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Cell-penetrating poly(disulfide)s: Focus on substrate-initiated co-polymerization

Polymer Chemistry, ISSN: 1759-9962, Vol: 5, Issue: 7, Page: 2433-2441
2014
  • 17
    Citations
  • 0
    Usage
  • 39
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    17
    • Citation Indexes
      17
  • Captures
    39

Article Description

Outperforming cell-penetrating peptides, cell-penetrating poly(disulfide)s are attracting increasing attention. Recently we have shown that cell-penetrating poly(disulfide)s can be grown directly on substrates of free choice before delivery and depolymerized right afterwards. These unique characteristics are compatible with the general, non-toxic, traceless yet covalent delivery of substrates in an unmodified form. The objective of this study was to elaborate on substrate-initiated co-polymerization. The original propagators contain a strained disulfide for ring-opening disulfide-exchange polymerization and a guanidinium cation to assure cell-penetrating activity. Here, we report individually optimized conditions to polymerize these original propagators together with several other propagators. The nature of these new propagators significantly affected polymerization efficiency and conditions as well as size, polydispersity and transport activity of the final co-polymers. According to gel permeation chromatography, the length of co-polymers increases with hydrophobicity, bulk and valency of the co-propagators, whereas ion pairing with boronates gives shorter co-polymers and branching increases polydispersity. The activity of co-polymers increases with length, π-acidity, superhydrophobicity and boronate counterions. Hydrophobicity, π-basicity, bulk and branching appear less important for activity in fluorogenic vesicles. The here reported design, synthesis and evaluation of substrate-initiated co-polymers will be essential to find the best cell-penetrating poly(disulfide)s. © 2014 The Royal Society of Chemistry.

Bibliographic Details

Eun Kyoung Bang; Sandra Ward; Giulio Gasparini; Naomi Sakai; Stefan Matile

Royal Society of Chemistry (RSC)

Chemical Engineering; Biochemistry, Genetics and Molecular Biology; Materials Science; Chemistry

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