Synthesis, FT-IR, 1H, 13CNMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic – Lasalocid acid and its complexes with Li+, Na+ and K+ cations

Huczyński, Adam; Rutkowski, Jacek; Brzeziński, Bogumił; Bartl, Franz

doi:10.1016/j.saa.2012.11.106

Cited by 7 publications

(8 citation statements)

References 25 publications

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“…At the physiological pH, the zwitterionic headgroup of DPPC assumes a net zero charge with the phosphate group having the negative charge and the quaternary amine, at the terminal end of the headgroup, having a positive charge . LA as a free acid has been shown to have a negative charge at the physiological pH due to deprotonation of its carboxylic acid group; therefore, we expect the molecule to be electrostatically attracted to the positively charged terminal quaternary amine . We next inject a monovalent salt, sodium chloride, into the trough (Figure A-IV).…”

Section: Resultsmentioning

confidence: 99%

“…50 LA as a free acid has been shown to have a negative charge at the physiological pH due to deprotonation of its carboxylic acid group; therefore, we expect the molecule to be electrostatically attracted to the positively charged terminal quaternary amine. 51 We next inject a monovalent salt, sodium chloride, into the trough (Figure 3A-IV). Thus, after the injection of sodium salt into the subphase of the lipid monolayer, we see that the pressure quickly climbs to an equilibrium pressure of approximately 32 mN/m (Figure 3A-V).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…It is suggested that the ionophore-mediated influx of Na + into bacteria leads to a pH change and an increase in osmotic pressure, resulting in cell swelling and cell death. 51 Future SFG experiments with lipid bilayer systems will allow us to determine the structure of LA within the hydrophobic core of the bilayer in more detail.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Lasalocid Acid Antibiotic at a Membrane Surface Probed by Sum Frequency Generation Spectroscopy

et al. 2020

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Carboxyl polyether ionophores (CPIs) are widely used as veterinary antibiotics and to increase food utilization in ruminating animals. Furthermore, CPIs can target drug-resistant bacteria, but detailed knowledge about their mode-of-action is needed to develop agents with a reasonable therapeutic index. It has been suggested that ionophores bind to membranes and incur large structural changes to shield a bound ion from the hydrophobic environment of the lipid bilayer for transport. One crucial piece of information is missing, however: Is it necessary for the free ionophore to adsorb on the membrane surface before interacting with a cation to facilitate cross-membrane ion transport? To answer this question, we applied sum-frequency generation (SFG) vibrational spectroscopy and surface tensiometry to identify the interaction between the prototypical CPI lasalocid acid (LA) and a model membrane. Observed changes in the surface pressure demonstrate that the free LA undergoes a self-assembly process with the lipid monolayer. Spectra taken from the lipid monolayer show that the free acid inserts partially into the lipid monolayer and then after complexation with sodium chloride disrupts the lipid monolayer. Overall, this study strongly suggests that this must be the crucial step of LA and metal ion complexation that allows the ionophore to traverse a lipid membrane.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Lasalocid Acid Antibiotic at a Membrane Surface Probed by Sum Frequency Generation Spectroscopy

et al. 2020

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“…Acylated OH slightly decreased K + transportation rate of salinomycin but esterified COOH (C1) made it lose its ionophoric activity 53 . Work on the modification of salinomycin to enhance its anticancer activity has generated more than 100 derivatives, via either structure modification or dimer synthesis 44,47–49,77,146–170 . Of note, derivatives with single or double modification of C1 and/or C20, or double modification of C17/C21, or dimers connected at C20 showed a noteworthy improvement in terms of anticancer activities 145 …”

Section: Chemically Modified Salinomycin Derivatives and Synthesized ...mentioning

confidence: 99%

Salinomycin as a potent anticancer stem cell agent: State of the art and future directions

Liu

et al. 2021

Medicinal Research Reviews

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“…Transition metals and their complexes played a vital role in the human health, are therefore of great interest as potential drugs [16][17][18]. The study of structural and binding features of various Mannich base complexes can play an important role in better understanding of the complex biological processes.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with Mannich base ligand

Imran¹,

Farooq²,

Latif³

et al. 2019

Bull. Chem. Soc. Eth.

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A Mannich base ligand (L) was prepared by reacting 2-mercaptobenzimidazole, diphenylamine and benzaldehyde. This ligand (L) was further used for the preparation of four metal complexes with Co(II), Ni(II), Cu(II) and Zn(II) ions. The reactions were monitored by TLC. The synthesized compounds were structurally characterized using FTIR spectroscopy, UV-Visible spectroscopy, 1 Hand 13 C-NMR spectroscopy, ICP-OES/atomic absorption spectroscopy. It has been observed that the ligand (L) behaved in a monoanionic bidentate mode and the geometry of resulting complexes was tetrahedral. Conductivity analysis revealed their non-electrolytic nature. Antibacterial activity of the synthesized compounds was assessed through an agar well diffusion method against four strains of Gram-negative bacteria. L-Zn(II) complex showed best activity at all four concentrations against the four strains of Gram-negative bacteria.

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Synthesis, FT-IR, 1H, 13CNMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic – Lasalocid acid and its complexes with Li+, Na+ and K+ cations

Cited by 7 publications

References 25 publications

Lasalocid Acid Antibiotic at a Membrane Surface Probed by Sum Frequency Generation Spectroscopy

Lasalocid Acid Antibiotic at a Membrane Surface Probed by Sum Frequency Generation Spectroscopy

Salinomycin as a potent anticancer stem cell agent: State of the art and future directions

Antibacterial activity studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with Mannich base ligand

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