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- Title
Exploring the Binding of Natural Compounds to Cancer-Related G-Quadruplex Structures: From 9,10-Dihydrophenanthrenes to Their Dimeric and Glucoside Derivatives.
- Authors
Platella, Chiara; Criscuolo, Andrea; Riccardi, Claudia; Gaglione, Rosa; Arciello, Angela; Musumeci, Domenica; DellaGreca, Marina; Montesarchio, Daniela
- Abstract
In-depth studies on the interaction of natural compounds with cancer-related G-quadruplex structures have been undertaken only recently, despite their high potential as anticancer agents, especially due to their well-known and various bioactivities. In this frame, aiming at expanding the repertoire of natural compounds able to selectively recognize G-quadruplexes, and particularly focusing on phenanthrenoids, a mini-library including dimeric (1–3) and glucoside (4–5) analogues of 9,10-dihydrophenanthrenes, a related tetrahydropyrene glucoside (6) along with 9,10-dihydrophenanthrene 7 were investigated here by several biophysical techniques and molecular docking. Compounds 3 and 6 emerged as the most selective G-quadruplex ligands within the investigated series. These compounds proved to mainly target the grooves/flanking residues of the hybrid telomeric and parallel oncogenic G-quadruplex models exploiting hydrophobic, hydrogen bond and π-π interactions, without perturbing the main folds of the G-quadruplex structures. Notably, a binding preference was found for both ligands towards the hybrid telomeric G-quadruplex. Moreover, compounds 3 and 6 proved to be active on different human cancer cells in the low micromolar range. Overall, these compounds emerged as useful ligands able to target G-quadruplex structures, which are of interest as promising starting scaffolds for the design of analogues endowed with high and selective anticancer activity.
- Subjects
MOLECULAR docking; HYDROGEN bonding; QUADRUPLEX nucleic acids; ANTINEOPLASTIC agents; CANCER cells; ANTHRACENE derivatives
- Publication
International Journal of Molecular Sciences, 2023, Vol 24, Issue 9, p7765
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms24097765