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Triarylborane Dyes as a Novel Non‐Covalent and Non‐Inhibitive Fluorimetric Markers for DPP III Enzyme

Ban, Željka; Karačić, Zrinka; Tomić, Sanja; Amini, Hashem; Marder, Todd B.; Piantanida, Ivo (2021) Triarylborane Dyes as a Novel Non‐Covalent and Non‐Inhibitive Fluorimetric Markers for DPP III Enzyme. Molecules, 26 . ISSN 1420-3049

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Novel dyes were prepared by simple “click CuAAC” attachment of a triarylborane–alkyne to the azide side chain of an amino acid yielding triarylborane dye 1 which was conjugated with pyrene (dye 2) forming a triarylborane–pyrene FRET pair. In contrast to previous cationic triarylboranes, the novel neutral dyes interact only with proteins, while their affinity to DNA/RNA is completely abolished. Both the reference triarylborane amino acid and triarylborane–pyrene conjugate bind to BSA and the hDPP III enzyme with high affinities, exhibiting a strong (up to 100‐fold) fluorescence increase, whereby the triarylborane–pyrene conjugate additionally retained FRET upon binding to the protein. Furthermore, the triarylborane dyes, upon binding to the hDPP III enzyme, did not impair its enzymatic activity under a wide range of experimental conditions, thus being the first non‐covalent fluorimetric markers for hDPP III, also applicable during enzymatic reactions with hDPP III substrates.

Item Type: Article
Uncontrolled Keywords: triarylborane ; pyrene ; click CuAAC synthesis ; DPP III enzyme ; BSA ; fluorescence
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteinaPiantanida, IvoIP-2018-01-5475HRZZ
Biološka važnost dipeptidil peptidaze III i njezin utjecaj na zdravlje čovjekaTomić, SanjaIP-2018-01-2936HRZZ
Depositing User: Ivo Piantanida
Date Deposited: 25 Aug 2021 08:58
DOI: 10.3390/molecules26164816

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