In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria
Objective: To evaluate the antibacterial activity of ten synthetic tetrahydroisoquinolines against eight bacterial strains. Methods: The ten tetrahydroisoquinolines synthesized via base-catalyzed Pictet–Spengler cyclization were screened against a total of eight bacterial strains comprising control...
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Wolters Kluwer Medknow Publications
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ftdoajarticles:oai:doaj.org/article:3e91e985532f41bd901945aceca51097 2023-05-15T15:10:51+02:00 In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria Moses Njutain Ngemenya Joelle Ngo Hanna Julios Armand Komtchou Simon Mbua Ngale Efange 2015-06-01T00:00:00Z https://doi.org/10.1016/j.apjtb.2015.03.005 https://doaj.org/article/3e91e985532f41bd901945aceca51097 EN eng Wolters Kluwer Medknow Publications http://www.sciencedirect.com/science/article/pii/S2221169115000726 https://doaj.org/toc/2221-1691 2221-1691 doi:10.1016/j.apjtb.2015.03.005 https://doaj.org/article/3e91e985532f41bd901945aceca51097 Asian Pacific Journal of Tropical Biomedicine, Vol 5, Iss 6, Pp 472-477 (2015) Antibiotics Drug discovery Antibacterial agents Tetrahydroisoquinolines Cytotoxicity Arctic medicine. Tropical medicine RC955-962 Biology (General) QH301-705.5 article 2015 ftdoajarticles https://doi.org/10.1016/j.apjtb.2015.03.005 2023-01-08T01:35:54Z Objective: To evaluate the antibacterial activity of ten synthetic tetrahydroisoquinolines against eight bacterial strains. Methods: The ten tetrahydroisoquinolines synthesized via base-catalyzed Pictet–Spengler cyclization were screened against a total of eight bacterial strains comprising control and pathogenic strains by the disc diffusion and micro-dilution methods. The most active compound was then assessed for cytotoxicity on human lymphocytes. Results: Six of the tetrahydroisoquinolines showed broad spectrum bacteriostatic activity. The zones of inhibition produced ranged from 7 to 23 mm for 200 μg per disc. The presence of a lipophilic substituent at the para position of the pendant phenyl group conferred the highest antibacterial activity. Compound 2 [1-(3,4-chlorophenyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline] was the most active and produced zones ranging from 9 to 20 mm against all eight bacterial strains. Compound 2 also showed the lowest minimum inhibitory concentration of 100 μg/mL against Escherichia coli ATCC11775 and the lowest minimum bactericidal concentration of 800 μg/mL against pathogenic Salmonella typhimurium. Overall, compound 2 was the most active with bacteriostatic and bactericidal activity against three and four bacterial strains respectively. A 50% cytotoxic concentration of 98.2 μg/mL was recorded for compound 2 indicating a low risk of toxicity. Conclusions: The 1-aryl-1,2,3,4-tetrahydroisoquinolines display structure-related antibacterial activity and further chemical exploration of the tetrahydroisoquinoline scaffold may yield more potent non-toxic derivatives for development into new antibacterials. Article in Journal/Newspaper Arctic Directory of Open Access Journals: DOAJ Articles Arctic Asian Pacific Journal of Tropical Biomedicine 5 6 472 477 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
Antibiotics Drug discovery Antibacterial agents Tetrahydroisoquinolines Cytotoxicity Arctic medicine. Tropical medicine RC955-962 Biology (General) QH301-705.5 |
spellingShingle |
Antibiotics Drug discovery Antibacterial agents Tetrahydroisoquinolines Cytotoxicity Arctic medicine. Tropical medicine RC955-962 Biology (General) QH301-705.5 Moses Njutain Ngemenya Joelle Ngo Hanna Julios Armand Komtchou Simon Mbua Ngale Efange In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria |
topic_facet |
Antibiotics Drug discovery Antibacterial agents Tetrahydroisoquinolines Cytotoxicity Arctic medicine. Tropical medicine RC955-962 Biology (General) QH301-705.5 |
description |
Objective: To evaluate the antibacterial activity of ten synthetic tetrahydroisoquinolines against eight bacterial strains. Methods: The ten tetrahydroisoquinolines synthesized via base-catalyzed Pictet–Spengler cyclization were screened against a total of eight bacterial strains comprising control and pathogenic strains by the disc diffusion and micro-dilution methods. The most active compound was then assessed for cytotoxicity on human lymphocytes. Results: Six of the tetrahydroisoquinolines showed broad spectrum bacteriostatic activity. The zones of inhibition produced ranged from 7 to 23 mm for 200 μg per disc. The presence of a lipophilic substituent at the para position of the pendant phenyl group conferred the highest antibacterial activity. Compound 2 [1-(3,4-chlorophenyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline] was the most active and produced zones ranging from 9 to 20 mm against all eight bacterial strains. Compound 2 also showed the lowest minimum inhibitory concentration of 100 μg/mL against Escherichia coli ATCC11775 and the lowest minimum bactericidal concentration of 800 μg/mL against pathogenic Salmonella typhimurium. Overall, compound 2 was the most active with bacteriostatic and bactericidal activity against three and four bacterial strains respectively. A 50% cytotoxic concentration of 98.2 μg/mL was recorded for compound 2 indicating a low risk of toxicity. Conclusions: The 1-aryl-1,2,3,4-tetrahydroisoquinolines display structure-related antibacterial activity and further chemical exploration of the tetrahydroisoquinoline scaffold may yield more potent non-toxic derivatives for development into new antibacterials. |
format |
Article in Journal/Newspaper |
author |
Moses Njutain Ngemenya Joelle Ngo Hanna Julios Armand Komtchou Simon Mbua Ngale Efange |
author_facet |
Moses Njutain Ngemenya Joelle Ngo Hanna Julios Armand Komtchou Simon Mbua Ngale Efange |
author_sort |
Moses Njutain Ngemenya |
title |
In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria |
title_short |
In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria |
title_full |
In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria |
title_fullStr |
In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria |
title_full_unstemmed |
In vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: Structure related activity against pathogenic bacteria |
title_sort |
in vitro screening of 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinolines: structure related activity against pathogenic bacteria |
publisher |
Wolters Kluwer Medknow Publications |
publishDate |
2015 |
url |
https://doi.org/10.1016/j.apjtb.2015.03.005 https://doaj.org/article/3e91e985532f41bd901945aceca51097 |
geographic |
Arctic |
geographic_facet |
Arctic |
genre |
Arctic |
genre_facet |
Arctic |
op_source |
Asian Pacific Journal of Tropical Biomedicine, Vol 5, Iss 6, Pp 472-477 (2015) |
op_relation |
http://www.sciencedirect.com/science/article/pii/S2221169115000726 https://doaj.org/toc/2221-1691 2221-1691 doi:10.1016/j.apjtb.2015.03.005 https://doaj.org/article/3e91e985532f41bd901945aceca51097 |
op_doi |
https://doi.org/10.1016/j.apjtb.2015.03.005 |
container_title |
Asian Pacific Journal of Tropical Biomedicine |
container_volume |
5 |
container_issue |
6 |
container_start_page |
472 |
op_container_end_page |
477 |
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1766341790746542080 |