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Fluoro-Crown Ether Phosphate as Efficient Cell-Permeable Drug Carrier by Disrupting Hydration Layer.
Goswami, Abir; Kohata, Ai; Okazoe, Takashi; Huang, Hubiao; Aida, Takuzo.
Afiliación
  • Goswami A; RIKEN Center for Emergent Matter Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • Kohata A; Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 2-11-16 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan.
  • Okazoe T; Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 2-11-16 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan.
  • Huang H; Yokohama Technical Center, AGC Inc., 1-1 Suehiro-cho, Tsurumi-ku, Yokohama 230-0045, Japan.
  • Aida T; RIKEN Center for Emergent Matter Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
J Am Chem Soc ; 146(33): 23406-23411, 2024 Aug 21.
Article en En | MEDLINE | ID: mdl-39082642
ABSTRACT
Fast and direct permeation of drug molecules is crucial for effective biotherapeutics. Inspired by a recent finding that fluorous compounds disrupt the hydrogen-bonded network of water, we developed fluoro-crown ether phosphate CyclicFP-X. This compound acts as a fast cell-permeating agent, enabling direct delivery of various bioactive cargos (X) into cancer cells without endocytic entrapment. In contrast, its nonfluorinated cyclic analog (CyclicP-X) failed to achieve cellular internalization. Although the acyclic fluorous analog AcyclicFP-X was internalized, this process occurred slowly owing to the involvement of an endocytic trapping pathway. Designed with a high fluorine density, CyclicFP-X exhibits compactness, polarity, and high-water solubility, facilitating lipid vesicle fusion by disrupting their hydration layers. Raman spectroscopy confirmed the generation of dangling -OH bonds upon addition of CyclicFP-OH to water. Furthermore, conjugating CyclicFP-X with fluorouracil (FU, an anticancer drug) via a reductively cleavable disulfide linker (CyclicFP-SS-FU) demonstrated the general utility of fluoro-crown ether phosphate as a potent carrier for biotherapeutics.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Portadores de Fármacos / Agua / Éteres Corona Límite: Humans Idioma: En Revista: J Am Chem Soc Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Portadores de Fármacos / Agua / Éteres Corona Límite: Humans Idioma: En Revista: J Am Chem Soc Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos