Synthesis, characterization, and photoinduced antibacterial activity of porphyrin-type photosensitizers conjugated to the antimicrobial peptide apidaecin 1b

Ryan Dosselli, Cristiano Tampieri, Rubén Ruiz-González, Sonia De Munari, Xavier Ragàs, David Sánchez-García, Montserrat Agut, Santi Nonell, Elena Reddi, Marina Gobbo

Research output: Indexed journal article Articlepeer-review

90 Citations (Scopus)

Abstract

Antimicrobial photodynamic therapy (aPDT) is an emerging treatment for bacterial infections that is becoming increasingly more attractive because of its effectiveness against multi-antibiotic-resistant strains and unlikelihood of inducing bacterial resistance. Among the strategies to enhance the efficacy of PDT against Gram-negative bacteria, the binding to a cationic antimicrobial peptide offers the attractive prospect for improving both the water solubilty and the localization of the photoactive drug in bacteria. In this work we have compared a number of free and apidaecin-conjugated photosensitizers (PSs) differing in structure and charge. Our results indicate that the conjugation of per se ineffective highly hydrophobic PSs to a cationic peptide produces a photosensitizing agent effective against Gram-negative bacteria. Apidaecin cannot improve the phototoxic activity of cationic PSs, which mainly depends on a very high yield of singlet oxygen production in the surroundings of the bacterial outer membrane. Apidaecin-PS conjugates appear most promising for treatment protocols requiring repeated washing after sensitizer delivery.

Original languageEnglish
Pages (from-to)1052-1063
Number of pages12
JournalJournal of Medicinal Chemistry
Volume56
Issue number3
DOIs
Publication statusPublished - 14 Feb 2013

Keywords

  • Singlet oxygen
  • Photodynamic therapy
  • Escherichia-coli
  • Spectrum
  • Luminescence
  • Biodiversity
  • Membrane

Fingerprint

Dive into the research topics of 'Synthesis, characterization, and photoinduced antibacterial activity of porphyrin-type photosensitizers conjugated to the antimicrobial peptide apidaecin 1b'. Together they form a unique fingerprint.

Cite this