Stibonic acids and related stibonate-phosphonate clusters: Synthesis, characterization and bioactivity evaluation

Ali, J.; Mubarak, Mohamad Mosa; Samuel, Calvin; Kantroo, Hadiya Amin; Malik, Abbass; Ahmad, Zahoor; Baskar, Viswanathan

doi:10.1016/j.jinorgbio.2022.111909

Cited by 4 publications

(3 citation statements)

References 27 publications

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“…Antimicrobial activity of the synthesized peptides was determined by measuring their bacteriostatic and bactericidal potential in terms of MIC and MBC using broth microdilution method against Escherichia coli (ATCC 25922), Bacillus subtilis (ATCC 6633), Pseudomonas aeruginosa (ATCC 9027), Staphylococcus epidermidis (ATCC 35984), Staphylococcus aureus (MTCC 6538), Klebsiella pneumoniae (MTCC 3040), Lactobacillus acidophilus (MTCC 10307), Streptococcus mutans (MTCC 497), Salmonella typhimurium (ATCC 14028), Enterococcus faecalis (ATCC 29212), Methicillin-resistant Staphylococcus aureus (MRSA) and one more clinical isolatemulti-drug resistant strain of E. coli. , Briefly, all the test pathogens were cultured in the Mueller–Hinton Broth medium to an OD 600 nm of 0.4–0.8 which corresponds to the mid logarithmic growth phase (10 8 CFU/mL) followed by serial dilutions to give an inoculum of 5 × 10 5 CFU/mL. The 50 μL aliquots of this diluted culture were added to 96-well flat-bottom microtiter plates containing 200 μL of 2-fold serially diluted peptides with concentrations ranging from 0.25 to 128 μg/mL and incubated at 37 °C for 12–16 h. Streptomycin and media were used as positive and blank control.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Antimicrobial Activity of Ultra-Short Cationic β-Peptides

et al. 2023

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The development of new antibiotics is urgently required because of the rapidly growing resistance against conventional antibiotics. The antimicrobial peptides show potential as small antibiotic molecules. The stability of peptides is a primary concern for the use of peptides as drugs. Introducing β-amino acids into peptide sequences can be useful in preventing biological degradation by proteolytic enzymes. Herein, we describe the synthesis, characterization, and antimicrobial activity of ultrashort cationic β-peptides, LA-β 3,3 -Pip-β 2,2 -Ac 6 c-PEA, P1; LA-β 3,3 -Pip(G)-β 2,2 -Ac 6 c-PEA, P2; LA U -β 3,3 -Pip-β 2,2 -Ac 6 c-PEA, P3, and LA U -β 3,3 -Pip(G)-β 2,2 -Ac 6 c-PEA, P4. Peptides P1−P4 were evaluated against Gram-negative, Gram-positive, MRSA, and multi-drug resistant E. coli (MDR-E. coli). P3 exhibited the most potent antimicrobial activity against E. coli, S. epidermidis, S. aureus, K. pneumoniae, S. mutans, and E. faecalis, with MIC values 0.5, 2, 0.5, 1, 2, and 1 μg/mL, respectively. P3 exhibited time-and concentration-dependent bactericidal activities against E. coli, S. aureus, and E. faecalis with a killing rate of 1.6 logs/h. The treatment of E. coli with peptide P3 showed membrane disruption. In addition, P3 exhibited the inhibition of biofilm produced by E. coli, synergism with antibiotics (ciprofloxacin, streptomycin, and ampicillin), 100% cell viability against AML12, RAW 264.7, and HEK-293 cell lines at 1, and 10 μg/mL concentrations.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Antimicrobial Activity of Ultra-Short Cationic β-Peptides

et al. 2023

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“…To determine the MIC, the broth micro-dilution method was used, as described previously ( Ali et al, 2022 ). The 96-well plates were labeled with the compound name, reference antibiotics (two wells/compound), and name of bacterial strains.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and unraveling the antibacterial and antibiofilm potential of 2-azidobenzothiazoles: insights from a comprehensive in vitro study

Qadir,

Kanth,

Aasif

et al. 2023

Front. Chem.

