hrvatski jezikClear Cookie - decide language by browser settings

Tetracationic bis-triarylborane 1, 3-butadiyne as a combined fluorimetric and Raman probe for simultaneous and selective sensing of various DNA, RNA and proteins

Amini, Hashem; Ban, Željka; Ferger, Matthias; Lorenzen, Sabine; Rauch, Florian; Friedrich, Alexandra; Crnolatac, Ivo; Kenđel, Adriana; Miljanić, Snežana; Piantanida, Ivo; Marder, Todd B. (2020) Tetracationic bis-triarylborane 1, 3-butadiyne as a combined fluorimetric and Raman probe for simultaneous and selective sensing of various DNA, RNA and proteins. Chemistry - A European Journal, 26 . pp. 6017-6028. ISSN 0947-6539

[img]
Preview
PDF - Published Version - article
Available under License Creative Commons Attribution.

Download (2MB) | Preview

Abstract

A new bis-triarylborane tetracation (4-Ar2B-3, 5-Me2C6H2)-C≡C- C≡C-(3, 5-Me2C6H2-4-BAr2 [Ar = (2, 6-Me2-4-NMe3-C6H2)+] (24+) shows distinctly different behaviour in its fluorimetric response than that of our recently published bis-triarylborane 5- (4-Ar2B-3, 5-Me2C6H2)-2, 2’-(C4H2S)2-5’-(3, 5-Me2C6H2-4-BAr2) (34+). Single-crystal X-ray diffraction data on the neutral bis- triarylborane precursor 2N confirm its rod-like dumbbell structure, which is shown to be important for DNA/RNA targeting and also for BSA protein binding. Fluorimetric titrations with DNA/RNA/BSA revealed the very strong affinity of 24+ and indicated the importance of the properties of the linker connecting the two triarylboranes. Using the butadiyne- rather than a bithiophene linker resulted in an opposite emission effect (quenching vs enhancement), and 24+ bound to BSA 100 times stronger than 34+. Moreover, 24+ interacted strongly with ss-RNA, and circular dichroism (CD) results suggest ss- RNA chain-wrapping around the rod-like bis-triarylborane dumbbell structure like a thread around a spindle, a very unusual mode of binding of ss-RNA with small molecules. Furthermore, 24+ yielded strong Raman/SERS signals, allowing DNA or protein detection at ca. 10 nM concentrations. The above observations, combined with low cytotoxicity, efficient human cell uptake and organelle-selective accumulation make such compounds intriguing novel lead structures for bio-oriented, dual fluorescence/Raman-based applications.

Item Type: Article
Uncontrolled Keywords: Borane ; Fluorescent probe ; Raman probe ; DNA/RNA Sensor ; Protein Sensor ; Circular Dichroism
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina-BioMultiChromoProbesIvo PiantanidaIP-2018-01-5475HRZZ
Depositing User: Ivo Piantanida
Date Deposited: 12 May 2020 09:23
Last Modified: 12 May 2020 09:25
URI: http://fulir.irb.hr/id/eprint/5793
DOI: 10.1002/chem.201905328

Actions (login required)

View Item View Item

Downloads

Downloads per month over past year