Sequential pore wall functionalization in covalent organic frameworks and application to stable camptothecin delivery systems

Fecha de publicación:

Autores de CIPF

Participantes ajenos a CIPF

  • Oliveira, AD
  • Rivero-Buceta, EM
  • Vidaurre-Agut, C
  • Misturini, A
  • Jorda, JL
  • Sastre, G
  • Pergher, SBC
  • Botella, P

Grupos de Investigación

Abstract

Post-synthetic modification of covalent organic frameworks (COFs) is strongly demanded in order to provide additional functionalities to their structures. However, the introduction of functional groups during the synthesis of two dimensional COFs (2D COFs) is highly discouraged, as they can interfere with the ox-ox stacking forces, compromising framework integrity. Here, we show that direct incorporation of nucleophyllic groups (e.g., primary amines) on pore wall during the synthesis of a 2D-COF (COF-5) is possible by sequential substitution of original monomers. Subsequent bonding of the antitumor drug camptothecin results in a stable hydrophobic drug delivery system. Water adsorption isotherms modelling indicates that the insertion of CPT ligand in the framework promotes a hydrophobic effect that protects a region of COF chain from boronate ester hydrolysis and resulting degradation, which is also proven by stability testing in physiological conditions. Furthermore, this hydrophobic nature favors cell internalization kinetics by promoting interactions with the lipophilic cell membrane. To the best of our knowledge, this is the first case of a stable drug delivery system based on covalently conjugated COFs.

Datos de la publicación

ISSN/ISSNe:
0928-4931, 1873-0191

Materials Science & Engineering C-Materials for Biological Applications  Elsevier BV

Tipo:
Article
Páginas:
-
PubMed:
32919629

Citas Recibidas en Web of Science: 18

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Keywords

  • Covalent organic framework; Sequential functionalization; Framework stability; Water adsorption isotherms; Drug delivery systems; Camptothecin

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