Adaptive Synthesis, Supramolecular Behavior, and Biological Properties of Amphiphilic Carbosilane-Phosphonium Dendrons with Tunable Structure
Here, we present a modular synthesis as well as physicochemical and biological evaluation of a new series of amphiphilic dendrons carrying triphenylphosphonium groups at their periphery. Within the series, the size and mutual balance of lipophilic and hydrophilic domains are systematically varied, changing the dendron shape from cylindrical to conical. In physiological solution, the dendrons exhibit very low critical micelle concentrations (2.6-4.9 μM) and form stable and uniform micelles 6-12 nm in diameter, depending on dendron shape; the results correlate well with molecular dynamics simulations. The compounds show relatively high cytotoxicity (IC<sub>50</sub> 1.2-21.0 μM) associated with micelle formation and inversely related to the size of assembled particles. Depending on their shape, the dendrons show promising results in terms of dendriplex formation and antibacterial activity. In addition to simple amphiphilic dendrons, a fluorescently labeled analogue was also prepared and utilized as an additive visualizing the dendron's cellular uptake.
Authors
- Alena Krupková (ORCID: https://orcid.org/0000-0001-9428-6393)
- Dominika Wróbel (ORCID: https://orcid.org/0000-0003-3920-9330)
- Evgeny Apartsin (ORCID: https://orcid.org/0000-0003-3334-0397)
- Jan Marek (ORCID: https://orcid.org/0000-0003-3708-0967)
- Marek Malý (ORCID: https://orcid.org/0000-0002-5930-563X)
- Tomáš Strašák (ORCID: https://orcid.org/0000-0001-6413-0494)
- Antonín Edr (ORCID: https://orcid.org/0000-0001-9400-5379)
- Lucie Červenková Šťastná (ORCID: https://orcid.org/0000-0002-9968-1082)
- Jan Malý (ORCID: https://orcid.org/0000-0002-7022-2157)
- Michaela Hympánová
Institutions
- Centre National de la Recherche Scientifique (FR)
- Jan Evangelista Purkyně University in Ústí nad Labem (CZ)
- Czech Academy of Sciences, Institute of Chemical Process Fundamentals (CZ)
- Chimie et Biologie des Membranes et des Nanoobjects (FR)
- University Hospital Hradec Králové (CZ)
- Institut Polytechnique de Bordeaux (FR)
- University of Defence (CZ)
Publication Details
- Journal
- Biomacromolecules
- Published
- 2024-11-11
- DOI
- https://doi.org/10.1021/acs.biomac.4c01092
- Citations
- 1
- Primary Topic
- Dendrimers and Hyperbranched Polymers
- Type
- article
- Field-Weighted Citation Impact
- 0.17
Funders
- Fakultní nemocnice Hradec Králové
- European Commission
- European Cooperation in Science and Technology
- Ministerstvo Školství, Mládeže a Tělovýchovy
- Agentura Pro Zdravotnický Výzkum České Republiky