Guanidinylated chitosan inspired by arginine-rich cell-penetrating peptides

Hironori Izawa; Mizuki Kinai; Shinsuke Ifuku; Minoru Morimoto; Hiroyuki Saimoto

doi:10.1016/j.ijbiomac.2018.12.138

Guanidinylated chitosan inspired by arginine-rich cell-penetrating peptides

Int J Biol Macromol. 2019 Mar 15:125:901-905. doi: 10.1016/j.ijbiomac.2018.12.138. Epub 2018 Dec 17.

Authors

Hironori Izawa¹, Mizuki Kinai², Shinsuke Ifuku³, Minoru Morimoto⁴, Hiroyuki Saimoto⁵

Affiliations

¹ Graduate School of Engineering, Tottori University, 4-101 Koyama-Minami, Tottori 680-8550, Japan; Center for Research on Green Sustainable Chemistry, Tottori University, Tottori 680-8550, Japan. Electronic address: h-izawa@tottori-u.ac.jp.
² Graduate School of Engineering, Tottori University, 4-101 Koyama-Minami, Tottori 680-8550, Japan.
³ Graduate School of Engineering, Tottori University, 4-101 Koyama-Minami, Tottori 680-8550, Japan; Center for Research on Green Sustainable Chemistry, Tottori University, Tottori 680-8550, Japan.
⁴ Division of Instrumental Analysis, Research Center for Bioscience and Technology, Tottori University, Tottori 680-8550, Japan.
⁵ Graduate School of Engineering, Tottori University, 4-101 Koyama-Minami, Tottori 680-8550, Japan; Center for Research on Green Sustainable Chemistry, Tottori University, Tottori 680-8550, Japan. Electronic address: saimoto@chem.tottori-u.ac.jp.

PMID: 30572038
DOI: 10.1016/j.ijbiomac.2018.12.138

Abstract

We introduce a simple method for producing guanidinylation of chitosan (CS) with 1‑amidinopyrazole hydrochloride (AP). Production of GCS is proved via NMR, IR, and elemental analyses. In a reaction using 4.5 eq of AP for 7 days at room temperature, we obtained GCS with 42.3% of degree of guanidinylation (DG). The DG value can be controlled by the reaction time and AP amount. Furthermore, remarkable enhancement of the interaction between GCS and bovine serum albumin by guanidinylation was observed. This simple guanidinylation method for CS could provide novel additives for protein/peptide delivery systems.

Keywords: 1‑Amidinopyrazole hydrochloride; Bovine serum albumin; Chitosan; Guanidinylation; Protein delivery system.

MeSH terms

Arginine / chemistry*
Cell-Penetrating Peptides / chemistry*
Chitosan / chemistry*
Drug Carriers / chemistry
Drug Delivery Systems / methods
Guanidine / chemistry*
Serum Albumin, Bovine / chemistry

Substances

Cell-Penetrating Peptides
Drug Carriers
Serum Albumin, Bovine
Chitosan
Arginine
Guanidine