Novel cationic fullerene derivatized s-triazine scaffolds as photoinduced DNA cleavage agents: design, synthesis, biological evaluation and computational investigation

Abstract

A series of novel cationic fullerene (C 60 ) derivatives, bearing substituted s-triazine moiety as a side arm, synthesized by using the 1,3 dipolar cycloaddition reaction of C 60 with azomethine ylides generated from the corresponding Schiff bases of substituted s-triazine is reported. All the synthesized compounds were characterized by elemental analysis, FT-IR, 1 H NMR, 13 C NMR and ESI-MS. The compounds 7a, 7d, 7e and 7f cleaved the supercoiled pBR322 DNA into nicked form efficiently upon visible light irradiation in the presence of NADH. The photoinduced superoxide radical and hydroxyl radical generated may act as molecular species causing the DNA scission. Further, the interaction of synthesized molecules with pBR322 plasmid DNA was investigated using computational approaches.

DNA-Guided Assemblies toward Nanoelectronic Applications

“…Therefore, one helical pitch of DNA (3.4 nm) can accommodate three fullerene units or a cluster containing 5–8 fullerenes. On the basis of the atomistic molecular simulation, it was found that the groove binding nature and intrinsic rich π-surface of fullerenes are the main driving force for their ability to self-assemble with DNA. , The suitable functionalization of fullerene with intercalating and cationic groups can make them more accessible to interact with the DNA backbone through electrostatic and van der Waals interactions. For example, Cassell et al studied the assembly of a cationic fullerene derivative, C 60 - N,N -dimethylpyrrolidinium iodide on DNA, in which they showed effective interactions between DNA and fullerene can lead to DNA supercoiling, as can be seen in the transmission electron microscopy (TEM) image (Figure A) .…”

2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides

“…Similarly, the tandem iminium condensation/thermal decarboxylation reaction manifold (via carboxylic acids 278 , Scheme ) is a popular method for in situ preparation of N -alkyl azomethine ylides. − In 1993, Prato and co-workers demonstrated that C 60 could be converted to the corresponding pyrrolidine by 1,3-dipolar cycloaddition with the N -methyl azomethine ylide generated via thermal decarboxylation of the iminium formed by condensation between sarcosine ( N -methlyglycine) and formaldehyde (Scheme ). This so-called “Prato reaction”, and variations thereof, have since been applied toward the functionalization of fullerenes, − graphene and single-walled carbon nanotubes and nanohorns, − …”

Secondary‐Rim γ‐Cyclodextrin Functionalization to Conjugate with C60: Improved Efficacy as a Photosensitizer

“…Cationic porphyrin not only enhanced the solubility of C 60 , but also strengthened the affinity to DNA . s‐Triazine scaffolds were attached to ameliorate the hydrophilicity of C 60 and bring C 60 to the DNA minor groove . Furthermore, sugar‐, protein‐, and polymer‐based C 60 derivatives were applied as well.…”