Naphtholylimino-tether on β-cyclodextrin: Selective G-quadruplex DNA binding

• Published in: Journal of molecular structure Vol. 1265; p. 133403
• Main Authors: Suganthi, Soundarapandian, Alexander, Aleyamma, Pillai, Archana Sumohan, Enoch, Israel VMV, Yousuf, Sameena
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.10.2022
• Subjects: 2D ROESY; Binding constant; G-quadruplex; Naphthoyl derivative; β-cyclodextrin; Naphthoyl derivative; β-cyclodextrin; 2D ROESY; G-quadruplex; Binding constant
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.133403

•A naphtholyl derivative of β-cyclodextrin is synthesized.•It binds to duplex and the quadruplexes with different binding strengths.•The naphtholyl derivative forms a 1:1 stoichiometric host: guest complex with berberine.•The naphtholyl derivative of β-CD is a selective quadruplex binder.•The host: guest complex also binds with the DNA targets with variable binding affinities. Guanine-rich sequences of DNA are located in certain important functional positions of the genome including the telomeric part. We explore the interactions of a naphtholylimino derivative of β-cyclodextrin with various G-quadruplex and duplex DNAs, probed by spectroscopic methods. The cyclodextrin derivative is characterized using FT-IR, NMR, and mass spectroscopy. The binding constant values for interaction of the modified β-CD with c-kit, c-myc, and telo sequences and calf thymus DNA are reported. The binding constants show a variation depending upon the type of DNA. The naphtholylimino derivative forms a host: guest complex with a G-quadruplex binder, Berberine. The complex's stoichiometry of binding is 1: 1. The mode of binding of the Berberine molecule to the host is investigated by ROESY. UV–vis and fluorescence spectroscopy are employed to investigate the interaction of the Berberine-complexed naphtholylimino-β-cyclodextrin to DNAs. The selectivity of the binding of the free- and Berberine-loaded modified β-CD are compared.