Characterization of 7-amino-4-methylcoumarin as an effective antitubercular agent: structure-activity relationships
Objectives The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in combination with isoniazid, rifampicin, streptomycin or ethambutol, and to decipher the mode of action of the most effective agent. Method...
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Published in | Journal of antimicrobial chemotherapy Vol. 66; no. 11; pp. 2543 - 2555 |
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Main Authors | , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Oxford University Press
01.11.2011
Oxford Publishing Limited (England) |
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Abstract | Objectives
The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in combination with isoniazid, rifampicin, streptomycin or ethambutol, and to decipher the mode of action of the most effective agent.
Methods
A series of amino and acyl amino coumarins were synthesized and screened for activity against the Mycobacterium tuberculosis H37Rv strain. These compounds were further evaluated by standard assay procedures to determine their MBCs, fractional inhibitory concentration index values and cytotoxicities. The MICs for a susceptible and a multidrug-resistant clinical isolate of M. tuberculosis were also determined. Electron and fluorescence microscopy of the test compound-treated mycobacterial samples were also carried out in an attempt to find out the target of action.
Results
7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) displayed the lowest MIC of 1 mg/L against not only H37Rv but also the susceptible as well as the multidrug-resistant clinical isolates. Certain acyl amino coumarins were also found to inhibit the aforementioned strains and isolates with MICs in the range of 1.0-3.5 mg/L. They were also found to act in synergy with isoniazid/rifampicin. Electron microscopy revealed the cell-wall-attacking characteristic of these compounds, while fluorescence microscopy indicated that mycolic acid might be the target of action.
Conclusions
The present study clearly demonstrated the in vitro antitubercular potential of the novel drug candidate NA5. Further studies are warranted to establish the in vivo efficacy and therapeutic potential of NA5. |
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AbstractList | OBJECTIVESThe objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in combination with isoniazid, rifampicin, streptomycin or ethambutol, and to decipher the mode of action of the most effective agent.METHODSA series of amino and acyl amino coumarins were synthesized and screened for activity against the Mycobacterium tuberculosis H37Rv strain. These compounds were further evaluated by standard assay procedures to determine their MBCs, fractional inhibitory concentration index values and cytotoxicities. The MICs for a susceptible and a multidrug-resistant clinical isolate of M. tuberculosis were also determined. Electron and fluorescence microscopy of the test compound-treated mycobacterial samples were also carried out in an attempt to find out the target of action.RESULTS7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) displayed the lowest MIC of 1 mg/L against not only H37Rv but also the susceptible as well as the multidrug-resistant clinical isolates. Certain acyl amino coumarins were also found to inhibit the aforementioned strains and isolates with MICs in the range of 1.0-3.5 mg/L. They were also found to act in synergy with isoniazid/rifampicin. Electron microscopy revealed the cell-wall-attacking characteristic of these compounds, while fluorescence microscopy indicated that mycolic acid might be the target of action.CONCLUSIONSThe present study clearly demonstrated the in vitro antitubercular potential of the novel drug candidate NA5. Further studies are warranted to establish the in vivo efficacy and therapeutic potential of NA5. Objectives The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in combination with isoniazid, rifampicin, streptomycin or ethambutol, and to decipher the mode of action of the most effective agent. Methods A series of amino and acyl amino coumarins were synthesized and screened for activity against the Mycobacterium tuberculosis H37Rv strain. These compounds were further evaluated by standard assay procedures to determine their MBCs, fractional inhibitory concentration index values and cytotoxicities. The MICs for a susceptible and a multidrug-resistant clinical isolate of M. tuberculosis were also determined. Electron and fluorescence microscopy of the test compound-treated mycobacterial samples were also carried out in an attempt to find out the target of action. Results 7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) displayed the lowest