Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts

Hikaru Kato; Aika Kai; Tetsuro Kawabata; James D. Sunderhaus; Timothy J. McAfoos; Jennifer M. Finefield; Yukihiko Sugimoto; Robert M. Williams; Sachiko Tsukamoto

doi:10.1016/j.bmcl.2017.10.017

Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts

Hikaru Kato, Aika Kai, Tetsuro Kawabata, James D. Sunderhaus, Timothy J. McAfoos, Jennifer M. Finefield, Yukihiko Sugimoto, Robert M. Williams, Sachiko Tsukamoto

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

11 Scopus citations

Abstract

The marine-derived Aspergillus protuberus MF297-2 and the terrestrial A. amoenus NRRL 35600 produce enantiomeric prenylated indole alkaloids. Investigation of biological activities of the natural and synthetic derivatives revealed that (−)-enantiomers of notoamides A and B, 6-epi-notoamide T, and stephacidin A inhibited receptor activator of nuclear factor-κB (NF-κB) ligand (RANKL)–induced osteoclastogenic differentiation of murine RAW264 cells more strongly than their respective (+)-enantiomers. Among them, (−)-6-epi-notoamide T was the most potent inhibitor with an IC₅₀ value of 1.7 μM.

Original language	English (US)
Pages (from-to)	4975-4978
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	27
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2017.10.017
State	Published - Nov 15 2017
Externally published	Yes

Keywords

Aspergillus
Enantiomer
Fungus
Notoamide
Osteoclastogenesis

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.2017.10.017

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Kato, H., Kai, A., Kawabata, T., Sunderhaus, J. D., McAfoos, T. J., Finefield, J. M., Sugimoto, Y., Williams, R. M., & Tsukamoto, S. (2017). Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts. Bioorganic and Medicinal Chemistry Letters, 27(22), 4975-4978. https://doi.org/10.1016/j.bmcl.2017.10.017

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title = "Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts",

abstract = "The marine-derived Aspergillus protuberus MF297-2 and the terrestrial A. amoenus NRRL 35600 produce enantiomeric prenylated indole alkaloids. Investigation of biological activities of the natural and synthetic derivatives revealed that (−)-enantiomers of notoamides A and B, 6-epi-notoamide T, and stephacidin A inhibited receptor activator of nuclear factor-κB (NF-κB) ligand (RANKL)–induced osteoclastogenic differentiation of murine RAW264 cells more strongly than their respective (+)-enantiomers. Among them, (−)-6-epi-notoamide T was the most potent inhibitor with an IC50 value of 1.7 μM.",

keywords = "Aspergillus, Enantiomer, Fungus, Notoamide, Osteoclastogenesis",

author = "Hikaru Kato and Aika Kai and Tetsuro Kawabata and Sunderhaus, {James D.} and McAfoos, {Timothy J.} and Finefield, {Jennifer M.} and Yukihiko Sugimoto and Williams, {Robert M.} and Sachiko Tsukamoto",

note = "Funding Information: This work was financially supported in part by Grants-in-Aid for Scientific Research (No. 17H0399400 to ST) from the Ministry of Education, Culture, Sports, Science and Technology of Japan . Financial support from the National Institutes of Health of United States (Grant CA 070375 to RMW) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

month = nov,

day = "15",

doi = "10.1016/j.bmcl.2017.10.017",

language = "English (US)",

volume = "27",

pages = "4975--4978",

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T1 - Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts

AU - Kato, Hikaru

AU - Kai, Aika

AU - Kawabata, Tetsuro

AU - Sunderhaus, James D.

AU - McAfoos, Timothy J.

AU - Finefield, Jennifer M.

AU - Sugimoto, Yukihiko

AU - Williams, Robert M.

AU - Tsukamoto, Sachiko

N1 - Funding Information: This work was financially supported in part by Grants-in-Aid for Scientific Research (No. 17H0399400 to ST) from the Ministry of Education, Culture, Sports, Science and Technology of Japan . Financial support from the National Institutes of Health of United States (Grant CA 070375 to RMW) is gratefully acknowledged. Publisher Copyright: © 2017 Elsevier Ltd

PY - 2017/11/15

Y1 - 2017/11/15

N2 - The marine-derived Aspergillus protuberus MF297-2 and the terrestrial A. amoenus NRRL 35600 produce enantiomeric prenylated indole alkaloids. Investigation of biological activities of the natural and synthetic derivatives revealed that (−)-enantiomers of notoamides A and B, 6-epi-notoamide T, and stephacidin A inhibited receptor activator of nuclear factor-κB (NF-κB) ligand (RANKL)–induced osteoclastogenic differentiation of murine RAW264 cells more strongly than their respective (+)-enantiomers. Among them, (−)-6-epi-notoamide T was the most potent inhibitor with an IC50 value of 1.7 μM.

AB - The marine-derived Aspergillus protuberus MF297-2 and the terrestrial A. amoenus NRRL 35600 produce enantiomeric prenylated indole alkaloids. Investigation of biological activities of the natural and synthetic derivatives revealed that (−)-enantiomers of notoamides A and B, 6-epi-notoamide T, and stephacidin A inhibited receptor activator of nuclear factor-κB (NF-κB) ligand (RANKL)–induced osteoclastogenic differentiation of murine RAW264 cells more strongly than their respective (+)-enantiomers. Among them, (−)-6-epi-notoamide T was the most potent inhibitor with an IC50 value of 1.7 μM.

KW - Aspergillus

KW - Enantiomer

KW - Fungus

KW - Notoamide

KW - Osteoclastogenesis

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JO - Bioorganic and Medicinal Chemistry Letters

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ER -

Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts

Abstract

Keywords

ASJC Scopus subject areas

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