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Recognition of ATT Triplex and DNA:RNA Hybrid Structures by Benzothiazole Ligands

Zonjić, Iva; Tumir, Lidija-Marija; Crnolatac, Ivo; Šupljika, Filip; Racané, Livio; Tomić, Sanja; Radić Stojković, Marijana (2022) Recognition of ATT Triplex and DNA:RNA Hybrid Structures by Benzothiazole Ligands. Biomolecules, 12 (3). ISSN 2218-273X

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Interactions of an array of nucleic acid structures with a small series of benzothiazole ligands (bis-benzothiazolyl-pyridines—group 1, 2- thienyl/2-benzothienyl-substituted 6-(2- imidazolinyl) benzothiazoles—group 2, and three 2- aryl/heteroaryl-substituted 6-(2- imidazolinyl)benzothiazoles—group 3) were screened by competition dialysis. Due to the involvement of DNA:RNA hybrids and triplex helices in many essential functions in cells, this study’s main aim is to detect benzothiazole based moieties with selective binding or spectroscopic response to these nucleic structures compared to regular (non- hybrid) DNA and RNA duplexes and single-stranded forms. Complexes of nucleic acids and benzothiazoles, selected by this method, were characterized by UV/Vis, fluorescence and circular dichroism (CD) spectroscopy, isothermal titration calorimetry, and molecular modeling. Two compounds (1 and 6) from groups 1 and 2 demonstrated the highest affinities against 13 nucleic acid structures, while another compound (5) from group 2, despite lower affinities, yielded higher selectivity among studied compounds. Compound 1 significantly inhibited RNase H. Compound 6 could differentiate between B- (binding of 6 dimers inside minor groove) and A- type (intercalation) helices by an induced CD signal, while both 5 and 6 selectively stabilized ATT triplex in regard to AT duplex. Compound 3 induced strong condensation-like changes in CD spectra of AT-rich DNA sequences.

Item Type: Article
Uncontrolled Keywords: benzothiazoles ; competition dialysis ; DNA:RNA hybrids ; ATT triplex ; circular dichroism spectroscopy ; RNase H
Subjects: NATURAL SCIENCES > Chemistry > Physical Chemistry
NATURAL SCIENCES > Chemistry > Analytic Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavima-DNARNAHyB-MolBioMarijana Radić StojkovićIP-2018-01-4694HRZZ
Depositing User: Marijana Radić Stojković
Date Deposited: 06 Feb 2024 13:34
DOI: 10.3390/biom12030374

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