Equipping nanocarriers specifically toward cargo: A competitive study on solubilizing related photosensitizers for photodynamic therapy

Wieczorek, S., Remmler, D., Masini, T., Kochovski, Z., Hirsch, A. K. H. & Boerner, H. G., 2017, In : BIOCONJUGATE CHEMISTRY. 28, 3, p. 760-767

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  • Fine-tuning Nanocarriers Speci fi cally toward Cargo: A Competitive Study on Solubilizing Related Photosensitizers for Photodynamic Therapy

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  • Sebastian Wieczorek
  • Dario Remmler
  • Tiziana Masini
  • Zdravko Kochovski
  • Anna K H Hirsch
  • Hans G Boerner

Advancing drug delivery systems by introducing peptide segments which constitute a binding motive for small molecule drugs is giving rise to next generation drug specific transporters or formulation additives. Programing the drug-carrier interactions precisely enables fine-tuning of drug binding, release profiles and reduction of potential adverse co-transport. Suitable peptides are selected via combinatorial means by screening one-bead-one-compound (OBOC) peptide libraries that cover large sequential spaces. The capability of the screening method to read out structural details of the drug entities is investigated by comparing three closely related photosensitizers for the photodynamic cancer therapy. Superior selectivity of the peptide sequences toward their drug guest molecule is found. Insights into relevant amino acids in the identified peptide sequences are gained by systematic point mutations (alanine scans), enabling understanding of drug binding motifs. This reveals the importance of appropriate H-bonding between polar functional groups of the peptide and the drugs, which agrees well with computational binding studies performed on stoichiometric drug/peptide complexes. The sequence-interaction relationships found are beyond unspecific hydrophobic interaction present in established amphipathic block copolymer drug solubilizers and thus give rise to highly purpose adapted formulation additives.

Original languageEnglish
Pages (from-to)760-767
Issue number3
Publication statusPublished - 2017

ID: 38596915