MIC of 1 mg/L against not only H37Rv but also the susceptible as well as the multidrug-resistant clinical isolates. Certain acyl amino coumarins were also found to inhibit the aforementioned strains and isolates with MICs in the range of 1.0-3.5 mg/L. They were also found to act in synergy with isoniazid/rifampicin. Electron microscopy revealed the cell-wall-attacking characteristic of these compounds, while fluorescence microscopy indicated that mycolic acid might be the target of action. Conclusions The present study clearly demonstrated the in vitro antitubercular potential of the novel drug candidate NA5. Further studies are warranted to establish the in vivo efficacy and therapeutic potential of NA5. The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in combination with isoniazid, rifampicin, streptomycin or ethambutol, and to decipher the mode of action of the most effective agent. A series of amino and acyl amino coumarins were synthesized and screened for activity against the Mycobacterium tuberculosis H37Rv strain. These compounds were further evaluated by standard assay procedures to determine their MBCs, fractional inhibitory concentration index values and cytotoxicities. The MICs for a susceptible and a multidrug-resistant clinical isolate of M. tuberculosis were also determined. Electron and fluorescence microscopy of the test compound-treated mycobacterial samples were also carried out in an attempt to find out the target of action. 7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) displayed the lowest MIC of 1 mg/L against not only H37Rv but also the susceptible as well as the multidrug-resistant clinical isolates. Certain acyl amino coumarins were also found to inhibit the aforementioned strains and isolates with MICs in the range of 1.0-3.5 mg/L. They were also found to act in synergy with isoniazid/rifampicin. Electron microscopy revealed the cell-wall-attacking characteristic of these compounds, while fluorescence microscopy indicated that mycolic acid might be the target of action. The present study clearly demonstrated the in vitro antitubercular potential of the novel drug candidate NA5. Further studies are warranted to establish the in vivo efficacy and therapeutic potential of NA5. The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in combination with isoniazid, rifampicin, streptomycin or ethambutol, and to decipher the mode of action of the most effective agent. A series of amino and acyl amino coumarins were synthesized and screened for activity against the Mycobacterium tuberculosis H37Rv strain. These compounds were further evaluated by standard assay procedures to determine their MBCs, fractional inhibitory concentration index values and cytotoxicities. The MICs for a susceptible and a multidrug-resistant clinical isolate of M. tuberculosis were also determined. Electron and fluorescence microscopy of the test compound-treated mycobacterial samples were also carried out in an attempt to find out the target of action. 7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) displayed the lowest MIC of 1 mg/L against not only H37Rv but also the susceptible as well as the multidrug-resistant clinical isolates. Certain acyl amino coumarins were also found to inhibit the aforementioned strains and isolates with MICs in the range of 1.0-3.5 mg/L. They were also found to act in synergy with isoniazid/rifampicin. Electron microscopy revealed the cell-wall-attacking characteristic of these compounds, while fluorescence microscopy indicated that mycolic acid might be the target of action. The present study clearly demonstrated the in vitro antitubercular potential of the novel drug candidate NA5. Further studies are warranted to establish the in vivo efficacy and therapeutic potential of NA5. Objectives The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in combination with isoniazid, rifampicin, streptomycin or ethambutol, and to decipher the mode of action of the most effective agent. Methods A series of amino and acyl amino coumarins were synthesized and screened for activity against the Mycobacterium tuberculosis H37Rv strain. These compounds were further evaluated by standard assay procedures to determine their MBCs, fractional inhibitory concentration index values and cytotoxicities. The MICs for a susceptible and a multidrug-resistant clinical isolate of M. tuberculosis were also determined. Electron and fluorescence microscopy of the test compound-treated mycobacterial samples were also carried out in an attempt to find out the target of action. Results 7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) displayed the lowest MIC of 1 mg/L against not only H37Rv but also the susceptible as well as the multidrug-resistant clinical isolates. Certain acyl amino coumarins were also found to inhibit the aforementioned strains and isolates with MICs in the range of 1.0-3.5 mg/L. They were also found to act in synergy with isoniazid/rifampicin. Electron microscopy revealed the cell-wall-attacking characteristic of these compounds, while fluorescence microscopy indicated that mycolic acid might be the target of action. Conclusions The present study clearly demonstrated the in vitro antitubercular potential of the novel drug candidate NA5. Further studies are warranted to establish the in vivo efficacy and therapeutic potential of NA5. |
