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Substituted sulfonamide bioisosteres of 8-hydroxyquinoline as zinc-dependent antibacterial compounds.
McGowan, John E; Harper, Andrew D; Davison, Emma K; Jeong, Joo Young; Mros, Sonya; Harbison-Price, Nichaela; Van Zuylen, Essie M; Knottenbelt, Melanie K; Heikal, Adam; Ferguson, Scott A; McConnell, Michelle A; Cook, Gregory M; Krittaphol, Woravimol; Walker, Greg F; Brimble, Margaret A; Rennison, David.
Afiliación
  • McGowan JE; School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
  • Harper AD; School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
  • Davison EK; School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
  • Jeong JY; School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
  • Mros S; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • Harbison-Price N; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • Van Zuylen EM; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • Knottenbelt MK; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • Heikal A; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • Ferguson SA; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • McConnell MA; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • Cook GM; Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Auckland 1042, New Zealand; Department of Microbiology and Immunology, University of Otago, 720 Cumberland Street, Dunedin, New Zealand.
  • Krittaphol W; School of Pharmacy, University of Otago, 18 Frederick Street, Dunedin, New Zealand.
  • Walker GF; School of Pharmacy, University of Otago, 18 Frederick Street, Dunedin, New Zealand.
  • Brimble MA; School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand; Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Auckland 1042, New Zealand.
  • Rennison D; School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand. Electronic address: d.rennison@auckland.ac.nz.
Bioorg Med Chem Lett ; 30(11): 127110, 2020 06 01.
Article en En | MEDLINE | ID: mdl-32229060
A series of substituted sulfonamide bioisosteres of 8-hydroxyquinoline were evaluated for their antibacterial activity against the common mastitis causative pathogens Streptococcus uberis, Staphylococcus aureus and Escherichia coli, both in the presence and absence of supplementary zinc. Compounds 9a-e, 10a-c, 11a-e, 12 and 13 were demonstrated to have MICs of 0.0625 µg/mL against S. uberis in the presence of 50 µM ZnSO4. Against S. aureus compounds 9g (MIC 4 µg/mL) and 11d (MIC 8 µg/mL) showed the greatest activity, whereas all compounds were found to be inactive against E. coli (MIC > 256 µg/mL); again in the presence of 50 µM ZnSO4. All compounds were demonstrated to be significantly less active in the absence of supplementary zinc. Compound 9g was subsequently confirmed to be bactericidal, with an MBC (≥3log10 cfu/mL reduction) of 0.125 µg/mL against S. uberis in the presence of 50 µM ZnSO4. To validate the sanitising activity of compound 9g in the presence of supplementary zinc, a quantitative suspension disinfection (sanitizer) test was performed. In this preliminary test, sanitizing activity (>5log10 reduction of CFU/mL in 5 min) was observed against S. uberis for compound 9g at concentrations as low as 1 mg/mL, validating the potential of this compound to function as a topical sanitizer against the major environmental mastitis-causing microorganism S. uberis.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Zinc / Oxiquinolina / Sulfanilamida / Antibacterianos Idioma: En Revista: Bioorg Med Chem Lett Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Nueva Zelanda Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Zinc / Oxiquinolina / Sulfanilamida / Antibacterianos Idioma: En Revista: Bioorg Med Chem Lett Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Nueva Zelanda Pais de publicación: Reino Unido