Spectrophotometric Studies of a Fluorescent Naphthalenediimide PET and ICT pH Indicator and DNA Intercalator

Three naphthalenedimides (NDIs) were studied by UV-visible absorbance, fluorescence and circular dichroism spectroscopy in aqueous methanolic solution as DNA intercalators. Distinct solution colours are observed for the compounds under room lighting and upon irradiation with 365 nm UV light. The tetra-substituted dimethylaminoethylene NDI is designed as a fluorescent pH indicator with a ‘fluorophore–spacer–receptor’ construct based on a photoinduced electron transfer (PET) mechanism. This NDI derivative exhibits a significant change in the ellipticity with calf-thymus DNA. Fluorescence DNA titrations further revealed strong binding towards DNA, resulting in pronounced emission quenching. Incubation of MCF-7 cells reveals localisation of the fluorescent probe in the nucleus, specifically in the nucleoli.

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Publication Details

Journal
Molecules
Published
2026-09-11
DOI
https://doi.org/10.3390/molecules31183211
Primary Topic
DNA and Nucleic Acid Chemistry
Type
article
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article

Spectrophotometric Studies of a Fluorescent Naphthalenediimide PET and ICT pH Indicator and DNA Intercalator

David C. Magri, Gary J. Hunter, Mario Valentino, Alex D. Johnson
Molecules
DNA and Nucleic Acid Chemistry
article

Spectrophotometric Studies of a Fluorescent Naphthalenediimide PET and ICT pH Indicator and DNA Intercalator

David C. Magri, Gary J. Hunter, Mario Valentino, Alex D. Johnson
article en

Abstract

Three naphthalenedimides (NDIs) were studied by UV-visible absorbance, fluorescence and circular dichroism spectroscopy in aqueous methanolic solution as DNA intercalators. Distinct solution colours are observed for the compounds under room lighting and upon irradiation with 365 nm UV light. The tetra-substituted dimethylaminoethylene NDI is designed as a fluorescent pH indicator with a ‘fluorophore–spacer–receptor’ construct based on a photoinduced electron transfer (PET) mechanism. This NDI derivative exhibits a significant change in the ellipticity with calf-thymus DNA. Fluorescence DNA titrations further revealed strong binding towards DNA, resulting in pronounced emission quenching. Incubation of MCF-7 cells reveals localisation of the fluorescent probe in the nucleus, specifically in the nucleoli.

MoleculesVol. 31(18)
University of Malta (MT)
Openalex Percentile: Top 18%
DNA and Nucleic Acid Chemistry
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Spectrophotometric Studies of a Fluorescent Naphthalenediimide PET and ICT pH Indicator and DNA Intercalator — David C. Magri, Gary J. Hunter, et al. · Molecules (2026) | TGRS Research Map | TGRS