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Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition.
Vacek, Jan; Zatloukalova, Martina; Bartheldyova, Eliska; Reha, David; Minofar, Babak; Bednarova, Klara; Renciuk, Daniel; Coufal, Jan; Fojta, Miroslav; Zadny, Jaroslav; Gessini, Alessandro; Rossi, Barbara; Storch, Jan; Kabelac, Martin.
Afiliação
  • Vacek J; Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacky University, Hnevotinska 3, 775 15 Olomouc, Czech Republic. Electronic address: jan.vacek@upol.cz.
  • Zatloukalova M; Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacky University, Hnevotinska 3, 775 15 Olomouc, Czech Republic.
  • Bartheldyova E; Nexars C2P, Palachovo namesti 2, 62500 Brno, Czech Republic.
  • Reha D; IT4Innovations, VSB-Technical University of Ostrava, 17. listopadu 2172/15, 708 00 Ostrava-Poruba, Czech Republic.
  • Minofar B; Department of Chemistry, Faculty of Science, University of South Bohemia, Branisovska 31, 370 05 Ceske Budejovice, Czech Republic.
  • Bednarova K; Institute of Biophysics of the Czech Academy of Sciences, Kralovopolska 135, 612 00 Brno, Czech Republic.
  • Renciuk D; Institute of Biophysics of the Czech Academy of Sciences, Kralovopolska 135, 612 00 Brno, Czech Republic.
  • Coufal J; Institute of Biophysics of the Czech Academy of Sciences, Kralovopolska 135, 612 00 Brno, Czech Republic.
  • Fojta M; Institute of Biophysics of the Czech Academy of Sciences, Kralovopolska 135, 612 00 Brno, Czech Republic.
  • Zadny J; Institute of Chemical Process Fundamentals of the AS CR, v.v.i., Rozvojova 135, 165 02 Prague 6, Czech Republic.
  • Gessini A; Elettra Sincrotrone Trieste S.C.p.A., S.S. 14 - Km 163.5, Basovizza, Trieste I-34149, Italy.
  • Rossi B; Elettra Sincrotrone Trieste S.C.p.A., S.S. 14 - Km 163.5, Basovizza, Trieste I-34149, Italy.
  • Storch J; Institute of Chemical Process Fundamentals of the AS CR, v.v.i., Rozvojova 135, 165 02 Prague 6, Czech Republic. Electronic address: storchj@icpf.cas.cz.
  • Kabelac M; Department of Chemistry, Faculty of Science, University of South Bohemia, Branisovska 31, 370 05 Ceske Budejovice, Czech Republic. Electronic address: mkabelac@prf.jcu.cz.
Int J Biol Macromol ; 250: 125905, 2023 Oct 01.
Article em En | MEDLINE | ID: mdl-37487990
ABSTRACT
In this contribution, we focused on a fundamental study targeting the interaction of water-soluble [6]helicene derivative 1 (1-butyl-3-(2-methyl[6]helicenyl)-imidazolium bromide) with double-stranded (ds) DNA. A synthetic 30-base pair duplex, plasmid, chromosomal calf thymus and salmon DNA were investigated using electrochemistry, electrophoresis and spectroscopic tools supported by molecular dynamics (MD) and quantum mechanical approaches. Both experimental and theoretical work revealed the minor groove binding of 1 to the dsDNA. Both the positively charged imidazole ring and hydrophobic part of the side chain contributed to the accommodation of 1 into the dsDNA structure. Neither intercalation into the duplex DNA nor the stable binding of 1 to single-stranded DNA were found in topoisomerase relaxation experiments with structural components of 1, i.e. [6]helicene (2) and 1-butyl-3-methylimidazolium bromide (3), nor by theoretical calculations. Finally, the binding of optically pure enantiomers (P)-1 and (M)-1 was studied using circular dichroism spectroscopy, isothermal titration calorimetry and UV Resonance Raman (UVRR) methods. Using MD and quantum mechanical methods, minor groove and semi-intercalation were proposed for compound 1 as the predominant binding modes. From the UVRR findings, we also can conclude that 1 tends to preferentially interact with adenine and guanine residues in the structure of dsDNA.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Int J Biol Macromol Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Int J Biol Macromol Ano de publicação: 2023 Tipo de documento: Article