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• W2418324983 endingPage "7364" @default.
• W2418324983 startingPage "7357" @default.
• W2418324983 abstract "Drug delivery to the brain can be achieved by various means, including blood-brain barrier (BBB) disruption, neurosurgical-based approaches, and molecular design. Recently, passive diffusion BBB shuttles have been developed to transport low-molecular-weight drug candidates to the brain which would not be able to cross unaided. The low water solubility of these BBB shuttles has, however, prevented them from becoming a mainstream tool to deliver cargos across membranes. Here, we describe the design, synthesis, physicochemical characterization, and BBB-transport properties of phenylproline tetrapeptides, (PhPro)4, an improved class of BBB shuttles that operates via passive diffusion. These PhPro-based BBB shuttles showed 3 orders of magnitude improvement in water solubility compared to the gold-standard (N-MePhe)4, while retaining very high transport values. Transport capacity was confirmed when two therapeutically relevant cargos, nipecotic acid and l-3,4-dihydroxyphenylalanine (i.e., l-DOPA), were attached to the shuttle. Additionally, we used the unique chiral and conformationally restricted character of the (PhPro)4 shuttle to probe its chiral interactions with the lipid bilayer of the BBB. We studied the transport properties of 16 (PhPro)4 stereoisomers using the parallel artificial membrane permeability assay and looked at differences in secondary structure. Most stereoisomers displayed excellent transport values, yet this study also revealed pairs of enantiomers with high enantiomeric discrimination and different secondary structure, where one enantiomer maintained its high transport values while the other had significantly lower values, thereby confirming that stereochemistry plays a significant role in passive diffusion. This could open the door to the design of chiral and membrane-specific shuttles with potential applications in cell labeling and oncology." @default.
• W2418324983 created "2016-06-24" @default.
• W2418324983 creator A5008504219 @default.
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• W2418324983 creator A5053483017 @default.
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• W2418324983 creator A5083622532 @default.
• W2418324983 date "2015-06-02" @default.
• W2418324983 modified "2023-10-17" @default.
• W2418324983 title "Lipid Bilayer Crossing—The Gate of Symmetry. Water-Soluble Phenylproline-Based Blood-Brain Barrier Shuttles" @default.
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• W2418324983 doi "https://doi.org/10.1021/jacs.5b02050" @default.
• W2418324983 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25992679" @default.
• W2418324983 hasPublicationYear "2015" @default.
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