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Research Articles

Synthesis and antibacterial properties of alkyl substituted sulfonium salt

ORCID Icon, , , , &
Pages 257-265 | Received 28 Jul 2023, Accepted 20 Feb 2024, Published online: 04 Mar 2024

References

  • Kong, Q.; Yang, Y. Recent Advances in Antibacterial Agents. Bioorg. Med. Chem. Lett. 2021, 35, 127799. DOI:10.1016/j.bmcl.2021.127799.
  • Vereshchagin, A. N.; Frolov, N. A.; Egorova, K. S.; Seitkalieva, M. M.; Ananikov, V. P. Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials. Int. J. Mol. Sci. 2021, 22, 6793. DOI:10.3390/ijms22136793.
  • Saidin, S.; Jumat, M. A.; Mohd Amin, N. A. A.; Saleh Al-Hammadi, A. S. S. Organic and Inorganic Antibacterial Approaches in Combating Bacterial Infection for Biomedical Application. Mater. Sci. Eng. C Mater. Biol. Appl. 2021, 118, 111382. DOI:10.1016/j.msec.2020.111382.
  • Almeida, M. C.; Resende, D. I. S. P.; da Costa, P. M.; Pinto, M. M. M.; Sousa, E. Tryptophan Derived Natural Marine Alkaloids and Synthetic Derivatives as Promising Antimicrobial Agents. Eur. J. Med. Chem. 2021, 209, 112945. DOI:10.1016/j.ejmech.2020.112945.
  • Jennings, M. C.; Minbiole, K. P.; Wuest, W. M. Quaternary Ammonium Compounds: An Antimicrobial Mainstay and Platform for Innovation to Address Bacterial Resistance. ACS Infect. Dis. 2015, 1, 288–303. DOI:10.1021/acsinfecdis.5b00047.
  • Lobiuc, A.; Pavăl, N. E.; Mangalagiu, I. I.; Gheorghiță, R.; Teliban, G. C.; Amăriucăi-Mantu, D.; Stoleru, V. Future Antimicrobials: Natural and Functionalized Phenolics. Molecules 2023, 28, 1114. DOI:10.3390/molecules28031114.
  • Yin, M.; Wang, Y.; Zhang, Y.; Ren, X.; Qiu, Y.; Huang, T. S. Novel Quaternarized N-Halamine Chitosan and Polyvinyl Alcohol Nanofibrous Membranes as Hemostatic Materials with Excellent Antibacterial Properties. Carbohydr. Polym. 2020, 232, 115823. DOI:10.1016/j.carbpol.2019.115823.
  • Ibrahim, M. K.; Haria, A.; Mehta, N. V.; Degani, M. S. Antimicrobial Potential of Quaternary Phosphonium Salt Compounds: A Review. Future Med. Chem. 2023, 15, 2113–2141. DOI:10.4155/fmc-2023-0188.
  • Kratky, M.; Vinsova, J. Antimycobacterial Activity of Quaternary Pyridinium Salts and Pyridinium N-Oxides - Review. CPD 2012, 19, 1343–1355. DOI:10.2174/138161213804805711.
  • Guzmán, L.; Parra-Cid, C.; Guerrero-Muñoz, E.; Peña-Varas, C.; Polo-Cuadrado, E.; Duarte, Y.; Castro, R. I.; Nerio, L. S.; Araya-Maturana, R.; Asefa, T.; et al. Antimicrobial Properties of Novel Ionic Liquids Derived from Imidazolium Cation with Phenolic Functional Groups. Bioorg. Chem. 2021, 115, 105289. DOI:10.1016/j.bioorg.2021.105289.
  • Leong, J.; Yang, C.; Tan, J.; Tan, B. Q.; Hor, S.; Hedrick, J. L.; Yang, Y. Y. Combination of Guanidinium and Quaternary Ammonium Polymers with Distinctive Antimicrobial Mechanisms Achieving a Synergistic Antimicrobial Effect. Biomater. Sci. 2020, 8, 6920–6929. DOI:10.1039/d0bm00752h.
