The Abyssomicin C family as in vitro inhibitors of Mycobacterium tuberculosis

Joel S. Freundlich; Mallikarjun Lalgondar; Jun Rong Wei; Stephanie Swanson; Erik J. Sorensen; Eric J. Rubin; James C. Sacchettini

doi:10.1016/j.tube.2010.08.002

The Abyssomicin C family as in vitro inhibitors of Mycobacterium tuberculosis

Joel S. Freundlich, Mallikarjun Lalgondar, Jun Rong Wei, Stephanie Swanson, Erik J. Sorensen, Eric J. Rubin, James C. Sacchettini

Chemistry

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

35 Scopus citations

Abstract

The antimycobacterial efficacy of the abyssomicin C family of natural products, in addition to a key synthetic intermediate, has been investigated given their reported inhibition of Bacillus subtilis p-aminobenzoate biosynthesis. The naturally occurring (-)-abyssomicin C and its atropisomer were found to exhibit low micromolar growth inhibition against the relatively fast-growing and non-virulent Mycobacterium smegmatis and the vaccine strain Mycobacterium bovis BCG, while their antipodes were slightly less active. (-)-Abyssomicin C and its atropisomer were particularly efficacious against Mycobacterium tuberculosis H37Rv, exhibiting MIC values of 3.6 and 7.2 μM, respectively. More specifically, (-)-abyssomicin C was bactericidal. This complex natural product and its analogs, thus, hold promise as chemical tools in the study of M. tuberculosis metabolism.

Original language	English (US)
Pages (from-to)	298-300
Number of pages	3
Journal	Tuberculosis
Volume	90
Issue number	5
DOIs	https://doi.org/10.1016/j.tube.2010.08.002
State	Published - Sep 2010

All Science Journal Classification (ASJC) codes

Microbiology
Immunology
Microbiology (medical)
Infectious Diseases

Keywords

Abyssomicin
Mycobacterium tuberculosis
p-Aminobenzoate metabolism

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title = "The Abyssomicin C family as in vitro inhibitors of Mycobacterium tuberculosis",

abstract = "The antimycobacterial efficacy of the abyssomicin C family of natural products, in addition to a key synthetic intermediate, has been investigated given their reported inhibition of Bacillus subtilis p-aminobenzoate biosynthesis. The naturally occurring (-)-abyssomicin C and its atropisomer were found to exhibit low micromolar growth inhibition against the relatively fast-growing and non-virulent Mycobacterium smegmatis and the vaccine strain Mycobacterium bovis BCG, while their antipodes were slightly less active. (-)-Abyssomicin C and its atropisomer were particularly efficacious against Mycobacterium tuberculosis H37Rv, exhibiting MIC values of 3.6 and 7.2 μM, respectively. More specifically, (-)-abyssomicin C was bactericidal. This complex natural product and its analogs, thus, hold promise as chemical tools in the study of M. tuberculosis metabolism.",

keywords = "Abyssomicin, Mycobacterium tuberculosis, p-Aminobenzoate metabolism",

author = "Freundlich, {Joel S.} and Mallikarjun Lalgondar and Wei, {Jun Rong} and Stephanie Swanson and Sorensen, {Erik J.} and Rubin, {Eric J.} and Sacchettini, {James C.}",

note = "Funding Information: This work was supported by the Bill and Melinda Gates Foundation (grant 42844 ). J.C.S. acknowledges the Robert A. Welch Foundation (grant A-0015 ). ",

year = "2010",

month = sep,

doi = "10.1016/j.tube.2010.08.002",

language = "English (US)",

volume = "90",

pages = "298--300",

journal = "Tuberculosis",

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AU - Freundlich, Joel S.

AU - Lalgondar, Mallikarjun

AU - Wei, Jun Rong

AU - Swanson, Stephanie

AU - Sorensen, Erik J.

AU - Rubin, Eric J.

AU - Sacchettini, James C.

N1 - Funding Information: This work was supported by the Bill and Melinda Gates Foundation (grant 42844 ). J.C.S. acknowledges the Robert A. Welch Foundation (grant A-0015 ).

PY - 2010/9

Y1 - 2010/9

N2 - The antimycobacterial efficacy of the abyssomicin C family of natural products, in addition to a key synthetic intermediate, has been investigated given their reported inhibition of Bacillus subtilis p-aminobenzoate biosynthesis. The naturally occurring (-)-abyssomicin C and its atropisomer were found to exhibit low micromolar growth inhibition against the relatively fast-growing and non-virulent Mycobacterium smegmatis and the vaccine strain Mycobacterium bovis BCG, while their antipodes were slightly less active. (-)-Abyssomicin C and its atropisomer were particularly efficacious against Mycobacterium tuberculosis H37Rv, exhibiting MIC values of 3.6 and 7.2 μM, respectively. More specifically, (-)-abyssomicin C was bactericidal. This complex natural product and its analogs, thus, hold promise as chemical tools in the study of M. tuberculosis metabolism.

AB - The antimycobacterial efficacy of the abyssomicin C family of natural products, in addition to a key synthetic intermediate, has been investigated given their reported inhibition of Bacillus subtilis p-aminobenzoate biosynthesis. The naturally occurring (-)-abyssomicin C and its atropisomer were found to exhibit low micromolar growth inhibition against the relatively fast-growing and non-virulent Mycobacterium smegmatis and the vaccine strain Mycobacterium bovis BCG, while their antipodes were slightly less active. (-)-Abyssomicin C and its atropisomer were particularly efficacious against Mycobacterium tuberculosis H37Rv, exhibiting MIC values of 3.6 and 7.2 μM, respectively. More specifically, (-)-abyssomicin C was bactericidal. This complex natural product and its analogs, thus, hold promise as chemical tools in the study of M. tuberculosis metabolism.

KW - Abyssomicin

KW - Mycobacterium tuberculosis

KW - p-Aminobenzoate metabolism

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