Synthesis of mono-glucose-branched cyclodextrins with a high inclusion ability for doxorubicin and their efficient glycosylation using Mucor hiemalis endo-beta-N-acetylglucosaminidase.
The mono-glucose-branched cyclodextrins having an appropriate spacer between the beta-cyclodextrin and a glucose moiety were synthesized from beta-cyclodextrin and arbutin. They had the significantly high association constants for doxorubicin, the anticancer agent, in the range of 10(5)-10(6)M(-1), and worked as highly reactive glycosyl acceptors for the transglycosylation reaction by endo-beta-N-acetylglucosaminidase of Mucor hiemalis to produce sialo-complex type oligosaccharide-branched cyclodextrins in the high yields of 65-67%.
Yamanoi
Takashi
T
The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan. tyama@noguchi.or.jp
Yoshida
Naomichi
N
Oda
Yoshiki
Y
Akaike
Eri
E
Tsutsumida
Maki
M
Kobayashi
Natsumi
N
Osumi
Kenji
K
Yamamoto
Kenji
K
Fujita
Kiyotaka
K
Takahashi
Keiko
K
Hattori
Kenjiro
K
D000118:Acetylglucosaminidase / Q000378:metabolism*; D000970:Antineoplastic Agents / Q000008:administration & dosage; D001665:Binding Sites; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D004317:Doxorubicin / Q000737:chemistry*; D004337:Drug Carriers / Q000138:chemical synthesis*; D016503:Drug Delivery Systems; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D008958:Models, Molecular; D009089:Mucor / Q000201:enzymology*; D009844:Oligosaccharides / Q000737:chemistry
D000970:Antineoplastic Agents; D003505:Cyclodextrins; D004337:Drug Carriers; D009844:Oligosaccharides; D004317:Doxorubicin; D000118:Acetylglucosaminidase; D005947:Glucose