Macrocyclic proteoglycan mimics. Potent inhibition of cell adhesion by a bundle of chondroitin sulfate chains assembled on the calix[4]resorcarene platform

Naotoshi Tomita; Shinsuke Sando; Takashi Sera; Yasuhiro Aoyama

doi:10.1016/j.bmcl.2004.02.041

Macrocyclic proteoglycan mimics. Potent inhibition of cell adhesion by a bundle of chondroitin sulfate chains assembled on the calix[4]resorcarene platform

Naotoshi Tomita, Shinsuke Sando, Takashi Sera, Yasuhiro Aoyama

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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 10ng/mL or 40pM concentration range.

Original language	English
Pages (from-to)	2087-2090
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2004.02.041
Publication status	Published - May 3 2004
Externally published	Yes

Keywords

Calix[4]resorcarene
Chondroitin sulfate
Fibronectin
Inhibition of cell adhesion
Proteoglycan mimic

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2004.02.041

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Macrocyclic proteoglycan mimics. Potent inhibition of cell adhesion by a bundle of chondroitin sulfate chains assembled on the calix[4]resorcarene platform. / Tomita, Naotoshi; Sando, Shinsuke; Sera, Takashi et al.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 14, No. 9, 03.05.2004, p. 2087-2090.

Research output: Contribution to journal › Article › peer-review

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abstract = "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 10ng/mL or 40pM concentration range.",

keywords = "Calix[4]resorcarene, Chondroitin sulfate, Fibronectin, Inhibition of cell adhesion, Proteoglycan mimic",

author = "Naotoshi Tomita and Shinsuke Sando and Takashi Sera and Yasuhiro Aoyama",

note = "Funding Information: This work was supported by RFTF of Japan Society for the Promotion of Science (JSPS) and by Grant-in-Aids for Scientific Research (No. 13490021) and for 21st COE on Kyoto University Alliance for Chemistry from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

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AU - Sando, Shinsuke

AU - Sera, Takashi

AU - Aoyama, Yasuhiro

N1 - Funding Information: This work was supported by RFTF of Japan Society for the Promotion of Science (JSPS) and by Grant-in-Aids for Scientific Research (No. 13490021) and for 21st COE on Kyoto University Alliance for Chemistry from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

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AB - 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 10ng/mL or 40pM concentration range.

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KW - Chondroitin sulfate

KW - Fibronectin

KW - Inhibition of cell adhesion

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Macrocyclic proteoglycan mimics. Potent inhibition of cell adhesion by a bundle of chondroitin sulfate chains assembled on the calix[4]resorcarene platform

Abstract

Keywords

ASJC Scopus subject areas

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