hrvatski jezikClear Cookie - decide language by browser settings

Para-N-Methylpyridinium Pyrenes: Impact of Positive Charge on ds- DNA/RNA and Protein Recognition, Photo-Induced Bioactivity, and Intracellular Localisation

Košćak, Marta; Pehar, Isabela; Božinović, Ksenija; Kumar Kole, Goutam; Sobočanec, Sandra; Podgorski, Iva I.; Pinterić, Marija; Müller-Buschbaum, Klaus; Majhen, Dragomira; Piantanida, Ivo; Marder, Todd B. (2022) Para-N-Methylpyridinium Pyrenes: Impact of Positive Charge on ds- DNA/RNA and Protein Recognition, Photo-Induced Bioactivity, and Intracellular Localisation. Pharmaceutics, 14 (11). ISSN 1999-4923

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

Download (4MB) | Preview


The 2- and 2, 7- substituted para-N-methylpyridinium pyrene cations show high-affinity intercalation into ds-DNAs, whereas their non- methylated analogues interacted with ds-DNA/RNA only in the protonated form (at pH 5), but not at physiological conditions (pH 7). The fluorescence from non-methylated analogues was strongly dependent on the protonation of the pyridines ; con- sequently, they act as fluorescence ratiometric probes for simultaneous detection of both ds-DNA and BSA at pH 5, relying on the ratio between intensities at 420 nm (BSA specific) and 520 nm (DNA specific), whereby exclusively ds-DNA sensing could be switched-off by adjustment to pH 7. Only methylated, permanently charged pyrenes show photoinduced cleavage of circular DNA, at- tributed to pyrene- mediated irradiation-induced production of singlet oxygen. Consequently, the moderate toxicity of these cations against human cell lines is strongly increased upon irradiation. Detailed studies revealed increased total ROS production in cells treated by the compounds studied, accompanied by cell swelling and augmentation of cellular complexity. The most photo-active 2- para-N- methylpyridinium pyrene showed significant localization at mitochondria, its photo-bioac- tivity likely due to mitochondrial DNA damage. Other derivatives were mostly non-selectively dis- tributed between various cytoplasmic organelles, thus being less photoactive.

Item Type: Article
Uncontrolled Keywords: N-methylpyridinium pyrene ; DNA sensing ; protein sensing ; singlet oxygen ; photodynamic therapy ; fluorescence ; theranostics
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Molecular Biology
Division of Molecular Medicine
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
Endocitoza adenovirusa i urođeni imunosni odgovorMajhen, DragomiraIP-2019-04-6048HRZZ
Depositing User: Sofija Konjević
Date Deposited: 09 Dec 2022 10:12
DOI: 10.3390/pharmaceutics14112499

Actions (login required)

View Item View Item


Downloads per month over past year

Increase Font
Decrease Font
Dyslexic Font