Related Experiment Video
Updated: Sep 20, 2025
Visualization of Bacterial Resistance using Fluorescent Antibiotic Probes
Published on: March 2, 2020
Aryl bismuth phosphinates [BiAr2(O(O)PRR')]: structure-activity relationships for antibacterial activity and
Megan E Herdman1, Melissa V Werrett1, Philip C Andrews1
1School of Chemistry, Monash University, Clayton, Melbourne, VIC 3800, Australia. phil.andrews@monash.edu.
Abstract:
To study and evaluate the structure-activity relationships in di-aryl bismuth phosphinates on antibacterial activity and cytotoxicity a series of complexes containing ortho-methoxyphenyl, meta-methoxyphenyl, meta-tolyl and para-tolyl aryl groups; [Bi(o-MeOPh)2(O(O)P(H)Ph)]1, [Bi(o-MeOPh)2(O(O)PPh2)]2, [Bi(o-MeOPh)2(O(O)P(p-MeOPh)2)]3, [Bi(m-MeOPh)2(O(O)P(H)Ph)]4, [Bi(m-MeOPh)2(O(O)PPh2)]5, [Bi(m-MeOPh)2(O(O)P(p-MeOPh)2)]6, [Bi(m-tol)2(O(O)P(H)Ph)]7, [Bi(m-tol)2(O(O)PPh2)]8, [Bi(m-tol)2(O(O)P(p-MeOPh)2)]9, [Bi(p-tol)2(O(O)P(H)Ph)]10, [Bi(p-tol)2(O(O)PPh2)]11 and [Bi(p-tol)2(O(O)P(p-MeOPh)2)]12, were synthesised and characterised. Complexes 4, 7, 8, 10 and 11 were structurally authenticated by X-ray crystallography. Evaluation of their antibacterial activity towards methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE), Escherichia coli (E. coli) and Pseudomonas aeruginosa (P. aeruginosa) showed that the bismuth bound aryl group has a profound influence on activity, with the o-MeOPh complexes 1-3 showing very little activity while the m-MeOPh complexes have the greatest activity towards MRSA and VRE in the range of 0.63 to 1.25 μM. Viability studies with Cos-7 cells showed that the di-aryl bismuth complexes 1-12 are less cytotoxic than their di-phenyl bismuth analogues, with a general trend of toxicity observed as p-tolyl > m-tolyl > m-methoxyphenyl > o-methoxyphenyl. The large difference in Cos-7 viability for complexes 1 (IC50 > 80 μM) and 4 (IC50 14.0 μM) was further investigated through bismuth uptake studies, where there was no obvious difference in Cos-7 bismuth uptake at 5 μM. This suggests that the bismuth-bound aryl group has a significant impact on biological activity, which is then further mediated by other ligands.
More Related Videos
07:20Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
07:28Metabolic Profiling to Determine Bactericidal or Bacteriostatic Effects of New Natural Products using Isothermal Microcalorimetry
Published on: October 29, 2020
Related Concept Videos
01:26Physical Properties of Amines
01:28Structure-Activity Relationships and Drug Design
SAR studies the intricate relationship between a drug's chemical structure and biological activity. It focuses on understanding how modifications to a drug's structure can influence...
01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...