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Pregled bibliografske jedinice broj: 1203954

Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents


Zonjić, Iva; Radić Stojković, Marijana; Crnolatac, Ivo; Tomašić Paić, Ana; Pšeničnik, Silvia; Vasilev, Aleksey; Kandinska, Meglena; Mondeshki, Mihail; Baluschev, Stanislav; Landfester, Katharina et al.
Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents // Bioorganic chemistry, 127 (2022), 105999, 15 doi:10.1016/j.bioorg.2022.105999 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1203954 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents

Autori
Zonjić, Iva ; Radić Stojković, Marijana ; Crnolatac, Ivo ; Tomašić Paić, Ana ; Pšeničnik, Silvia ; Vasilev, Aleksey ; Kandinska, Meglena ; Mondeshki, Mihail ; Baluschev, Stanislav ; Landfester, Katharina ; Glavaš-Obrovac, Ljubica ; Jukić, Marijana ; Kralj, Juran ; Brozovic, Anamaria ; Horvat, Lucija ; Tumir, Lidija-Marija

Izvornik
Bioorganic chemistry (0045-2068) 127 (2022); 105999, 15

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

Ključne riječi
DYES ; Benzothiazole ; Piperazine ; DNA and RNA binding ; Fluorescence ; CD spectroscopy ; G-quadruplex binding ; Antiproliferative activity ; Mitochondrial dye ; Theragnostic activity

Sažetak
New monomethine, unsymmetrical styryl dyes consisting of benzothiazole and N-methylpiperazine or N-phenylpiperazine scaffolds were synthesized, and their binding affinities for different ds-polynucleotides and G-quadruplex were studied. Substitution of piperazine unit with methyl or phenyl group strongly influenced their binding modes, binding affinities, spectroscopic responses and antiproliferative activities. Compounds with N-methylpiperazine substituents showed a significant preference for AT-DNA polynucleotides and demonstrated AT-minor groove binding, which manifested in strong fluorescence increase, significant double helix stabilization, and positive induced circular dichroism spectra. These compounds formed complexes with G-quadruplex by π-π stacking interactions of dye with the top or bottom G-tetrad. Bulkier compounds with N-phenylpiperazine function are probably bound to ds-polynucleotide by partial intercalation between base pairs. On the other hand, they showed stronger stabilization of G-quadruplex compared to methyl-substituted compounds. Fluorimetric titrations pointed to possible mixed stoichiometry’s: 1:1 complex with π-π stacking interactions of dye on the top or bottom G- tetrad and 1:2 complex with dye positioned between two G-quadruplex molecules. Bulkier dyes with N-phenylpiperazine fragments demonstrated micromolar and submicromolar antiproliferative activity that was especially pronounced for leukaemia and lymphoma. Flow cytometric assay shows dose- and time-dependent increase in SubG0/G1 phase. Furthermore, the compounds enter the cells readily and accumulate in the mitochondrial space, co-localize with the standard mitochondrial markers.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Interdisciplinarne prirodne znanosti



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-4694 - Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavima (DNARNAHyB-MolBio) (Radić Stojković, Marijana, HRZZ - 2018-01) ( POIROT)

Ustanove:
Institut "Ruđer Bošković", Zagreb,
Medicinski fakultet, Osijek

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com doi.org

Citiraj ovu publikaciju:

Zonjić, Iva; Radić Stojković, Marijana; Crnolatac, Ivo; Tomašić Paić, Ana; Pšeničnik, Silvia; Vasilev, Aleksey; Kandinska, Meglena; Mondeshki, Mihail; Baluschev, Stanislav; Landfester, Katharina et al.
Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents // Bioorganic chemistry, 127 (2022), 105999, 15 doi:10.1016/j.bioorg.2022.105999 (međunarodna recenzija, članak, znanstveni)
Zonjić, I., Radić Stojković, M., Crnolatac, I., Tomašić Paić, A., Pšeničnik, S., Vasilev, A., Kandinska, M., Mondeshki, M., Baluschev, S. & Landfester, K. (2022) Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents. Bioorganic chemistry, 127, 105999, 15 doi:10.1016/j.bioorg.2022.105999.
@article{article, author = {Zonji\'{c}, Iva and Radi\'{c} Stojkovi\'{c}, Marijana and Crnolatac, Ivo and Toma\v{s}i\'{c} Pai\'{c}, Ana and P\v{s}eni\v{c}nik, Silvia and Vasilev, Aleksey and Kandinska, Meglena and Mondeshki, Mihail and Baluschev, Stanislav and Landfester, Katharina and Glava\v{s}-Obrovac, Ljubica and Juki\'{c}, Marijana and Kralj, Juran and Brozovic, Anamaria and Horvat, Lucija and Tumir, Lidija-Marija}, year = {2022}, pages = {15}, DOI = {10.1016/j.bioorg.2022.105999}, chapter = {105999}, keywords = {DYES, Benzothiazole, Piperazine, DNA and RNA binding, Fluorescence, CD spectroscopy, G-quadruplex binding, Antiproliferative activity, Mitochondrial dye, Theragnostic activity}, journal = {Bioorganic chemistry}, doi = {10.1016/j.bioorg.2022.105999}, volume = {127}, issn = {0045-2068}, title = {Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents}, keyword = {DYES, Benzothiazole, Piperazine, DNA and RNA binding, Fluorescence, CD spectroscopy, G-quadruplex binding, Antiproliferative activity, Mitochondrial dye, Theragnostic activity}, chapternumber = {105999} }
@article{article, author = {Zonji\'{c}, Iva and Radi\'{c} Stojkovi\'{c}, Marijana and Crnolatac, Ivo and Toma\v{s}i\'{c} Pai\'{c}, Ana and P\v{s}eni\v{c}nik, Silvia and Vasilev, Aleksey and Kandinska, Meglena and Mondeshki, Mihail and Baluschev, Stanislav and Landfester, Katharina and Glava\v{s}-Obrovac, Ljubica and Juki\'{c}, Marijana and Kralj, Juran and Brozovic, Anamaria and Horvat, Lucija and Tumir, Lidija-Marija}, year = {2022}, pages = {15}, DOI = {10.1016/j.bioorg.2022.105999}, chapter = {105999}, keywords = {DYES, Benzothiazole, Piperazine, DNA and RNA binding, Fluorescence, CD spectroscopy, G-quadruplex binding, Antiproliferative activity, Mitochondrial dye, Theragnostic activity}, journal = {Bioorganic chemistry}, doi = {10.1016/j.bioorg.2022.105999}, volume = {127}, issn = {0045-2068}, title = {Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents}, keyword = {DYES, Benzothiazole, Piperazine, DNA and RNA binding, Fluorescence, CD spectroscopy, G-quadruplex binding, Antiproliferative activity, Mitochondrial dye, Theragnostic activity}, chapternumber = {105999} }

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
  • MEDLINE


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