Quadruplex-duplex junction in LTR-III: A molecular insight into the complexes with BMH-21, namitecan and doxorubicin

PLoS One. 2024 Jul 24;19(7):e0306239. doi: 10.1371/journal.pone.0306239. eCollection 2024.

Abstract

Quadruplex-Duplex (Q-D) junctions are unique structural motifs garnering increasing interest as drug targets, due to their frequent occurrence in genomic sequences. The viral HIV LTR-III sequence was chosen as a Q-D junction model to study the affinity of the selected compounds BMH-21, namitecan (ST-1968), and doxorubicin (DOXO), all containing a planar polycyclic aromatic moiety, linked to either one short aminoalkyl or an aminoglycosyl group. A multidisciplinary approach that combines NMR spectroscopy, molecular modelling, circular dichroism (CD) and fluorescence spectroscopy was employed. The studied ligands induced moderate but clear stabilization to the Q-D junction by interacting with the interfacial tetrad. DOXO was found to be the best Q-D junction binder. Interestingly, the removal of the aminoglycosyl group significantly changed the pattern of the interactions, indicating that highly polar substituents have a stronger affinity with the exposed regions of the Q-D junction, particularly at the level of the interfacial tetrad.

MeSH terms

  • Camptothecin / analogs & derivatives
  • Camptothecin / chemistry
  • Circular Dichroism
  • Doxorubicin* / chemistry
  • G-Quadruplexes*
  • HIV Long Terminal Repeat / genetics
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular

Substances

  • Doxorubicin
  • Camptothecin

Grants and funding

The author(s) received no specific funding for this work.