  • Huang, W.; Meng, L.; Chen, Y.; Dong, Z.; Peng, Q. Bacterial Outer Membrane Vesicles as Potential Biological Nanomaterials for Antibacterial Therapy. Acta Biomater. 2022, 140, 102–115. DOI:10.1016/j.actbio.2021.12.005.
  • Bortolotti, A.; Troiano, C.; Bobone, S.; Konai, M. M.; Ghosh, C.; Bocchinfuso, G.; Acharya, Y.; Santucci, V.; Bonacorsi, S.; Di Stefano, C.; et al. Mechanism of Lipid Bilayer Perturbation by Bactericidal Membrane-Active Small Molecules. Biochim. Biophys. Acta. Biomembr. 2023, 1865, 184079. DOI:10.1016/j.bbamem.2022.184079.
  • Hirayama, M. The Antimicrobial Activity, Hydrophobicity and Toxicity of Sulfonium Compounds, and Their Relationship. Biocontrol Sci. 2011, 16, 23–31. DOI:10.4265/bio.16.23.
  • Carden, R. G.; Sommers, K. J.; Schrank, C. L.; Leitgeb, A. J.; Feliciano, J. A.; Wuest, W. M.; Minbiole, K. P. C. Advancements in the Development of Non-Nitrogen-Based Amphiphilic Antiseptics to Overcome Pathogenic Bacterial Resistance. ChemMedChem 2020, 15, 1974–1984. DOI:10.1002/cmdc.202000612.
  • Oh, J.; Khan, A. Main-Chain Polysulfonium Salts: Development of Non-Ammonium Antibacterial Polymers Similar in Their Activity to Antibiotic Drugs Vancomycin and Kanamycin. Biomacromolecules 2021, 22, 3534–3542. DOI:10.1021/acs.biomac.1c00627.
  • Zhang, B.; Li, M.; Lin, M.; Yang, X.; Sun, J. A Convenient Approach for Antibacterial Polypeptoids Featuring Sulfonium and Oligo(Ethylene Glycol) Subunits. Biomater. Sci. 2020, 8, 6969–6977. DOI:10.1039/d0bm01384f.
  • Feliciano, J. A.; Leitgeb, A. J.; Schrank, C. L.; Allen, R. A.; Minbiole, K. P. C.; Wuest, W. M.; Carden, R. G. Trivalent Sulfonium Compounds (TSCs): Tetrahydrothiophene-Based Amphiphiles Exhibit Similar Antimicrobial Activity to Analogous Ammonium-Based Amphiphiles. Bioorg. Med. Chem. Lett. 2021, 37, 127809. DOI:10.1016/j.bmcl.2021.127809.
  • Sun, J.; Li, M.; Lin, M.; Zhang, B.; Chen, X. High Antibacterial Activity and Selectivity of the Versatile Polysulfoniums That Combat Drug Resistance. Adv. Mater. 2021, 33, e2104402. DOI:10.1002/adma.202104402.
  • Wang, X.; Wang, G.; Zhao, J.; Zhu, Z.; Rao, J. Main-Chain Sulfonium-Containing Homopolymers with Negligible Hemolytic Toxicity for Eradication of Bacterial and Fungal Biofilms. ACS Macro Lett. 2021, 10, 1643–1649. DOI:10.1021/acsmacrolett.1c00698.
  • Guan, D.; Chen, F.; Qiu, Y.; Jiang, B.; Gong, L.; Lan, L.; Huang, W. Sulfonium, an Underestimated Moiety for Structural Modification, Alters the Antibacterial Profile of Vancomycin against Multidrug-Resistant Bacteria. Angew. Chem. Int. Ed. Engl. 2019, 58, 6678–6682. DOI:10.1002/anie.201902210.
  • Patel, A.; Dey, S.; Shokeen, K.; Karpiński, T. M.; Sivaprakasam, S.; Kumar, S.; Manna, D. Sulfonium-Based Liposome-Encapsulated Antibiotics Deliver a Synergistic Antibacterial Activity. RSC Med. Chem. 2021, 12, 1005–1015. DOI:10.1039/d1md00091h.
  • Hirayama, M. The Antimicrobial Activity, Toxicity and Antimicrobial Mechanism of a New Type of Tris(Alkylphenyl)Sulfonium. Biocontrol Sci. 2012, 17, 27–35. DOI:10.4265/bio.17.27.

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