Sensing and Microbiological Activity of a New Blue Fluorescence Polyamidoamine Dendrimer Modified with 1,8-Naphthalimide Units

Molecules. 2024 Apr 25;29(9):1960. doi: 10.3390/molecules29091960.

Abstract

A novel second-generation blue fluorescent polyamidoamine dendrimer peripherally modified with sixteen 4-N,N-dimethylaninoethyloxy-1,8-naphthalimide units was synthesized. Its basic photophysical characteristics were investigated in organic solvents of different polarity. It was found that in these solvents, the dendrimer is colorless and emitted blue fluorescence with different intensities depending on their polarity. The effect of the pH of the medium on the fluorescence intensity was investigated and it was found that in the acidic medium, the fluorescence is intense and is quenched in the alkaline medium. The ability of the dendrimer to detect metal ions (Pb2+, Zn2+, Mg2+, Sn2+, Ba2+, Ni2+, Sn2+, Mn2+, Co2+, Fe3+, and Al3+) was also investigated, and it was found that in the presence of Fe3+, the fluorescent intensity was amplified more than 66 times. The antimicrobial activity of the new compound has been tested in vitro against Gram-positive B. cereus and Gram-negative P. aeruginosa. The tests were performed in the dark and after irradiation with visible light. The antimicrobial activity of the compound enhanced after light irradiation and B. cereus was found slightly more sensitive than P. aeruginosa. The increase in antimicrobial activity after light irradiation is due to the generation of singlet oxygen particles, which attack bacterial cell membranes.

Keywords: 1,8-naphthalimide; antimicrobial; dendrimer; photophysics; sensors.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Bacillus cereus / drug effects
  • Dendrimers* / chemistry
  • Dendrimers* / pharmacology
  • Fluorescence
  • Fluorescent Dyes / chemistry
  • Hydrogen-Ion Concentration
  • Light
  • Microbial Sensitivity Tests*
  • Naphthalimides* / chemistry
  • Naphthalimides* / pharmacology
  • Polyamines* / chemistry
  • Polyamines* / pharmacology
  • Pseudomonas aeruginosa / drug effects
  • Spectrometry, Fluorescence

Substances

  • Naphthalimides
  • Dendrimers
  • Polyamines
  • Poly(amidoamine)
  • Anti-Bacterial Agents
  • Fluorescent Dyes