hrvatski jezikClear Cookie - decide language by browser settings

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

Matić, Josipa; Tandarić, Tana; Radić Stojković, Marijana; Šupljika, Filip; Karačić, Zrinka; Tomašić Paić, Ana; Horvat, Lucija; Vianello, Robert; Tumir, Lidija-Marija (2023) Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme. Beilstein journal of organic chemistry, 19 . pp. 550-565. ISSN 2195-951X

PDF - Published Version - article
Available under License Creative Commons Attribution.

Download (1MB) | Preview


Two novel conjugate molecules were designed: pyrene and phenanthridine-amino acid units with a different linker length between the aromatic fragments. Molecular modelling combined with spectrophotometric experiments revealed that in neutral and acidic buffered water solutions conjugates predominantly exist in intramolecularly stacked conformations because of the π–π stacking interaction between pyrene and phenanthridine moieties. The investigated systems exhibited a pH- dependent excimer formation that is significantly red-shifted relative to the pyrene and phenanthridine fluorescence. While the conjugate with a short linker showed negligible spectrophotometric changes due to the polynucleotide addition, the conjugate with a longer and more flexible linker exhibited a micromolar and submicromolar binding affinity for ds-polynucleotides and inactivated a mutant of dipeptidyl peptidase enzyme E451A. Confocal microscopy revealed that the conjugate with the longer linker entered the HeLa cell membranes and blue fluorescence was visualized as the dye accumulated in the cell membrane.

Item Type: Article
Uncontrolled Keywords: dipeptidyl peptidase enzyme ; excimer ; molecular dynamics simulations ; phenanthridine ; polynucleotide ; pyrene
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Molecular Biology
Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavimaRadić Stojković, MarijanaIP-2018-01-4694HRZZ
Dizajn, sinteza i računalna analiza novih optičkih kemijskih pH osjetilnih derivata benzazolaVianello, RobertIP-2020-02-8090HRZZ
Depositing User: Lidija-Marija Tumir
Date Deposited: 21 Jun 2023 11:59
DOI: 10.3762/bjoc.19.40

Actions (login required)

View Item View Item


Downloads per month over past year

Increase Font
Decrease Font
Dyslexic Font