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Synthesis, DNA/RNA-interaction and biological activity of benzo[k,l]xanthene lignans

Tumir, Lidija-Marija; Zonjić, Iva; Žuna, Kristina; Radić Brkanac, Sandra; Jukić, Marijana; Huđek, Ana; Durgo, Ksenija; Crnolatac, Ivo; Glavaš-Obrovac, Ljubica; Cardullo, Nunzio; Pulvirenti, Luana; Muccilli, Vera; Tringali, Corrado; Radić Stojković, Marijana (2020) Synthesis, DNA/RNA-interaction and biological activity of benzo[k,l]xanthene lignans. Bioorganic chemistry, 104 . ISSN 0045-2068

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Abstract

Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double- stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram- positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth- inhibitory activity and cytotoxicity.

Item Type: Article
Uncontrolled Keywords: DNA/RNA recognition ; Benzo[k, l]xanthene lignans ; G-quadruplex interaction ; HSA interaction ; Antiproliferative effect
Subjects: NATURAL SCIENCES > Chemistry > Analytic Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
NATURAL SCIENCES > Biology
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavimaRadić Stojković, MarijanaIP-2018-01-4694HRZZ
Depositing User: Marijana Radić Stojković
Date Deposited: 19 Nov 2021 14:09
URI: http://fulir.irb.hr/id/eprint/6748
DOI: 10.1016/j.bioorg.2020.104190

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