Synthesis, anti-microbial, toxicity and molecular docking studies of N-nitroso-N-phenylhydroxylamine (cupferron) and its derivatives.

Waziri, I; Isa, MA; Sonopo, M; Williams, DBG; Muller, A

Synthesis, anti-microbial, toxicity and molecular docking studies of N-nitroso-N-phenylhydroxylamine (cupferron) and its derivatives.

Waziri, I Isa, MA Sonopo, M Williams, DBG Muller, A

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Publisher:: Elsevier BV
Publication Type:: Journal Article
Citation:: Bioorg Med Chem Lett, 2021, 52, pp. 128381
Issue Date:: 2021-11-15

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Field	Value	Language
dc.contributor.author	Waziri, I
dc.contributor.author	Isa, MA
dc.contributor.author	Sonopo, M
dc.contributor.author	Williams, DBG
dc.contributor.author	Muller, A
dc.date.accessioned	2022-01-17T00:39:02Z
dc.date.available	2021-09-20
dc.date.available	2022-01-17T00:39:02Z
dc.date.issued	2021-11-15
dc.identifier.citation	Bioorg Med Chem Lett, 2021, 52, pp. 128381
dc.identifier.issn	0960-894X
dc.identifier.issn	1464-3405
dc.identifier.uri	http://hdl.handle.net/10453/153188
dc.description.abstract	Bacterial resistance to antimicrobial agents is increasing at an alarming rate globally and requires new lead compounds for antibiotics. In this study, N-phenyl-N-nitroso hydroxylamine (cupferron) and its derivatives have been synthesised using readily available starting materials. The compounds were obtained in high yield and purity. They show activity towards a range of Gram-positive and Gram-negative pathogenic bacteria, with minimum inhibitory concentration (MIC) values as low as 2 μg.mL-1 against the tested organisms, especially for Gram-positive species. Toxicity studies on the lead compound 3b indicate insignificant effects on healthy cell lines. Molecular docking studies on the lead compound identify possible binding modes of the compound, and the results obtained correlate with those of in vitro and MIC studies. The lead compound shows excellent drug-likeness properties.
dc.format	Print-Electronic
dc.language	eng
dc.publisher	Elsevier BV
dc.relation.ispartof	Bioorg Med Chem Lett
dc.relation.isbasedon	10.1016/j.bmcl.2021.128381
dc.rights	info:eu-repo/semantics/embargoedAccess
dc.subject	0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, 1115 Pharmacology and Pharmaceutical Sciences
dc.subject.classification	Medicinal & Biomolecular Chemistry
dc.subject.mesh	Anti-Bacterial Agents
dc.subject.mesh	Dose-Response Relationship, Drug
dc.subject.mesh	Gram-Negative Bacteria
dc.subject.mesh	Gram-Positive Bacteria
dc.subject.mesh	Microbial Sensitivity Tests
dc.subject.mesh	Molecular Docking Simulation
dc.subject.mesh	Molecular Structure
dc.subject.mesh	Nitrosamines
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Gram-Negative Bacteria
dc.subject.mesh	Gram-Positive Bacteria
dc.subject.mesh	Nitrosamines
dc.subject.mesh	Anti-Bacterial Agents
dc.subject.mesh	Microbial Sensitivity Tests
dc.subject.mesh	Molecular Structure
dc.subject.mesh	Structure-Activity Relationship
dc.subject.mesh	Dose-Response Relationship, Drug
dc.subject.mesh	Molecular Docking Simulation
dc.title	Synthesis, anti-microbial, toxicity and molecular docking studies of N-nitroso-N-phenylhydroxylamine (cupferron) and its derivatives.
dc.type	Journal Article
utslib.citation.volume	52
utslib.location.activity	England
utslib.for	0304 Medicinal and Biomolecular Chemistry
utslib.for	0305 Organic Chemistry
utslib.for	1115 Pharmacology and Pharmaceutical Sciences
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
utslib.copyright.status	open_access	*
utslib.copyright.embargo	2023-11-15T00:00:00+1000Z
dc.date.updated	2022-01-17T00:39:01Z
pubs.publication-status	Published
pubs.volume	52

Abstract:

Bacterial resistance to antimicrobial agents is increasing at an alarming rate globally and requires new lead compounds for antibiotics. In this study, N-phenyl-N-nitroso hydroxylamine (cupferron) and its derivatives have been synthesised using readily available starting materials. The compounds were obtained in high yield and purity. They show activity towards a range of Gram-positive and Gram-negative pathogenic bacteria, with minimum inhibitory concentration (MIC) values as low as 2 μg.mL-1 against the tested organisms, especially for Gram-positive species. Toxicity studies on the lead compound 3b indicate insignificant effects on healthy cell lines. Molecular docking studies on the lead compound identify possible binding modes of the compound, and the results obtained correlate with those of in vitro and MIC studies. The lead compound shows excellent drug-likeness properties.

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http://hdl.handle.net/10453/153188