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Article

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

1
Division of Organic Chemistry & Biochemistry, Ruđer Bošković Institute, P.O. Box 180, HR-10002 Zagreb, Croatia
2
Institut für Anorganische Chemie and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, 97074 Würzburg, Germany
*
Authors to whom correspondence should be addressed.
Molecules 2021, 26(16), 4816; https://doi.org/10.3390/molecules26164816
Received: 2 July 2021 / Revised: 23 July 2021 / Accepted: 29 July 2021 / Published: 9 August 2021
(This article belongs to the Section Bioorganic Chemistry)
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. View Full-Text
Keywords: triarylborane; pyrene; click CuAAC synthesis; DPP III enzyme; BSA; fluorescence triarylborane; pyrene; click CuAAC synthesis; DPP III enzyme; BSA; fluorescence
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MDPI and ACS Style

Ban, Ž.; Karačić, Z.; Tomić, S.; Amini, H.; Marder, T.B.; Piantanida, I. Triarylborane Dyes as a Novel Non-Covalent and Non-Inhibitive Fluorimetric Markers for DPP III Enzyme. Molecules 2021, 26, 4816. https://doi.org/10.3390/molecules26164816

AMA Style

Ban Ž, Karačić Z, Tomić S, Amini H, Marder TB, Piantanida I. Triarylborane Dyes as a Novel Non-Covalent and Non-Inhibitive Fluorimetric Markers for DPP III Enzyme. Molecules. 2021; 26(16):4816. https://doi.org/10.3390/molecules26164816

Chicago/Turabian Style

Ban, Željka, Zrinka Karačić, Sanja Tomić, Hashem Amini, Todd B. Marder, and Ivo Piantanida. 2021. "Triarylborane Dyes as a Novel Non-Covalent and Non-Inhibitive Fluorimetric Markers for DPP III Enzyme" Molecules 26, no. 16: 4816. https://doi.org/10.3390/molecules26164816

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