Homologous Copolymerization Route to Functional and Biocompatible Polyvinylpyrrolidone

Abstract

Linear multifunctional polyvinylpyrrolidone (PVP) chains bearing carboxylate (COO−) or/and sulfonate (SO3−) groups are prepared by standard radical copolymerization of homologous vinylpyrrolidone (VP) and the VP derivatives 3‐carboxyvinylpyrrolidone (VPC) and 3‐sulfoalkylvinylpyrrolidone (VPS). Functional PVP networks with homogeneous crosslinking density are also prepared using a new homologous water‐compatible VP‐R‐VP crosslinker. This homologous approach for the preparation of functionalized PVP systems is compared theoretically with the preparation of VP with commercial acrylic comonomers bearing similar functionalities. All the linear chains and networks are tested under basic in vitro cell cultures.

Synthesis and self-assembly of thermosensitive double-hydrophilic poly(N-vinylcaprolactam)-b-poly(N-vinyl-2-pyrrolidone) diblock copolymers

“…This makes PVCL highly useful for biomedical applications such as drug delivery and in vivo release systems . The hydrophilic homologue of PVCL, poly( N ‐vinyl‐2‐pyrrolidone) (PVPON) is a water soluble polymer with its monomer unit structure similar to PVCL and is broadly used in biomedical field because of its hydrophilicity and biocompatibility …”

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

“…Besides classical alkylation reactions, Reinecke et al performed ring-opening reactions to insert functional groups and aromatic side chains [20–21]. Furthermore, they investigated the formation of homogeneous [22] and amphiphilic [23] N -VP networks. However, in contrast to the restricted monoalkylation of N -vinylcaprolactam [24], the five-membered ring of N -VP can be double alkylated in α-position.…”

“…In this connection, 1-bromo-2-(2-bromoethoxy)ethane was used as alkylation reagent to allow the preparation of a spiro-type monomer [25] due to intramolecular reaction. Until now, dibromo compounds were mainly used to synthesize symmetric cross linker [22,26–27]. To the best of our knowledge, the synthesis of modified paraffin-like oligomers via double alkylation of N -VP with aliphatic dibromides was not yet described in literature.…”

Macromolecular Prodrugs for Controlled Delivery of Ribavirin

“…This aspect minimizes opportunities in copolymerization with, for example, activated ester monomer units for bioconjugation through polymer analogous reaction . Production of ‘NVP‐alike’ monomers, i.e., derivatives of lactam structure, is a viable strategy which ensures compatibility of the monomers towards copolymerization with NVP; nonetheless this approach is yet to be implemented in the design of MPs. Successful examples of bioconjugation with PVP include the control of polymer terminal groups via the choice of chain transfer reagents and subsequent conjugation of chain termini with proteins .…”