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Pregled bibliografske jedinice broj: 1209065

Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift


Čipor, Ivona; Kurutos, Atanas; Dobrikov, Georgi M.; Kamounah, Fadhil S.; Majhen, Dragomira; Nestić, Davor; Piantanida, Ivo
Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift // Dyes and pigments, 206 (2022), 110626, 12 doi:10.1016/j.dyepig.2022.110626 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1209065 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift

Autori
Čipor, Ivona ; Kurutos, Atanas ; Dobrikov, Georgi M. ; Kamounah, Fadhil S. ; Majhen, Dragomira ; Nestić, Davor ; Piantanida, Ivo

Izvornik
Dyes and pigments (0143-7208) 206 (2022); 110626, 12

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Styryl dyes ; DNA/RNA binding ; BSA binding ; confocal microscopy

Sažetak
A series of 9 monocationic styryl dyes was prepared in moderate to good yields via Knoevenagel condensation between various CH active N-quaternary heterocycles and 4-(4-methylpiperazin-1-yl)benzaldehyde. Structural elucidation of the newly synthesized fluorophores was achieved by 1H NMR, 13C NMR, 77Se-NMR and high-resolution mass spectrometry (HRMS) in ESI mode. Novel dyes are characterised by very pronounced Stokes shift (94–203 nm), while fluorescence quantum yields (0.18–2.38 × 10􀀀 2) were strongly dependent on the selection of N-quaternary heterocycle. New dyes bind to DNA/RNA by micromolar affinity, yielding strong fluorescence increase. Among the studied series the strongest enhancement was observed for the two quinolinium derivatives and the benzo[e]indole analogue. The dye emission response selectivity between ds-DNA and ds-RNA was opposite for para-quinolinium and ortho-quinolinium analogue, stressing the importance of fine tuning of fluorophore by means of electronic properties and positioning within the DNA/RNA binding site. Combined results of several methods support binding of dyes within DNA minor or RNA major groove, with exception of indole and benzo[e]indole analogues, which show partial intercalation. Majority of dyes investigated in this work showed negligible cytotoxic activity, with an exception of the benzo[e]indole-dye micromolar cytotoxicity. The majority of the studied dyes exhibit localization within mitochondria, with two exceptions. The benzo[d] [1, 3] selenazole-derived dye preferentially localizes in lysosomes, while benzo[e]indole-dye is equally distributed between mitochondria and lysosomes at variance to indole-dye highly selective for mitochondria, suggesting different intracellular mechanisms of these two related dyes. Observed bioactivity of benzo[e]indole-dye combined with easily monitored localization by strong fluorescence makes this dye potential theranostic agent.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-5475 - Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina (BioMultiChromoProbes) (Piantanida, Ivo, HRZZ - 2018-01) ( POIROT)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Ivo Piantanida (autor)

Avatar Url Dragomira Majhen (autor)

Avatar Url Ivona Čipor (autor)

Avatar Url Davor Nestić (autor)

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com doi.org

Citiraj ovu publikaciju:

Čipor, Ivona; Kurutos, Atanas; Dobrikov, Georgi M.; Kamounah, Fadhil S.; Majhen, Dragomira; Nestić, Davor; Piantanida, Ivo
Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift // Dyes and pigments, 206 (2022), 110626, 12 doi:10.1016/j.dyepig.2022.110626 (međunarodna recenzija, članak, znanstveni)
Čipor, I., Kurutos, A., Dobrikov, G., Kamounah, F., Majhen, D., Nestić, D. & Piantanida, I. (2022) Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift. Dyes and pigments, 206, 110626, 12 doi:10.1016/j.dyepig.2022.110626.
@article{article, author = {\v{C}ipor, Ivona and Kurutos, Atanas and Dobrikov, Georgi M. and Kamounah, Fadhil S. and Majhen, Dragomira and Nesti\'{c}, Davor and Piantanida, Ivo}, year = {2022}, pages = {12}, DOI = {10.1016/j.dyepig.2022.110626}, chapter = {110626}, keywords = {Styryl dyes, DNA/RNA binding, BSA binding, confocal microscopy}, journal = {Dyes and pigments}, doi = {10.1016/j.dyepig.2022.110626}, volume = {206}, issn = {0143-7208}, title = {Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift}, keyword = {Styryl dyes, DNA/RNA binding, BSA binding, confocal microscopy}, chapternumber = {110626} }
@article{article, author = {\v{C}ipor, Ivona and Kurutos, Atanas and Dobrikov, Georgi M. and Kamounah, Fadhil S. and Majhen, Dragomira and Nesti\'{c}, Davor and Piantanida, Ivo}, year = {2022}, pages = {12}, DOI = {10.1016/j.dyepig.2022.110626}, chapter = {110626}, keywords = {Styryl dyes, DNA/RNA binding, BSA binding, confocal microscopy}, journal = {Dyes and pigments}, doi = {10.1016/j.dyepig.2022.110626}, volume = {206}, issn = {0143-7208}, title = {Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift}, keyword = {Styryl dyes, DNA/RNA binding, BSA binding, confocal microscopy}, chapternumber = {110626} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


Citati:





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