Synthesis, antimicrobial evaluation, DNA gyrase inhibition, and in silico pharmacokinetic studies of novel quinoline derivatives.

Anti-Bacterial Agents / chemical synthesis Antifungal Agents / chemical synthesis DNA Gyrase / metabolism Dose-Response Relationship, Drug Fungi / drug effects Gram-Negative Bacteria / drug effects Gram-Positive Bacteria / drug effects Humans Microbial Sensitivity Tests Molecular Structure Quinolines / chemical synthesis Structure-Activity Relationship Topoisomerase II Inhibitors / chemical synthesis
DNA gyrase antimicrobial molecular docking quinoline synthesis

Journal

Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167

Informations de publication

Date de publication:
Feb 2021
Historique:
received: 29 07 2020
revised: 17 09 2020
accepted: 23 09 2020
pubmed: 21 10 2020
medline: 7 10 2021
entrez: 20 10 2020
Statut: ppublish

Résumé

Herein, we report the synthesis and in vitro antimicrobial evaluation of novel quinoline derivatives as DNA gyrase inhibitors. The preliminary antimicrobial activity was assessed against a panel of pathogenic microbes including Gram-positive bacteria (Streptococcus pneumoniae and Bacillus subtilis), Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), and fungal strains (Aspergillus fumigatus, Syncephalastrum racemosum, Geotrichum candidum, and Candida albicans). Compounds that revealed the best activity were subjected to further biological studies to determine their minimum inhibitory concentrations (MICs) against the selected pathogens as well as their in vitro activity against the E. coli DNA gyrase, to realize whether their antimicrobial action is mediated via inhibition of this enzyme. Four of the new derivatives (14, 17, 20, and 23) demonstrated a relatively potent antimicrobial activity with MIC values in the range of 0.66-5.29 μg/ml. Among them, compound 14 exhibited a particularly potent broad-spectrum antimicrobial activity against most of the tested strains of bacteria and fungi, with MIC values in the range of 0.66-3.98 μg/ml. A subsequent in vitro investigation against the bacterial DNA gyrase target enzyme revealed a significant potent inhibitory activity of quinoline derivative 14, which can be observed from its IC

Identifiants

DOI: 10.1002/ardp.202000277 PMID: 33078877
pubmed: 33078877
doi: 10.1002/ardp.202000277
doi:

Substances chimiques

Anti-Bacterial Agents 0
Antifungal Agents 0
Quinolines 0
Topoisomerase II Inhibitors 0
quinoline E66400VT9R
DNA Gyrase EC 5.99.1.3

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e2000277

Informations de copyright

© 2020 Deutsche Pharmazeutische Gesellschaft.

Références

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Auteurs

Mohamed H El-Shershaby (MH)

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.

Kamal M El-Gamal (KM)

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.

Ashraf H Bayoumi (AH)

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.

Khaled El-Adl (K)

Pharmaceutical Medicinal Chemistry & Drug Design Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Heliopolis University for Sustainable Development, Cairo, Egypt.
ORCID: 0000-0002-8922-9770

Hany E A Ahmed (HEA)

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.
Pharmacognosy and Pharmaceutical Chemistry Department, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia.
ORCID: 0000-0001-8898-8452

Hamada S Abulkhair (HS)

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.
Pharmaceutical Chemistry Department, Faculty of Pharmacy, Horus University, New Damietta, Egypt.
ORCID: 0000-0001-6479-4573

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Classifications MeSH

questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Anti-infectieux › Antibactériens › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Anti-infectieux › Antifongiques › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines bactériennes › DNA gyrase › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Eucaryotes › Champignons › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Bactéries › Bactéries à Gram négatif › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Bactéries › Bactéries à Gram positif › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Techniques d'investigation › Évaluation préclinique de médicament › Tests de sensibilité microbienne › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Quinoléines › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Synthesis, antimicrobial evaluation, DNA...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Antinéoplasiques › Inhibiteurs des topoisomérases › Inhibiteurs de la topoisomérase-II › Synthesis, antimicrobial evaluation, DNA...