Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

Anita Mahapatra; Sannah P. N. Mativandlela; B. Binneman; P. B. Fourie; Chris J. Hamilton; J. J. M. Meyer; F. van der Kooy; Peter Houghton; Namrita Lall

doi:10.1016/j.bmc.2007.08.064

Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

Anita Mahapatra, Sannah P. N. Mativandlela, B. Binneman, P. B. Fourie, Chris J. Hamilton, J. J. M. Meyer, F. van der Kooy, Peter Houghton, Namrita Lall

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Abstract

The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plant-derived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e. g. other disulfide reductases). (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7638-7646
Number of pages	9
Journal	Bioorganic & Medicinal Chemistry
Volume	15
Issue number	24
DOIs	https://doi.org/10.1016/j.bmc.2007.08.064
Publication status	Published - 15 Dec 2007

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Cite this

Mahapatra, A., Mativandlela, S. P. N., Binneman, B., Fourie, P. B., Hamilton, C. J., Meyer, J. J. M., van der Kooy, F., Houghton, P., & Lall, N. (2007). Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase. Bioorganic & Medicinal Chemistry, 15(24), 7638-7646. https://doi.org/10.1016/j.bmc.2007.08.064

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title = "Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase",

abstract = "The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plant-derived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e. g. other disulfide reductases). (c) 2007 Elsevier Ltd. All rights reserved.",

author = "Anita Mahapatra and Mativandlela, {Sannah P. N.} and B. Binneman and Fourie, {P. B.} and Hamilton, {Chris J.} and Meyer, {J. J. M.} and {van der Kooy}, F. and Peter Houghton and Namrita Lall",

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Mahapatra, A, Mativandlela, SPN, Binneman, B, Fourie, PB, Hamilton, CJ, Meyer, JJM, van der Kooy, F, Houghton, P & Lall, N 2007, 'Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase', Bioorganic & Medicinal Chemistry, vol. 15, no. 24, pp. 7638-7646. https://doi.org/10.1016/j.bmc.2007.08.064

TY - JOUR

T1 - Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

AU - Mahapatra, Anita

AU - Mativandlela, Sannah P. N.

AU - Binneman, B.

AU - Fourie, P. B.

AU - Hamilton, Chris J.

AU - Meyer, J. J. M.

AU - van der Kooy, F.

AU - Houghton, Peter

AU - Lall, Namrita

PY - 2007/12/15

Y1 - 2007/12/15

N2 - The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plant-derived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e. g. other disulfide reductases). (c) 2007 Elsevier Ltd. All rights reserved.

AB - The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plant-derived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e. g. other disulfide reductases). (c) 2007 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.bmc.2007.08.064

DO - 10.1016/j.bmc.2007.08.064

M3 - Article

VL - 15

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EP - 7646

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

SN - 0968-0896

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