toxicity
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry NATURAL SCIENCES > Biology
Divisions:	Division of Molecular Biology Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Novi peptid-oligonukleotid-kromofor konjugati za biokemijsku dijagnostiku I bioaktivnost Ivo Piantanida IP-2022-10-9829 Znanstveno-istraživački projekti
Depositing User:	Lorena Palameta
Date Deposited:	28 Aug 2024 12:20
URI:	http://fulir.irb.hr/id/eprint/9030
DOI:	10.3390/ijms25115724

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