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Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates


Racane, Livio; Stojković, Ranko; Tralić- Kulenović, Vesna; Cerić, Helena; Đaković, Marijana; Ester, Katja; Mišir Krpan, Ana; Radić Stojković, Marijana
Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates // European journal of medicinal chemistry, 86 (2014), 406-419 doi:10.1016/j.ejmech.2014.08.072 (međunarodna recenzija, članak, znanstveni)


Naslov
Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates

Autori
Racane, Livio ; Stojković, Ranko ; Tralić- Kulenović, Vesna ; Cerić, Helena ; Đaković, Marijana ; Ester, Katja ; Mišir Krpan, Ana ; Radić Stojković, Marijana

Izvornik
European journal of medicinal chemistry (0223-5234) 86 (2014); 406-419

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

Ključne riječi
Amino-amidino disubstituted 2-phenylbenzothiazoles; DNA/RNA; intercalation; minor groove binding; antiproliferative activity

Sažetak
Based on previously reported antiproliferative activity screening, four most promising disubstituted 2-phenylbenzothiazole hydrochlorides were chosen for detailed study. Water solubility, as well as liphophilicity/hydrophilicity balance of organic core were modified by conversion to mesylate salts. For purpose of structure/activity studies their structures were determined by X-ray structure analysis. Detailed analysis of interactions of new compounds with double stranded (ds-) DNA/RNA by UV/Vis and CD titrations, thermal melting and viscometry experiments revealed that most of studied compounds intercalate into ds-RNA but bind into minor groove of AT-DNA, and agglomerate along GC-DNA. Furthermore, compounds also interact with ss-RNA, but only amino- imidazolinyl 2-phenylbenzothiazole, 4b displayed well defined orientation and dominant binding mode (by induced CD signals) with poly A and poly G. Besides, in vitro investigations revealed moderate to high antiproliferative activity of benzothiazoles against seven human cancer cell lines, while in some cases (HTC 116, SW620, MIA PaCa-2) high correlation between the type of the amidino group and cytotoxic activity was observed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982464-2390 - Novi terapijski modaliteti u liječenju malignih bolesti (Ranko Stojković, )
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Marijeta Kralj, )
098-0982914-2918 - Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima (Ivo Piantanida, )
117-0000000-3283 - Istraživanje novih višenamjenskih bojila i optičkih bjelila (Livio Racane, )
119-1193079-1332 - Kemija metalnih kompleksa u reakcijama od biološkog značaja i novim materijalima (Zora Popović, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Tekstilno-tehnološki fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb,
Klinički bolnički centar Zagreb,
PLIVA HRVATSKA d.o.o.

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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