Literature DB >> 33197298

Metallocene QACs: The Incorporation of Ferrocene Moieties into monoQAC and bisQAC Structures.

Kyle J Sommers1, Brian S Bentley1, Robert G Carden1, Savannah J Post2, Ryan A Allen2, Renee C Kontos1, Jacob W Black1, William M Wuest2, Kevin P C Minbiole1.   

Abstract

Inspired by the incorporation of metallocene functionalities into a variety of bioactive structures, particularly antimicrobial peptides, we endeavored to broaden the structural variety of quaternary ammonium compounds (QACs) by the incorporation of the ferrocene moiety. Accordingly, 23 ferrocene-containing mono- and bisQACs were prepared in high yields and tested for activity against a variety of bacteria, including Gram-negative strains and a panel of clinically isolated MRSA strains. Ferrocene QACs were shown to be effective antiseptics with some displaying single-digit micromolar activity against all bacteria tested, demonstrating yet another step in the expansion of structural variety of antiseptic QACs.
© 2020 Wiley-VCH GmbH.

Entities:  

Keywords:  antiseptics; benzalkonium chloride; bisQAC; ferrocene; methicillin-resistant Staphylococcus aureus (MRSA); quaternary ammonium compounds

Mesh:

Substances:

Year:  2020        PMID: 33197298      PMCID: PMC7864880          DOI: 10.1002/cmdc.202000605

Source DB:  PubMed          Journal:  ChemMedChem        ISSN: 1860-7179            Impact factor:   3.466


  34 in total

Review 1.  Studies and syntheses of siderophores, microbial iron chelators, and analogs as potential drug delivery agents.

Authors:  J M Roosenberg; Y M Lin; Y Lu; M J Miller
Journal:  Curr Med Chem       Date:  2000-02       Impact factor: 4.530

Review 2.  Control of membrane lipid fluidity by molecular thermosensors.

Authors:  María C Mansilla; Larisa E Cybulski; Daniela Albanesi; Diego de Mendoza
Journal:  J Bacteriol       Date:  2004-10       Impact factor: 3.490

3.  Scaffold-Hopping of Multicationic Amphiphiles Yields Three New Classes of Antimicrobials.

Authors:  Myles A Mitchell; Anthony A Iannetta; Megan C Jennings; Madison H Fletcher; William M Wuest; Kevin P C Minbiole
Journal:  Chembiochem       Date:  2015-09-11       Impact factor: 3.164

4.  Characterization of a strain of community-associated methicillin-resistant Staphylococcus aureus widely disseminated in the United States.

Authors:  Fred C Tenover; Linda K McDougal; Richard V Goering; George Killgore; Steven J Projan; Jean B Patel; Paul M Dunman
Journal:  J Clin Microbiol       Date:  2006-01       Impact factor: 5.948

5.  Purification and characterization of E37, a major chloroplast envelope protein.

Authors:  M A Block; J Joyard; R Douce
Journal:  FEBS Lett       Date:  1991-08-05       Impact factor: 4.124

6.  Analysis of the Destabilization of Bacterial Membranes by Quaternary Ammonium Compounds: A Combined Experimental and Computational Study.

Authors:  Saleh Alkhalifa; Megan C Jennings; Daniele Granata; Michael Klein; William M Wuest; Kevin P C Minbiole; Vincenzo Carnevale
Journal:  Chembiochem       Date:  2020-02-18       Impact factor: 3.164

Review 7.  Design Strategies and Medicinal Applications of Metal-Peptidic Bioconjugates.

Authors:  Samuel M Meier-Menches; Angela Casini
Journal:  Bioconjug Chem       Date:  2020-04-14       Impact factor: 4.774

8.  An Investigation into Rigidity-Activity Relationships in BisQAC Amphiphilic Antiseptics.

Authors:  Renee C Kontos; Stephanie A Schallenhammer; Brian S Bentley; Kelly R Morrison; Javier A Feliciano; Julia A Tasca; Anna R Kaplan; Mark W Bezpalko; W Scott Kassel; William M Wuest; Kevin P C Minbiole
Journal:  ChemMedChem       Date:  2018-12-18       Impact factor: 3.466

9.  TMEDA-derived biscationic amphiphiles: An economical preparation of potent antibacterial agents.

Authors:  Jacob W Black; Megan C Jennings; Julianne Azarewicz; Thomas J Paniak; Melissa C Grenier; William M Wuest; Kevin P C Minbiole
Journal:  Bioorg Med Chem Lett       Date:  2013-12-04       Impact factor: 2.823

10.  Membrane fluidity adjustments in ethanol-stressed Oenococcus oeni cells.

Authors:  M Graça Da Silveira; Elena A Golovina; Folkert A Hoekstra; Frank M Rombouts; Tjakko Abee
Journal:  Appl Environ Microbiol       Date:  2003-10       Impact factor: 4.792

View more
  2 in total

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

Authors:  Kyle J Sommers; Marina E Michaud; Cody E Hogue; Amber M Scharnow; Lauren E Amoo; Ashley A Petersen; Robert G Carden; Kevin P C Minbiole; William M Wuest
Journal:  ACS Infect Dis       Date:  2022-01-25       Impact factor: 5.084

2.  An Efficient Synthesis of 3-Alkylpyridine Alkaloids Enables Their Biological Evaluation.

Authors:  Anna R Kaplan; Cassandra L Schrank; William M Wuest
Journal:  ChemMedChem       Date:  2021-04-14       Impact factor: 3.540

  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.