3-(Phenethylamino)demethyl(oxy)aaptamine as an anti-dormant mycobacterial substance: Isolation, evaluation and total synthesis

Yuji Sumii; Naoyuki Kotoku; Chisu Han; Kentaro Kamiya; Andi Setiawan; Catherine Vilchèze; William R. Jacobs; Masayoshi Arai

doi:10.1016/j.tetlet.2020.151924

3-(Phenethylamino)demethyl(oxy)aaptamine as an anti-dormant mycobacterial substance: Isolation, evaluation and total synthesis

Yuji Sumii, Naoyuki Kotoku, Chisu Han, Kentaro Kamiya, Andi Setiawan, Catherine Vilchèze, William R. Jacobs, Masayoshi Arai

Microbiology & Immunology

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

9 Scopus citations

Abstract

3-(Phenethylamino)demethyl(oxy)aaptamine (1) was re-discovered from the marine sponge of Aaptos sp. as an anti-dormant mycobacterial substance through the bioassay-guided separation. Compound 1 showed potent anti-microbial activity against Mycobacterium bovis BCG with a minimum inhibitory concentration of 0.75 µg/mL under both aerobic conditions and hypoxic conditions inducing dormant state. Compound 1 was also effective against pathogenic M. tuberculosis strains including clinical multidrug-resistant strains. Furthermore, the successful total syntheses of 1 and its analog 3-aminodemethyl(oxy)aaptamine (2) afford sufficient quantities for further biological studies.

Original language	English (US)
Article number	151924
Journal	Tetrahedron Letters
Volume	61
Issue number	22
DOIs	https://doi.org/10.1016/j.tetlet.2020.151924
State	Published - May 28 2020

Keywords

Aaptamine derivative
Antimicrobial
Dormant
Tuberculosis
ZIWLGKRCCRFXQK-UHFFFAOYSA-N

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2020.151924

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title = "3-(Phenethylamino)demethyl(oxy)aaptamine as an anti-dormant mycobacterial substance: Isolation, evaluation and total synthesis",

abstract = "3-(Phenethylamino)demethyl(oxy)aaptamine (1) was re-discovered from the marine sponge of Aaptos sp. as an anti-dormant mycobacterial substance through the bioassay-guided separation. Compound 1 showed potent anti-microbial activity against Mycobacterium bovis BCG with a minimum inhibitory concentration of 0.75 µg/mL under both aerobic conditions and hypoxic conditions inducing dormant state. Compound 1 was also effective against pathogenic M. tuberculosis strains including clinical multidrug-resistant strains. Furthermore, the successful total syntheses of 1 and its analog 3-aminodemethyl(oxy)aaptamine (2) afford sufficient quantities for further biological studies.",

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author = "Yuji Sumii and Naoyuki Kotoku and Chisu Han and Kentaro Kamiya and Andi Setiawan and Catherine Vilch{\`e}ze and Jacobs, {William R.} and Masayoshi Arai",

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language = "English (US)",

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T1 - 3-(Phenethylamino)demethyl(oxy)aaptamine as an anti-dormant mycobacterial substance

T2 - Isolation, evaluation and total synthesis

AU - Sumii, Yuji

AU - Kotoku, Naoyuki

AU - Han, Chisu

AU - Kamiya, Kentaro

AU - Setiawan, Andi

AU - Vilchèze, Catherine

AU - Jacobs, William R.

AU - Arai, Masayoshi

PY - 2020/5/28

Y1 - 2020/5/28

N2 - 3-(Phenethylamino)demethyl(oxy)aaptamine (1) was re-discovered from the marine sponge of Aaptos sp. as an anti-dormant mycobacterial substance through the bioassay-guided separation. Compound 1 showed potent anti-microbial activity against Mycobacterium bovis BCG with a minimum inhibitory concentration of 0.75 µg/mL under both aerobic conditions and hypoxic conditions inducing dormant state. Compound 1 was also effective against pathogenic M. tuberculosis strains including clinical multidrug-resistant strains. Furthermore, the successful total syntheses of 1 and its analog 3-aminodemethyl(oxy)aaptamine (2) afford sufficient quantities for further biological studies.

AB - 3-(Phenethylamino)demethyl(oxy)aaptamine (1) was re-discovered from the marine sponge of Aaptos sp. as an anti-dormant mycobacterial substance through the bioassay-guided separation. Compound 1 showed potent anti-microbial activity against Mycobacterium bovis BCG with a minimum inhibitory concentration of 0.75 µg/mL under both aerobic conditions and hypoxic conditions inducing dormant state. Compound 1 was also effective against pathogenic M. tuberculosis strains including clinical multidrug-resistant strains. Furthermore, the successful total syntheses of 1 and its analog 3-aminodemethyl(oxy)aaptamine (2) afford sufficient quantities for further biological studies.

KW - Aaptamine derivative

KW - Antimicrobial

KW - Dormant

KW - Tuberculosis

KW - ZIWLGKRCCRFXQK-UHFFFAOYSA-N

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DO - 10.1016/j.tetlet.2020.151924

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JF - Tetrahedron Letters

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ER -

3-(Phenethylamino)demethyl(oxy)aaptamine as an anti-dormant mycobacterial substance: Isolation, evaluation and total synthesis

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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