10.1021/acsanm.9b02187.s001
Goutam Kulsi
Goutam
Kulsi
Annie Agnes Suganya Samson
Annie Agnes Suganya
Samson
Baskaran Purushothaman
Baskaran
Purushothaman
Joon Myong Song
Joon Myong
Song
Side-Chain-Dependent Binding of bis-Naphthalimide
Self-Assembled Nanoparticles to G‑Quadruplex DNA for Potential
Anticancer Therapy
American Chemical Society
2020
bis-NI 1
bis-NI 3
bis-NI 6
side chain
G 4-DNA groove
G 4-DNAs
cell cycle arrest
Potential Anticancer Therapy Novel bis-naphthalimide
IC 50 values
NP
space linkers
bis-Naphthalimide Self-Assembled Nanoparticles
groove binding
needle-shaped bis-NI 6
2020-02-04 20:34:02
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Side-Chain-Dependent_Binding_of_bis-Naphthalimide_Self-Assembled_Nanoparticles_to_G_Quadruplex_DNA_for_Potential_Anticancer_Therapy/11803170
Novel
bis-naphthalimide (NI)-based molecules composed of space
linkers of phenyl dialkyne (bis-NI1 and bis-NI2), triazole (bis-NI3
and bis-NI4), and alkyne (bis-NI5 and bis-NI6) with the distinctive
side chain of 2,6-diisopropylaniline or 2,4,6-trimethylaniline were
designed and synthesized as nanoparticles (NPs) that bind to G-quadruplex
(G4) DNA. The supramolecular assemblies of the bis-NIs were found
to form isolated spheres (bis-NI1, bis-NI3), dumbbells with or without
a cylindrical bridge (bis-NI2, bis-NI4), and needle-like structures
(bis-NI6). The side chain of 2,4,6-trimethylaniline is suggested to
play a key role in the self-assembly of the bridge-connected shape
such as dumbbells or needle in bis-NIs with three different space
linkers. The small sphere shaped NP formed by bis-NI1 displayed both
intercalation and groove binding to G4-DNAs, while a larger sphere
shaped NP of bis-NI3 represented binding to the G4-DNA groove. The
dumbbells of bis-NI2 showed both intercalation and groove binding
to G4-DNAs, whereas the dumbbells of bis-NI4 represented binding to
the G4-DNA groove. The needle-shaped bis-NI6 exhibited both intercalation
and groove binding to G4-DNAs. Different morphologies of self-assembled
bis-NIs provided different IC<sub>50</sub> values. Furthermore, bis-NI1,
bis-NI4, and bis-NI6 induced cell cycle arrest (G1/S phase) and apoptosis
in cancer cells. This suggests bis-NI1, bis-NI4, and bis-NI6 are potential
anticancer agents.