The guanidiniocarbonylpyrrole - fluorophore conjugates as theragnostic tools for DPP III monitoring and inhibition

Čehić, Mirsada; Suć Sajko, Josipa; Karačić, Zrinka; Piotrowski, Patryciusz; Šmidlehner, Tamara; Jerić, Ivanka; Schmuck, Carsten; Piantanida, Ivo; Tomić, Sanja (2020) The guanidiniocarbonylpyrrole - fluorophore conjugates as theragnostic tools for DPP III monitoring and inhibition. Journal of Biomolecular Structure and Dynamics, 38 . pp. 3790-3800. ISSN 0739-1102

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Abstract

Study of seven new guanidiniocarbonylpyrrole (GCP)–fluorophore conjugates interactions with dipeptidyl peptidase III (DPP III) showed that all compounds bind strongly (Ks ≈ µM) to enzyme active site, but with very different fluorimetric response (varying from quenching to strong increase), dependent on the fluorophore type and intramolecular pre-organisation of molecule. Positively charged lysine side chain improved significantly compound solubility but diminished fluorescence increase upon DPP III binding and completely abolished inhibitory effect on DPP III activity, whereas linker-neutral analogues showed stronger emission increase and were efficient enzyme inhibitors. By far the best fluorimetric response and inhibitive properties showed cyanine–GCP analogue, thus being promising lead compound for both enzyme sensing and bio-activity inhibiting (theragnostic) studies of DPP III in the future.

Item Type:	Article
Uncontrolled Keywords:	DPP III inhibitor; fluorescence; pyrene; cyanine; guanidiniocarbonyl-pyrrole
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry NATURAL SCIENCES > Biology > Biochemistry and Molecular Biology
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Biološka važnost dipeptidil peptidaze III i njezin utjecaj na zdravlje čovjeka-DPP3BioRe Sanja Tomić; Hrvoje Brkić IP-2018-01-2936 HRZZ Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina-BioMultiChromoProbes Ivo Piantanida IP-2018-01-5475 HRZZ
Depositing User:	Zrinka Karačić
Date Deposited:	07 Jan 2026 15:30
URI:	http://fulir.irb.hr/id/eprint/10740
DOI:	10.1080/07391102.2019.1664936

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