Polyrotaxane composed of poly-L-lactide and alpha-cyclodextrin exhibiting protease-triggered hydrolysis.
Biodegradable polyrotaxanes (PRXs) were synthesized from bis-amino-terminated poly(L-lactide) (PLLA) and alpha-cyclodextrin (alpha-CD), combined with capping by bulky end groups at the amino-termini of PLLA through enzymatically cleavable peptide linkages. The crystalline structure of the PRXs in the solid state was investigated by wide-angle X-ray diffraction (WAXRD), and the results suggested that PRX forms a column-type crystalline structure. Hydrolysis of ester bonds of the PLLA in PRX was prevented due to the supramolecular structure. However, in the presence of a protease (papain), the hydrolysis of PLLA in PRX was induced. The removal of the bulky end groups by the protease acted as a trigger for the release of alpha-CD and allowed hydrolysis of the PLLA ester bonds. Such unique hydrolysis behavior, that is, proteinase-triggered degradation of a polyester, was achieved by the combination of the supramolecular architecture, biodegradable PLLA, and enzymatically cleavable end groups.
Ohya
Yuichi
Y
Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, and High Technology Research Center, Kansai University, Suita, Osaka 564-8680, Japan. yohya@ipcku.kansai-u.ac.jp
Takamido
Seigo
S
Nagahama
Koji
K
Ouchi
Tatsuro
T
Katoono
Ryo
R
Yui
Nobuhiko
N
D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D003505:Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D006868:Hydrolysis; D010206:Papain / Q000494:pharmacology*; D020442:Poloxamer / Q000138:chemical synthesis / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry*; D043862:Rotaxanes / Q000138:chemical synthesis / Q000737:chemistry*; D014961:X-Ray Diffraction; D047391:alpha-Cyclodextrins / Q000737:chemistry* / Q000378:metabolism
D001672:Biocompatible Materials; D003505:Cyclodextrins; D004952:Esters; D011091:Polyesters; D043862:Rotaxanes; D047391:alpha-Cyclodextrins; C475673:polyrotaxane; D020442:Poloxamer; C033616:poly(lactide); D010206:Papain