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).

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

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

@article{8a4d1b06b36a4bf688f1da75da98cbcd,

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).",

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 Kooy, {F. van der} and Peter Houghton and Namrita Lall",

year = "2007",

doi = "10.1016/j.bmc.2007.08.064",

language = "English",

volume = "15",

pages = "7638--7646",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Pergamon",

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}

Mahapatra, A, Mativandlela, SPN, Binneman, B, Fourie, PB, Hamilton, CJ, Meyer, JJM, Kooy, FVD, Houghton, P & Lall, N 2007, 'Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase', Bioorganic and 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 - Kooy, F. van der

AU - Houghton, Peter

AU - Lall, Namrita

PY - 2007

Y1 - 2007

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).

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).

UR - http://handle.uws.edu.au:8081/1959.7/528777

U2 - 10.1016/j.bmc.2007.08.064

DO - 10.1016/j.bmc.2007.08.064

M3 - Article

SN - 0968-0896

VL - 15

SP - 7638

EP - 7646

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 24

ER -

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

Abstract

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