Natural Product-derived Quaternary Ammonium Compounds with Potent Antimicrobial Activity

Overview

Journal J Antibiot (Tokyo)

Specialties Infectious Diseases
Pharmacology

Date 2015 Nov 19

PMID 26577453

Citations 9

Authors

Maureen D Joyce

Megan C Jennings

Celina N Santiago

Madison H Fletcher

William M Wuest

Kevin Pc Minbiole

Affiliations

Soon will be listed here.

Citing Articles

Naturally derived 3-aminoquinuclidine salts as new promising therapeutic agents.

Crncevic D, Ramic A, Kastelic A, Odzak R, Krce L, Weber I Sci Rep. 2024; 14(1):26211.

PMID: 39482460 PMC: 11528103. DOI: 10.1038/s41598-024-77647-5.

Deriving Novel Quaternary Ammonium Compound Disinfectant Scaffolds from a Natural Product: Mechanistic Insights of the Quaternization of Ianthelliformisamine C.

Allen R, McCormack C, Wuest W ChemMedChem. 2023; 18(22):e202300253.

PMID: 37770411 PMC: 10841702. DOI: 10.1002/cmdc.202300253.

Quinine Esters with 1,2-Azole, Pyridine and Adamantane Fragments.

Mukusheva G, Zhasymbekova A, Seidakhmetova R, Nurkenov O, Akishina E, Petkevich S Molecules. 2022; 27(11).

PMID: 35684414 PMC: 9182173. DOI: 10.3390/molecules27113476.

Quaternary Phosphonium Compounds: An Examination of Non-Nitrogenous Cationic Amphiphiles That Evade Disinfectant Resistance.

Sommers K, Michaud M, Hogue C, Scharnow A, Amoo L, Petersen A ACS Infect Dis. 2022; 8(2):387-397.

PMID: 35077149 PMC: 8996050. DOI: 10.1021/acsinfecdis.1c00611.

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials.

Vereshchagin A, Frolov N, Egorova K, Seitkalieva M, Ananikov V Int J Mol Sci. 2021; 22(13).

PMID: 34202677 PMC: 8268321. DOI: 10.3390/ijms22136793.

References

Park C, Kim S, Choi W, Lee Y, Kim J, Kang S . Novel anticholinesterase and antiamnesic activities of dehydroevodiamine, a constituent of Evodia rutaecarpa. Planta Med. 1996; 62(5):405-9. DOI: 10.1055/s-2006-957926. View

Guani-Guerra E, Santos-Mendoza T, Lugo-Reyes S, Teran L . Antimicrobial peptides: general overview and clinical implications in human health and disease. Clin Immunol. 2010; 135(1):1-11. DOI: 10.1016/j.clim.2009.12.004. View

Crooks P, Ayers J, Xu R, Sumithran S, Grinevich V, Wilkins L . Development of subtype-selective ligands as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release. Bioorg Med Chem Lett. 2004; 14(8):1869-74. DOI: 10.1016/j.bmcl.2003.10.074. View

Wabo H, Tane P, Connolly J, Okunji C, Schuster B, Iwu M . Tabouensinium chloride, a novel quaternary pyranoquinoline alkaloid from Araliopsis tabouensis. Nat Prod Res. 2005; 19(6):591-5. DOI: 10.1080/14786410412331280078. View

Jennings M, Minbiole K, Wuest W . Quaternary Ammonium Compounds: An Antimicrobial Mainstay and Platform for Innovation to Address Bacterial Resistance. ACS Infect Dis. 2016; 1(7):288-303. DOI: 10.1021/acsinfecdis.5b00047. View

Rochfort S, Towerzey L, Carroll A, King G, Michael A, Pierens G . Latifolians A and B, novel JNK3 kinase inhibitors from the Papua New Guinean plant Gnetum latifolium. J Nat Prod. 2005; 68(7):1080-2. DOI: 10.1021/np049616i. View

Baidya M, Horn M, Zipse H, Mayr H . Organocatalytic activity of cinchona alkaloids: which nitrogen is more nucleophilic?. J Org Chem. 2009; 74(18):7157-64. DOI: 10.1021/jo901670w. View

Lv J, Qian Y, Liu T, Wang Y . Synthesis and evaluation of amphiphilic cationic quinine-derived for antibacterial activity against methicillin-resistant Staphylococcus aureus. Bioorg Med Chem Lett. 2007; 17(15):4102-6. DOI: 10.1016/j.bmcl.2007.05.065. View

Martin F, Grkovic T, Sykes M, Shelper T, Avery V, Camp D . Alkaloids from the Chinese vine Gnetum montanum. J Nat Prod. 2011; 74(11):2425-30. DOI: 10.1021/np200700f. View

10.

Cernakova M, Kostalova D . Antimicrobial activity of berberine--a constituent of Mahonia aquifolium. Folia Microbiol (Praha). 2002; 47(4):375-8. DOI: 10.1007/BF02818693. View

11.

Palomo C, Oiarbide M, Lopez R . Asymmetric organocatalysis by chiral Brønsted bases: implications and applications. Chem Soc Rev. 2009; 38(2):632-53. DOI: 10.1039/b708453f. View

12.

Hertiani T, Edrada-Ebel R, Ortlepp S, Soest R, de Voogd N, Wray V . From anti-fouling to biofilm inhibition: new cytotoxic secondary metabolites from two Indonesian Agelas sponges. Bioorg Med Chem. 2010; 18(3):1297-311. DOI: 10.1016/j.bmc.2009.12.028. View