A Unique Perylene‐Based DNA Intercalator: Localization in Cell Nuclei and Inhibition of Cancer Cells and Tumors

Abstract

To date, perylene derivatives have not been explored as DNA intercalator to inhibit cancer cells by intercalating into the base pairs of DNA. Herein, a water-soluble perylene bisimide (PBDI) that efficiently intercalates into the base pairs of DNA is synthesized. Excitingly, PBDI is superior to the commercial DNA intercalator, amonafide, for specific nuclear accumulation and effective suppression of cancer cells and tumors.

Luminescent Rhenium(I)–Polypyridine Complexes Appended with a Perylene Diimide or Benzoperylene Monoimide Moiety: Photophysics, Intracellular Sensing, and Photocytotoxic Activity

“…Additionally, fluorescent multi‐cationic and amphiphilic PDI compounds have been used as gene‐delivery vectors and imaging reagents . Water‐soluble PDI and BPMI compounds have also been designed to study enzyme activity and DNA intercalation …”

Fluorescent Nucleic Acid Analogues in Research and Clinical Diagnostics

“…Intercalating dyes find broad application in detection and quantification of nucleic acids, as well as therapeutics. For example, Xu et al synthesized a water-soluble PBDI and used it for nuclear intercalation and suppression of cancer cells and tumors (Xu et al 2014). Previously applied intercalating dyes have the disadvantage of high toxicity (e.g., EB).…”

“…Non-covalently intercalating dyes represent a broad class of organic compounds (e.g., ethidium bromide (EB), perylene bisimide (PBDI), BODIPY, SYBR Green, and the recently introduced EvaGreen dyes), which change fluorescence properties upon intercalation into double-stranded nucleic acids (Xu et al 2014;Ikeda et al 2009;Brzezinska et al 2012;Zhao et al 2013;Morgan et al 1979;Ahn et al 1996;Miotke et al 2014). The main advantage of this class of dyes is their low cost and higher availability compared to other nucleoside-based sensors due to shorter synthetic route.…”

Amphiphilic DNA Organic Hybrids: Functional Materials in Nanoscience and Potential Application in Biomedicine

“…Moreover, water soluble PDI molecules with biocompatibility and photostability have been successfully applied in the biological field [39]. Recently, PDI molecules were also attached to the DNA strand, at different locations [40,41,42,43,44]. Lewis and coworkers reported that PDI-linked bis(oligonucleotide) conjugates could form a hairpin dimer structure, driven by the hydrophobic interaction among PDI molecules [45].…”