N-Acyl derivatives of glucosamine as acceptor substrates for galactosyltransferase from bone and cartilage cells.
Glucosamine is commonly used as a nutraceutical by arthritis patients. However, its mode of action is still unknown, and there is controversy about its clinical efficacy. Synthetic N-acyl glucosamines (acyl group>2 carbons) comprise a new class of drugs. We examined these derivatives for their effect in bone and cartilage cells, and for their ability to serve as acceptor substrates for galactosyltransferase. With the exception of N-benzoylglucosamine, compounds of the series were good substrates for galactosyltransferases from bone and cartilage cells, and for purified enzyme from bovine milk. When N-butyrylglucosamine (GlcNBu) was added to the cell medium of primary bovine chondrocytes and human osteoblasts, small amounts were found to enter the cells and a radiolabeled metabolite appeared in the medium. However, GlcNBu did not appear to be incorporated directly into oligosaccharides. GlcNBu at 1 and 5mM concentrations in the glucose-free cell medium of primary human osteoblasts from osteoarthritis patients did not significantly alter cell proliferation or cell differentiation.
Department of Medicine, The Arthritis Centre, Queen's University, Kingston General Hospital, Kingston, Ontario, Canada K7L 2V7. brockhau@post.queensu.ca
Inka
I
Brockhausen
John
J
Carran
Kevin
K
McEleney
Michael
M
Lehotay
Xiaojing
X
Yang
Liyuan
L
Yin
Tassos
T
Anastassiades
D000818:Animals; D002417:Cattle; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D019902:Chondrocytes / Q000187:drug effects / Q000201:enzymology*; D002851:Chromatography, High Pressure Liquid; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000378:metabolism* / Q000494:pharmacology; D006801:Humans; D008892:Milk / Q000201:enzymology; D009237:N-Acetyllactosamine Synthase / Q000378:metabolism*; D010006:Osteoblasts / Q000201:enzymology*; D012516:Osteosarcoma / Q000201:enzymology
C502362:N-butyrylglucosamine; D009237:N-Acetyllactosamine Synthase; D005944:Glucosamine