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The present study reports the synthesis of 2-azidobenzothiazoles from substituted 2-aminobenzothiazoles using sodium nitrite and sodium azide under mild conditions. All the synthesized compounds were examined for their antibacterial activity against Gram (+) bacteria, Staphylococcus aureus (ATCC 25923), Enterococcus faecalis (ATCC 51299), Bacillus cereus (ATCC 10876) and Gram (−) bacteria, Escherichia coli (ATCC 10536), Pseudomonas aeruginosa (ATCC 10145), Klebsiella pneumonia (ATCC BAA-2146)and clinical isolates of Gram (+) Methicillin Resistant S. aureus (MRSA) and Multi Drug Resistant E. coli. The Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) values by broth dilution method revealed that compound 2d exhibited significant antibacterial potential against E. faecalis and S. aureus with MIC of 8 μg/mL, while other synthesized compounds had only moderate effects against all the tested species. The compound significantly inhibited the biofilm formation of the bacterial strains below its MIC. The selective cytotoxicity of Compound 2d towards bacterial cells was evidenced on extended exposure of Human Embryonic Kidney-293 cell line to higher concentrations of the compound. Hence, the present study confirmed that compound 2d can be a potential drug candidate for future development as an antibacterial drug.

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“…Organostibonic acids have been shown to behave as versatile building blocks in synthesizing discrete molecular architectures . Recently, biological studies on organostibonic acids have shown that they can act as potent anticancer drugs and antimicrobial agents . Rare molecular architectures like triangles, cubes, and adamantane-type motifs have been stabilized on reacting stibonic acids with various protic ligands. − Interestingly, the solid-state structure of organostibonic acids that have been retained in the solution state has been validated by ESI-MS data .…”

Section: Introductionmentioning

confidence: 97%

Discrete Molecular Aggregates Based on Zn^II and Sb^III/V Ions Displaying Efficient Antibacterial and Antioxidant Properties

et al. 2023

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The reactions of [Zn3Cl2(3,5-Me2PzH)4(t-BuPO3)2] with organostibonic acid in varying reaction conditions have been investigated. Single-crystal X-ray diffraction studies reveal the formation of [Zn2(p-ClC6H4Sb)2(O)2(OCH3)2(t-BuPO3)3(py)2] (1), [Zn2(p-ClC6H4SbV)4(SbIII)2(O)8(t-BuPO3H)4(t-BuPO3)2(py)2Cl2] (2), and [Zn2(RSb)4(O)4(OCH3)4(t-BuPO3)4(py)2], where R = p-ClC6H4 (3) and R = p-iPrC6H4 (4), respectively. Interestingly, in the synthesis of 2, complete dearylation of organoantimony moieties followed by C–F bond formation, a reduction from Sb (V) to Sb (III), and Sb···Cl weak intermolecular interactions have been observed. ESI-MS studies suggested that clusters 1–4 maintained their structural integrity in the solution state also. Solution NMR studies (1H, 31P, and 13C) support well the observed solid-state structures. 1–4 were tested for antibacterial activity using a microdilution assay. 1 and 4 showed the best activity with lower MIC values (0.78–6.25 μg/mL) against all the tested pathogens. The total antioxidant activity of 1–4 was evaluated through the phosphomolybdenum assay, which showed a total antioxidant activity ranging from 28.96 to 86.46 mg AAE/g compound with the ascorbic acid standard.

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Stibonic acids and related stibonate-phosphonate clusters: Synthesis, characterization and bioactivity evaluation

Cited by 4 publications

References 27 publications

Synthesis, Characterization, and Antimicrobial Activity of Ultra-Short Cationic β-Peptides

Synthesis, Characterization, and Antimicrobial Activity of Ultra-Short Cationic β-Peptides

Design, synthesis, and unraveling the antibacterial and antibiofilm potential of 2-azidobenzothiazoles: insights from a comprehensive in vitro study

Discrete Molecular Aggregates Based on Zn^II and Sb^III/V Ions Displaying Efficient Antibacterial and Antioxidant Properties

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Stibonic acids and related stibonate-phosphonate clusters: Synthesis, characterization and bioactivity evaluation

Cited by 4 publications

References 27 publications

Synthesis, Characterization, and Antimicrobial Activity of Ultra-Short Cationic β-Peptides

Synthesis, Characterization, and Antimicrobial Activity of Ultra-Short Cationic β-Peptides

Design, synthesis, and unraveling the antibacterial and antibiofilm potential of 2-azidobenzothiazoles: insights from a comprehensive in vitro study

Discrete Molecular Aggregates Based on ZnII and SbIII/V Ions Displaying Efficient Antibacterial and Antioxidant Properties

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Product

Resources

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Discrete Molecular Aggregates Based on Zn^II and Sb^III/V Ions Displaying Efficient Antibacterial and Antioxidant Properties