ArticleBioorganic & medicinal chemistry letters2016
Pterin-sulfa conjugates as dihydropteroate synthase inhibitors and antibacterial agents.
Article in Bioorganic & medicinal chemistry letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 103 citations in OpenAlex.
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- Metabolism-Based Biomarkers for Rapid Phenotypic Antibiotic Susceptibility Testing.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Review
- Design and synthesis of novel sulfa-azo dyes: a sustainable approach to textile dyeing combined with microwave energy.RSC advances · 2026Article
- A virtual screening and molecular dynamics approach in search of novel antibiotic chemotypes.PloS one · 2026Article
- Hybrids/Conjugates/Chimera Drugs-Antimicrobial Hybrids: Antibiotics, Antifungals, Antituberculars, Antimalarials.Current medicinal chemistry · 2026Review
- Development of Pyrimido Pyridazine Analogs through Increased Whole Cell Target Engagement of the Dihydropteroate Synthase Pterin Binding Site in Gram-Negative Bacteria.ACS infectious diseases · 2025Article
- Preparation of Lipophilic Derivatives ofACS omega · 2025Article
- The crystal structures and Hirshfeld surface analysis of the 2-iodophenyl- and 4,5-difluoro-2-iodophenyl derivatives of benzenesulfonamide.Acta crystallographica. Section E, Crystallographic communications · 2025Article
- The crystal structures determination and Hirshfeld surface analysis ofActa crystallographica. Section E, Crystallographic communications · 2024Article
- Synthesis, docking and characterization of some novel 5-(S-alkyl)-1.3.4-thiadiazole-2-carboxamide derivatives as anti-inflammatory and antibacterial agents.BMC chemistry · 2024Article
- The aminosalicylate - folate connection.Drug metabolism reviews · 2024Review
- Synthesis, Characterization, and Antimicrobial Evaluation of Schiff Base-mixed Ligand Complexes with Divalent Metal Ions Derived from Amoxicillin and Vanillin/Nicotinamide.Current pharmaceutical design · 2024Article
- Molecular mechanism of plasmid-borne resistance to sulfonamide antibiotics.Nature communications · 2023Article
- New Ni(II) and Pd(II) complexes bearing derived sulfa drug ligands: synthesis, characterization, DFT calculations, and in silico and in vitro biological activity studies.Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine · 2023Article
- Crystallographic study, biological assessment and POM/Docking studies of pyrazoles-sulfonamide hybrids (PSH): Identification of a combined Antibacterial/Antiviral pharmacophore sites leading toJournal of molecular structure · 2022Article
- Sulfamethoxazole Enhances Specific Enzymatic Activities under Aerobic Heterotrophic Conditions: A Metaproteomic Approach.Environmental science & technology · 2022Article
- Crystal structure of Arabidopsis thaliana HPPK/DHPS, a bifunctional enzyme and target of the herbicide asulam.Plant communications · 2022Article
- Synthesis and Structure-Activity Relationship of Thioacetamide-Triazoles againstMolecules (Basel, Switzerland) · 2022Article
- Folic acid-sulfonamide conjugates as antibacterial agents: design, synthesis and molecular docking studies.RSC advances · 2020Article
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Authors and funding
9 authors at 2 institutions in 1 country.
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Abstract
The sulfonamide class of antibiotics has been in continuous use for over 70years. They are thought to act by directly inhibiting dihydropteroate synthase (DHPS), and also acting as prodrugs that sequester pterin pools by forming dead end pterin-sulfonamide conjugates. In this study, eight pterin-sulfonamide conjugates were synthesized using a novel synthetic strategy and their biochemical and microbiological properties were investigated. The conjugates were shown to competitively inhibit DHPS, and inhibition was enhanced by the presence of pyrophosphate that is crucial to catalysis and is known to promote an ordering of the DHPS active site. The co-crystal structure of Yersinia pestis DHPS bound to one of the more potent conjugates revealed a mode of binding that is similar to that of the enzymatic product analog pteroic acid. The antimicrobial activities of the pterin-sulfonamide conjugates were measured against Escherichia coli in the presence and absence of folate precursors and dependent metabolites. These results show that the conjugates have appreciable antibacterial activity and act by an on target, anti-folate pathway mechanism rather than as simple dead end products.
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