Macrocyclic proteoglycan mimics. Potent inhibition of cell adhesion by a bundle of chondroitin sulfate chains assembled on the calix[4]resorcarene platform.
Tailed calix[4]resorcarene macrocycle (tail=undecyl) can be used as a platform to assemble four glycosaminoglycan polysaccharide chains to give a new type of proteoglycan mimics. A tetra(chondroitin sulfate) derivative thus obtained from the reaction of macrocyclic octaamine and chondroitin sulfate lactone is readily immobilized on a tissue culture plastic (polystyrene) plate and inhibits fibronectin-mediated adhesion of BHK (baby hamster kidney) cells thereon remarkably strongly with 50% inhibition occurring at a 10 ng/mL or 40 pM concentration range.
Tomita
Naotoshi
N
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Sando
Shinsuke
S
Sera
Takashi
T
Aoyama
Yasuhiro
Y
D000818:Animals; D047250:Calixarenes / Q000737:chemistry*; D002448:Cell Adhesion / Q000187:drug effects*; D002460:Cell Line; D002809:Chondroitin Sulfates / Q000737:chemistry / Q000494:pharmacology*; D006224:Cricetinae; D047028:Macrocyclic Compounds / Q000737:chemistry*; D018716:Molecular Mimicry; D011509:Proteoglycans / Q000737:chemistry / Q000494:pharmacology*
D047028:Macrocyclic Compounds; D011509:Proteoglycans; C494074:calix(4)resorcarene; D047250:Calixarenes; D002809:Chondroitin Sulfates