Author | Raj, Hanumantharao G. Gupta, Garima Arya, Anu Aggarwal, Neha Parmar, Virinder S. Pathak, Rakesh Ponnan, Prija Bose, Mridula Tandon, Rashmi Prasad, Ashok K. Nath, Mahendra Baghel, Anil S. |
Author_xml | – sequence: 1 givenname: Rashmi surname: Tandon fullname: Tandon, Rashmi organization: 1 Department of Biochemistry, V. P. Chest Institute, University of Delhi, Delhi 110 007, India – sequence: 2 givenname: Prija surname: Ponnan fullname: Ponnan, Prija organization: 1 Department of Biochemistry, V. P. Chest Institute, University of Delhi, Delhi 110 007, India – sequence: 3 givenname: Neha surname: Aggarwal fullname: Aggarwal, Neha organization: 2 Department of Chemistry, University of Delhi, Delhi 110 007, India – sequence: 4 givenname: Rakesh surname: Pathak fullname: Pathak, Rakesh organization: 3 Department of Microbiology, V. P. Chest Institute, University of Delhi, Delhi 110 007, India – sequence: 5 givenname: Anil S. surname: Baghel fullname: Baghel, Anil S. organization: 1 Department of Biochemistry, V. P. Chest Institute, University of Delhi, Delhi 110 007, India – sequence: 6 givenname: Garima surname: Gupta fullname: Gupta, Garima organization: 1 Department of Biochemistry, V. P. Chest Institute, University of Delhi, Delhi 110 007, India – sequence: 7 givenname: Anu surname: Arya fullname: Arya, Anu organization: 2 Department of Chemistry, University of Delhi, Delhi 110 007, India – sequence: 8 givenname: Mahendra surname: Nath fullname: Nath, Mahendra organization: 2 Department of Chemistry, University of Delhi, Delhi 110 007, India – sequence: 9 givenname: Virinder S. surname: Parmar fullname: Parmar, Virinder S. organization: 2 Department of Chemistry, University of Delhi, Delhi 110 007, India – sequence: 10 givenname: Hanumantharao G. surname: Raj fullname: Raj, Hanumantharao G. organization: 1 Department of Biochemistry, V. P. Chest Institute, University of Delhi, Delhi 110 007, India – sequence: 11 givenname: Ashok K. surname: Prasad fullname: Prasad, Ashok K. organization: 2 Department of Chemistry, University of Delhi, Delhi 110 007, India – sequence: 12 givenname: Mridula surname: Bose fullname: Bose, Mridula email: mridulabose@hotmail.com organization: 3 Department of Microbiology, V. P. Chest Institute, University of Delhi, Delhi 110 007, India |
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Copyright | The Author 2011. Published by Oxford University Press on behalf of the British Society for Antimicrobial Chemotherapy. All rights reserved. For Permissions, please e-mail: journals.permissions@oup.com 2011 2015 INIST-CNRS Copyright Oxford Publishing Limited(England) Nov 2011 |
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Keywords | cell-wall attacking synergy amino coumarins multidrug resistant Coumarine derivatives Coumarin Cell wall Characterization Structure activity relation Efficiency Multiple resistance Antituberculous agent Antibacterial agent |
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The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and... The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and in... OBJECTIVESThe objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and... Objectives The objective of the present study was to evaluate the antitubercular activity of amino and acyl amino derivatives of coumarins when used alone and... |
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SubjectTerms | Antibiotics. Antiinfectious agents. Antiparasitic agents Antitubercular Agents - pharmacology Biological and medical sciences Cell Wall - drug effects Chemical compounds Coumarins - chemistry Coumarins - pharmacology Cytotoxicity Drug resistance Drug Resistance, Multiple, Bacterial Drug Synergism Ethambutol - pharmacology Gram-positive bacteria Isoniazid - pharmacology Medical sciences Microbial Sensitivity Tests Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects Mycolic Acids - metabolism Pharmacology. Drug treatments Prescription drugs Rifampin - pharmacology Streptomycin - pharmacology Structure-Activity Relationship |
Title | Characterization of 7-amino-4-methylcoumarin as an effective antitubercular agent: structure-activity relationships |
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