Dual structure-activity relationship of osteoclastogenesis inhibitor methyl gerfelin based on teg scanning

Naoki Kanoh; Takahiro Suzuki; Makoto Kawatani; Yasuhiro Katou; Hiroyuki Osada; Yoshiharu Iwabuchi

doi:10.1021/bc3003666

Dual structure-activity relationship of osteoclastogenesis inhibitor methyl gerfelin based on teg scanning

Naoki Kanoh, Takahiro Suzuki, Makoto Kawatani, Yasuhiro Katou, Hiroyuki Osada, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

8 Citations (Scopus)

Abstract

Methyl gerfelin derivatives, each having an amine-terminated tri(ethylene glycol) linker at the peripheral position, were designed and systematically synthesized. These "TEGylated" derivatives were then subjected to a structure-activity relationship (SAR) study to examine their glyoxalase 1-inhibition activity and binding affinity toward the three binding proteins identified. Among the derivatives synthesized, that with a NH₂-TEG linker at the C6-methyl group showed the most potent glyoxalase 1-inhibiting activity and glyoxalase 1 selectivity. These results indicated that derivatization at the C6-methyl group would be suitable for the further development of selective glyoxalase 1 inhibitors.

Original language	English
Pages (from-to)	44-52
Number of pages	9
Journal	Bioconjugate chemistry
Volume	24
Issue number	1
DOIs	https://doi.org/10.1021/bc3003666
Publication status	Published - 2013 Jan 16

ASJC Scopus subject areas

Biotechnology
Bioengineering
Biomedical Engineering
Pharmacology
Pharmaceutical Science
Organic Chemistry

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T1 - Dual structure-activity relationship of osteoclastogenesis inhibitor methyl gerfelin based on teg scanning

AU - Kanoh, Naoki

AU - Suzuki, Takahiro

AU - Kawatani, Makoto

AU - Katou, Yasuhiro

AU - Osada, Hiroyuki

AU - Iwabuchi, Yoshiharu

PY - 2013/1/16

Y1 - 2013/1/16

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AB - Methyl gerfelin derivatives, each having an amine-terminated tri(ethylene glycol) linker at the peripheral position, were designed and systematically synthesized. These "TEGylated" derivatives were then subjected to a structure-activity relationship (SAR) study to examine their glyoxalase 1-inhibition activity and binding affinity toward the three binding proteins identified. Among the derivatives synthesized, that with a NH2-TEG linker at the C6-methyl group showed the most potent glyoxalase 1-inhibiting activity and glyoxalase 1 selectivity. These results indicated that derivatization at the C6-methyl group would be suitable for the further development of selective glyoxalase 1 inhibitors.

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Dual structure-activity relationship of osteoclastogenesis inhibitor methyl gerfelin based on teg scanning

Abstract

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