The Nature of the (Oligo/Hetero)Arene Linker Connecting Two Triarylborane Cations Controls Fluorimetric and Circular Dichroism Sensing of Various ds-DNAs and ds-RNAs

Tumir, Lidija-Marija; Pavlović Saftić, Dijana; Crnolatac, Ivo; Ban, Željka; Maslać, Matea; Griesbeck, Stefanie; Marder, Todd B.; Piantanida, Ivo (2023) The Nature of the (Oligo/Hetero)Arene Linker Connecting Two Triarylborane Cations Controls Fluorimetric and Circular Dichroism Sensing of Various ds-DNAs and ds-RNAs. Molecules, 28 . ISSN 1420-3049

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Abstract

A series of tetracationic bis-triarylborane dyes, differing in the aromatic linker connecting two dicationic triarylborane moieties, showed very high submicromolar affinities toward ds-DNA and ds-RNA. The linker strongly influenced the emissive properties of triarylborane cations and controlled the fluorimetric response of dyes. The fluorene-analog shows the most selective fluorescence response between AT-DNA, GC-DNA, and AU-RNA, the pyrene-analog’s emission is non-selectively enhanced by all DNA/RNA, and the dithienyl-diketopyrrolopyrrole analog’s emission is strongly quenched upon DNA/RNA binding. The emission properties of the biphenyl-analog were not applicable, but the compound showed specific induced circular dichroism (ICD) signals only for AT-sequence containing ds-DNAs, whereas the pyrene-analog ICD signals were specific for AT-DNA with respect to GC-DNA, and also recognized AU-RNA by giving a different ICD pattern from that observed upon interaction with AT-DNA. The fluorene- and dithienyl-diketopyrrolopyrrole analogs were ICD-signal silent. Thus, fine-tuning of the aromatic linker properties connecting two triarylborane dications can be used for the dual sensing (fluorimetric and CD) of various ds-DNA/RNA secondary structures, depending on the steric properties of the DNA/RNA grooves.

Item Type:	Article
Uncontrolled Keywords:	triarylborane ; fluorescent probe ; circular dichroism ; DNA recognition ; RNA recognition
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina Piantanida, Ivo IP-2018-01-5475 HRZZ
Depositing User:	Sofija Konjević
Date Deposited:	16 Jun 2023 09:09
URI:	http://fulir.irb.hr/id/eprint/8024
DOI:	10.3390/molecules28114348

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